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Synthesis and evaluation of keto-glutamine analogues as potent inhibitors of severe acute respiratory syndrome 3CLpro

Identifieur interne : 000758 ( PascalFrancis/Checkpoint ); précédent : 000757; suivant : 000759

Synthesis 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. Vederas

Source :

RBID : Pascal:05-0097618

Descripteurs français

English descriptors

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.


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Pascal:05-0097618

Le document en format XML

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<div type="abstract" xml:lang="en">The 3C-like proteinase (3CL
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<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>
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<s0>Tetrapeptide</s0>
<s5>18</s5>
</fC03>
<fC03 i1="13" i2="X" l="SPA">
<s0>Tetrapéptido</s0>
<s5>18</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE">
<s0>Aminocétone</s0>
<s5>19</s5>
</fC03>
<fC03 i1="14" i2="X" l="ENG">
<s0>Aminoketone</s0>
<s5>19</s5>
</fC03>
<fC03 i1="14" i2="X" l="SPA">
<s0>Aminocetona</s0>
<s5>19</s5>
</fC03>
<fC03 i1="15" i2="X" l="FRE">
<s0>Phtalazine dérivé</s0>
<s2>FR</s2>
<s5>20</s5>
</fC03>
<fC03 i1="15" i2="X" l="ENG">
<s0>Phthalazine derivatives</s0>
<s2>FR</s2>
<s5>20</s5>
</fC03>
<fC03 i1="16" i2="X" l="FRE">
<s0>Valine dérivé</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>78</s5>
</fC03>
<fC03 i1="17" i2="X" l="FRE">
<s0>Thréonine dérivé</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>79</s5>
</fC03>
<fC03 i1="18" i2="X" l="FRE">
<s0>Glutamine analogue</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>80</s5>
</fC03>
<fC07 i1="01" i2="X" l="FRE">
<s0>Coronavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="01" i2="X" l="ENG">
<s0>Coronavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="01" i2="X" l="SPA">
<s0>Coronavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="02" i2="X" l="FRE">
<s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="02" i2="X" l="ENG">
<s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="02" i2="X" l="SPA">
<s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="FRE">
<s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="ENG">
<s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="SPA">
<s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="FRE">
<s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="ENG">
<s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="SPA">
<s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="FRE">
<s0>Virose</s0>
</fC07>
<fC07 i1="05" i2="X" l="ENG">
<s0>Viral disease</s0>
</fC07>
<fC07 i1="05" i2="X" l="SPA">
<s0>Virosis</s0>
</fC07>
<fC07 i1="06" i2="X" l="FRE">
<s0>Infection</s0>
</fC07>
<fC07 i1="06" i2="X" l="ENG">
<s0>Infection</s0>
</fC07>
<fC07 i1="06" i2="X" 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>

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