Discovery of potent anilide inhibitors against the severe acute respiratory syndrome 3CL protease
Identifieur interne : 000663 ( PascalFrancis/Checkpoint ); précédent : 000662; suivant : 000664Discovery of potent anilide inhibitors against the severe acute respiratory syndrome 3CL protease
Auteurs : Jiun-Jie Shie [Taïwan] ; Jim-Min Fang [Taïwan] ; Chih-Jung Kuo [Taïwan] ; Tun-Hsun Kuo [Taïwan] ; Po-Huang Liang [Taïwan] ; Hung-Jyun Huang [Taïwan] ; Wen-Bin Yang [Taïwan] ; Chun-Hung Lin [Taïwan] ; Jiun-Ling Chen [Taïwan] ; Yin-Ta Wu [Taïwan] ; Chi-Huey Wong [Taïwan, États-Unis]Source :
- Journal of medicinal chemistry : (Print) [ 0022-2623 ] ; 2005.
Descripteurs français
- Pascal (Inist)
- Anilide, Inhibiteur enzyme, Virus syndrome respiratoire aigu sévère, Peptidases, Antiviral, Peptide, Composé non peptide, Aminoamide, Benzène dérivé, Composé nitro, Relation structure activité, Tripeptide, Tétrapeptide, In vitro, Carboxamide, Phénylalanamide(N-[2-chloro-4-nitrophényl]-N-[4-(diméthylamino)benzoyl]).
English descriptors
- KwdEn :
Abstract
A diversified library of peptide anilides was prepared, and their inhibition activities against the SARS-CoV 3CL protease were examined by a fluorogenic tetradecapeptide substrate. The most potent inhibitor is an anilide derived from 2-chloro-4-nitroaniline, L-phenylalanine and 4-(dimethylamino)benzoic acid. This anilide is a competitive inhibitor of the SARS-CoV 3CL protease with Ki = 0.03 μM. The molecular docking experiment indicates that the PI residue of this anilide inhibitor is distant from the nucleophilic SH of Cys145 in the active site.
Affiliations:
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Pascal:05-0450262Le document en format XML
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<series><title level="j" type="main">Journal of medicinal chemistry : (Print)</title>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aminoamide</term>
<term>Anilide</term>
<term>Antiviral</term>
<term>Benzene derivatives</term>
<term>Carboxamide</term>
<term>Enzyme inhibitor</term>
<term>In vitro</term>
<term>Nitro compound</term>
<term>Non peptide compound</term>
<term>Peptidases</term>
<term>Peptides</term>
<term>Severe acute respiratory syndrome virus</term>
<term>Structure activity relation</term>
<term>Tetrapeptide</term>
<term>Tripeptide</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Anilide</term>
<term>Inhibiteur enzyme</term>
<term>Virus syndrome respiratoire aigu sévère</term>
<term>Peptidases</term>
<term>Antiviral</term>
<term>Peptide</term>
<term>Composé non peptide</term>
<term>Aminoamide</term>
<term>Benzène dérivé</term>
<term>Composé nitro</term>
<term>Relation structure activité</term>
<term>Tripeptide</term>
<term>Tétrapeptide</term>
<term>In vitro</term>
<term>Carboxamide</term>
<term>Phénylalanamide(N-[2-chloro-4-nitrophényl]-N-[4-(diméthylamino)benzoyl])</term>
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<front><div type="abstract" xml:lang="en">A diversified library of peptide anilides was prepared, and their inhibition activities against the SARS-CoV 3CL protease were examined by a fluorogenic tetradecapeptide substrate. The most potent inhibitor is an anilide derived from 2-chloro-4-nitroaniline, L-phenylalanine and 4-(dimethylamino)benzoic acid. This anilide is a competitive inhibitor of the SARS-CoV 3CL protease with K<sub>i</sub>
= 0.03 μM. The molecular docking experiment indicates that the PI residue of this anilide inhibitor is distant from the nucleophilic SH of Cys145 in the active site.</div>
</front>
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<fA11 i1="02" i2="1"><s1>FANG (Jim-Min)</s1>
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<fA11 i1="11" i2="1"><s1>WONG (Chi-Huey)</s1>
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<sZ>11 aut.</sZ>
</fA14>
<fA20><s1>4469-4473</s1>
</fA20>
<fA21><s1>2005</s1>
</fA21>
<fA23 i1="01"><s0>ENG</s0>
</fA23>
<fA43 i1="01"><s1>INIST</s1>
<s2>9165</s2>
<s5>354000138558210310</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>05-0450262</s0>
</fA47>
<fA60><s1>P</s1>
</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>A diversified library of peptide anilides was prepared, and their inhibition activities against the SARS-CoV 3CL protease were examined by a fluorogenic tetradecapeptide substrate. The most potent inhibitor is an anilide derived from 2-chloro-4-nitroaniline, L-phenylalanine and 4-(dimethylamino)benzoic acid. This anilide is a competitive inhibitor of the SARS-CoV 3CL protease with K<sub>i</sub>
= 0.03 μM. The molecular docking experiment indicates that the PI residue of this anilide inhibitor is distant from the nucleophilic SH of Cys145 in the active site.</s0>
</fC01>
<fC02 i1="01" i2="X"><s0>002B02S05</s0>
</fC02>
<fC03 i1="01" i2="X" l="FRE"><s0>Anilide</s0>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="ENG"><s0>Anilide</s0>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="SPA"><s0>Anilido</s0>
<s5>01</s5>
</fC03>
<fC03 i1="02" i2="X" l="FRE"><s0>Inhibiteur enzyme</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="ENG"><s0>Enzyme inhibitor</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="SPA"><s0>Inhibidor enzima</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" i2="X" l="FRE"><s0>Peptidases</s0>
<s2>FE</s2>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="ENG"><s0>Peptidases</s0>
<s2>FE</s2>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="SPA"><s0>Peptidases</s0>
<s2>FE</s2>
<s5>04</s5>
</fC03>
<fC03 i1="05" i2="X" l="FRE"><s0>Antiviral</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="ENG"><s0>Antiviral</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="SPA"><s0>Antiviral</s0>
<s5>05</s5>
</fC03>
<fC03 i1="06" i2="X" l="FRE"><s0>Peptide</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="ENG"><s0>Peptides</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="SPA"><s0>Péptido</s0>
<s5>06</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE"><s0>Composé non peptide</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="ENG"><s0>Non peptide compound</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="SPA"><s0>Compuesto no péptido</s0>
<s5>07</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE"><s0>Aminoamide</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG"><s0>Aminoamide</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA"><s0>Aminoamida</s0>
<s5>08</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE"><s0>Benzène dérivé</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG"><s0>Benzene derivatives</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Benceno derivado</s0>
<s5>09</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE"><s0>Composé nitro</s0>
<s2>FX</s2>
<s5>11</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG"><s0>Nitro compound</s0>
<s2>FX</s2>
<s5>11</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA"><s0>Compuesto nitro</s0>
<s2>FX</s2>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE"><s0>Relation structure activité</s0>
<s5>12</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG"><s0>Structure activity relation</s0>
<s5>12</s5>
</fC03>
<fC03 i1="11" i2="X" l="SPA"><s0>Relación estructura actividad</s0>
<s5>12</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE"><s0>Tripeptide</s0>
<s5>13</s5>
</fC03>
<fC03 i1="12" i2="X" l="ENG"><s0>Tripeptide</s0>
<s5>13</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA"><s0>Tripéptido</s0>
<s5>13</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Tétrapeptide</s0>
<s5>14</s5>
</fC03>
<fC03 i1="13" i2="X" l="ENG"><s0>Tetrapeptide</s0>
<s5>14</s5>
</fC03>
<fC03 i1="13" i2="X" l="SPA"><s0>Tetrapéptido</s0>
<s5>14</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>In vitro</s0>
<s5>15</s5>
</fC03>
<fC03 i1="14" i2="X" l="ENG"><s0>In vitro</s0>
<s5>15</s5>
</fC03>
<fC03 i1="14" i2="X" l="SPA"><s0>In vitro</s0>
<s5>15</s5>
</fC03>
<fC03 i1="15" i2="X" l="FRE"><s0>Carboxamide</s0>
<s5>32</s5>
</fC03>
<fC03 i1="15" i2="X" l="ENG"><s0>Carboxamide</s0>
<s5>32</s5>
</fC03>
<fC03 i1="15" i2="X" l="SPA"><s0>Carboxamida</s0>
<s5>32</s5>
</fC03>
<fC03 i1="16" i2="X" l="FRE"><s0>Phénylalanamide(N-[2-chloro-4-nitrophényl]-N-[4-(diméthylamino)benzoyl])</s0>
<s2>NK</s2>
<s2>FR</s2>
<s4>INC</s4>
<s5>76</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>Hydrolases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="05" i2="X" l="ENG"><s0>Hydrolases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="05" i2="X" l="SPA"><s0>Hydrolases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="06" i2="X" l="FRE"><s0>Enzyme</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="06" i2="X" l="ENG"><s0>Enzyme</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="06" i2="X" l="SPA"><s0>Enzima</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="07" i2="X" l="FRE"><s0>Chlore Composé organique</s0>
<s2>NC</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>10</s5>
</fC07>
<fC07 i1="07" i2="X" l="ENG"><s0>Chlorine Organic compounds</s0>
<s2>NC</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>10</s5>
</fC07>
<fC07 i1="07" i2="X" l="SPA"><s0>Cloro Compuesto orgánico</s0>
<s2>NC</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>10</s5>
</fC07>
<fN21><s1>318</s1>
</fN21>
</pA>
</standard>
</inist>
<affiliations><list><country><li>Taïwan</li>
<li>États-Unis</li>
</country>
</list>
<tree><country name="Taïwan"><noRegion><name sortKey="Shie, Jiun Jie" sort="Shie, Jiun Jie" uniqKey="Shie J" first="Jiun-Jie" last="Shie">Jiun-Jie Shie</name>
</noRegion>
<name sortKey="Chen, Jiun Ling" sort="Chen, Jiun Ling" uniqKey="Chen J" first="Jiun-Ling" last="Chen">Jiun-Ling Chen</name>
<name sortKey="Fang, Jim Min" sort="Fang, Jim Min" uniqKey="Fang J" first="Jim-Min" last="Fang">Jim-Min Fang</name>
<name sortKey="Fang, Jim Min" sort="Fang, Jim Min" uniqKey="Fang J" first="Jim-Min" last="Fang">Jim-Min Fang</name>
<name sortKey="Huang, Hung Jyun" sort="Huang, Hung Jyun" uniqKey="Huang H" first="Hung-Jyun" last="Huang">Hung-Jyun Huang</name>
<name sortKey="Kuo, Chih Jung" sort="Kuo, Chih Jung" uniqKey="Kuo C" first="Chih-Jung" last="Kuo">Chih-Jung Kuo</name>
<name sortKey="Kuo, Tun Hsun" sort="Kuo, Tun Hsun" uniqKey="Kuo T" first="Tun-Hsun" last="Kuo">Tun-Hsun Kuo</name>
<name sortKey="Liang, Po Huang" sort="Liang, Po Huang" uniqKey="Liang P" first="Po-Huang" last="Liang">Po-Huang Liang</name>
<name sortKey="Lin, Chun Hung" sort="Lin, Chun Hung" uniqKey="Lin C" first="Chun-Hung" last="Lin">Chun-Hung Lin</name>
<name sortKey="Wong, Chi Huey" sort="Wong, Chi Huey" uniqKey="Wong C" first="Chi-Huey" last="Wong">Chi-Huey Wong</name>
<name sortKey="Wu, Yin Ta" sort="Wu, Yin Ta" uniqKey="Wu Y" first="Yin-Ta" last="Wu">Yin-Ta Wu</name>
<name sortKey="Yang, Wen Bin" sort="Yang, Wen Bin" uniqKey="Yang W" first="Wen-Bin" last="Yang">Wen-Bin Yang</name>
</country>
<country name="États-Unis"><noRegion><name sortKey="Wong, Chi Huey" sort="Wong, Chi Huey" uniqKey="Wong C" first="Chi-Huey" last="Wong">Chi-Huey Wong</name>
</noRegion>
</country>
</tree>
</affiliations>
</record>
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