Chitosan Derivatives and Their Application in Biomedicine
Identifieur interne : 000A29 ( Pmc/Corpus ); précédent : 000A28; suivant : 000A30Chitosan Derivatives and Their Application in Biomedicine
Auteurs : Wenqian Wang ; Qiuyu Meng ; Qi Li ; Jinbao Liu ; Mo Zhou ; Zheng Jin ; Kai ZhaoSource :
- International Journal of Molecular Sciences [ 1422-0067 ] ; 2020.
Abstract
Chitosan is a product of the deacetylation of chitin, which is widely found in nature. Chitosan is insoluble in water and most organic solvents, which seriously limits both its application scope and applicable fields. However, chitosan contains active functional groups that are liable to chemical reactions; thus, chitosan derivatives can be obtained through the chemical modification of chitosan. The modification of chitosan has been an important aspect of chitosan research, showing a better solubility, pH-sensitive targeting, an increased number of delivery systems, etc. This review summarizes the modification of chitosan by acylation, carboxylation, alkylation, and quaternization in order to improve the water solubility, pH sensitivity, and the targeting of chitosan derivatives. The applications of chitosan derivatives in the antibacterial, sustained slowly release, targeting, and delivery system fields are also described. Chitosan derivatives will have a large impact and show potential in biomedicine for the development of drugs in future.
Url:
DOI: 10.3390/ijms21020487
PubMed: 31940963
PubMed Central: 7014278
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Chitosan Derivatives and Their Application in Biomedicine</title><author><name sortKey="Wang, Wenqian" sort="Wang, Wenqian" uniqKey="Wang W" first="Wenqian" last="Wang">Wenqian Wang</name><affiliation><nlm:aff id="af1-ijms-21-00487">Key Laboratory of Chemical Engineering Process and Technology for High-efficiency Conversion, College of Heilongjiang Province, College of Chemistry Engineering and Materials, Heilongjiang University, Harbin 150080, China;<email>wangwenqian3104@163.com</email> (W.W.);<email>m940584524@163.com</email> (Q.M.);<email>liqi114013@163.com</email> (Q.L.);<email>ljb19970107@163.com</email> (J.L.)</nlm:aff></affiliation></author><author><name sortKey="Meng, Qiuyu" sort="Meng, Qiuyu" uniqKey="Meng Q" first="Qiuyu" last="Meng">Qiuyu Meng</name><affiliation><nlm:aff id="af1-ijms-21-00487">Key Laboratory of Chemical Engineering Process and Technology for High-efficiency Conversion, College of Heilongjiang Province, College of Chemistry Engineering and Materials, Heilongjiang University, Harbin 150080, China;<email>wangwenqian3104@163.com</email> (W.W.);<email>m940584524@163.com</email> (Q.M.);<email>liqi114013@163.com</email> (Q.L.);<email>ljb19970107@163.com</email> (J.L.)</nlm:aff></affiliation></author><author><name sortKey="Li, Qi" sort="Li, Qi" uniqKey="Li Q" first="Qi" last="Li">Qi Li</name><affiliation><nlm:aff id="af1-ijms-21-00487">Key Laboratory of Chemical Engineering Process and Technology for High-efficiency Conversion, College of Heilongjiang Province, College of Chemistry Engineering and Materials, Heilongjiang University, Harbin 150080, China;<email>wangwenqian3104@163.com</email> (W.W.);<email>m940584524@163.com</email> (Q.M.);<email>liqi114013@163.com</email> (Q.L.);<email>ljb19970107@163.com</email> (J.L.)</nlm:aff></affiliation></author><author><name sortKey="Liu, Jinbao" sort="Liu, Jinbao" uniqKey="Liu J" first="Jinbao" last="Liu">Jinbao Liu</name><affiliation><nlm:aff id="af1-ijms-21-00487">Key Laboratory of Chemical Engineering Process and Technology for High-efficiency Conversion, College of Heilongjiang Province, College of Chemistry Engineering and Materials, Heilongjiang University, Harbin 150080, China;<email>wangwenqian3104@163.com</email> (W.W.);<email>m940584524@163.com</email> (Q.M.);<email>liqi114013@163.com</email> (Q.L.);<email>ljb19970107@163.com</email> (J.L.)</nlm:aff></affiliation></author><author><name sortKey="Zhou, Mo" sort="Zhou, Mo" uniqKey="Zhou M" first="Mo" last="Zhou">Mo Zhou</name><affiliation><nlm:aff id="af2-ijms-21-00487">Engineering Research Center of Agricultural Microbiology Technology, Ministry of Education, Heilongjiang University, Harbin 150080, China;<email>zhoumo_wk@hotmail.com</email></nlm:aff></affiliation><affiliation><nlm:aff id="af3-ijms-21-00487">Key Laboratory of Microbiology, College of Heilongjiang Province, School of Life Science, Heilongjiang University, Harbin 150080, China</nlm:aff></affiliation></author><author><name sortKey="Jin, Zheng" sort="Jin, Zheng" uniqKey="Jin Z" first="Zheng" last="Jin">Zheng Jin</name><affiliation><nlm:aff id="af1-ijms-21-00487">Key Laboratory of Chemical Engineering Process and Technology for High-efficiency Conversion, College of Heilongjiang Province, College of Chemistry Engineering and Materials, Heilongjiang University, Harbin 150080, China;<email>wangwenqian3104@163.com</email> (W.W.);<email>m940584524@163.com</email> (Q.M.);<email>liqi114013@163.com</email> (Q.L.);<email>ljb19970107@163.com</email> (J.L.)</nlm:aff></affiliation></author><author><name sortKey="Zhao, Kai" sort="Zhao, Kai" uniqKey="Zhao K" first="Kai" last="Zhao">Kai Zhao</name><affiliation><nlm:aff id="af2-ijms-21-00487">Engineering Research Center of Agricultural Microbiology Technology, Ministry of Education, Heilongjiang University, Harbin 150080, China;<email>zhoumo_wk@hotmail.com</email></nlm:aff></affiliation><affiliation><nlm:aff id="af3-ijms-21-00487">Key Laboratory of Microbiology, College of Heilongjiang Province, School of Life Science, Heilongjiang University, Harbin 150080, China</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">31940963</idno><idno type="pmc">7014278</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7014278</idno><idno type="RBID">PMC:7014278</idno><idno type="doi">10.3390/ijms21020487</idno><date when="2020">2020</date><idno type="wicri:Area/Pmc/Corpus">000A29</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000A29</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Chitosan Derivatives and Their Application in Biomedicine</title><author><name sortKey="Wang, Wenqian" sort="Wang, Wenqian" uniqKey="Wang W" first="Wenqian" last="Wang">Wenqian Wang</name><affiliation><nlm:aff id="af1-ijms-21-00487">Key Laboratory of Chemical Engineering Process and Technology for High-efficiency Conversion, College of Heilongjiang Province, College of Chemistry Engineering and Materials, Heilongjiang University, Harbin 150080, China;<email>wangwenqian3104@163.com</email> (W.W.);<email>m940584524@163.com</email> (Q.M.);<email>liqi114013@163.com</email> (Q.L.);<email>ljb19970107@163.com</email> (J.L.)</nlm:aff></affiliation></author><author><name sortKey="Meng, Qiuyu" sort="Meng, Qiuyu" uniqKey="Meng Q" first="Qiuyu" last="Meng">Qiuyu Meng</name><affiliation><nlm:aff id="af1-ijms-21-00487">Key Laboratory of Chemical Engineering Process and Technology for High-efficiency Conversion, College of Heilongjiang Province, College of Chemistry Engineering and Materials, Heilongjiang University, Harbin 150080, China;<email>wangwenqian3104@163.com</email> (W.W.);<email>m940584524@163.com</email> (Q.M.);<email>liqi114013@163.com</email> (Q.L.);<email>ljb19970107@163.com</email> (J.L.)</nlm:aff></affiliation></author><author><name sortKey="Li, Qi" sort="Li, Qi" uniqKey="Li Q" first="Qi" last="Li">Qi Li</name><affiliation><nlm:aff id="af1-ijms-21-00487">Key Laboratory of Chemical Engineering Process and Technology for High-efficiency Conversion, College of Heilongjiang Province, College of Chemistry Engineering and Materials, Heilongjiang University, Harbin 150080, China;<email>wangwenqian3104@163.com</email> (W.W.);<email>m940584524@163.com</email> (Q.M.);<email>liqi114013@163.com</email> (Q.L.);<email>ljb19970107@163.com</email> (J.L.)</nlm:aff></affiliation></author><author><name sortKey="Liu, Jinbao" sort="Liu, Jinbao" uniqKey="Liu J" first="Jinbao" last="Liu">Jinbao Liu</name><affiliation><nlm:aff id="af1-ijms-21-00487">Key Laboratory of Chemical Engineering Process and Technology for High-efficiency Conversion, College of Heilongjiang Province, College of Chemistry Engineering and Materials, Heilongjiang University, Harbin 150080, China;<email>wangwenqian3104@163.com</email> (W.W.);<email>m940584524@163.com</email> (Q.M.);<email>liqi114013@163.com</email> (Q.L.);<email>ljb19970107@163.com</email> (J.L.)</nlm:aff></affiliation></author><author><name sortKey="Zhou, Mo" sort="Zhou, Mo" uniqKey="Zhou M" first="Mo" last="Zhou">Mo Zhou</name><affiliation><nlm:aff id="af2-ijms-21-00487">Engineering Research Center of Agricultural Microbiology Technology, Ministry of Education, Heilongjiang University, Harbin 150080, China;<email>zhoumo_wk@hotmail.com</email></nlm:aff></affiliation><affiliation><nlm:aff id="af3-ijms-21-00487">Key Laboratory of Microbiology, College of Heilongjiang Province, School of Life Science, Heilongjiang University, Harbin 150080, China</nlm:aff></affiliation></author><author><name sortKey="Jin, Zheng" sort="Jin, Zheng" uniqKey="Jin Z" first="Zheng" last="Jin">Zheng Jin</name><affiliation><nlm:aff id="af1-ijms-21-00487">Key Laboratory of Chemical Engineering Process and Technology for High-efficiency Conversion, College of Heilongjiang Province, College of Chemistry Engineering and Materials, Heilongjiang University, Harbin 150080, China;<email>wangwenqian3104@163.com</email> (W.W.);<email>m940584524@163.com</email> (Q.M.);<email>liqi114013@163.com</email> (Q.L.);<email>ljb19970107@163.com</email> (J.L.)</nlm:aff></affiliation></author><author><name sortKey="Zhao, Kai" sort="Zhao, Kai" uniqKey="Zhao K" first="Kai" last="Zhao">Kai Zhao</name><affiliation><nlm:aff id="af2-ijms-21-00487">Engineering Research Center of Agricultural Microbiology Technology, Ministry of Education, Heilongjiang University, Harbin 150080, China;<email>zhoumo_wk@hotmail.com</email></nlm:aff></affiliation><affiliation><nlm:aff id="af3-ijms-21-00487">Key Laboratory of Microbiology, College of Heilongjiang Province, School of Life Science, Heilongjiang University, Harbin 150080, China</nlm:aff></affiliation></author></analytic><series><title level="j">International Journal of Molecular Sciences</title><idno type="eISSN">1422-0067</idno><imprint><date when="2020">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>Chitosan is a product of the deacetylation of chitin, which is widely found in nature. Chitosan is insoluble in water and most organic solvents, which seriously limits both its application scope and applicable fields. However, chitosan contains active functional groups that are liable to chemical reactions; thus, chitosan derivatives can be obtained through the chemical modification of chitosan. The modification of chitosan has been an important aspect of chitosan research, showing a better solubility, pH-sensitive targeting, an increased number of delivery systems, etc. This review summarizes the modification of chitosan by acylation, carboxylation, alkylation, and quaternization in order to improve the water solubility, pH sensitivity, and the targeting of chitosan derivatives. The applications of chitosan derivatives in the antibacterial, sustained slowly release, targeting, and delivery system fields are also described. 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<front><journal-meta><journal-id journal-id-type="nlm-ta">Int J Mol Sci</journal-id><journal-id journal-id-type="iso-abbrev">Int J Mol Sci</journal-id><journal-id journal-id-type="publisher-id">ijms</journal-id><journal-title-group><journal-title>International Journal of Molecular Sciences</journal-title></journal-title-group><issn pub-type="epub">1422-0067</issn><publisher><publisher-name>MDPI</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">31940963</article-id><article-id pub-id-type="pmc">7014278</article-id><article-id pub-id-type="doi">10.3390/ijms21020487</article-id><article-id pub-id-type="publisher-id">ijms-21-00487</article-id><article-categories><subj-group subj-group-type="heading"><subject>Review</subject></subj-group></article-categories><title-group><article-title>Chitosan Derivatives and Their Application in Biomedicine</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Wang</surname><given-names>Wenqian</given-names></name><xref ref-type="aff" rid="af1-ijms-21-00487">1</xref></contrib><contrib contrib-type="author"><name><surname>Meng</surname><given-names>Qiuyu</given-names></name><xref ref-type="aff" rid="af1-ijms-21-00487">1</xref></contrib><contrib contrib-type="author"><name><surname>Li</surname><given-names>Qi</given-names></name><xref ref-type="aff" rid="af1-ijms-21-00487">1</xref></contrib><contrib contrib-type="author"><name><surname>Liu</surname><given-names>Jinbao</given-names></name><xref ref-type="aff" rid="af1-ijms-21-00487">1</xref></contrib><contrib contrib-type="author"><name><surname>Zhou</surname><given-names>Mo</given-names></name><xref ref-type="aff" rid="af2-ijms-21-00487">2</xref><xref ref-type="aff" rid="af3-ijms-21-00487">3</xref></contrib><contrib contrib-type="author"><name><surname>Jin</surname><given-names>Zheng</given-names></name><xref ref-type="aff" rid="af1-ijms-21-00487">1</xref><xref rid="c1-ijms-21-00487" ref-type="corresp">*</xref></contrib><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0001-6139-1912</contrib-id><name><surname>Zhao</surname><given-names>Kai</given-names></name><xref ref-type="aff" rid="af2-ijms-21-00487">2</xref><xref ref-type="aff" rid="af3-ijms-21-00487">3</xref><xref rid="c1-ijms-21-00487" ref-type="corresp">*</xref></contrib></contrib-group><aff id="af1-ijms-21-00487"><label>1</label>Key Laboratory of Chemical Engineering Process and Technology for High-efficiency Conversion, College of Heilongjiang Province, College of Chemistry Engineering and Materials, Heilongjiang University, Harbin 150080, China;<email>wangwenqian3104@163.com</email> (W.W.);<email>m940584524@163.com</email> (Q.M.);<email>liqi114013@163.com</email> (Q.L.);<email>ljb19970107@163.com</email> (J.L.)</aff><aff id="af2-ijms-21-00487"><label>2</label>Engineering Research Center of Agricultural Microbiology Technology, Ministry of Education, Heilongjiang University, Harbin 150080, China;<email>zhoumo_wk@hotmail.com</email></aff><aff id="af3-ijms-21-00487"><label>3</label>Key Laboratory of Microbiology, College of Heilongjiang Province, School of Life Science, Heilongjiang University, Harbin 150080, China</aff><author-notes><corresp id="c1-ijms-21-00487"><label>*</label>Correspondence: <email>jinzheng@hlju.edu.cn</email> (Z.J.); <email>zybin395@126.com</email> (K.Z.); Tel.: +86-451-8660-8131 (Z.J.); +86-451-8660-8586 (K.Z.)</corresp></author-notes><pub-date pub-type="epub"><day>12</day><month>1</month><year>2020</year></pub-date><pub-date pub-type="collection"><month>1</month><year>2020</year></pub-date><volume>21</volume><issue>2</issue><elocation-id>487</elocation-id><history><date date-type="received"><day>25</day><month>11</month><year>2019</year></date><date date-type="accepted"><day>09</day><month>1</month><year>2020</year></date></history><permissions><copyright-statement>© 2020 by the authors.</copyright-statement><copyright-year>2020</copyright-year><license license-type="open-access"><license-p>Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (<ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/4.0/">http://creativecommons.org/licenses/by/4.0/</ext-link>).</license-p></license></permissions><abstract><p>Chitosan is a product of the deacetylation of chitin, which is widely found in nature. Chitosan is insoluble in water and most organic solvents, which seriously limits both its application scope and applicable fields. However, chitosan contains active functional groups that are liable to chemical reactions; thus, chitosan derivatives can be obtained through the chemical modification of chitosan. The modification of chitosan has been an important aspect of chitosan research, showing a better solubility, pH-sensitive targeting, an increased number of delivery systems, etc. This review summarizes the modification of chitosan by acylation, carboxylation, alkylation, and quaternization in order to improve the water solubility, pH sensitivity, and the targeting of chitosan derivatives. The applications of chitosan derivatives in the antibacterial, sustained slowly release, targeting, and delivery system fields are also described. Chitosan derivatives will have a large impact and show potential in biomedicine for the development of drugs in future.</p></abstract><kwd-group><kwd>chitosan derivative</kwd><kwd>nanoparticles</kwd><kwd>biomedicine</kwd><kwd>drug delivery</kwd><kwd>immunology</kwd></kwd-group></article-meta></front><body><sec sec-type="intro" id="sec1-ijms-21-00487"><title>1. Introduction</title><p>With the improvement of living standards, people have been paying more attention to the development of health and medical technology. In recent years, many polymer compounds, extracted from starch, liver sugar, inulin, cellulose, chitin, and alginates, have been widely used in biology, medicine, beauty, healthcare, and other fields [<xref rid="B1-ijms-21-00487" ref-type="bibr">1</xref>,<xref rid="B2-ijms-21-00487" ref-type="bibr">2</xref>,<xref rid="B3-ijms-21-00487" ref-type="bibr">3</xref>]. Here, chitosan is one area of focus. Chitosan is a deacetylated product of chitin, which is an abundant natural resource that features less storage than cellulose [<xref rid="B4-ijms-21-00487" ref-type="bibr">4</xref>,<xref rid="B5-ijms-21-00487" ref-type="bibr">5</xref>]. Chitosan is a renewable natural alkaline polysaccharide that has no toxicity and no side effects, and it features good moisturizing and adsorption properties. The United States Food and Drug Administration (FDA) has approved that chitosan is safe in the use of foods and drugs.</p><p>However, chitosan is insoluble in water and most organic solvents, which limits its applications in various fields. Chitosan derivatives can be obtained by the chemical modification of chitosan-reactive functional groups. Here, the −OH and −NH<sub>2</sub> active groups on the chitosan molecule are prone to chemical reactions [<xref rid="B6-ijms-21-00487" ref-type="bibr">6</xref>,<xref rid="B7-ijms-21-00487" ref-type="bibr">7</xref>]. Chemical modification can not only improve the physical and chemical properties of chitosan, it can also retain the unique properties of chitosan and expand the application range of chitosan derivatives. Modified chitosan derivatives have better biocompatibility, bioactivity, biodegradability, and non-toxicity, and they still possess the original bactericidal, antibacterial, anticancer, and antiviral pharmacological effects, including the ability to induce erythrocyte aggregation, promote platelet activation, and activate complement systems other than that of chitosan [<xref rid="B8-ijms-21-00487" ref-type="bibr">8</xref>,<xref rid="B9-ijms-21-00487" ref-type="bibr">9</xref>,<xref rid="B10-ijms-21-00487" ref-type="bibr">10</xref>,<xref rid="B11-ijms-21-00487" ref-type="bibr">11</xref>,<xref rid="B12-ijms-21-00487" ref-type="bibr">12</xref>,<xref rid="B13-ijms-21-00487" ref-type="bibr">13</xref>]. At present, chitosan derivatives have been widely used in both medical materials and biomedicine. With the development of nanotechnology, chitosan derivatives have been prepared as nanomaterials, including nanoparticles, hydrogels, microspheres, and micelles. Chitosan derivatives can be used as targeted delivery vehicles for drugs, as well as adjuvants and delivery carriers for vaccines [<xref rid="B14-ijms-21-00487" ref-type="bibr">14</xref>,<xref rid="B15-ijms-21-00487" ref-type="bibr">15</xref>,<xref rid="B16-ijms-21-00487" ref-type="bibr">16</xref>,<xref rid="B17-ijms-21-00487" ref-type="bibr">17</xref>,<xref rid="B18-ijms-21-00487" ref-type="bibr">18</xref>,<xref rid="B19-ijms-21-00487" ref-type="bibr">19</xref>,<xref rid="B20-ijms-21-00487" ref-type="bibr">20</xref>]. Therefore, chitosan derivatives and their nanomaterials can be widely used and expanded upon in terms of the fields of chitosan application [<xref rid="B21-ijms-21-00487" ref-type="bibr">21</xref>,<xref rid="B22-ijms-21-00487" ref-type="bibr">22</xref>]. The properties of materials determine their applications, so this review focuses on the preparation of chitosan derivatives with excellent solubility, pH sensitivity, targeting, and mucosal adhesion; additionally, this review introduces the application fields of chitosan derivatives in medicine in three aspects, namely as drug carriers, drug materials, and for mucosal immunity. The effects of chemical modification and different material states (nanoparticles, fibers, gels, etc.) of the properties of chitosan derivatives have been researched. We hope that the review can provide some guidance for research on improving the good properties of chitosan and expanding the potential applications of chitosan.</p></sec><sec id="sec2-ijms-21-00487"><title>2. Modification of Chitosan</title><p>Functional groups on the chitosan molecules include C<sub>3</sub>–OH, C<sub>6</sub>–OH, C<sub>2</sub>–NH<sub>2</sub>, and acetyl amino and glycoside bonds [<xref rid="B6-ijms-21-00487" ref-type="bibr">6</xref>]. Among them, the acetyl amino bond is as stable as the glycosidic bond, which is not easy to fracture. C<sub>3</sub>–OH belongs to a secondary hydroxyl, it cannot rotate freely, and its steric hindrance is so big that it does not easily react. The active chemical properties of C<sub>6</sub>–OH and C<sub>2</sub>–NH<sub>2</sub> take advantage of these groups in chitosan molecules to introduce other groups through various kinds of molecular design. The chemical modification of chitosan can improve its physical and chemical properties, as well as expand its applications and relevant research fields [<xref rid="B23-ijms-21-00487" ref-type="bibr">23</xref>,<xref rid="B24-ijms-21-00487" ref-type="bibr">24</xref>,<xref rid="B25-ijms-21-00487" ref-type="bibr">25</xref>]. A schematic diagram of chitosan modification is shown in <xref ref-type="fig" rid="ijms-21-00487-f001">Figure 1</xref>.</p><sec id="sec2dot1-ijms-21-00487"><title>2.1. Improving the Solubility of Chitosan</title><p>Though chitosan has a wide range of applications, its intermolecular and intramolecular hydrogen bonds are highly crystalline, which makes it almost insoluble in water and therefore limits its applications to some extent. Therefore, it is important to improve the water solubility of chitosan. At present, there are generally three considered methods for improving the solubility of chitosan: (1) Chitin deacetylation, where the chitosan, after deacetylation, can only be dissolved in an acidic solution, thus limiting its applications; (2) chemical modification, where a hydrophilic group is introduced on an amino group or a hydroxyl group in a chitosan molecule. At the same time, this method destroys the original hydrogen bond and crystallinity of chitosan; (3) chitosan degrades into a water-soluble product of small molecules under the action of an enzyme, where the molecular weight distribution of chitosan during the degradation is extremely uneven and the product is difficult to separate. Therefore, chemical modification is often used to improve the water solubility of chitosan.</p><sec id="sec2dot1dot1-ijms-21-00487"><title>2.1.1. Destruction of Hydrogen Bonding</title><sec><title>Acylated Modified Chitosan</title><p>Acylation modification is the most common modification of chitosan. The acylation of chitosan refers to the reaction of chitosan with a variety of organic acids and derivatives of organic acids (mainly anhydride and acyl chloride), introducing aliphatic or aromatic acyl groups to the molecular chain [<xref rid="B26-ijms-21-00487" ref-type="bibr">26</xref>]. The acylation reaction destroys the intramolecular and intermolecular hydrogen bonding of chitosan, which weakens its crystallinity and enhances its water solubility. There are two hydroxyl groups on the molecular chain of chitosan, with one being the primary hydroxyl group of C<sub>6</sub>–OH and the other being the secondary hydroxyl group of C<sub>3</sub>–OH. The primary hydroxyl group is free to rotate in the spatial conformation, with low steric hindrance, while the secondary hydroxyl group is not able to rotate, with high steric hindrance, and the activity of C<sub>2</sub>–NH<sub>2</sub> is higher than that of the primary hydroxyl group. Therefore, the order of activity of the acylation reaction is C<sub>2</sub>–NH<sub>2</sub> > C<sub>6</sub>–OH > C<sub>3</sub>–OH [<xref rid="B27-ijms-21-00487" ref-type="bibr">27</xref>,<xref rid="B28-ijms-21-00487" ref-type="bibr">28</xref>]. An acylation reaction that occurs with C<sub>2</sub>–NH<sub>2</sub> to form an amide is called N-acylation [<xref rid="B29-ijms-21-00487" ref-type="bibr">29</xref>]. An ester is formed by the acylation reaction of C<sub>6</sub>–OH when there is a protective functional group on C<sub>2</sub>–NH<sub>2</sub>, and this is referred to as O-acylation [<xref rid="B30-ijms-21-00487" ref-type="bibr">30</xref>].</p><p>N-acylated chitosan derivatives show enhanced biocompatibility, anticoagulability, and blood compatibility. Moreover, N-acylated chitosan derivatives do not cause an inflammatory reaction in the human body, so N-acylated chitosan can be used as a carrier or sustained release agent in pharmaceutical applications [<xref rid="B24-ijms-21-00487" ref-type="bibr">24</xref>,<xref rid="B29-ijms-21-00487" ref-type="bibr">29</xref>,<xref rid="B31-ijms-21-00487" ref-type="bibr">31</xref>,<xref rid="B32-ijms-21-00487" ref-type="bibr">32</xref>]. A schematic diagram of the N-acylation reaction of chitosan is shown in <xref ref-type="fig" rid="ijms-21-00487-f002">Figure 2</xref>A.</p><p>The solubility of N-acylated chitosan depends on the degree of substitution (DS) and the length of the side chain. Studies have shown that when the DS is less than 50%, the DS is proportional to the solubility; the higher the DS is, the greater the solubility. The length of the side chain is proportional to the crystallinity, and a longer side chain results in a higher crystallinity and lower relative solubility [<xref rid="B6-ijms-21-00487" ref-type="bibr">6</xref>,<xref rid="B29-ijms-21-00487" ref-type="bibr">29</xref>]. N-acylated chitosan, with high solubility, can be used as a carrier for hydrophobic drugs [<xref rid="B33-ijms-21-00487" ref-type="bibr">33</xref>], while N-acylated chitosan, with high crystallinity, can increase fiber toughness and thermal stability, making it suitable for applications such as use in polyvinyl chloride (PVC) fiber film materials [<xref rid="B34-ijms-21-00487" ref-type="bibr">34</xref>,<xref rid="B35-ijms-21-00487" ref-type="bibr">35</xref>]. Additionally, N-acylated chitosan can also be used as a template additive for bone tissue materials, such as 3D templates for hydroxyapatite [<xref rid="B24-ijms-21-00487" ref-type="bibr">24</xref>].</p><p>C<sub>6</sub>–OH does not react until C<sub>2</sub>–NH<sub>2</sub> completely reacts [<xref rid="B36-ijms-21-00487" ref-type="bibr">36</xref>]. If only O-acylated chitosan is required, it is necessary to add a solvent to protect the ammonium group, such as trifluoroacetic acid or methanesulfonic acid [<xref rid="B37-ijms-21-00487" ref-type="bibr">37</xref>,<xref rid="B38-ijms-21-00487" ref-type="bibr">38</xref>,<xref rid="B39-ijms-21-00487" ref-type="bibr">39</xref>]. Methanesulfonic acid is both a solvent and a catalyst in the chitosan O-acylation process [<xref rid="B37-ijms-21-00487" ref-type="bibr">37</xref>,<xref rid="B38-ijms-21-00487" ref-type="bibr">38</xref>]. A schematic diagram of the O-acylation reaction of chitosan is shown in <xref ref-type="fig" rid="ijms-21-00487-f002">Figure 2</xref>B.</p><p>O-acylation modification destroys the hydrogen bond structure of chitosan and improves its fat solubility and hydrophobicity. However, the properties of O-acylated chitosan and N-acylated chitosan are also different. O-acylated chitosan is lipid-soluble and can be dissolved in non-polar solvents such as pyridine and chloroform [<xref rid="B37-ijms-21-00487" ref-type="bibr">37</xref>], while N-acylated chitosan improves water solubility [<xref rid="B29-ijms-21-00487" ref-type="bibr">29</xref>,<xref rid="B31-ijms-21-00487" ref-type="bibr">31</xref>]. O-acylated chitosan is commonly used in the films of fibers or polymeric materials to enhance the hydrophobicity and stability of the material [<xref rid="B30-ijms-21-00487" ref-type="bibr">30</xref>,<xref rid="B38-ijms-21-00487" ref-type="bibr">38</xref>]. N-acylated chitosan can be used as a carrier or a sustained release agent in the delivery of drugs and can also be used as a material additive in biological scaffolds [<xref rid="B28-ijms-21-00487" ref-type="bibr">28</xref>,<xref rid="B29-ijms-21-00487" ref-type="bibr">29</xref>].</p></sec><sec><title>Alkylation Modified Chitosan</title><p>An alkyl group can be introduced into chitosan, and this leads to the latter having significantly weakened intermolecular hydrogen bonds, leading to an improvement in its solubility [<xref rid="B40-ijms-21-00487" ref-type="bibr">40</xref>]. However, the alkyl group is a hydrophobic group. The solubility is lowered when alkyl chain that is too long is introduced, showing that the solubility of a chitosan derivative can be controlled by manipulating the length of an alkyl chain [<xref rid="B41-ijms-21-00487" ref-type="bibr">41</xref>,<xref rid="B42-ijms-21-00487" ref-type="bibr">42</xref>]. An alkylation reaction is caused by the introduction of an alkyl group to the C<sub>2</sub>–NH<sub>2</sub>, C<sub>6</sub>–OH, or C<sub>3</sub>–OH groups of chitosan to form an alkyl group-containing chitosan derivative. N-alkylation occurs with the alkylation of the C<sub>2</sub>–NH<sub>2</sub> group in chitosan, and O-alkylation occurs with the alkylation of the C<sub>6</sub>–OH or C<sub>3</sub>–OH groups in chitosan [<xref rid="B43-ijms-21-00487" ref-type="bibr">43</xref>,<xref rid="B44-ijms-21-00487" ref-type="bibr">44</xref>]. Here, the C<sub>2</sub>–NH<sub>2</sub> group has strong nucleophilic lone pair electrons, and, thus, N-alkylation is more likely to occur.</p><p>N-alkylated chitosan can be prepared from a halogenated alkane. The reaction equation of this process is shown in <xref ref-type="fig" rid="ijms-21-00487-f003">Figure 3</xref>A [<xref rid="B45-ijms-21-00487" ref-type="bibr">45</xref>]. The material can also be prepared from higher fatty aldehydes and long chain fatty acyl groups. In this case, the reaction equation is shown in <xref ref-type="fig" rid="ijms-21-00487-f003">Figure 3</xref>B [<xref rid="B46-ijms-21-00487" ref-type="bibr">46</xref>,<xref rid="B47-ijms-21-00487" ref-type="bibr">47</xref>,<xref rid="B48-ijms-21-00487" ref-type="bibr">48</xref>]. Alkylated chitosan can be used to prepare medical gauze due to its coagulation and antibacterial properties [<xref rid="B42-ijms-21-00487" ref-type="bibr">42</xref>,<xref rid="B47-ijms-21-00487" ref-type="bibr">47</xref>,<xref rid="B49-ijms-21-00487" ref-type="bibr">49</xref>], and it can be used to absorb anionic surfactants in water purification engineering due to its positive charge [<xref rid="B50-ijms-21-00487" ref-type="bibr">50</xref>].</p></sec></sec><sec id="sec2dot1dot2-ijms-21-00487"><title>2.1.2. Introduction of Hydrophilic Group</title><p>A hydrophilic group has an atomic group that is soluble in water or that which is readily compatible with water. Common hydrophilic groups include the carboxylic acid group, the quaternary ammonium group, the sulfonic acid group, the phosphoric acid group, amino group, ether bonds composed of an oxygen group, the hydroxyl group, the carboxylate group, and the block polyether group.</p><sec><title>Carboxylated Chitosan</title><p>A carboxylation reaction mainly utilizes glyoxylic acid or chloroalkanoic acid to react with the C<sub>6</sub>–OH or C<sub>2</sub>–NH<sub>2</sub> groups of chitosan, the product of which is a −COOH group [<xref rid="B51-ijms-21-00487" ref-type="bibr">51</xref>]. Carboxylated chitosan has good water solubility and can be dissolved in neutral and alkaline solutions. Carboxylated chitosan also has better thickening, heat preservation, film formation, flocculation, and kneading properties than chitosan. At the same time, carboxylated chitosan has wider applications than chitosan in the industrial, agricultural, medical, health, and biochemical fields [<xref rid="B47-ijms-21-00487" ref-type="bibr">47</xref>,<xref rid="B50-ijms-21-00487" ref-type="bibr">50</xref>,<xref rid="B52-ijms-21-00487" ref-type="bibr">52</xref>,<xref rid="B53-ijms-21-00487" ref-type="bibr">53</xref>,<xref rid="B54-ijms-21-00487" ref-type="bibr">54</xref>,<xref rid="B55-ijms-21-00487" ref-type="bibr">55</xref>,<xref rid="B56-ijms-21-00487" ref-type="bibr">56</xref>,<xref rid="B57-ijms-21-00487" ref-type="bibr">57</xref>].</p><p>Most studies on carboxylated chitosan have concerned carboxymethylation reactions [<xref rid="B58-ijms-21-00487" ref-type="bibr">58</xref>,<xref rid="B59-ijms-21-00487" ref-type="bibr">59</xref>,<xref rid="B60-ijms-21-00487" ref-type="bibr">60</xref>]. The steric hindrance effect on the chitosan C<sub>3</sub>–OH group makes the carboxymethylation of the C<sub>3</sub>–OH group more difficult. Therefore, the carboxylation reaction mostly occurs with the C<sub>6</sub>–OH group. Under an alkaline condition, the activity of the C<sub>6</sub>–OH group on the molecular level of chitosan is greater than that of the C<sub>2</sub>–NH<sub>2</sub> group. Therefore, when the DS is less than 1, the product is C<sub>6</sub>-<italic>O</italic>-carboxymethyl, and the reaction equation of this is shown in <xref ref-type="fig" rid="ijms-21-00487-f004">Figure 4</xref>A. When the DS is greater than or equal to 1, carboxymethyl substitution occurs simultaneously with the C<sub>6</sub>–OH and C<sub>2</sub>–NH<sub>2</sub> groups to form N, O-carboxymethyl chitosan [<xref rid="B61-ijms-21-00487" ref-type="bibr">61</xref>,<xref rid="B62-ijms-21-00487" ref-type="bibr">62</xref>], and the reaction equation of this is shown in <xref ref-type="fig" rid="ijms-21-00487-f004">Figure 4</xref>B.</p><p>The property of carboxymethyl chitosan (CMCS) is related to the DS, where the DS depends on the amount of the carboxylating agent and the molecular weight of chitosan (CSMW). The relationship between the CSMW and the DS is that the DS decreases with the increase of the CSMW [<xref rid="B63-ijms-21-00487" ref-type="bibr">63</xref>]. CMCS is active in the biomedical and pharmaceutical fields due to its antibacterial properties, which promote wound healing, as well as its lipid-lowering, anti-arteriosclerosis, antiviral, anti-tumor, anti-coagulation, and hypoglycemic effects [<xref rid="B51-ijms-21-00487" ref-type="bibr">51</xref>,<xref rid="B64-ijms-21-00487" ref-type="bibr">64</xref>].</p></sec><sec><title>Quaternary Ammonium Chitosan</title><p>The quaternary ammonium group is a hydrophilic group and is positively charged. The introduction of a quaternary ammonium salt group not only improves water solubility, it also increases chargeability. The quaternization occurs with C<sub>2</sub>–NH<sub>2</sub>. Quaternization generally occurs via three methods, namely direct quaternary ammonium substitution, N-alkylation, and the epoxy derivative open loop method [<xref rid="B65-ijms-21-00487" ref-type="bibr">65</xref>,<xref rid="B66-ijms-21-00487" ref-type="bibr">66</xref>,<xref rid="B67-ijms-21-00487" ref-type="bibr">67</xref>,<xref rid="B68-ijms-21-00487" ref-type="bibr">68</xref>,<xref rid="B69-ijms-21-00487" ref-type="bibr">69</xref>]. In recent years, the most commonly used quaternary ammonium salts have been GTA (2,3-epoxypropyl trimethyl ammonium chloride) and CTA (3-chloro-2-hydroxypropyl trimethyl) [<xref rid="B15-ijms-21-00487" ref-type="bibr">15</xref>,<xref rid="B70-ijms-21-00487" ref-type="bibr">70</xref>].</p><p>N,N,N-trimethyl chitosan (TMC) is a quaternary ammonium chitosan. TMC can be synthesized by two methods. One method is direct quaternary ammonium substitution (<xref ref-type="fig" rid="ijms-21-00487-f005">Figure 5</xref>A) [<xref rid="B71-ijms-21-00487" ref-type="bibr">71</xref>,<xref rid="B72-ijms-21-00487" ref-type="bibr">72</xref>], and the other is the N-alkylation method (<xref ref-type="fig" rid="ijms-21-00487-f005">Figure 5</xref>B) [<xref rid="B73-ijms-21-00487" ref-type="bibr">73</xref>,<xref rid="B74-ijms-21-00487" ref-type="bibr">74</xref>,<xref rid="B75-ijms-21-00487" ref-type="bibr">75</xref>]. The epoxy-derivative ring-opening process is the reaction of C<sub>2</sub>-NH<sub>2</sub> with GTA or CTA under alkaline conditions. The reaction of chitosan and epoxypropyl trimethyl ammonium chloride gives <italic>N</italic>-2-Hydroxypropyl trimethyl ammonium chloride chitosan (N-2-HACC) [<xref rid="B76-ijms-21-00487" ref-type="bibr">76</xref>,<xref rid="B77-ijms-21-00487" ref-type="bibr">77</xref>]. The reaction equation of this is shown in <xref ref-type="fig" rid="ijms-21-00487-f005">Figure 5</xref>C.</p><p>Quaternary ammonium salt increases charging strength and weakens hydrogen bonds, thus increasing water solubility. In addition, a higher DS leads to a better water-solubility and a higher potential [<xref rid="B78-ijms-21-00487" ref-type="bibr">78</xref>,<xref rid="B79-ijms-21-00487" ref-type="bibr">79</xref>]. Quaternary ammonium chitosan salt also has better antibacterial, biocompatibility, biodegradability, non-toxicity, and biological effects, as well as innate mucoadhesiveness and the ability to penetrate mucus layers and bind to epithelial surfaces. Therefore, it is widely used in medicine [<xref rid="B80-ijms-21-00487" ref-type="bibr">80</xref>,<xref rid="B81-ijms-21-00487" ref-type="bibr">81</xref>,<xref rid="B82-ijms-21-00487" ref-type="bibr">82</xref>]. Due to its antibacterial properties, quaternary ammonium chitosan can be used in anti-inflammatory drugs or as a filler fiber in materials for dressing wounds [<xref rid="B82-ijms-21-00487" ref-type="bibr">82</xref>,<xref rid="B83-ijms-21-00487" ref-type="bibr">83</xref>].</p></sec></sec><sec id="sec2dot1dot3-ijms-21-00487"><title>2.1.3. Formation of Hydrophilic Group</title><sec><title>Chitosan Esterification Reaction</title><p>The esterification reaction of chitosan is the reaction of chitosan with carboxylic acid or an oxy-containing mineral acid. The common acids of chitosan esterification are sulfuric acid, phosphoric acid, and chlorosulfonic acid [<xref rid="B84-ijms-21-00487" ref-type="bibr">84</xref>,<xref rid="B85-ijms-21-00487" ref-type="bibr">85</xref>]. Sulfated chitosan has a significant anticoagulant activity due to its structural similarity to heparin, and it can be used as an alternative to anticoagulants [<xref rid="B86-ijms-21-00487" ref-type="bibr">86</xref>].</p></sec><sec><title>Chitosan Etherification Modification</title><p>The hydroxyl group in the chitosan molecule reacts with a alkylating reagent agent (e.g., dimethyl sulfate, chloroacetic acid, and ethylene oxide) to form a chitosan-etherified derivative. Chitosan-etherified derivatives are soluble in water and have the dual structure and function of high molecular chitosan and low molecular ether [<xref rid="B87-ijms-21-00487" ref-type="bibr">87</xref>]. The etherified product has good moisture retention, bacteriostasis, and non-toxicity, and it can be used in medical materials and pharmaceutical fields [<xref rid="B88-ijms-21-00487" ref-type="bibr">88</xref>].</p></sec></sec></sec><sec id="sec2dot2-ijms-21-00487"><title>2.2. Improving Chitosan Mucoadhesion</title><p>Mucosal adhesion is the ability of a material to adhere to the mucosa and provide temporary retention. Polymers with mucosal adhesion typically have strong hydrogen bond groups (carboxyl, hydroxyl, amino, and sulfate groups) or strong anion/cation charges, such as chitosan and its derivatives [<xref rid="B89-ijms-21-00487" ref-type="bibr">89</xref>]. Chitosan achieves a mucosal adsorption effect through electrostatic attraction with mucosal proteins, along with hydrogen bonding and the material’s hydrophobic properties [<xref rid="B90-ijms-21-00487" ref-type="bibr">90</xref>]. Chitosan derivatives generally achieve mucosal adhesion through hydrogen bonding or non-specific, non-covalent, and electrostatic interactions [<xref rid="B91-ijms-21-00487" ref-type="bibr">91</xref>]. Strong hydrogen bonding groups can also be introduced to improve mucosal adhesion, such as carboxylated chitosan [<xref rid="B89-ijms-21-00487" ref-type="bibr">89</xref>]. Thiolated chitosan derivatives enhance mucosal adhesion through the formation of covalent bonds between free thiol groups and cysteine-containing glycoproteins in mucus [<xref rid="B91-ijms-21-00487" ref-type="bibr">91</xref>]. Thiolated chitosan derivatives prepared by the annealing method have stronger adhesion, hydration ability, and drug release properties than thiolated chitosan derivatives that are prepared by other methods [<xref rid="B92-ijms-21-00487" ref-type="bibr">92</xref>]. Compared with pure drugs, the amount of insulin that is released by thiolated chitosan xerogels has been shown to increase by 1.7 times. Consequently, thiolated chitosan derivatives can be used in oral drug delivery systems [<xref rid="B93-ijms-21-00487" ref-type="bibr">93</xref>,<xref rid="B94-ijms-21-00487" ref-type="bibr">94</xref>]. Enhancing the charge of chitosan can improve mucosal adhesion, such as in the case of quaternary ammonium chitosan [<xref rid="B95-ijms-21-00487" ref-type="bibr">95</xref>,<xref rid="B96-ijms-21-00487" ref-type="bibr">96</xref>]. Here, ovalbumin was conjugated with N-trimethylaminoethylmethacrylate chitosan. After intranasal administration, the conjugated polymer significantly increased the amount of ovalbumin that was absorbed by mouse mononuclear macrophages and improved the efficiency of transporting ovalbumin to deep neck lymph nodes. After three nasal immunizations with a conjugate, a strong systemic and mucosal immune response in mice was induced. Quaternary ammonium chitosan derivatives can be administered via the nasal cavity to prevent respiratory infection diseases [<xref rid="B97-ijms-21-00487" ref-type="bibr">97</xref>]. The mucosal adhesion of chitosan derivatives has broad application prospects in both oral and respiratory drug delivery systems.</p></sec><sec id="sec2dot3-ijms-21-00487"><title>2.3. Improving of Chitosan pH Sensitivity</title><p>A pH-sensitive material is a type of material that changes its volume or shape as the pH of its environment changes [<xref rid="B98-ijms-21-00487" ref-type="bibr">98</xref>,<xref rid="B99-ijms-21-00487" ref-type="bibr">99</xref>]. A change in the intramolecular or intermolecular force of the polymer can be produced, depending on the change in pH. Here, this is manifested as a macroscopic change in the properties of the polymer. A pH-sensitive material can achieve the controlled release of a drug in a delivery system based on continuous changes in the pH of the gastrointestinal tract in the body. Targeted administration can be achieved according to the difference in pH between the lesion and the normal physiological state of the body [<xref rid="B100-ijms-21-00487" ref-type="bibr">100</xref>].</p><p>pH sensitivity can be increased by introducing a sensitive acyl group in chitosan. A hydrogel with good pH sensitivity was prepared by an alginate and graft copolymer of methoxypolyethylene glycol and carboxymethyl chitosan (mPEG-g-CMC) [<xref rid="B101-ijms-21-00487" ref-type="bibr">101</xref>]. Hydrogel materials are sensitive to pH reactions. A pH-sensitive hydrogel that was obtained by crosslinking chitosan with polyacrylic acid contained amoxicillin and meloxicam, and its release rate increased with increase of pH [<xref rid="B102-ijms-21-00487" ref-type="bibr">102</xref>]. The methacrylic chitosan hydrogel swelled at a pH < 5, while it shrunk at a pH ≥ 7.4. Cytocompatibility studies were performed with NIH/3T3 fibroblasts (embryonic fibroblasts); cell proliferation or adhesion was suppressed when seeded on hydrogel surfaces compared to tissue culture plastic, but no measurable cell death was observed. It can be seen that the methacrylic chitosan hydrogel is not toxic to fibroblasts, showing specific wound healing stages and accelerated pH-dependent wound healing [<xref rid="B103-ijms-21-00487" ref-type="bibr">103</xref>]. Bovine serum albumin (BSA), as a protein drug, was encapsulated in a hydrogel. Here, the results showed that the release rate was lower at a pH of 1.2 and was increased at a pH of 7.4 [<xref rid="B101-ijms-21-00487" ref-type="bibr">101</xref>]. A carboxymethyl chitosan/alginate (PECs) hydrogel showed significant pH sensitivity, and the cumulative release amount of a protein at a pH of 7.4 was higher than at a pH of 1.2. Therefore, PECs hydrogels can deliver proteins to the intestine for targeted administration [<xref rid="B104-ijms-21-00487" ref-type="bibr">104</xref>].</p></sec><sec id="sec2dot4-ijms-21-00487"><title>2.4. Targeting Modification</title><p>The targeted delivery of drugs is critical to improving treatment outcomes and reducing side effects. There are currently many ways to deliver drugs to specific sites of action. Chitosan derivatives have been driving the development of safe and effective drug delivery systems due to their unique physicochemical and biological properties [<xref rid="B105-ijms-21-00487" ref-type="bibr">105</xref>,<xref rid="B106-ijms-21-00487" ref-type="bibr">106</xref>].</p><sec id="sec2dot4dot1-ijms-21-00487"><title>2.4.1. Colon-Specific Delivery</title><p>Colon-specific drug delivery systems have been paid increasing attention for the treatment of diseases such as Crohn’s disease, ulcerative colitis, and irritable bowel syndrome. The main obstacle to delivery here is absorption and degradation via the upper gastrointestinal tract. Therefore, elucidating how to prevent the degradation of drugs in the stomach and small intestine is the research direction of colon-specific drug delivery systems [<xref rid="B107-ijms-21-00487" ref-type="bibr">107</xref>,<xref rid="B108-ijms-21-00487" ref-type="bibr">108</xref>].</p><p>5-fluorouracil (5-FU) is a hydrophilic drug that has been widely used for the treatment of colorectal cancer. The water-soluble amphoteric chitosan derivative (CTAA) is formed by using trimellitic acid chloride, where CTAA is crosslinked with alginate to prepare a film and the CTAA/alginate film can protect 5-FU from being absorbed and degraded by the upper gastrointestinal tract before reaching the colon [<xref rid="B109-ijms-21-00487" ref-type="bibr">109</xref>]. O-carboxymethyl chitosan (OCMC) is a carboxymethylated derivative. When compared with other natural forms, OCMC has a better water solubility and more desirable pH sensitivity, and, thus, it can be used as a carrier for intestine-targeted drug delivery. Spherical microcapsules (GA-OCMC LbL) with a core-shell structure were prepared by a layer-by-layer assembly (LbL) with the use of gum arabic (GA) and OCMC. Pharmacokinetic analysis showed that the GA-OCMC LbL not only improved the bioavailability of omeprazole, it also enhanced stability in simulated gastric fluid, indicating that the GA-OCMC LbL is a promising vector for intestine-targeted delivery [<xref rid="B110-ijms-21-00487" ref-type="bibr">110</xref>].</p></sec><sec id="sec2dot4dot2-ijms-21-00487"><title>2.4.2. Liver-Targeted Delivery</title><p>Typically, liver targeting systems employ reticulated endothelial passive capture microparticles or active targeting based on recognition between liver receptors and ligand-bearing microparticles [<xref rid="B111-ijms-21-00487" ref-type="bibr">111</xref>]. Fatty-acid-modified quaternary ammonium chitosan derivative nanoparticles were used as a carrier to deliver insulin into the liver, and the results showed that the nanoparticles had a higher hepatocyte uptake and a better anti-diabetic efficacy [<xref rid="B80-ijms-21-00487" ref-type="bibr">80</xref>].</p><p>Ferulic acid is a promising antioxidant drug that can treat liver cancer. Glycyrrhizic acid and modified chitosan nanoparticles have been used for the liver-targeted delivery of ferulic acid. Here, the results showed a cell viability of 70.6% at a concentration of 300 μg/mL, indicating that the nanoparticles had biocompatibility and non-toxicity. The release of ferulic acid from chitosan nanoparticles loaded with ferulic acid reached 13.34% of the total injected dose after 6 h, showing that the nanoparticles could effectively deliver ferulic acid to the liver [<xref rid="B111-ijms-21-00487" ref-type="bibr">111</xref>].</p></sec><sec id="sec2dot4dot3-ijms-21-00487"><title>2.4.3. Kidney and Lung Targeted Delivery</title><p>Proximal tubular cells and mesenchymal fibroblasts are major targets for the delivery of renal drugs, as they play a key role in many kidney diseases. A carrier that has been successfully used for targeted delivery to the kidneys is acetylated low molecular weight chitosan (LMWC). Here, researchers coupled prednisone with LMWC (19 kDa), and the distribution of prednisone in the kidney was 13 times higher than that of the prednisone alone, which showed that the LMWC could serve as a renal targeting delivery carrier [<xref rid="B112-ijms-21-00487" ref-type="bibr">112</xref>]. LMWC may be specifically taken up by tubular cells by megalin, and it can be cleared from the kidneys faster than the lysozyme [<xref rid="B113-ijms-21-00487" ref-type="bibr">113</xref>].</p><p>A novel folic acid-grafted polyethylene glycol chitosan copolymer (F-PEG-HTCC) was synthesized, and F-PEG-HTCC nanoparticles loaded with Taxol were prepared. The results showed that the nanoparticles had good pharmacokinetic characteristics after reaching the lungs, where the distribution of paclitaxel was limited to the lungs for 6 h; this showed that the nanoparticle delivery method can effectively reduce the side effects of highly toxic drugs [<xref rid="B114-ijms-21-00487" ref-type="bibr">114</xref>].</p></sec></sec></sec><sec id="sec3-ijms-21-00487"><title>3. Application of Chitosan Derivatives as Biomedical Materials</title><sec id="sec3dot1-ijms-21-00487"><title>3.1. Application in the Antibacterial Materials</title><p>Antibacterial materials refer to a new class of functional materials that have the function of killing or inhibiting microbes [<xref rid="B115-ijms-21-00487" ref-type="bibr">115</xref>]. There are many substances in nature that have good bactericidal or microbicidal activities [<xref rid="B116-ijms-21-00487" ref-type="bibr">116</xref>,<xref rid="B117-ijms-21-00487" ref-type="bibr">117</xref>,<xref rid="B118-ijms-21-00487" ref-type="bibr">118</xref>]; however, antibacterial materials are a kind of new functional material that have the ability to inhibit or kill bacteria through the addition of certain antibacterial substances, such as antibacterial plastics, antibacterial fibers and fabrics, antibacterial ceramics, and antibacterial metal materials [<xref rid="B119-ijms-21-00487" ref-type="bibr">119</xref>,<xref rid="B120-ijms-21-00487" ref-type="bibr">120</xref>,<xref rid="B121-ijms-21-00487" ref-type="bibr">121</xref>,<xref rid="B122-ijms-21-00487" ref-type="bibr">122</xref>]. Chitosan and chitosan derivatives have been widely used as non-toxic or low-toxicity antibacterial materials [<xref rid="B123-ijms-21-00487" ref-type="bibr">123</xref>]. Among them, chitosan quaternary ammonium salt is the most widely used [<xref rid="B15-ijms-21-00487" ref-type="bibr">15</xref>,<xref rid="B83-ijms-21-00487" ref-type="bibr">83</xref>]. <xref rid="ijms-21-00487-t001" ref-type="table">Table 1</xref> summarizes the antimicrobial species and applications of quaternized chitosan derivatives.</p><p>Compared with chitosan, quaternized chitosan has a significantly increased antibacterial activity and can be used in anti-inflammatory drugs or as a filler fiber in materials for dressing wounds [<xref rid="B82-ijms-21-00487" ref-type="bibr">82</xref>,<xref rid="B83-ijms-21-00487" ref-type="bibr">83</xref>]. The antibacterial mechanism of chitosan and quaternized chitosan is still inconclusive. There are only three speculations [<xref rid="B15-ijms-21-00487" ref-type="bibr">15</xref>,<xref rid="B81-ijms-21-00487" ref-type="bibr">81</xref>]: (1) Chitosan and chitosan derivatives are positively charged, while bacteria are negatively charged, causing them to attract and interact with each other due to electrostatic adsorption; (2) after adsorbing bacteria, chitosan and chitosan derivatives enter the inside of bacterial cells and bind to DNA, which interferes with the transcription of bacterial DNA, thereby inhibiting the growth of bacteria; (3) chitosan and chitosan derivatives inhibit the uptake of trace elements and nutrients that are necessary for cell growth. The antibacterial mechanism of TMC is to form a complex with the cell membrane or interfere with gene expression to achieve an antibacterial effect [<xref rid="B130-ijms-21-00487" ref-type="bibr">130</xref>]. Cationic molecules are the active site of the polymer. Therefore, with an increase in positive charge, the antibacterial activity of TMC is enhanced. The antibacterial activity of TMC decreases with the decrease of pH under acidic conditions, and the antibacterial activity is lower under weak alkaline conditions than acidic conditions [<xref rid="B72-ijms-21-00487" ref-type="bibr">72</xref>,<xref rid="B75-ijms-21-00487" ref-type="bibr">75</xref>,<xref rid="B131-ijms-21-00487" ref-type="bibr">131</xref>].</p></sec><sec id="sec3dot2-ijms-21-00487"><title>3.2. Bone Tissue Engineering Material</title><p>Bone tissue engineering (BTE) refers to the high-concentration osteoblasts, bone marrow stromal stem cells or chondrocytes that are isolated from the organism itself and which are cultured in vitro and transplanted into a cell scaffold [<xref rid="B132-ijms-21-00487" ref-type="bibr">132</xref>,<xref rid="B133-ijms-21-00487" ref-type="bibr">133</xref>,<xref rid="B134-ijms-21-00487" ref-type="bibr">134</xref>]. A perfect scaffold must be biodegradable and biocompatible, promote cell adhesion and proliferation, and preserve cell metabolism. An implantable stent must have a high degree of compatibility with the body, with suitable mechanical properties, morphology, porosity, healing, and tissue replacement capabilities [<xref rid="B1-ijms-21-00487" ref-type="bibr">1</xref>].</p><p>A bone graft or stent should mimic the structure and properties of the natural bone extracellular matrix (ECM) and provide all the necessary environmental conditions in the natural bone, which is an area of BTE that needs to be addressed. Current synthetic bone tissue engineering materials consist essentially of hydroxyapatite, protein, and polysaccharides [<xref rid="B135-ijms-21-00487" ref-type="bibr">135</xref>,<xref rid="B136-ijms-21-00487" ref-type="bibr">136</xref>]. <xref rid="ijms-21-00487-t002" ref-type="table">Table 2</xref> shows the applications of common chitosan derivatives in bone tissue engineering.</p><p>CMCS is a commonly used in bone tissue engineering [<xref rid="B137-ijms-21-00487" ref-type="bibr">137</xref>,<xref rid="B138-ijms-21-00487" ref-type="bibr">138</xref>,<xref rid="B139-ijms-21-00487" ref-type="bibr">139</xref>,<xref rid="B140-ijms-21-00487" ref-type="bibr">140</xref>,<xref rid="B141-ijms-21-00487" ref-type="bibr">141</xref>]. In addition to the applications shown in <xref rid="ijms-21-00487-t002" ref-type="table">Table 2</xref>, CMCS can also be used to make nanofiber scaffolds [<xref rid="B144-ijms-21-00487" ref-type="bibr">144</xref>]. In BTE, TMC and heparinoid are commonly used materials for the preparation of periosteal mimics. Almodovar et al. developed an LbL assembly of polyelectrolyte complexes by using TMC as a polycation and heparin as a polyanion, and the LbL assembly was used as a periosteal mimetic to provide osteoprogenitor cells and improve bone and allograft compatibility [<xref rid="B145-ijms-21-00487" ref-type="bibr">145</xref>]. Hydroxyalkyl chitosan derivatives are also used in BTE; however, only hydroxypropyl chitosan (HPCS), hydroxybutyl chitosan (HBCS), and hydroxyethyl chitosan (HECS) are currently in use for bone tissue engineering [<xref rid="B146-ijms-21-00487" ref-type="bibr">146</xref>,<xref rid="B147-ijms-21-00487" ref-type="bibr">147</xref>,<xref rid="B148-ijms-21-00487" ref-type="bibr">148</xref>].</p></sec></sec><sec id="sec4-ijms-21-00487"><title>4. Application of Chitosan Derivative Nanoparticles in Drug Delivery</title><p>A drug delivery system is a technical system that comprehensively regulates the distribution of drugs in a living body in terms of delivery space, time, and dosage [<xref rid="B149-ijms-21-00487" ref-type="bibr">149</xref>]. The goal is to deliver the right amount of the drug to the right place at the right time, increasing drug bioavailability and reducing costs and side effects [<xref rid="B150-ijms-21-00487" ref-type="bibr">150</xref>]. A drug delivery system is a fusion of medicine, engineering (materials, mechanics, and electronics), and pharmacy. The objectives of research here include the drug itself, the drug carrier, and the related delivery technology, as well as the physical and chemical modification of the drug or carrier [<xref rid="B151-ijms-21-00487" ref-type="bibr">151</xref>,<xref rid="B152-ijms-21-00487" ref-type="bibr">152</xref>]. Chitosan derivative nanoparticles have better bioadhesion and permeability, which can improve the delivery and transport of drugs. Chitosan derivative nanoparticles have important applications in targeting, sustained release, and increasing drug absorption. At present, chitosan derivative nanoparticles are mainly used for sustained release, the preparation of targeted drugs, and as vectors for gene therapy.</p><sec id="sec4dot1-ijms-21-00487"><title>4.1. Delivery Carrier</title><p>Chitosan and its derivatives are mainly found as microspheres, nanoparticles, micelles, and gels in delivery carriers [<xref rid="B153-ijms-21-00487" ref-type="bibr">153</xref>,<xref rid="B154-ijms-21-00487" ref-type="bibr">154</xref>,<xref rid="B155-ijms-21-00487" ref-type="bibr">155</xref>]. The particle sizes of these microspheres are generally in the range of 1–500 μm, and the particle sizes of the nanoparticles are smaller than the particle sizes of the microspheres and are within 100 nm. The small size of nanoparticles enables them to pass through various biological barriers in order to deliver drugs to target sites [<xref rid="B156-ijms-21-00487" ref-type="bibr">156</xref>]. A micelle is a core-shell structural material with good stability, tissue permeability, and sustained drug release properties [<xref rid="B157-ijms-21-00487" ref-type="bibr">157</xref>]. Amphiphilic chitosan, with a self-assembling micelle, can improve the solubility, biological activity, and targeted delivery of fat-soluble drugs [<xref rid="B158-ijms-21-00487" ref-type="bibr">158</xref>]. A gel is a material that has a three-dimensional spatial polymerization capability and is capable of accommodating a large amount of water in its slightly crosslinked network structure. Gels have many adjustable properties, including their flexibility and deformability, dispersibility in biological fluids, controlled stability, biodegradability, and chemical function [<xref rid="B159-ijms-21-00487" ref-type="bibr">159</xref>,<xref rid="B160-ijms-21-00487" ref-type="bibr">160</xref>]. Compared with nanoparticles, gels have better mucoadhesivity and permeability and can transport small molecules, all of which gives them great potential in biomedical fields [<xref rid="B161-ijms-21-00487" ref-type="bibr">161</xref>].</p></sec><sec id="sec4dot2-ijms-21-00487"><title>4.2. Controlled Drug Delivery</title><p>Drug control and sustained release are promising areas of research [<xref rid="B162-ijms-21-00487" ref-type="bibr">162</xref>]. Some drugs have a very short release time and are rapidly consumed, resulting in a decrease in plasma levels. Therefore, more doses of the drug are needed to maintain plasma balance, causing discomfort to the patient. Scientists are working hard to develop novel drug delivery systems in order to provide appropriate drug concentrations to meet therapeutic needs [<xref rid="B163-ijms-21-00487" ref-type="bibr">163</xref>]. The ideal drug release is rapid, at a constant rate, and sustained so that the drug be immediately effective while achieving a long effect [<xref rid="B164-ijms-21-00487" ref-type="bibr">164</xref>]. Chitosan derivative nanoparticles can easily achieve a sustained slow release, increasing bioavailability and therapeutic efficacy while reducing side effects [<xref rid="B165-ijms-21-00487" ref-type="bibr">165</xref>].</p><p>Proteins are the drugs of choice for the treatment of various diseases due to their targeting and good biocompatibility. However, protein drugs also have some drawbacks [<xref rid="B166-ijms-21-00487" ref-type="bibr">166</xref>]. For example, proteins are easily degraded by enzymes, have low permeability in the intestinal epithelium, and have poor oral absorption. These factors limit the applications of protein drugs [<xref rid="B167-ijms-21-00487" ref-type="bibr">167</xref>]. In recent years, chitosan derivative nanoparticles have received considerable attention for use as protein drug delivery vehicles. These nanoparticles have received considerable attention and can be used to deliver proteins.</p><sec id="sec4dot2dot1-ijms-21-00487"><title>4.2.1. Chitosan Derivative Nanoparticles for the Delivery of Polypeptide</title><p>Chitosan derivative nanoparticles interact with peptides through strong hydrogen bonds and static electricity, obtaining peptide-loaded nanoparticles. Nanoparticle-loaded peptides have a better thermal stability and are controllable via in vitro release when compared to free peptides [<xref rid="B168-ijms-21-00487" ref-type="bibr">168</xref>]. Fatty acid-modified quaternary ammonium chitosan nanoparticles loaded with insulin have been shown to have an encapsulation efficiency and loading capacity of over 98%, as nanoparticle-loaded insulin is more efficient than a free insulin group [<xref rid="B80-ijms-21-00487" ref-type="bibr">80</xref>]. The oral delivery of insulin needs to overcome the barrier of gastrointestinal tract digestion and absorption [<xref rid="B169-ijms-21-00487" ref-type="bibr">169</xref>]. Fucoidan (FD) has hypoglycemic effects. Nanoparticles (NPs) prepared by TMC and FD were loaded with insulin. Here, the TMC/FD NPs were pH sensitive and could protect insulin from degradation in the gastrointestinal tract, and TMC/FD NPs enhanced the cellular transport of insulin across the intestinal barrier [<xref rid="B170-ijms-21-00487" ref-type="bibr">170</xref>]. The delivery of insulin by glycerol monocaprylate-modified chitosan nanoparticles has also achieved the same effects as delivery via TMC/FD NPs [<xref rid="B171-ijms-21-00487" ref-type="bibr">171</xref>].</p></sec><sec id="sec4dot2dot2-ijms-21-00487"><title>4.2.2. Chitosan Derivative Nanoparticles for the Delivery of Gene</title><p>Gene therapy is a promising strategy for challenging diseases. A key step in gene therapy is the successful delivery of genes [<xref rid="B172-ijms-21-00487" ref-type="bibr">172</xref>]. Therefore, a safe and effective gene delivery system is critical for the successful application of gene therapy [<xref rid="B173-ijms-21-00487" ref-type="bibr">173</xref>]. The delivery carriers of genes include viral and non-viral vectors. Compared with non-viral vectors, the transfection rate and immunogenicity of the viral vector are both higher, but the vector is more toxic, the capacity of the target gene is smaller, the targeting specificity is worse, the preparation is more complicated, and the cost is higher. Compared with viral vectors, non-viral vectors feature an ease of production, high yield, and low cost, and they can be widely used for drug delivery [<xref rid="B174-ijms-21-00487" ref-type="bibr">174</xref>,<xref rid="B175-ijms-21-00487" ref-type="bibr">175</xref>,<xref rid="B176-ijms-21-00487" ref-type="bibr">176</xref>,<xref rid="B177-ijms-21-00487" ref-type="bibr">177</xref>,<xref rid="B178-ijms-21-00487" ref-type="bibr">178</xref>]. Chitosan derivative nanoparticles, as non-viral vectors, have excellent solubility, biodegradability, biocompatibility, non-toxicity, and a higher transfection rate than chitosan nanoparticles [<xref rid="B73-ijms-21-00487" ref-type="bibr">73</xref>,<xref rid="B98-ijms-21-00487" ref-type="bibr">98</xref>,<xref rid="B179-ijms-21-00487" ref-type="bibr">179</xref>]. <xref rid="ijms-21-00487-t003" ref-type="table">Table 3</xref> shows a gene delivery carrier-containing a chitosan derivative and its applications.</p><p>Genes can regulate signaling networks and promote tumor suppression through chemotherapy, which is important for the treatment of tumors [<xref rid="B189-ijms-21-00487" ref-type="bibr">189</xref>]. However, naked nucleic acids cannot cross cell membranes and are easily degraded by nucleases [<xref rid="B190-ijms-21-00487" ref-type="bibr">190</xref>]. TMC can be further modified to protect genes from degradation by nucleases in serum [<xref rid="B191-ijms-21-00487" ref-type="bibr">191</xref>,<xref rid="B192-ijms-21-00487" ref-type="bibr">192</xref>,<xref rid="B193-ijms-21-00487" ref-type="bibr">193</xref>]. For example, methoxy polyethylene glycol-modified trimethyl chitosan (mPEG-TMC) has been covalently linked to doxorubicin (DOX) and cis-itaconic anhydride (CA) in order to give mPEG-TCD NPs, where anti-tumor effects have shown that the mPEG-TCD NPs exhibit better anti-tumor activities when compared with DOX and plasmid DNA alone [<xref rid="B194-ijms-21-00487" ref-type="bibr">194</xref>,<xref rid="B195-ijms-21-00487" ref-type="bibr">195</xref>]. O-carboxymethyl chitosan nanoparticles have been shown to have the ability to inhibit tumor cell migration in vitro [<xref rid="B7-ijms-21-00487" ref-type="bibr">7</xref>]. The poly-β-amino ester nanoparticle loading gene, after the addition of thiolated O-carboxymethyl chitosan, showed a higher cell transfection rate, as the loaded genes of the poly-β-amino ester and thiolated O-carboxymethyl chitosan composite nanoparticles had higher cell transfection rates than the nanoparticles of the former alone [<xref rid="B184-ijms-21-00487" ref-type="bibr">184</xref>]. The target ligand can also be used to modify chitosan derivatives in order to improve the targeted delivery of genes. Target ligands have been shown to improve tumor-specific delivery, promote cellular uptake, and reduce side effects [<xref rid="B196-ijms-21-00487" ref-type="bibr">196</xref>].</p></sec></sec></sec><sec id="sec5-ijms-21-00487"><title>5. Applications of Chitosan Derivative Nanoparticles in Mucosal Immunity</title><p>The body mainly relies on immune response to destroy and repel pathogenic microorganisms that enter the body for the prevention of infectious diseases. There are three immune defense systems in human and animal bodies, with mucosal immunity being the first defense system against infection. The mucosal immune system refers to lymphoid tissues that are widely distributed in the respiratory tract, gastrointestinal tract, genitourinary mucosa, and some exocrine glands, and this system is the main site for performing local specific immune function [<xref rid="B197-ijms-21-00487" ref-type="bibr">197</xref>,<xref rid="B198-ijms-21-00487" ref-type="bibr">198</xref>].</p><p>Nowadays, vaccination is one of the most effective and economical strategies for humans and animals to control and prevent the spread of infectious diseases. It is worth noting that, in recent years, with the advancement of immunology, biotechnology, and nanotechnology, etc., some intractable cancers have been included in the scope of vaccination targets, and great therapeutic effects in some patients have been achieved [<xref rid="B199-ijms-21-00487" ref-type="bibr">199</xref>,<xref rid="B200-ijms-21-00487" ref-type="bibr">200</xref>]. Traditionally, vaccines are mainly delivered by intramuscular injection, but this route generally cannot induce effective mucosal immunity. Mucosal vaccines have some advantages compared with traditionally vaccines, and most infections occur at a mucosal surface or spread from mucosal surfaces [<xref rid="B201-ijms-21-00487" ref-type="bibr">201</xref>]. Studies have shown that mucosal administration could provide an early defense against invading pathogens, as the local antibodies of the mucosa work faster than serum antibodies, are higher in level, and have a greater maintenance time [<xref rid="B202-ijms-21-00487" ref-type="bibr">202</xref>,<xref rid="B203-ijms-21-00487" ref-type="bibr">203</xref>]. The process of immunity is shown in <xref ref-type="fig" rid="ijms-21-00487-f006">Figure 6</xref> [<xref rid="B204-ijms-21-00487" ref-type="bibr">204</xref>].</p><p>Chitosan and chitosan derivatives can open tight junctions between epithelial cells to facilitate the transmembranal delivery of drugs. Compared with chitosan nanoparticles, chitosan derivative nanoparticles have a better mucoadhesivity, higher water solubility, and promote the better absorption of antigens; thus, chitosan derivative nanoparticles can serve as vaccine adjuvants or delivery carriers in the case of mucosal immunity [<xref rid="B204-ijms-21-00487" ref-type="bibr">204</xref>]. In our previous study, our group prepared a Newcastle disease live vaccine/<italic>O</italic>-2′-Hydroxypropyl trimethyl ammonium chloride chitosan nanoparticles, where the results showed that the chickens that were intranasally immunized with the nanoparticles had stronger cellular, humoral, and mucosal immunity than those intramuscularly immunized with the live attenuated Newcastle disease vaccine, indicating that <italic>O</italic>-2′-Hydroxypropyl trimethyl ammonium chloride chitosan nanoparticles can be used as vaccine adjuvants and delivery carriers in the case of mucosal immunity [<xref rid="B205-ijms-21-00487" ref-type="bibr">205</xref>].</p><p>To achieve a higher mucosal immune effect, composite biological nanomaterials were synthesized [<xref rid="B206-ijms-21-00487" ref-type="bibr">206</xref>,<xref rid="B207-ijms-21-00487" ref-type="bibr">207</xref>]. Reshma et al. prepared a peptide vaccine by binding TMC to a peptide antigen and polyglutamic acid (PGA), and the vaccine induced higher levels of mucosal antibodies compared with the mucosal adjuvant cholera toxin B subunit [<xref rid="B208-ijms-21-00487" ref-type="bibr">208</xref>]. N-2-HACC and CMCS were synthesized as vaccine adjuvants and delivery systems in our group, where an animal experiment showed that the intranasal N-2-HACC/CMCS nanoparticles produced higher IgG (immunoglobulin G) and sIgA (secretory immunoglobulin A) antibody titers and higher levels of cytokines than the commercially available vaccine did [<xref rid="B209-ijms-21-00487" ref-type="bibr">209</xref>]. Additionally, our team also synthesized chitosan-coated PLGA(poly(lactic-co-glycolic acid) nanoparticles, and NDV (Newcastle disease virus) energy-containing DNA that was encapsulated in the nanoparticles was prepared to evaluate the mucosal immune response; the results indicated that the nanoparticles induced stronger cellular, humoral, and mucosal immune responses than the plasmid DNA alone, showing that the chitosan-coated PLGA nanoparticles could be used as an efficient delivery system for mucosal immunization in the case of DNA vaccines [<xref rid="B210-ijms-21-00487" ref-type="bibr">210</xref>].</p></sec><sec id="sec6-ijms-21-00487"><title>6. Prospects</title><p>As a kind of biodegradable polymer material with excellent performance, chitosan is widely used in medical materials and biomedicines. In order to improve the water solubility of chitosan and broaden the scope and fields of its applications, chitosan derivatives with excellent properties, such as hydrophilicity, pH sensitivity, and targeting, have been synthesized through chemical reactions. Chitosan derivatives are promising drug excipients. A drug-loading system, including micelles, nanoparticles, microspheres, and hydrogels, that is prepared by chitosan derivatives, can increase the stability of drugs and release drugs in a sustained and slow manner. Thus, chitosan derivative delivery systems for drugs or vaccines can reduce side effects and improve the bioavailability of drugs, which has increased interest for chitosan derivatives in the field of biomedicine.</p><p>In order to improve current drug delivery systems, it is necessary to study the properties of drugs and new carrier materials. It is important to study new biodegradable materials that are non-toxic to humans and the environment that can overcome the shortcomings of specific drugs. The preparation of multifunctional composite nanoparticles is required to prevent the effects of drugs from adverse conditions and to prolong the release of drugs at the target site. Among the existing polymers, chitosan derivatives seem to be more attractive and can be used for the controlled release of drugs, and their modification with new solvents can be converted into drug delivery systems, especially for the controlled release and persistence of the released drugs. With additional research, it is believed that the physical and chemical properties of chitosan derivative nanomaterials can be continuously improved by chemical modification methods and can also be made to be more suitable for use in medical materials and drug delivery systems. Chitosan derivatives will have broader prospects in biomedicine in the future.</p></sec></body><back><notes><title>Author Contributions</title><p>K.Z. and Z.J. designed and conceived the manuscript. W.W. conducted the article writing work under the supervision of K.Z. and Z.J. W.W., Q.M., Q.L., J.L., M.Z., Z.J. and K.Z. revised the manuscript. All authors have read and agreed to the published version of the manuscript.</p></notes><notes><title>Funding</title><p>We gratefully acknowledge the Heilongjiang Provincial Key Laboratory of Plant Genetic Engineering and Biological Fermentation Engineering for Cold Region to carry out this work. This work was supported in part by the National Key Research and Development Program of China (2017YFD0500603), National Natural Science Foundation of China (31771000), Natural Science Foundation of Heilongjiang Province of China (C2017058), Cultivation Project of Scientific and Technological Achievements for Provincial Universities in Heilongjiang (TSTAU-C2018017) and Technological innovation talent of special funds for outstanding subject leaders in Harbin (2017RAXXJ001).</p></notes><notes notes-type="COI-statement"><title>Conflicts of Interest</title><p>The authors declare no competing financial interest.</p></notes><ref-list><title>References</title><ref id="B1-ijms-21-00487"><label>1.</label><element-citation publication-type="journal"><person-group person-group-type="author"><name><surname>Baranwal</surname><given-names>A.</given-names></name><name><surname>Kumar</surname><given-names>A.</given-names></name><name><surname>Priyadharshini</surname><given-names>A.</given-names></name><name><surname>Oggu</surname><given-names>G.S.</given-names></name><name><surname>Bhatnagar</surname><given-names>I.</given-names></name><name><surname>Srivastava</surname><given-names>A.</given-names></name><name><surname>Chandra</surname><given-names>P.</given-names></name></person-group><article-title>Chitosan: An undisputed bio-fabrication material for tissue engineering and bio-sensing applications</article-title><source>Int. 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Nanomed.</source><year>2014</year><volume>9</volume><fpage>4609</fpage><lpage>4619</lpage><pub-id pub-id-type="doi">10.2147/IJN.S70633</pub-id></element-citation></ref><ref id="B210-ijms-21-00487"><label>210.</label><element-citation publication-type="journal"><person-group person-group-type="author"><name><surname>Zhao</surname><given-names>K.</given-names></name><name><surname>Li</surname><given-names>S.</given-names></name><name><surname>Li</surname><given-names>W.</given-names></name><name><surname>Yu</surname><given-names>L.</given-names></name><name><surname>Duan</surname><given-names>X.</given-names></name><name><surname>Han</surname><given-names>J.</given-names></name><name><surname>Wang</surname><given-names>X.</given-names></name><name><surname>Jin</surname><given-names>Z.</given-names></name></person-group><article-title>Quaternized chitosan nanoparticles loaded with the combined attenuated live vaccine against Newcastle disease and infectious bronchitis elicit immune response in chicken after intranasal administration</article-title><source>Drug Deliv.</source><year>2017</year><volume>24</volume><fpage>1574</fpage><lpage>1586</lpage><pub-id pub-id-type="doi">10.1080/10717544.2017.1388450</pub-id><pub-id pub-id-type="pmid">29029568</pub-id></element-citation></ref></ref-list></back><floats-group><fig id="ijms-21-00487-f001" orientation="portrait" position="float"><label>Figure 1</label><caption><p>Schematic diagram of chitosan chemical reaction.</p></caption><graphic xlink:href="ijms-21-00487-g001"></graphic></fig><fig id="ijms-21-00487-f002" orientation="portrait" position="float"><label>Figure 2</label><caption><p>Reaction equations for acylated chitosan derivatives. (<bold>A</bold>) N-acylated chitosan; (<bold>B</bold>) O-acylated chitosan.</p></caption><graphic xlink:href="ijms-21-00487-g002"></graphic></fig><fig id="ijms-21-00487-f003" orientation="portrait" position="float"><label>Figure 3</label><caption><p>Alkylation chitosan derivative reaction equations. (<bold>A</bold>) Halogenated alkane to prepare N-alkylated chitosan; (<bold>B</bold>) advanced fatty aldehyde prepares N-alkylated chitosan.</p></caption><graphic xlink:href="ijms-21-00487-g003"></graphic></fig><fig id="ijms-21-00487-f004" orientation="portrait" position="float"><label>Figure 4</label><caption><p>Carboxylated chitosan derivative reaction equation. (<bold>A</bold>) O-carboxymethyl chitosan (degree of substitution (DS) < 1); (<bold>B</bold>) N, O-carboxymethyl chitosan (DS ≥ 1).</p></caption><graphic xlink:href="ijms-21-00487-g004"></graphic></fig><fig id="ijms-21-00487-f005" orientation="portrait" position="float"><label>Figure 5</label><caption><p>Reaction equations for quaternized chitosan derivatives. (<bold>A</bold>), N,N-trimethyl chitosan (TMC) direct quaternary ammonium salt substitution method; (<bold>B</bold>) TMC N-alkylation; (<bold>C</bold>) chitosan 2,3-epoxypropyl trimethyl ammonium chloride (GTA) ring opening method.</p></caption><graphic xlink:href="ijms-21-00487-g005"></graphic></fig><fig id="ijms-21-00487-f006" orientation="portrait" position="float"><label>Figure 6</label><caption><p>Immunity causes antibody production to be immune.</p></caption><graphic xlink:href="ijms-21-00487-g006"></graphic></fig><table-wrap id="ijms-21-00487-t001" orientation="portrait" position="float"><object-id pub-id-type="pii">ijms-21-00487-t001_Table 1</object-id><label>Table 1</label><caption><p>Applications of quaternary ammonium chitosan in antibacterial.</p></caption><table frame="hsides" rules="groups"><thead><tr><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Name</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Antibacterial Species</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Application</th></tr></thead><tbody><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Ammonium N-alkyl chitosan particles</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>Staphylococcus aureus</italic>, <italic>Escherichia coli</italic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Biomedical devices, textile industry [<xref rid="B124-ijms-21-00487" ref-type="bibr">124</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Quaternized N-alkyl chitosan film</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>Staphylococcus aureus</italic>, <italic>Escherichia coli</italic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Antibacterial material [<xref rid="B125-ijms-21-00487" ref-type="bibr">125</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Quaternized N-aryl chitosan</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>Staphylococcus aureus</italic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Antibacterial material [<xref rid="B126-ijms-21-00487" ref-type="bibr">126</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Quaternary ammonium chitosan-containing monosaccharide or disaccharide moiety</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>Staphylococcus aureus</italic>, <italic>Escherichia coli</italic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Antibacterial agents [<xref rid="B127-ijms-21-00487" ref-type="bibr">127</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">O-imidazolyl quaternary ammonium chitosan</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>Botrytis cinerea</italic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Anti-cancer, anti-virus, anti-diabetes, enzyme inhibition and anti-tuberculosis [<xref rid="B128-ijms-21-00487" ref-type="bibr">128</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Trimethyl ammonium chitosan</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>Aspergillus flavus</italic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Biodegradable fungicide [<xref rid="B129-ijms-21-00487" ref-type="bibr">129</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Glutaraldehyde cross-linked chitosan quaternary ammonium salt film</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>Escherichia coli</italic>, <italic>Staphylococcus aureus</italic>, <italic>Pseudomonas aeruginosa</italic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Antibacterial coating [<xref rid="B81-ijms-21-00487" ref-type="bibr">81</xref>]</td></tr></tbody></table></table-wrap><table-wrap id="ijms-21-00487-t002" orientation="portrait" position="float"><object-id pub-id-type="pii">ijms-21-00487-t002_Table 2</object-id><label>Table 2</label><caption><p>Applications of common chitosan derivatives in bone tissue engineering.</p></caption><table frame="hsides" rules="groups"><thead><tr><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Chitosan Derivative</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Complex</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Application</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Attributes</th></tr></thead><tbody><tr><td rowspan="5" align="center" valign="middle" style="border-bottom:solid thin" colspan="1">Carboxymethyl chitosan</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Fibroin/CMCS/strontium replaces hydroxyapatite/cellulose nanocrystals</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Preparation bracket</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Improving adhesion and proliferation of osteoblasts [<xref rid="B137-ijms-21-00487" ref-type="bibr">137</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Tyrosinase/CMCS/gelatin/nano hydroxyapatite</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Treatment of irregular small bone defects</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Injectable gel to promote osteoblast differentiation and maturation [<xref rid="B138-ijms-21-00487" ref-type="bibr">138</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Silk fibroin/CMCS/vitamin C</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Preparation bracket</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Enhanced cell proliferation, proliferation, and alkaline phosphatase activity, promoting calcium phosphate deposition in the scaffold [<xref rid="B53-ijms-21-00487" ref-type="bibr">53</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CMCS/nano hydroxyapatite/graphene oxide</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Preparation bracket</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Enhances osteoinductivity and promotes new bone formation [<xref rid="B139-ijms-21-00487" ref-type="bibr">139</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Gelatin/CMCS/LAPONITE</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Preparation bracket</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Enhances mechanical properties and promotes bone marrow stem cell attachment, proliferation and osteogenic differentiation [<xref rid="B140-ijms-21-00487" ref-type="bibr">140</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Carboxymethyl chitosan nanofiber</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Hydroxyapatite coated electrospun CMCS nanofibers</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Preparation bracket</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Enhances ALP activity and promotes osteoblast differentiation and maturation [<xref rid="B141-ijms-21-00487" ref-type="bibr">141</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">N, O-carboxymethyl chitosan</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Hydroxyapatite/N, O-carboxymethyl chitosan/fucoidan</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Preparation bracket</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Increased pore size and mechanical properties promote osteoblast differentiation [<xref rid="B61-ijms-21-00487" ref-type="bibr">61</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Trimethyl chitosan</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">N,N,N-trimethyl chitosan-heparin polyelectrolyte multilayer</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Bionic periosteum</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Good cell compatibility and support osteoblast differentiation [<xref rid="B142-ijms-21-00487" ref-type="bibr">142</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Hydroxypropyltrimethylammonium chloride chitosan</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Alginate/HACC/oyster shell powder</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Preparation bracket</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Improve mechanical properties and enhance stent surface area [<xref rid="B143-ijms-21-00487" ref-type="bibr">143</xref>]</td></tr></tbody></table></table-wrap><table-wrap id="ijms-21-00487-t003" orientation="portrait" position="float"><object-id pub-id-type="pii">ijms-21-00487-t003_Table 3</object-id><label>Table 3</label><caption><p>Gene carrier-containing chitosan derivative and applications.</p></caption><table frame="hsides" rules="groups"><thead><tr><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Carrier</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Drug</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Application</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Main Findings/Features</th></tr></thead><tbody><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Polyethyleneimine/chitosan-4-thio-butyl-oxime</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">siRNA</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Colorectal cancer</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Increased transfection rate [<xref rid="B180-ijms-21-00487" ref-type="bibr">180</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Polyethylene glycol/O-carboxymethyl chitosan/low molecular weight polyethylene imine</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">siRNA</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Breast cancer</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Enhanced targeting and cell transfection rates [<xref rid="B181-ijms-21-00487" ref-type="bibr">181</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Methyl methacrylate-modified chitosan</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Curcumin</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Mammalian cancer cell line (A549, HeLa, HepG2)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Increased transfection rate [<xref rid="B182-ijms-21-00487" ref-type="bibr">182</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Ethylene glycol chitosan–dequalinium nanoparticles</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Curcumin</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Tumor treatment</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Targeted delivery [<xref rid="B183-ijms-21-00487" ref-type="bibr">183</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Poly-β-amino ester/thiolated O-carboxymethyl chitosan nanoparticles</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">RNAi</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Lung cancer</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Increased transfection rate and increased cellular uptake [<xref rid="B184-ijms-21-00487" ref-type="bibr">184</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Aminotetrazole functionalized magnetic chitosan nanocomposites</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Plasmid DNA </td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">HEK-293T cell line</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Increased transfection rate [<xref rid="B185-ijms-21-00487" ref-type="bibr">185</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Polyethylene glycol grafted chitosan nanoparticles</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">p53</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Tumor cell</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">High transfection efficiency and increased cellular uptake [<xref rid="B186-ijms-21-00487" ref-type="bibr">186</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Chitosan derivative-modified mesoporous silica microspheres</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">DOX, p53</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Tumor treatment</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Increased transfection rate, sustained release [<xref rid="B187-ijms-21-00487" ref-type="bibr">187</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Trans transcriptional activator/poly(N-3-benzyloxycarbonyl-lysine) chitosan</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">p53, DOX</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Cancer treatment</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Improve transfection efficiency and drug delivery efficiency 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