Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents.
Identifieur interne : 001008 ( PubMed/Curation ); précédent : 001007; suivant : 001009Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents.
Auteurs : Hao Chen [République populaire de Chine] ; Yun-Bao Ma [République populaire de Chine] ; Xiao-Yan Huang [République populaire de Chine] ; Chang-An Geng [République populaire de Chine] ; Yong Zhao [République populaire de Chine] ; Li-Jun Wang [République populaire de Chine] ; Rui-Hua Guo [République populaire de Chine] ; Wen-Juan Liang [République populaire de Chine] ; Xue-Mei Zhang [République populaire de Chine] ; Ji-Jun Chen [République populaire de Chine]Source :
- Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2014.
Descripteurs français
- KwdFr :
- ADN viral (biosynthèse), ADN viral (génétique), Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Diterpènes (), Diterpènes (pharmacologie), Diterpènes (synthèse chimique), Produits biologiques, Relation structure-activité, Réplication de l'ADN (), Réplication virale (), Virus de l'hépatite B (), Virus de l'hépatite B (génétique), Virus de l'hépatite B (physiologie).
- MESH :
- biosynthèse : ADN viral.
- génétique : ADN viral, Virus de l'hépatite B.
- pharmacologie : Antiviraux, Diterpènes.
- physiologie : Virus de l'hépatite B.
- synthèse chimique : Antiviraux, Diterpènes.
- Antiviraux, Diterpènes, Produits biologiques, Relation structure-activité, Réplication de l'ADN, Réplication virale, Virus de l'hépatite B.
English descriptors
- KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Biological Products, DNA Replication (drug effects), DNA, Viral (biosynthesis), DNA, Viral (genetics), Diterpenes (chemical synthesis), Diterpenes (chemistry), Diterpenes (pharmacology), Hepatitis B virus (drug effects), Hepatitis B virus (genetics), Hepatitis B virus (physiology), Structure-Activity Relationship, Virus Replication (drug effects).
- MESH :
- chemical , biosynthesis : DNA, Viral.
- chemical , chemical synthesis : Antiviral Agents, Diterpenes.
- chemical , chemistry : Antiviral Agents, Diterpenes.
- chemical , genetics : DNA, Viral.
- chemical , pharmacology : Antiviral Agents, Diterpenes.
- chemical : Biological Products.
- drug effects : DNA Replication, Hepatitis B virus, Virus Replication.
- genetics : Hepatitis B virus.
- physiology : Hepatitis B virus.
- Structure-Activity Relationship.
Abstract
Dehydroandrographolide and andrographolide, two natural diterpenoids isolated from Andrographis paniculata possessed activity against HBV DNA replication with IC50 values of 22.58 and 54.07μM and low SI values of 8.7 and 3.7 in our random assay. Consequently, 48 derivatives of dehydroandrographolide and andrographolide were synthesized and evaluated for their anti-HBV properties to yield a series of active derivatives with lower cytotoxicity, including 14 derivatives against HBsAg secretion, 19 derivatives against HBeAg secretion and 38 derivatives against HBV DNA replication. Interestingly, compound 4e could inhibit not only HBsAg and HBeAg secretions but also HBV DNA replication with SI values of 20.3, 125.0 and 104.9. Furthermore, the most active compound 2c with SI value higher than 165.1 inhibiting HBV DNA replication was revealed with the optimal logP value of 1.78 and logD values. Structure-activity relationships (SARs) of the derivatives were disclosed for guiding the future research toward the discovery of new anti-HBV drugs.
DOI: 10.1016/j.bmcl.2014.03.060
PubMed: 24731274
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University of Chinese Academy of Sciences, Beijing 100049, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; University of Chinese Academy of Sciences, Beijing 100049</wicri:regionArea></affiliation></author><author><name sortKey="Zhang, Xue Mei" sort="Zhang, Xue Mei" uniqKey="Zhang X" first="Xue-Mei" last="Zhang">Xue-Mei Zhang</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201</wicri:regionArea></affiliation></author><author><name sortKey="Chen, Ji Jun" sort="Chen, Ji Jun" uniqKey="Chen J" first="Ji-Jun" last="Chen">Ji-Jun Chen</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China. Electronic address: chenjj@mail.kib.ac.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201</wicri:regionArea></affiliation></author></analytic><series><title level="j">Bioorganic & medicinal chemistry letters</title><idno type="eISSN">1464-3405</idno><imprint><date when="2014" type="published">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Biological Products</term><term>DNA Replication (drug effects)</term><term>DNA, Viral (biosynthesis)</term><term>DNA, Viral (genetics)</term><term>Diterpenes (chemical synthesis)</term><term>Diterpenes (chemistry)</term><term>Diterpenes (pharmacology)</term><term>Hepatitis B virus (drug effects)</term><term>Hepatitis B virus (genetics)</term><term>Hepatitis B virus (physiology)</term><term>Structure-Activity Relationship</term><term>Virus Replication (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN viral (biosynthèse)</term><term>ADN viral (génétique)</term><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Diterpènes ()</term><term>Diterpènes (pharmacologie)</term><term>Diterpènes (synthèse chimique)</term><term>Produits biologiques</term><term>Relation structure-activité</term><term>Réplication de l'ADN ()</term><term>Réplication virale ()</term><term>Virus de l'hépatite B ()</term><term>Virus de l'hépatite B (génétique)</term><term>Virus de l'hépatite B (physiologie)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="biosynthesis" xml:lang="en"><term>DNA, Viral</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Diterpenes</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Diterpenes</term></keywords><keywords scheme="MESH" type="chemical" qualifier="genetics" xml:lang="en"><term>DNA, Viral</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Diterpenes</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Biological Products</term></keywords><keywords scheme="MESH" qualifier="biosynthèse" xml:lang="fr"><term>ADN viral</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>DNA Replication</term><term>Hepatitis B virus</term><term>Virus Replication</term></keywords><keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Hepatitis B virus</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>ADN viral</term><term>Virus de l'hépatite B</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term><term>Diterpènes</term></keywords><keywords scheme="MESH" qualifier="physiologie" xml:lang="fr"><term>Virus de l'hépatite B</term></keywords><keywords scheme="MESH" qualifier="physiology" xml:lang="en"><term>Hepatitis B virus</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term><term>Diterpènes</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Antiviraux</term><term>Diterpènes</term><term>Produits biologiques</term><term>Relation structure-activité</term><term>Réplication de l'ADN</term><term>Réplication virale</term><term>Virus de l'hépatite B</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Dehydroandrographolide and andrographolide, two natural diterpenoids isolated from Andrographis paniculata possessed activity against HBV DNA replication with IC50 values of 22.58 and 54.07μM and low SI values of 8.7 and 3.7 in our random assay. Consequently, 48 derivatives of dehydroandrographolide and andrographolide were synthesized and evaluated for their anti-HBV properties to yield a series of active derivatives with lower cytotoxicity, including 14 derivatives against HBsAg secretion, 19 derivatives against HBeAg secretion and 38 derivatives against HBV DNA replication. Interestingly, compound 4e could inhibit not only HBsAg and HBeAg secretions but also HBV DNA replication with SI values of 20.3, 125.0 and 104.9. Furthermore, the most active compound 2c with SI value higher than 165.1 inhibiting HBV DNA replication was revealed with the optimal logP value of 1.78 and logD values. Structure-activity relationships (SARs) of the derivatives were disclosed for guiding the future research toward the discovery of new anti-HBV drugs. </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">24731274</PMID><DateCompleted><Year>2015</Year><Month>02</Month><Day>20</Day></DateCompleted><DateRevised><Year>2017</Year><Month>11</Month><Day>16</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1464-3405</ISSN><JournalIssue CitedMedium="Internet"><Volume>24</Volume><Issue>10</Issue><PubDate><Year>2014</Year><Month>May</Month><Day>15</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry letters</Title><ISOAbbreviation>Bioorg. Med. Chem. Lett.</ISOAbbreviation></Journal><ArticleTitle>Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents.</ArticleTitle><Pagination><MedlinePgn>2353-9</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bmcl.2014.03.060</ELocationID><ELocationID EIdType="pii" ValidYN="Y">S0960-894X(14)00287-X</ELocationID><Abstract><AbstractText>Dehydroandrographolide and andrographolide, two natural diterpenoids isolated from Andrographis paniculata possessed activity against HBV DNA replication with IC50 values of 22.58 and 54.07μM and low SI values of 8.7 and 3.7 in our random assay. Consequently, 48 derivatives of dehydroandrographolide and andrographolide were synthesized and evaluated for their anti-HBV properties to yield a series of active derivatives with lower cytotoxicity, including 14 derivatives against HBsAg secretion, 19 derivatives against HBeAg secretion and 38 derivatives against HBV DNA replication. Interestingly, compound 4e could inhibit not only HBsAg and HBeAg secretions but also HBV DNA replication with SI values of 20.3, 125.0 and 104.9. Furthermore, the most active compound 2c with SI value higher than 165.1 inhibiting HBV DNA replication was revealed with the optimal logP value of 1.78 and logD values. Structure-activity relationships (SARs) of the derivatives were disclosed for guiding the future research toward the discovery of new anti-HBV drugs. </AbstractText><CopyrightInformation>Copyright © 2014 Elsevier Ltd. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Chen</LastName><ForeName>Hao</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; University of Chinese Academy of Sciences, Beijing 100049, PR China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ma</LastName><ForeName>Yun-Bao</ForeName><Initials>YB</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Huang</LastName><ForeName>Xiao-Yan</ForeName><Initials>XY</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Geng</LastName><ForeName>Chang-An</ForeName><Initials>CA</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhao</LastName><ForeName>Yong</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; University of Chinese Academy of Sciences, Beijing 100049, PR China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Wang</LastName><ForeName>Li-Jun</ForeName><Initials>LJ</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Guo</LastName><ForeName>Rui-Hua</ForeName><Initials>RH</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Liang</LastName><ForeName>Wen-Juan</ForeName><Initials>WJ</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; University of Chinese Academy of Sciences, Beijing 100049, PR China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhang</LastName><ForeName>Xue-Mei</ForeName><Initials>XM</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Chen</LastName><ForeName>Ji-Jun</ForeName><Initials>JJ</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China. Electronic address: chenjj@mail.kib.ac.cn.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2014</Year><Month>03</Month><Day>28</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Bioorg Med Chem Lett</MedlineTA><NlmUniqueID>9107377</NlmUniqueID><ISSNLinking>0960-894X</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001688">Biological Products</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D004279">DNA, Viral</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D004224">Diterpenes</NameOfSubstance></Chemical><Chemical><RegistryNumber>410105JHGR</RegistryNumber><NameOfSubstance UI="C030419">andrographolide</NameOfSubstance></Chemical><Chemical><RegistryNumber>TKB45D7LVX</RegistryNumber><NameOfSubstance UI="C478098">dehydroandrographolide</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000998" MajorTopicYN="N">Antiviral Agents</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001688" MajorTopicYN="N">Biological Products</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004261" MajorTopicYN="N">DNA Replication</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004279" MajorTopicYN="N">DNA, Viral</DescriptorName><QualifierName UI="Q000096" MajorTopicYN="N">biosynthesis</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004224" MajorTopicYN="N">Diterpenes</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006515" MajorTopicYN="N">Hepatitis B virus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName><QualifierName UI="Q000502" MajorTopicYN="N">physiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D014779" MajorTopicYN="N">Virus Replication</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Anti-HBV activity</Keyword><Keyword MajorTopicYN="N">Dehydroandrographolide and andrographolide derivatives</Keyword><Keyword MajorTopicYN="N">Octanol–water partition coefficients</Keyword><Keyword MajorTopicYN="N">Structure–activity relationships</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2014</Year><Month>02</Month><Day>02</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2014</Year><Month>03</Month><Day>10</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2014</Year><Month>03</Month><Day>19</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2014</Year><Month>4</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2014</Year><Month>4</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>2</Month><Day>24</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">24731274</ArticleId><ArticleId IdType="pii">S0960-894X(14)00287-X</ArticleId><ArticleId IdType="doi">10.1016/j.bmcl.2014.03.060</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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