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Synthesis, characterization, and antifungal evaluation of diethoxyphosphoryl polyaminoethyl chitosan derivatives.

Identifieur interne : 000653 ( Main/Exploration ); précédent : 000652; suivant : 000654

Synthesis, characterization, and antifungal evaluation of diethoxyphosphoryl polyaminoethyl chitosan derivatives.

Auteurs : Zhaoqian Fan [République populaire de Chine] ; Yukun Qin [République populaire de Chine] ; Song Liu [République populaire de Chine] ; Ronge Xing [République populaire de Chine] ; Huahua Yu [République populaire de Chine] ; Xiaolin Chen [République populaire de Chine] ; Kecheng Li [République populaire de Chine] ; Pengcheng Li [République populaire de Chine]

Source :

RBID : pubmed:29628225

Descripteurs français

English descriptors

Abstract

Botrytis cinerea, Phytophthora capsici Leonian, and Fusarium solani are important plant pathogenic fungi which can cause great crop losses worldwide, but their control methods are limited. It is necessary to develop efficient and green fungicides from abundant marine resources. Chitosan is a non-toxic, biodegradable, biocompatible marine polysaccharide which has prospective applications in agriculture. In this paper, to increase the antifungal activity of chitosan for application, novel water-soluble functional chitosan derivatives were synthesized by grafting polyaminoethyl and diethoxyphosphoryl groups in accordance with a strategy of improving protonation potential. The derivatives were characterized by FTIR, NMR, XRD, SEM, Gaussian 09 and elemental analysis. The antifungal activities against the three fungi and the cytotoxicity were estimated in vitro. The results showed that the derivatives had better antifungal activities and water solubility than chitosan, and had good biocompatibility. They confirmed that these chitosan derivatives can be developed as antifungal agents for plant protection purposes.

DOI: 10.1016/j.carbpol.2018.02.056
PubMed: 29628225


Affiliations:


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Le document en format XML

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<div type="abstract" xml:lang="en">Botrytis cinerea, Phytophthora capsici Leonian, and Fusarium solani are important plant pathogenic fungi which can cause great crop losses worldwide, but their control methods are limited. It is necessary to develop efficient and green fungicides from abundant marine resources. Chitosan is a non-toxic, biodegradable, biocompatible marine polysaccharide which has prospective applications in agriculture. In this paper, to increase the antifungal activity of chitosan for application, novel water-soluble functional chitosan derivatives were synthesized by grafting polyaminoethyl and diethoxyphosphoryl groups in accordance with a strategy of improving protonation potential. The derivatives were characterized by FTIR, NMR, XRD, SEM, Gaussian 09 and elemental analysis. The antifungal activities against the three fungi and the cytotoxicity were estimated in vitro. The results showed that the derivatives had better antifungal activities and water solubility than chitosan, and had good biocompatibility. They confirmed that these chitosan derivatives can be developed as antifungal agents for plant protection purposes.</div>
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<ELocationID EIdType="doi" ValidYN="Y">10.1016/j.carbpol.2018.02.056</ELocationID>
<Abstract>
<AbstractText>Botrytis cinerea, Phytophthora capsici Leonian, and Fusarium solani are important plant pathogenic fungi which can cause great crop losses worldwide, but their control methods are limited. It is necessary to develop efficient and green fungicides from abundant marine resources. Chitosan is a non-toxic, biodegradable, biocompatible marine polysaccharide which has prospective applications in agriculture. In this paper, to increase the antifungal activity of chitosan for application, novel water-soluble functional chitosan derivatives were synthesized by grafting polyaminoethyl and diethoxyphosphoryl groups in accordance with a strategy of improving protonation potential. The derivatives were characterized by FTIR, NMR, XRD, SEM, Gaussian 09 and elemental analysis. The antifungal activities against the three fungi and the cytotoxicity were estimated in vitro. The results showed that the derivatives had better antifungal activities and water solubility than chitosan, and had good biocompatibility. They confirmed that these chitosan derivatives can be developed as antifungal agents for plant protection purposes.</AbstractText>
<CopyrightInformation>Copyright © 2018 Elsevier Ltd. All rights reserved.</CopyrightInformation>
</Abstract>
<AuthorList CompleteYN="Y">
<Author ValidYN="Y">
<LastName>Fan</LastName>
<ForeName>Zhaoqian</ForeName>
<Initials>Z</Initials>
<AffiliationInfo>
<Affiliation>Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, No. 7 Nanhai Road, Qingdao 266071, China; Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, No. 1 Wenhai Road, Qingdao 266237, China; University of Chinese Academy of Sciences, Beijing 100049, China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Qin</LastName>
<ForeName>Yukun</ForeName>
<Initials>Y</Initials>
<AffiliationInfo>
<Affiliation>Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, No. 7 Nanhai Road, Qingdao 266071, China; Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, No. 1 Wenhai Road, Qingdao 266237, China. Electronic address: ykqin@qdio.ac.cn.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Liu</LastName>
<ForeName>Song</ForeName>
<Initials>S</Initials>
<AffiliationInfo>
<Affiliation>Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, No. 7 Nanhai Road, Qingdao 266071, China; Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, No. 1 Wenhai Road, Qingdao 266237, China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Xing</LastName>
<ForeName>Ronge</ForeName>
<Initials>R</Initials>
<AffiliationInfo>
<Affiliation>Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, No. 7 Nanhai Road, Qingdao 266071, China; Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, No. 1 Wenhai Road, Qingdao 266237, China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Yu</LastName>
<ForeName>Huahua</ForeName>
<Initials>H</Initials>
<AffiliationInfo>
<Affiliation>Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, No. 7 Nanhai Road, Qingdao 266071, China; Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, No. 1 Wenhai Road, Qingdao 266237, China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Chen</LastName>
<ForeName>Xiaolin</ForeName>
<Initials>X</Initials>
<AffiliationInfo>
<Affiliation>Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, No. 7 Nanhai Road, Qingdao 266071, China; Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, No. 1 Wenhai Road, Qingdao 266237, China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Li</LastName>
<ForeName>Kecheng</ForeName>
<Initials>K</Initials>
<AffiliationInfo>
<Affiliation>Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, No. 7 Nanhai Road, Qingdao 266071, China; Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, No. 1 Wenhai Road, Qingdao 266237, China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Li</LastName>
<ForeName>Pengcheng</ForeName>
<Initials>P</Initials>
<AffiliationInfo>
<Affiliation>Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, No. 7 Nanhai Road, Qingdao 266071, China; Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, No. 1 Wenhai Road, Qingdao 266237, China. Electronic address: pcli@qdio.ac.cn.</Affiliation>
</AffiliationInfo>
</Author>
</AuthorList>
<Language>eng</Language>
<PublicationTypeList>
<PublicationType UI="D016428">Journal Article</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic">
<Year>2018</Year>
<Month>02</Month>
<Day>22</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo>
<Country>England</Country>
<MedlineTA>Carbohydr Polym</MedlineTA>
<NlmUniqueID>8307156</NlmUniqueID>
<ISSNLinking>0144-8617</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList>
<Chemical>
<RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000935">Antifungal Agents</NameOfSubstance>
</Chemical>
<Chemical>
<RegistryNumber>9012-76-4</RegistryNumber>
<NameOfSubstance UI="D048271">Chitosan</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList>
<MeshHeading>
<DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D000935" MajorTopicYN="N">Antifungal Agents</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
<QualifierName UI="Q000633" MajorTopicYN="N">toxicity</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D002470" MajorTopicYN="N">Cell Survival</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D060326" MajorTopicYN="N">Chemistry Techniques, Synthetic</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D048271" MajorTopicYN="N">Chitosan</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
<QualifierName UI="Q000633" MajorTopicYN="N">toxicity</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D005658" MajorTopicYN="N">Fungi</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D056945" MajorTopicYN="N">Hep G2 Cells</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D051379" MajorTopicYN="N">Mice</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D008958" MajorTopicYN="N">Models, Molecular</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D008968" MajorTopicYN="N">Molecular Conformation</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D010944" MajorTopicYN="N">Plants</DescriptorName>
<QualifierName UI="Q000382" MajorTopicYN="N">microbiology</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D000067996" MajorTopicYN="N">RAW 264.7 Cells</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D012995" MajorTopicYN="N">Solubility</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName>
</MeshHeading>
</MeshHeadingList>
<KeywordList Owner="NOTNLM">
<Keyword MajorTopicYN="N">Antifungal</Keyword>
<Keyword MajorTopicYN="N">Chitosan</Keyword>
<Keyword MajorTopicYN="N">Phosphoryl</Keyword>
<Keyword MajorTopicYN="N">Polyaminoethyl</Keyword>
</KeywordList>
</MedlineCitation>
<PubmedData>
<History>
<PubMedPubDate PubStatus="received">
<Year>2017</Year>
<Month>10</Month>
<Day>26</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="revised">
<Year>2018</Year>
<Month>02</Month>
<Day>14</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="accepted">
<Year>2018</Year>
<Month>02</Month>
<Day>20</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez">
<Year>2018</Year>
<Month>4</Month>
<Day>10</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed">
<Year>2018</Year>
<Month>4</Month>
<Day>10</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline">
<Year>2018</Year>
<Month>9</Month>
<Day>13</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList>
<ArticleId IdType="pubmed">29628225</ArticleId>
<ArticleId IdType="pii">S0144-8617(18)30214-5</ArticleId>
<ArticleId IdType="doi">10.1016/j.carbpol.2018.02.056</ArticleId>
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<affiliations>
<list>
<country>
<li>République populaire de Chine</li>
</country>
<settlement>
<li>Pékin</li>
</settlement>
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<name sortKey="Fan, Zhaoqian" sort="Fan, Zhaoqian" uniqKey="Fan Z" first="Zhaoqian" last="Fan">Zhaoqian Fan</name>
</noRegion>
<name sortKey="Chen, Xiaolin" sort="Chen, Xiaolin" uniqKey="Chen X" first="Xiaolin" last="Chen">Xiaolin Chen</name>
<name sortKey="Li, Kecheng" sort="Li, Kecheng" uniqKey="Li K" first="Kecheng" last="Li">Kecheng Li</name>
<name sortKey="Li, Pengcheng" sort="Li, Pengcheng" uniqKey="Li P" first="Pengcheng" last="Li">Pengcheng Li</name>
<name sortKey="Liu, Song" sort="Liu, Song" uniqKey="Liu S" first="Song" last="Liu">Song Liu</name>
<name sortKey="Qin, Yukun" sort="Qin, Yukun" uniqKey="Qin Y" first="Yukun" last="Qin">Yukun Qin</name>
<name sortKey="Xing, Ronge" sort="Xing, Ronge" uniqKey="Xing R" first="Ronge" last="Xing">Ronge Xing</name>
<name sortKey="Yu, Huahua" sort="Yu, Huahua" uniqKey="Yu H" first="Huahua" last="Yu">Huahua Yu</name>
</country>
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</affiliations>
</record>

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