Binding interaction of quercetin -3 -β -galactoside and its synthetic derivatives with SARS-CoV 3CLpro : Structure-activity relationship studies reveal salient pharmacophore features
Identifieur interne : 004472 ( Main/Exploration ); précédent : 004471; suivant : 004473Binding interaction of quercetin -3 -β -galactoside and its synthetic derivatives with SARS-CoV 3CLpro : Structure-activity relationship studies reveal salient pharmacophore features
Auteurs : LILI CHEN [République populaire de Chine] ; JIAN LI [République populaire de Chine] ; CHENG LUO [République populaire de Chine] ; HONG LIU [République populaire de Chine] ; WEIJUN XU [Singapour] ; GANG CHEN [Singapour] ; OI WAH LIEW [Singapour] ; WEILIANG ZHU [République populaire de Chine] ; CHUM MOK PUAH [Singapour] ; XU SHEN [République populaire de Chine] ; HUALIANG JIANG [République populaire de Chine]Source :
- Bioorganic & medicinal chemistry [ 0968-0896 ] ; 2006.
Descripteurs français
- Pascal (Inist)
- Quercétine, Virus syndrome respiratoire aigu sévère, Relation structure activité, Modélisation, Peptidases, Syndrome respiratoire aigu sévère, Médicament, Cycle développement, Composé naturel, Inhibiteur protease, Modèle moléculaire, Prédiction, Spectrométrie fluorescence, Transfert énergie résonnant, Mutagenèse, Mutation, Structure secondaire, Fixation biologique, Synthèse chimique, Antiviral, Mécanisme action, Galactose, In vitro, Flavone dérivé, Polyphénol, Inhibiteur enzyme, Flavonoïde, Glycoside, Interaction moléculaire, Galactopyranoside dérivé, Criblage virtuel.
- Wicri :
- topic : Médicament.
English descriptors
- KwdEn :
- Antiviral, Biological fixation, Chemical synthesis, Drug, Enzyme inhibitor, Flavone derivatives, Flavonoid, Fluorescence spectrometry, Galactose, Glycoside, In vitro, Life cycle, Mechanism of action, Modeling, Molecular interaction, Molecular model, Mutagenesis, Mutation, Natural compound, Peptidases, Polyphenol, Prediction, Protease inhibitor, Quercetin, Resonant energy transfer, Secondary structure, Severe acute respiratory syndrome, Severe acute respiratory syndrome virus, Structure activity relation, Virtual screening.
Abstract
The 3C-like protease (3CLpro) of severe acute respiratory syndrome-associated coronavirus (SARS-CoV) is one of the most promising targets for discovery of drugs against SARS, because of its critical role in the viral life cycle. In this study, a natural compound called quercetin-3-β-galactoside was identified as an inhibitor of the protease by molecular docking, SPR/FRET-based bioassays, and mutagenesis studies. Both molecular modeling and Q189A mutation revealed that Glnl89 plays a key role in the binding. Furthermore, experimental evidence showed that the secondary structure and enzymatic activity of SARS-CoV 3CLpro were not affected by the Q189A mutation. With the help of molecular modeling, eight new derivatives of the natural product were designed and synthesized. Bioassay results reveal salient features of the structure-activity relationship of the new compounds: (1) removal of the 7-hydroxy group of the quercetin moiety decreases the bioactivity of the derivatives; (2) acetoxylation of the sugar moiety abolishes inhibitor action; (3) introduction of a large sugar substituent on 7-hydroxy of quercetin can be tolerated; (4) replacement of the galactose moiety with other sugars does not affect inhibitor potency. This study not only reveals a new class of compounds as potential drug leads against the SARS virus, but also provides a solid understanding of the mechanism of inhibition against the target enzyme.
Affiliations:
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wicri:level="1"><inist:fA14 i1="02"><s1>Technology Centre for Life Sciences, Singapore Polytechnic, 500 Dover Road</s1><s2>139651 Singapore</s2><s3>SGP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Singapour</country><wicri:noRegion>139651 Singapore</wicri:noRegion></affiliation></author><author><name sortKey="Oi Wah Liew" sort="Oi Wah Liew" uniqKey="Oi Wah Liew" last="Oi Wah Liew">OI WAH LIEW</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Technology Centre for Life Sciences, Singapore Polytechnic, 500 Dover Road</s1><s2>139651 Singapore</s2><s3>SGP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Singapour</country><wicri:noRegion>139651 Singapore</wicri:noRegion></affiliation></author><author><name sortKey="Weiliang Zhu" sort="Weiliang Zhu" uniqKey="Weiliang Zhu" last="Weiliang Zhu">WEILIANG ZHU</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences</s1><s2>Shanghai 201203</s2><s3>CHN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>République populaire de Chine</country><wicri:noRegion>Shanghai 201203</wicri:noRegion></affiliation></author><author><name sortKey="Chum Mok Puah" sort="Chum Mok Puah" uniqKey="Chum Mok Puah" last="Chum Mok Puah">CHUM MOK PUAH</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Technology Centre for Life Sciences, Singapore Polytechnic, 500 Dover Road</s1><s2>139651 Singapore</s2><s3>SGP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Singapour</country><wicri:noRegion>139651 Singapore</wicri:noRegion></affiliation></author><author><name sortKey="Xu Shen" sort="Xu Shen" uniqKey="Xu Shen" last="Xu Shen">XU SHEN</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Drug Discovery and Design Center, Shanghai 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uniqKey="Lili Chen" last="Lili Chen">LILI CHEN</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences</s1><s2>Shanghai 201203</s2><s3>CHN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>République populaire de Chine</country><wicri:noRegion>Shanghai 201203</wicri:noRegion></affiliation></author><author><name sortKey="Jian Li" sort="Jian Li" uniqKey="Jian Li" last="Jian Li">JIAN LI</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences</s1><s2>Shanghai 201203</s2><s3>CHN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>République populaire de Chine</country><wicri:noRegion>Shanghai 201203</wicri:noRegion></affiliation></author><author><name sortKey="Cheng Luo" sort="Cheng Luo" uniqKey="Cheng Luo" last="Cheng Luo">CHENG LUO</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences</s1><s2>Shanghai 201203</s2><s3>CHN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>République populaire de Chine</country><wicri:noRegion>Shanghai 201203</wicri:noRegion></affiliation></author><author><name sortKey="Hong Liu" sort="Hong Liu" uniqKey="Hong Liu" last="Hong Liu">HONG LIU</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences</s1><s2>Shanghai 201203</s2><s3>CHN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>République populaire de Chine</country><wicri:noRegion>Shanghai 201203</wicri:noRegion></affiliation></author><author><name sortKey="Weijun Xu" sort="Weijun Xu" uniqKey="Weijun Xu" last="Weijun Xu">WEIJUN XU</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Technology Centre for Life Sciences, Singapore Polytechnic, 500 Dover Road</s1><s2>139651 Singapore</s2><s3>SGP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Singapour</country><wicri:noRegion>139651 Singapore</wicri:noRegion></affiliation></author><author><name sortKey="Gang Chen" sort="Gang Chen" uniqKey="Gang Chen" last="Gang Chen">GANG CHEN</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Technology Centre for Life Sciences, Singapore Polytechnic, 500 Dover Road</s1><s2>139651 Singapore</s2><s3>SGP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Singapour</country><wicri:noRegion>139651 Singapore</wicri:noRegion></affiliation></author><author><name sortKey="Oi Wah Liew" sort="Oi Wah Liew" uniqKey="Oi Wah Liew" last="Oi Wah Liew">OI WAH LIEW</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Technology Centre for Life Sciences, Singapore Polytechnic, 500 Dover Road</s1><s2>139651 Singapore</s2><s3>SGP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Singapour</country><wicri:noRegion>139651 Singapore</wicri:noRegion></affiliation></author><author><name sortKey="Weiliang Zhu" sort="Weiliang Zhu" uniqKey="Weiliang Zhu" last="Weiliang Zhu">WEILIANG ZHU</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences</s1><s2>Shanghai 201203</s2><s3>CHN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>République populaire de Chine</country><wicri:noRegion>Shanghai 201203</wicri:noRegion></affiliation></author><author><name sortKey="Chum Mok Puah" sort="Chum Mok Puah" uniqKey="Chum Mok Puah" last="Chum Mok Puah">CHUM MOK PUAH</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Technology Centre for Life Sciences, Singapore Polytechnic, 500 Dover Road</s1><s2>139651 Singapore</s2><s3>SGP</s3><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Singapour</country><wicri:noRegion>139651 Singapore</wicri:noRegion></affiliation></author><author><name sortKey="Xu Shen" sort="Xu Shen" uniqKey="Xu Shen" last="Xu Shen">XU SHEN</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences</s1><s2>Shanghai 201203</s2><s3>CHN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>République populaire de Chine</country><wicri:noRegion>Shanghai 201203</wicri:noRegion></affiliation></author><author><name sortKey="Hualiang Jiang" sort="Hualiang Jiang" uniqKey="Hualiang Jiang" last="Hualiang Jiang">HUALIANG JIANG</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences</s1><s2>Shanghai 201203</s2><s3>CHN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>République populaire de Chine</country><wicri:noRegion>Shanghai 201203</wicri:noRegion></affiliation></author></analytic><series><title level="j" type="main">Bioorganic & medicinal chemistry</title><title level="j" type="abbreviated">Bioorg. med. chem.</title><idno type="ISSN">0968-0896</idno><imprint><date when="2006">2006</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Bioorganic & medicinal chemistry</title><title level="j" type="abbreviated">Bioorg. med. chem.</title><idno type="ISSN">0968-0896</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral</term><term>Biological fixation</term><term>Chemical synthesis</term><term>Drug</term><term>Enzyme inhibitor</term><term>Flavone derivatives</term><term>Flavonoid</term><term>Fluorescence spectrometry</term><term>Galactose</term><term>Glycoside</term><term>In vitro</term><term>Life cycle</term><term>Mechanism of action</term><term>Modeling</term><term>Molecular interaction</term><term>Molecular model</term><term>Mutagenesis</term><term>Mutation</term><term>Natural compound</term><term>Peptidases</term><term>Polyphenol</term><term>Prediction</term><term>Protease inhibitor</term><term>Quercetin</term><term>Resonant energy transfer</term><term>Secondary structure</term><term>Severe acute respiratory syndrome</term><term>Severe acute respiratory syndrome virus</term><term>Structure activity relation</term><term>Virtual screening</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Quercétine</term><term>Virus syndrome respiratoire aigu sévère</term><term>Relation structure activité</term><term>Modélisation</term><term>Peptidases</term><term>Syndrome respiratoire aigu sévère</term><term>Médicament</term><term>Cycle développement</term><term>Composé naturel</term><term>Inhibiteur protease</term><term>Modèle moléculaire</term><term>Prédiction</term><term>Spectrométrie fluorescence</term><term>Transfert énergie résonnant</term><term>Mutagenèse</term><term>Mutation</term><term>Structure secondaire</term><term>Fixation biologique</term><term>Synthèse chimique</term><term>Antiviral</term><term>Mécanisme action</term><term>Galactose</term><term>In vitro</term><term>Flavone dérivé</term><term>Polyphénol</term><term>Inhibiteur enzyme</term><term>Flavonoïde</term><term>Glycoside</term><term>Interaction moléculaire</term><term>Galactopyranoside dérivé</term><term>Criblage virtuel</term></keywords><keywords scheme="Wicri" type="topic" xml:lang="fr"><term>Médicament</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The 3C-like protease (3CL<sup>pro</sup>) of severe acute respiratory syndrome-associated coronavirus (SARS-CoV) is one of the most promising targets for discovery of drugs against SARS, because of its critical role in the viral life cycle. In this study, a natural compound called quercetin-3-β-galactoside was identified as an inhibitor of the protease by molecular docking, SPR/FRET-based bioassays, and mutagenesis studies. Both molecular modeling and Q189A mutation revealed that Glnl89 plays a key role in the binding. Furthermore, experimental evidence showed that the secondary structure and enzymatic activity of SARS-CoV 3CL<sup>pro</sup> were not affected by the Q189A mutation. With the help of molecular modeling, eight new derivatives of the natural product were designed and synthesized. Bioassay results reveal salient features of the structure-activity relationship of the new compounds: (1) removal of the 7-hydroxy group of the quercetin moiety decreases the bioactivity of the derivatives; (2) acetoxylation of the sugar moiety abolishes inhibitor action; (3) introduction of a large sugar substituent on 7-hydroxy of quercetin can be tolerated; (4) replacement of the galactose moiety with other sugars does not affect inhibitor potency. This study not only reveals a new class of compounds as potential drug leads against the SARS virus, but also provides a solid understanding of the mechanism of inhibition against the target enzyme.</div></front></TEI><affiliations><list><country><li>République populaire de Chine</li><li>Singapour</li></country></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Lili Chen" sort="Lili Chen" uniqKey="Lili Chen" last="Lili Chen">LILI CHEN</name></noRegion><name sortKey="Cheng Luo" sort="Cheng Luo" uniqKey="Cheng Luo" last="Cheng Luo">CHENG LUO</name><name sortKey="Hong Liu" sort="Hong Liu" uniqKey="Hong Liu" last="Hong Liu">HONG LIU</name><name sortKey="Hualiang Jiang" sort="Hualiang Jiang" uniqKey="Hualiang Jiang" last="Hualiang Jiang">HUALIANG JIANG</name><name sortKey="Jian Li" sort="Jian Li" uniqKey="Jian Li" last="Jian Li">JIAN LI</name><name sortKey="Weiliang Zhu" sort="Weiliang Zhu" uniqKey="Weiliang Zhu" last="Weiliang Zhu">WEILIANG ZHU</name><name sortKey="Xu Shen" sort="Xu Shen" uniqKey="Xu Shen" last="Xu Shen">XU SHEN</name></country><country name="Singapour"><noRegion><name sortKey="Weijun Xu" sort="Weijun Xu" uniqKey="Weijun Xu" last="Weijun Xu">WEIJUN XU</name></noRegion><name sortKey="Chum Mok Puah" sort="Chum Mok Puah" uniqKey="Chum Mok Puah" last="Chum Mok Puah">CHUM MOK PUAH</name><name sortKey="Gang Chen" sort="Gang Chen" uniqKey="Gang Chen" last="Gang Chen">GANG CHEN</name><name sortKey="Oi Wah Liew" sort="Oi Wah Liew" uniqKey="Oi Wah Liew" last="Oi Wah Liew">OI WAH LIEW</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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