Synthesis and evaluation of keto-glutamine analogues as potent inhibitors of severe acute respiratory syndrome 3CLpro
Identifieur interne : 000758 ( PascalFrancis/Checkpoint ); précédent : 000757; suivant : 000759Synthesis and evaluation of keto-glutamine analogues as potent inhibitors of severe acute respiratory syndrome 3CLpro
Auteurs : Rajendra P. Jain [Canada] ; Hanna I. Pettersson ; JIANMIN ZHANG ; Katherine D. Aull ; Pascal D. Fortin ; Carly Huitema ; Lindsay D. Eltis ; Jonathan C. Parrish ; Michael N. G. James ; David S. Wishart ; John C. VederasSource :
- Journal of medicinal chemistry : (Print) [ 0022-2623 ] ; 2004.
Descripteurs français
- Pascal (Inist)
- Activité biologique, Antiviral, Virus syndrome respiratoire aigu sévère, Syndrome respiratoire aigu sévère, Inhibiteur protease, Inhibiteur enzyme, Peptidases, In vitro, Modélisation, Modèle moléculaire, Synthèse chimique, Peptide, Tétrapeptide, Aminocétone, Phtalazine dérivé, Valine dérivé, Thréonine dérivé, Glutamine analogue.
English descriptors
- KwdEn :
Abstract
The 3C-like proteinase (3CLpro) of severe acute respiratory syndrome (SARS) coronavirus is a key target for structure-based drug design against this viral infection. The enzyme recognizes peptide substrates with a glutamine residue at the P1 site. A series of keto-glutamine analogues with a phthalhydrazido group at the α-position were synthesized and tested as reversible inhibitiors against SARS 3CLpro. Attachment of tripeptide (Ac-Val-Thr-Leu) to these glutamine-based "warheads" generated significantly better inhibitors (4a-c, 8a-d) with IC50 values ranging from 0.60 to 70 μM.
Affiliations:
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Pascal:05-0097618Le document en format XML
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Jain</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Chemistry, University of Alberta</s1><s2>Edmonton, Alberta, T6G 2G2</s2><s3>CAN</s3></inist:fA14><country>Canada</country><wicri:noRegion>Edmonton, Alberta, T6G 2G2</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Departments of Microbiology and Biochemistry, University of British Columbia</s1><s2>Vancouver, British Columbia, V6T 1Z3</s2><s3>CAN</s3></inist:fA14><country>Canada</country><wicri:noRegion>Vancouver, British Columbia, V6T 1Z3</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="03"><s1>Alberta Synchroton Institute, University of Alberta</s1><s2>Edmonton, AB, T6G 2E1</s2><s3>CAN</s3></inist:fA14><country>Canada</country><wicri:noRegion>Edmonton, AB, T6G 2E1</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>Department of Biochemistry, University of Alberta</s1><s2>Edmonton, Alberta, T6G 2H7</s2><s3>CAN</s3></inist:fA14><country>Canada</country><wicri:noRegion>Edmonton, Alberta, T6G 2H7</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="05"><s1>Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta</s1><s2>Edmonton, AB, T6G 2N8</s2><s3>CAN</s3></inist:fA14><country>Canada</country><wicri:noRegion>Edmonton, AB, T6G 2N8</wicri:noRegion></affiliation></author><author><name sortKey="Pettersson, Hanna I" sort="Pettersson, Hanna I" uniqKey="Pettersson H" first="Hanna I." last="Pettersson">Hanna I. Pettersson</name></author><author><name sortKey="Jianmin Zhang" sort="Jianmin Zhang" uniqKey="Jianmin Zhang" last="Jianmin Zhang">JIANMIN ZHANG</name></author><author><name sortKey="Aull, Katherine D" sort="Aull, Katherine D" uniqKey="Aull K" first="Katherine D." last="Aull">Katherine D. Aull</name></author><author><name sortKey="Fortin, Pascal D" sort="Fortin, Pascal D" uniqKey="Fortin P" first="Pascal D." last="Fortin">Pascal D. Fortin</name></author><author><name sortKey="Huitema, Carly" sort="Huitema, Carly" uniqKey="Huitema C" first="Carly" last="Huitema">Carly Huitema</name></author><author><name sortKey="Eltis, Lindsay D" sort="Eltis, Lindsay D" uniqKey="Eltis L" first="Lindsay D." last="Eltis">Lindsay D. Eltis</name></author><author><name sortKey="Parrish, Jonathan C" sort="Parrish, Jonathan C" uniqKey="Parrish J" first="Jonathan C." last="Parrish">Jonathan C. Parrish</name></author><author><name sortKey="James, Michael N G" sort="James, Michael N G" uniqKey="James M" first="Michael N. G." last="James">Michael N. G. James</name></author><author><name sortKey="Wishart, David S" sort="Wishart, David S" uniqKey="Wishart D" first="David S." last="Wishart">David S. Wishart</name></author><author><name sortKey="Vederas, John C" sort="Vederas, John C" uniqKey="Vederas J" first="John C." last="Vederas">John C. Vederas</name></author></analytic><series><title level="j" type="main">Journal of medicinal chemistry : (Print)</title><title level="j" type="abbreviated">J. med. chem. : (Print)</title><idno type="ISSN">0022-2623</idno><imprint><date when="2004">2004</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Journal of medicinal chemistry : (Print)</title><title level="j" type="abbreviated">J. med. chem. : (Print)</title><idno type="ISSN">0022-2623</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aminoketone</term><term>Antiviral</term><term>Biological activity</term><term>Chemical synthesis</term><term>Enzyme inhibitor</term><term>In vitro</term><term>Modeling</term><term>Molecular model</term><term>Peptidases</term><term>Peptides</term><term>Phthalazine derivatives</term><term>Protease inhibitor</term><term>Severe acute respiratory syndrome</term><term>Severe acute respiratory syndrome virus</term><term>Tetrapeptide</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Activité biologique</term><term>Antiviral</term><term>Virus syndrome respiratoire aigu sévère</term><term>Syndrome respiratoire aigu sévère</term><term>Inhibiteur protease</term><term>Inhibiteur enzyme</term><term>Peptidases</term><term>In vitro</term><term>Modélisation</term><term>Modèle moléculaire</term><term>Synthèse chimique</term><term>Peptide</term><term>Tétrapeptide</term><term>Aminocétone</term><term>Phtalazine dérivé</term><term>Valine dérivé</term><term>Thréonine dérivé</term><term>Glutamine analogue</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The 3C-like proteinase (3CL<sup>pro</sup>) of severe acute respiratory syndrome (SARS) coronavirus is a key target for structure-based drug design against this viral infection. The enzyme recognizes peptide substrates with a glutamine residue at the P1 site. A series of keto-glutamine analogues with a phthalhydrazido group at the α-position were synthesized and tested as reversible inhibitiors against SARS 3CL<sup>pro</sup>. Attachment of tripeptide (Ac-Val-Thr-Leu) to these glutamine-based "warheads" generated significantly better inhibitors (4a-c, 8a-d) with IC<sub>50</sub> values ranging from 0.60 to 70 μM.</div></front></TEI><inist><standard h6="B"><pA><fA01 i1="01" i2="1"><s0>0022-2623</s0></fA01><fA02 i1="01"><s0>JMCMAR</s0></fA02><fA03 i2="1"><s0>J. med. chem. : (Print)</s0></fA03><fA05><s2>47</s2></fA05><fA06><s2>25</s2></fA06><fA08 i1="01" i2="1" l="ENG"><s1>Synthesis and evaluation of keto-glutamine analogues as potent inhibitors of severe acute respiratory syndrome 3CL<sup>pro</sup></s1></fA08><fA11 i1="01" i2="1"><s1>JAIN (Rajendra P.)</s1></fA11><fA11 i1="02" i2="1"><s1>PETTERSSON (Hanna I.)</s1></fA11><fA11 i1="03" i2="1"><s1>JIANMIN ZHANG</s1></fA11><fA11 i1="04" i2="1"><s1>AULL (Katherine D.)</s1></fA11><fA11 i1="05" i2="1"><s1>FORTIN (Pascal D.)</s1></fA11><fA11 i1="06" i2="1"><s1>HUITEMA (Carly)</s1></fA11><fA11 i1="07" i2="1"><s1>ELTIS (Lindsay D.)</s1></fA11><fA11 i1="08" i2="1"><s1>PARRISH (Jonathan C.)</s1></fA11><fA11 i1="09" i2="1"><s1>JAMES (Michael N. G.)</s1></fA11><fA11 i1="10" i2="1"><s1>WISHART (David S.)</s1></fA11><fA11 i1="11" i2="1"><s1>VEDERAS (John C.)</s1></fA11><fA14 i1="01"><s1>Department of Chemistry, University of Alberta</s1><s2>Edmonton, Alberta, T6G 2G2</s2><s3>CAN</s3></fA14><fA14 i1="02"><s1>Departments of Microbiology and Biochemistry, University of British Columbia</s1><s2>Vancouver, British Columbia, V6T 1Z3</s2><s3>CAN</s3></fA14><fA14 i1="03"><s1>Alberta Synchroton Institute, University of Alberta</s1><s2>Edmonton, AB, T6G 2E1</s2><s3>CAN</s3></fA14><fA14 i1="04"><s1>Department of Biochemistry, University of Alberta</s1><s2>Edmonton, Alberta, T6G 2H7</s2><s3>CAN</s3></fA14><fA14 i1="05"><s1>Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta</s1><s2>Edmonton, AB, T6G 2N8</s2><s3>CAN</s3></fA14><fA20><s1>6113-6116</s1></fA20><fA21><s1>2004</s1></fA21><fA23 i1="01"><s0>ENG</s0></fA23><fA43 i1="01"><s1>INIST</s1><s2>9165</s2><s5>354000122546380010</s5></fA43><fA44><s0>0000</s0><s1>© 2005 INIST-CNRS. All rights reserved.</s1></fA44><fA45><s0>18 ref.</s0></fA45><fA47 i1="01" i2="1"><s0>05-0097618</s0></fA47><fA60><s1>P</s1><s3>CR</s3></fA60><fA61><s0>A</s0></fA61><fA64 i1="01" i2="1"><s0>Journal of medicinal chemistry : (Print)</s0></fA64><fA66 i1="01"><s0>USA</s0></fA66><fC01 i1="01" l="ENG"><s0>The 3C-like proteinase (3CL<sup>pro</sup>) of severe acute respiratory syndrome (SARS) coronavirus is a key target for structure-based drug design against this viral infection. The enzyme recognizes peptide substrates with a glutamine residue at the P1 site. A series of keto-glutamine analogues with a phthalhydrazido group at the α-position were synthesized and tested as reversible inhibitiors against SARS 3CL<sup>pro</sup>. Attachment of tripeptide (Ac-Val-Thr-Leu) to these glutamine-based "warheads" generated significantly better inhibitors (4a-c, 8a-d) with IC<sub>50</sub> values ranging from 0.60 to 70 μM.</s0></fC01><fC02 i1="01" i2="X"><s0>002B02S05</s0></fC02><fC03 i1="01" i2="X" l="FRE"><s0>Activité biologique</s0><s5>01</s5></fC03><fC03 i1="01" i2="X" l="ENG"><s0>Biological activity</s0><s5>01</s5></fC03><fC03 i1="01" i2="X" l="SPA"><s0>Actividad biológica</s0><s5>01</s5></fC03><fC03 i1="02" i2="X" l="FRE"><s0>Antiviral</s0><s5>02</s5></fC03><fC03 i1="02" i2="X" l="ENG"><s0>Antiviral</s0><s5>02</s5></fC03><fC03 i1="02" i2="X" l="SPA"><s0>Antiviral</s0><s5>02</s5></fC03><fC03 i1="03" i2="X" l="FRE"><s0>Virus syndrome respiratoire aigu sévère</s0><s2>NW</s2><s5>03</s5></fC03><fC03 i1="03" i2="X" l="ENG"><s0>Severe acute respiratory syndrome virus</s0><s2>NW</s2><s5>03</s5></fC03><fC03 i1="03" i2="X" l="SPA"><s0>Severe acute respiratory syndrome virus</s0><s2>NW</s2><s5>03</s5></fC03><fC03 i1="04" 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l="SPA"><s0>Infección</s0></fC07><fC07 i1="07" i2="X" l="FRE"><s0>Appareil respiratoire pathologie</s0><s5>06</s5></fC07><fC07 i1="07" i2="X" l="ENG"><s0>Respiratory disease</s0><s5>06</s5></fC07><fC07 i1="07" i2="X" l="SPA"><s0>Aparato respiratorio patología</s0><s5>06</s5></fC07><fC07 i1="08" i2="X" l="FRE"><s0>Hydrolases</s0><s2>FE</s2></fC07><fC07 i1="08" i2="X" l="ENG"><s0>Hydrolases</s0><s2>FE</s2></fC07><fC07 i1="08" i2="X" l="SPA"><s0>Hydrolases</s0><s2>FE</s2></fC07><fC07 i1="09" i2="X" l="FRE"><s0>Enzyme</s0><s2>FE</s2></fC07><fC07 i1="09" i2="X" l="ENG"><s0>Enzyme</s0><s2>FE</s2></fC07><fC07 i1="09" i2="X" l="SPA"><s0>Enzima</s0><s2>FE</s2></fC07><fN21><s1>066</s1></fN21><fN44 i1="01"><s1>PSI</s1></fN44><fN82><s1>PSI</s1></fN82></pA></standard></inist><affiliations><list><country><li>Canada</li></country></list><tree><noCountry><name sortKey="Aull, Katherine D" sort="Aull, Katherine D" uniqKey="Aull K" first="Katherine D." last="Aull">Katherine D. Aull</name><name sortKey="Eltis, Lindsay D" sort="Eltis, Lindsay D" uniqKey="Eltis L" first="Lindsay D." last="Eltis">Lindsay D. Eltis</name><name sortKey="Fortin, Pascal D" sort="Fortin, Pascal D" uniqKey="Fortin P" first="Pascal D." last="Fortin">Pascal D. Fortin</name><name sortKey="Huitema, Carly" sort="Huitema, Carly" uniqKey="Huitema C" first="Carly" last="Huitema">Carly Huitema</name><name sortKey="James, Michael N G" sort="James, Michael N G" uniqKey="James M" first="Michael N. G." last="James">Michael N. G. James</name><name sortKey="Jianmin Zhang" sort="Jianmin Zhang" uniqKey="Jianmin Zhang" last="Jianmin Zhang">JIANMIN ZHANG</name><name sortKey="Parrish, Jonathan C" sort="Parrish, Jonathan C" uniqKey="Parrish J" first="Jonathan C." last="Parrish">Jonathan C. Parrish</name><name sortKey="Pettersson, Hanna I" sort="Pettersson, Hanna I" uniqKey="Pettersson H" first="Hanna I." last="Pettersson">Hanna I. Pettersson</name><name sortKey="Vederas, John C" sort="Vederas, John C" uniqKey="Vederas J" first="John C." last="Vederas">John C. Vederas</name><name sortKey="Wishart, David S" sort="Wishart, David S" uniqKey="Wishart D" first="David S." last="Wishart">David S. Wishart</name></noCountry><country name="Canada"><noRegion><name sortKey="Jain, Rajendra P" sort="Jain, Rajendra P" uniqKey="Jain R" first="Rajendra P." last="Jain">Rajendra P. Jain</name></noRegion><name sortKey="Jain, Rajendra P" sort="Jain, Rajendra P" uniqKey="Jain R" first="Rajendra P." last="Jain">Rajendra P. Jain</name><name sortKey="Jain, Rajendra P" sort="Jain, Rajendra P" uniqKey="Jain R" first="Rajendra P." last="Jain">Rajendra P. Jain</name><name sortKey="Jain, Rajendra P" sort="Jain, Rajendra P" uniqKey="Jain R" first="Rajendra P." last="Jain">Rajendra P. Jain</name><name sortKey="Jain, Rajendra P" sort="Jain, Rajendra P" uniqKey="Jain R" first="Rajendra P." last="Jain">Rajendra P. Jain</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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