Structure-activity relationships of 3-O-β-chacotriosyl oleanane-type triterpenoids as potential H5N1 entry inhibitors.
Identifieur interne : 000F37 ( Main/Exploration ); précédent : 000F36; suivant : 000F38Structure-activity relationships of 3-O-β-chacotriosyl oleanane-type triterpenoids as potential 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] ; Hongzong Si [République populaire de Chine] ; Jihong Fan [République populaire de Chine] ; Junhua Li [République populaire de Chine] ; Erqiang Gao [République populaire de Chine] ; Shuwen Liu [République populaire de Chine]Source :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2016.
Descripteurs français
- KwdFr :
- Acide oléanolique (), Acide oléanolique (analogues et dérivés), Animaux, Antiviraux (), Antiviraux (métabolisme), Antiviraux (pharmacologie), Antiviraux (toxicité), Cellules rénales canines Madin-Darby, Chiens, Glycoprotéine hémagglutinine du virus influenza (), Glycoprotéine hémagglutinine du virus influenza (métabolisme), Poulets, Pénétration virale (), Relation structure-activité, Simulation de docking moléculaire, Sous-type H5N1 du virus de la grippe A (), Sous-type H5N1 du virus de la grippe A (physiologie), Structure quaternaire des protéines, Triterpènes (), Triterpènes (métabolisme), Triterpènes (pharmacologie), Triterpènes (toxicité), Érythrocytes (métabolisme).
- MESH :
- analogues et dérivés : Acide oléanolique.
- métabolisme : Antiviraux, Glycoprotéine hémagglutinine du virus influenza, Triterpènes, Érythrocytes.
- pharmacologie : Antiviraux, Triterpènes.
- physiologie : Sous-type H5N1 du virus de la grippe A.
- toxicité : Antiviraux, Triterpènes.
- Acide oléanolique, Animaux, Antiviraux, Cellules rénales canines Madin-Darby, Chiens, Glycoprotéine hémagglutinine du virus influenza, Poulets, Pénétration virale, Relation structure-activité, Simulation de docking moléculaire, Sous-type H5N1 du virus de la grippe A, Structure quaternaire des protéines, Triterpènes.
English descriptors
- KwdEn :
- Animals, Antiviral Agents (chemistry), Antiviral Agents (metabolism), Antiviral Agents (pharmacology), Antiviral Agents (toxicity), Chickens, Dogs, Erythrocytes (metabolism), Hemagglutinin Glycoproteins, Influenza Virus (chemistry), Hemagglutinin Glycoproteins, Influenza Virus (metabolism), Influenza A Virus, H5N1 Subtype (drug effects), Influenza A Virus, H5N1 Subtype (physiology), Madin Darby Canine Kidney Cells, Molecular Docking Simulation, Oleanolic Acid (analogs & derivatives), Oleanolic Acid (chemistry), Protein Structure, Quaternary, Structure-Activity Relationship, Triterpenes (chemistry), Triterpenes (metabolism), Triterpenes (pharmacology), Triterpenes (toxicity), Virus Internalization (drug effects).
- MESH :
- chemical , analogs & derivatives : Oleanolic Acid.
- chemical , chemistry : Antiviral Agents, Hemagglutinin Glycoproteins, Influenza Virus, Oleanolic Acid, Triterpenes.
- chemical , metabolism : Antiviral Agents, Hemagglutinin Glycoproteins, Influenza Virus, Triterpenes.
- chemical , pharmacology : Antiviral Agents, Triterpenes.
- chemical , toxicity : Antiviral Agents, Triterpenes.
- drug effects : Influenza A Virus, H5N1 Subtype, Virus Internalization.
- metabolism : Erythrocytes.
- physiology : Influenza A Virus, H5N1 Subtype.
- Animals, Chickens, Dogs, Madin Darby Canine Kidney Cells, Molecular Docking Simulation, Protein Structure, Quaternary, Structure-Activity Relationship.
Abstract
A series of 3-O-β-chacotriosyl oleanolic acid analogs have been designed, synthesized and evaluated as H5N1 entry inhibitors based on a small molecule inhibitor saponin 1 previously discovered by us. Detailed structure-activity relationships (SARs) studies on the aglycone of compound 1 indicated that the subtle modification of oleanolic acid as an aglycon has key influences on the antiviral activity. These results suggested that either the introduction of a disubstituted amide structure at the 17-COOH of OA or alteration of the C-3 configuration of OA from 3β-to 3α-forms can significantly improve the selective index while maintaining their antiviral activities in vitro. Compound 8 was selected for further mechanistic study because of its distinguished inhibition activity and good selective index. Molecular simulation study and surface plasmon resonance analysis confirmed that compound 8 stabilized HA2 subunit of hemagglutinin (HA) by binding with amino acid residues LYS-26, ASN-53, ASN-27 and ASN-50, therefore may prevent HA from conformational rearranging, which is a critical step for viral entry.
DOI: 10.1016/j.ejmech.2016.04.061
PubMed: 27153348
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 Materials and Energy, 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>Department of Pharmacy, Maternal and Child Health Hospital of Bao'an District, Shenzhen, 518133, China; School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Pharmacy, Maternal and Child Health Hospital of Bao'an District, Shenzhen, 518133, China; 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 Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Si, Hongzong" sort="Si, Hongzong" uniqKey="Si H" first="Hongzong" last="Si">Hongzong Si</name><affiliation wicri:level="1"><nlm:affiliation>Institute for Computational Science and Engineering, Qingdao University, Qingdao, 266071, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Institute for Computational Science and Engineering, Qingdao University, Qingdao, 266071</wicri:regionArea><wicri:noRegion>266071</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 Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Li, Junhua" sort="Li, Junhua" uniqKey="Li J" first="Junhua" last="Li">Junhua Li</name><affiliation wicri:level="1"><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Gao, Erqiang" sort="Gao, Erqiang" uniqKey="Gao E" first="Erqiang" last="Gao">Erqiang Gao</name><affiliation wicri:level="1"><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, 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>Department of Pharmacy, Maternal and Child Health Hospital of Bao'an District, Shenzhen, 518133, China. Electronic address: liusw@smu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Pharmacy, Maternal and Child Health Hospital of Bao'an District, Shenzhen, 518133</wicri:regionArea><wicri:noRegion>518133</wicri:noRegion></affiliation></author></analytic><series><title level="j">European journal of medicinal chemistry</title><idno type="eISSN">1768-3254</idno><imprint><date when="2016" type="published">2016</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 (metabolism)</term><term>Antiviral Agents (pharmacology)</term><term>Antiviral Agents (toxicity)</term><term>Chickens</term><term>Dogs</term><term>Erythrocytes (metabolism)</term><term>Hemagglutinin Glycoproteins, Influenza Virus (chemistry)</term><term>Hemagglutinin Glycoproteins, Influenza Virus (metabolism)</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>Molecular Docking Simulation</term><term>Oleanolic Acid (analogs & derivatives)</term><term>Oleanolic Acid (chemistry)</term><term>Protein Structure, Quaternary</term><term>Structure-Activity Relationship</term><term>Triterpenes (chemistry)</term><term>Triterpenes (metabolism)</term><term>Triterpenes (pharmacology)</term><term>Triterpenes (toxicity)</term><term>Virus Internalization (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acide oléanolique ()</term><term>Acide oléanolique (analogues et dérivés)</term><term>Animaux</term><term>Antiviraux ()</term><term>Antiviraux (métabolisme)</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (toxicité)</term><term>Cellules rénales canines Madin-Darby</term><term>Chiens</term><term>Glycoprotéine hémagglutinine du virus influenza ()</term><term>Glycoprotéine hémagglutinine du virus influenza (métabolisme)</term><term>Poulets</term><term>Pénétration virale ()</term><term>Relation structure-activité</term><term>Simulation de docking moléculaire</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>Structure quaternaire des protéines</term><term>Triterpènes ()</term><term>Triterpènes (métabolisme)</term><term>Triterpènes (pharmacologie)</term><term>Triterpènes (toxicité)</term><term>Érythrocytes (métabolisme)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Oleanolic Acid</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Hemagglutinin Glycoproteins, Influenza Virus</term><term>Oleanolic Acid</term><term>Triterpenes</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Antiviral Agents</term><term>Hemagglutinin Glycoproteins, Influenza Virus</term><term>Triterpenes</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Triterpenes</term></keywords><keywords scheme="MESH" type="chemical" qualifier="toxicity" xml:lang="en"><term>Antiviral Agents</term><term>Triterpenes</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Acide oléanolique</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="metabolism" xml:lang="en"><term>Erythrocytes</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Antiviraux</term><term>Glycoprotéine hémagglutinine du virus influenza</term><term>Triterpènes</term><term>Érythrocytes</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" qualifier="toxicité" xml:lang="fr"><term>Antiviraux</term><term>Triterpènes</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Chickens</term><term>Dogs</term><term>Madin Darby Canine Kidney Cells</term><term>Molecular Docking Simulation</term><term>Protein Structure, Quaternary</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Acide oléanolique</term><term>Animaux</term><term>Antiviraux</term><term>Cellules rénales canines Madin-Darby</term><term>Chiens</term><term>Glycoprotéine hémagglutinine du virus influenza</term><term>Poulets</term><term>Pénétration virale</term><term>Relation structure-activité</term><term>Simulation de docking moléculaire</term><term>Sous-type H5N1 du virus de la grippe A</term><term>Structure quaternaire des protéines</term><term>Triterpènes</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A series of 3-O-β-chacotriosyl oleanolic acid analogs have been designed, synthesized and evaluated as H5N1 entry inhibitors based on a small molecule inhibitor saponin 1 previously discovered by us. Detailed structure-activity relationships (SARs) studies on the aglycone of compound 1 indicated that the subtle modification of oleanolic acid as an aglycon has key influences on the antiviral activity. These results suggested that either the introduction of a disubstituted amide structure at the 17-COOH of OA or alteration of the C-3 configuration of OA from 3β-to 3α-forms can significantly improve the selective index while maintaining their antiviral activities in vitro. Compound 8 was selected for further mechanistic study because of its distinguished inhibition activity and good selective index. Molecular simulation study and surface plasmon resonance analysis confirmed that compound 8 stabilized HA2 subunit of hemagglutinin (HA) by binding with amino acid residues LYS-26, ASN-53, ASN-27 and ASN-50, therefore may prevent HA from conformational rearranging, which is a critical step for viral entry. </div></front></TEI><affiliations><list><country><li>République populaire de Chine</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="Gao, Erqiang" sort="Gao, Erqiang" uniqKey="Gao E" first="Erqiang" last="Gao">Erqiang Gao</name><name sortKey="Li, Junhua" sort="Li, Junhua" uniqKey="Li J" first="Junhua" last="Li">Junhua Li</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="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="Si, Hongzong" sort="Si, Hongzong" uniqKey="Si H" first="Hongzong" last="Si">Hongzong Si</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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