Structure-activity relationships of 3-O-β-chacotriosyl ursolic acid derivatives as novel H5N1 entry inhibitors.
Identifieur interne : 001238 ( Main/Exploration ); précédent : 001237; suivant : 001239Structure-activity relationships of 3-O-β-chacotriosyl ursolic acid derivatives as novel H5N1 entry inhibitors.
Auteurs : Gaopeng Song [République populaire de Chine] ; Xintian Shen [République populaire de Chine] ; Sumei Li [République populaire de Chine] ; Yibin Li [République populaire de Chine] ; Yunpeng Liu [États-Unis] ; Yushan Zheng [République populaire de Chine] ; Ruheng Lin [République populaire de Chine] ; Jihong Fan [République populaire de Chine] ; Hanming Ye [République populaire de Chine] ; Shuwen Liu [République populaire de Chine]Source :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2015.
Descripteurs français
- KwdFr :
- Animaux, Antiviraux (), Antiviraux (pharmacologie), Cellules HEK293, Cellules rénales canines Madin-Darby, Chiens, Humains, Pénétration virale (), Relation structure-activité, Sous-type H5N1 du virus de la grippe A (), Sous-type H5N1 du virus de la grippe A (physiologie), Triterpènes (), Triterpènes (pharmacologie), Tropanes ().
- MESH :
English descriptors
- KwdEn :
- Animals, Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Dogs, HEK293 Cells, Humans, Influenza A Virus, H5N1 Subtype (drug effects), Influenza A Virus, H5N1 Subtype (physiology), Madin Darby Canine Kidney Cells, Structure-Activity Relationship, Triterpenes (chemistry), Triterpenes (pharmacology), Tropanes (chemistry), Virus Internalization (drug effects).
- MESH :
- chemical , chemistry : Antiviral Agents, Triterpenes, Tropanes.
- chemical , pharmacology : Antiviral Agents, Triterpenes.
- drug effects : Influenza A Virus, H5N1 Subtype, Virus Internalization.
- physiology : Influenza A Virus, H5N1 Subtype.
- Animals, Dogs, HEK293 Cells, Humans, Madin Darby Canine Kidney Cells, Structure-Activity Relationship.
Abstract
A series of methyl ursolate 3-O-β-chacotrioside analogs have been designed, synthesized and evaluated as H5N1 entry inhibitors based on a small molecule inhibitor saponin 3 previously discovered by us. Detailed structure-activity relationships (SARs) studies on the aglycone of compound 3 indicated that both the type of pentacyclic triterpene and the subtle modification of ursolic acid as an aglycon had key influences on the antiviral activity. These results suggested that either the introduction of a disubstituted amide structure at the 17-COOH of ursolic acid or alteration of the C-3 configuration of ursolic acid from 3β-to 3α-forms was helpful to significantly improve the selective index while keeping their antiviral activities.
DOI: 10.1016/j.ejmech.2015.02.029
PubMed: 25728024
Affiliations:
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Electronic address: vinsin1021@126.com.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Resources and Environment, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Shen, Xintian" sort="Shen, Xintian" uniqKey="Shen X" first="Xintian" last="Shen">Xintian Shen</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515</wicri:regionArea><wicri:noRegion>510515</wicri:noRegion></affiliation></author><author><name sortKey="Li, Sumei" sort="Li, Sumei" uniqKey="Li S" first="Sumei" last="Li">Sumei Li</name><affiliation wicri:level="1"><nlm:affiliation>Department of Human Anatomy, School of Medicine, Jinan University, Guangzhou, 510632, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Human Anatomy, School of Medicine, Jinan University, Guangzhou, 510632</wicri:regionArea><wicri:noRegion>510632</wicri:noRegion></affiliation></author><author><name sortKey="Li, Yibin" sort="Li, Yibin" uniqKey="Li Y" first="Yibin" last="Li">Yibin Li</name><affiliation wicri:level="1"><nlm:affiliation>College of Resources and Environment, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Resources and Environment, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Liu, Yunpeng" sort="Liu, Yunpeng" uniqKey="Liu Y" first="Yunpeng" last="Liu">Yunpeng Liu</name><affiliation wicri:level="1"><nlm:affiliation>Center for Diagnostics and Therapeutics, Department of Chemistry, Georgia State University, Atlanta, GA, 30303, United States.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Diagnostics and Therapeutics, Department of Chemistry, Georgia State University, Atlanta, GA, 30303</wicri:regionArea><wicri:noRegion>30303</wicri:noRegion></affiliation></author><author><name sortKey="Zheng, Yushan" sort="Zheng, Yushan" uniqKey="Zheng Y" first="Yushan" last="Zheng">Yushan Zheng</name><affiliation wicri:level="1"><nlm:affiliation>College of Resources and Environment, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Resources and Environment, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Lin, Ruheng" sort="Lin, Ruheng" uniqKey="Lin R" first="Ruheng" last="Lin">Ruheng Lin</name><affiliation wicri:level="1"><nlm:affiliation>College of Resources and Environment, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Resources and Environment, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Fan, Jihong" sort="Fan, Jihong" uniqKey="Fan J" first="Jihong" last="Fan">Jihong Fan</name><affiliation wicri:level="1"><nlm:affiliation>College of Resources and Environment, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Resources and Environment, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Ye, Hanming" sort="Ye, Hanming" uniqKey="Ye H" first="Hanming" last="Ye">Hanming Ye</name><affiliation wicri:level="1"><nlm:affiliation>College of Resources and Environment, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Resources and Environment, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Liu, Shuwen" sort="Liu, Shuwen" uniqKey="Liu S" first="Shuwen" last="Liu">Shuwen Liu</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China. Electronic address: liusw@smu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515</wicri:regionArea><wicri:noRegion>510515</wicri:noRegion></affiliation></author></analytic><series><title level="j">European journal of medicinal chemistry</title><idno type="eISSN">1768-3254</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Dogs</term><term>HEK293 Cells</term><term>Humans</term><term>Influenza A Virus, H5N1 Subtype (drug effects)</term><term>Influenza A Virus, H5N1 Subtype (physiology)</term><term>Madin Darby Canine Kidney Cells</term><term>Structure-Activity Relationship</term><term>Triterpenes (chemistry)</term><term>Triterpenes (pharmacology)</term><term>Tropanes (chemistry)</term><term>Virus Internalization (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Cellules HEK293</term><term>Cellules rénales canines Madin-Darby</term><term>Chiens</term><term>Humains</term><term>Pénétration virale ()</term><term>Relation structure-activité</term><term>Sous-type H5N1 du virus de la grippe A ()</term><term>Sous-type H5N1 du virus de la grippe A (physiologie)</term><term>Triterpènes ()</term><term>Triterpènes (pharmacologie)</term><term>Tropanes ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Triterpenes</term><term>Tropanes</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Triterpenes</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Influenza A Virus, H5N1 Subtype</term><term>Virus Internalization</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term><term>Triterpènes</term></keywords><keywords scheme="MESH" qualifier="physiologie" xml:lang="fr"><term>Sous-type H5N1 du virus de la grippe A</term></keywords><keywords scheme="MESH" qualifier="physiology" xml:lang="en"><term>Influenza A Virus, H5N1 Subtype</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Dogs</term><term>HEK293 Cells</term><term>Humans</term><term>Madin Darby Canine Kidney Cells</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Animaux</term><term>Antiviraux</term><term>Cellules HEK293</term><term>Cellules rénales canines Madin-Darby</term><term>Chiens</term><term>Humains</term><term>Pénétration virale</term><term>Relation structure-activité</term><term>Sous-type H5N1 du virus de la grippe A</term><term>Triterpènes</term><term>Tropanes</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A series of methyl ursolate 3-O-β-chacotrioside analogs have been designed, synthesized and evaluated as H5N1 entry inhibitors based on a small molecule inhibitor saponin 3 previously discovered by us. Detailed structure-activity relationships (SARs) studies on the aglycone of compound 3 indicated that both the type of pentacyclic triterpene and the subtle modification of ursolic acid as an aglycon had key influences on the antiviral activity. These results suggested that either the introduction of a disubstituted amide structure at the 17-COOH of ursolic acid or alteration of the C-3 configuration of ursolic acid from 3β-to 3α-forms was helpful to significantly improve the selective index while keeping their antiviral activities. </div></front></TEI><affiliations><list><country><li>République populaire de Chine</li><li>États-Unis</li></country></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Song, Gaopeng" sort="Song, Gaopeng" uniqKey="Song G" first="Gaopeng" last="Song">Gaopeng Song</name></noRegion><name sortKey="Fan, Jihong" sort="Fan, Jihong" uniqKey="Fan J" first="Jihong" last="Fan">Jihong Fan</name><name sortKey="Li, Sumei" sort="Li, Sumei" uniqKey="Li S" first="Sumei" last="Li">Sumei Li</name><name sortKey="Li, Yibin" sort="Li, Yibin" uniqKey="Li Y" first="Yibin" last="Li">Yibin Li</name><name sortKey="Lin, Ruheng" sort="Lin, Ruheng" uniqKey="Lin R" first="Ruheng" last="Lin">Ruheng Lin</name><name sortKey="Liu, Shuwen" sort="Liu, Shuwen" uniqKey="Liu S" first="Shuwen" last="Liu">Shuwen Liu</name><name sortKey="Shen, Xintian" sort="Shen, Xintian" uniqKey="Shen X" first="Xintian" last="Shen">Xintian Shen</name><name sortKey="Ye, Hanming" sort="Ye, Hanming" uniqKey="Ye H" first="Hanming" last="Ye">Hanming Ye</name><name sortKey="Zheng, Yushan" sort="Zheng, Yushan" uniqKey="Zheng Y" first="Yushan" last="Zheng">Yushan Zheng</name></country><country name="États-Unis"><noRegion><name sortKey="Liu, Yunpeng" sort="Liu, Yunpeng" uniqKey="Liu Y" first="Yunpeng" last="Liu">Yunpeng Liu</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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