Stable Benzotriazole Esters as Mechanism-Based Inactivators of the Severe Acute Respiratory Syndrome 3CL Protease
Identifieur interne : 003C96 ( Main/Exploration ); précédent : 003C95; suivant : 003C97Stable Benzotriazole Esters as Mechanism-Based Inactivators of the Severe Acute Respiratory Syndrome 3CL Protease
Auteurs : Chung-Yi Wu [Taïwan, États-Unis] ; Ke-Yung King [Taïwan] ; Chih-Jung Kuo [Taïwan] ; Jim-Min Fang [Taïwan] ; Ying-Ta Wu [Taïwan] ; Ming-Yi Ho [Taïwan] ; Chung-Lin Liao [Taïwan] ; Jiun-Jie Shie [Taïwan] ; Po-Huang Liang [Taïwan] ; Chi-Huey Wong [Taïwan, États-Unis]Source :
- Chemistry & Biology [ 1074-5521 ] ; 2006.
Abstract
Severe acute respiratory syndrome (SARS) is caused by a newly emerged coronavirus that infected more than 8000 individuals and resulted in more than 800 fatalities in 2003. Currently, there is no effective treatment for this epidemic. SARS-3CLpro has been shown to be essential for replication and is thus a target for drug discovery. Here, a class of stable benzotriazole esters was reported as mechanism-based inactivators of 3CLpro, and the most potent inactivator exhibited a
Url:
DOI: 10.1016/j.chembiol.2005.12.008
PubMed: 16638531
PubMed Central: 7111201
Affiliations:
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xml:lang="fr">Taïwan</country><wicri:regionArea>The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115</wicri:regionArea><wicri:noRegion>115</wicri:noRegion></affiliation><affiliation wicri:level="2"><nlm:aff id="aff2">Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037</nlm:aff><country xml:lang="fr">États-Unis</country><placeName><region type="state">Californie</region></placeName><wicri:cityArea>Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla</wicri:cityArea></affiliation></author><author><name sortKey="King, Ke Yung" sort="King, Ke Yung" uniqKey="King K" first="Ke-Yung" last="King">Ke-Yung King</name><affiliation wicri:level="1"><nlm:aff id="aff1">The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115</wicri:regionArea><wicri:noRegion>115</wicri:noRegion></affiliation></author><author><name sortKey="Kuo, Chih Jung" sort="Kuo, Chih Jung" uniqKey="Kuo C" first="Chih-Jung" last="Kuo">Chih-Jung Kuo</name><affiliation wicri:level="1"><nlm:aff id="aff1">The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115</wicri:regionArea><wicri:noRegion>115</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:aff id="aff3">Taiwan International Graduate Program, Academia Sinica, Nan-Kang, Taipei, 115, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>Taiwan International Graduate Program, Academia Sinica, Nan-Kang, Taipei, 115</wicri:regionArea><wicri:noRegion>115</wicri:noRegion></affiliation></author><author><name sortKey="Fang, Jim Min" sort="Fang, Jim Min" uniqKey="Fang J" first="Jim-Min" last="Fang">Jim-Min Fang</name><affiliation wicri:level="1"><nlm:aff id="aff1">The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115</wicri:regionArea><wicri:noRegion>115</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:aff id="aff4">Department of Chemistry, National Taiwan University, Taipei, 106, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>Department of Chemistry, National Taiwan University, Taipei, 106</wicri:regionArea><wicri:noRegion>106</wicri:noRegion></affiliation></author><author><name sortKey="Wu, Ying Ta" sort="Wu, Ying Ta" uniqKey="Wu Y" first="Ying-Ta" last="Wu">Ying-Ta Wu</name><affiliation wicri:level="1"><nlm:aff id="aff1">The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115</wicri:regionArea><wicri:noRegion>115</wicri:noRegion></affiliation></author><author><name sortKey="Ho, Ming Yi" sort="Ho, Ming Yi" uniqKey="Ho M" first="Ming-Yi" last="Ho">Ming-Yi Ho</name><affiliation wicri:level="1"><nlm:aff id="aff1">The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115</wicri:regionArea><wicri:noRegion>115</wicri:noRegion></affiliation></author><author><name sortKey="Liao, Chung Lin" sort="Liao, Chung Lin" uniqKey="Liao C" first="Chung-Lin" last="Liao">Chung-Lin Liao</name><affiliation wicri:level="1"><nlm:aff id="aff1">The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115</wicri:regionArea><wicri:noRegion>115</wicri:noRegion></affiliation></author><author><name sortKey="Shie, Jiun Jie" sort="Shie, Jiun Jie" uniqKey="Shie J" first="Jiun-Jie" last="Shie">Jiun-Jie Shie</name><affiliation wicri:level="1"><nlm:aff id="aff1">The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115</wicri:regionArea><wicri:noRegion>115</wicri:noRegion></affiliation></author><author><name sortKey="Liang, Po Huang" sort="Liang, Po Huang" uniqKey="Liang P" first="Po-Huang" last="Liang">Po-Huang Liang</name><affiliation wicri:level="1"><nlm:aff id="aff1">The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115</wicri:regionArea><wicri:noRegion>115</wicri:noRegion></affiliation></author><author><name sortKey="Wong, Chi Huey" sort="Wong, Chi Huey" uniqKey="Wong C" first="Chi-Huey" last="Wong">Chi-Huey Wong</name><affiliation wicri:level="1"><nlm:aff id="aff1">The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>The Genomics Research Center and Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 115</wicri:regionArea><wicri:noRegion>115</wicri:noRegion></affiliation><affiliation wicri:level="2"><nlm:aff id="aff2">Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037</nlm:aff><country xml:lang="fr">États-Unis</country><placeName><region type="state">Californie</region></placeName><wicri:cityArea>Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla</wicri:cityArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff4">Department of Chemistry, National Taiwan University, Taipei, 106, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>Department of Chemistry, National Taiwan University, Taipei, 106</wicri:regionArea><wicri:noRegion>106</wicri:noRegion></affiliation></author></analytic><series><title level="j">Chemistry & Biology</title><idno type="ISSN">1074-5521</idno><idno type="eISSN">1879-1301</idno><imprint><date when="2006">2006</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><title>Summary</title><p>Severe acute respiratory syndrome (SARS) is caused by a newly emerged coronavirus that infected more than 8000 individuals and resulted in more than 800 fatalities in 2003. Currently, there is no effective treatment for this epidemic. SARS-3CL<sup>pro</sup> has been shown to be essential for replication and is thus a target for drug discovery. Here, a class of stable benzotriazole esters was reported as mechanism-based inactivators of 3CL<sup>pro</sup>, and the most potent inactivator exhibited a <italic>k</italic><sub>inact</sub> of 0.0011 s<sup>−1</sup> and a <italic>K</italic><sub>i</sub> of 7.5 nM. Mechanistic investigation with kinetic and mass spectrometry analyses indicates that the active site Cys145 is acylated, and that no irreversible inactivation was observed with the use of the C145A mutant. In addition, a noncovalent, competitive inhibition became apparent by using benzotriazole ester surrogates in which the bridged ester-oxygen group is replaced with carbon.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Ksiazek, T G" uniqKey="Ksiazek T">T.G. 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Liang</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>Taïwan</li><li>États-Unis</li></country><region><li>Californie</li></region></list><tree><country name="Taïwan"><noRegion><name sortKey="Wu, Chung Yi" sort="Wu, Chung Yi" uniqKey="Wu C" first="Chung-Yi" last="Wu">Chung-Yi Wu</name></noRegion><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="Ho, Ming Yi" sort="Ho, Ming Yi" uniqKey="Ho M" first="Ming-Yi" last="Ho">Ming-Yi Ho</name><name sortKey="King, Ke Yung" sort="King, Ke Yung" uniqKey="King K" first="Ke-Yung" last="King">Ke-Yung King</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, Chih Jung" sort="Kuo, Chih Jung" uniqKey="Kuo C" first="Chih-Jung" last="Kuo">Chih-Jung 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="Liao, Chung Lin" sort="Liao, Chung Lin" uniqKey="Liao C" first="Chung-Lin" last="Liao">Chung-Lin Liao</name><name sortKey="Shie, Jiun Jie" sort="Shie, Jiun Jie" uniqKey="Shie J" first="Jiun-Jie" last="Shie">Jiun-Jie Shie</name><name sortKey="Wong, Chi Huey" sort="Wong, Chi Huey" uniqKey="Wong C" first="Chi-Huey" last="Wong">Chi-Huey Wong</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, Ying Ta" sort="Wu, Ying Ta" uniqKey="Wu Y" first="Ying-Ta" last="Wu">Ying-Ta Wu</name></country><country name="États-Unis"><region name="Californie"><name sortKey="Wu, Chung Yi" sort="Wu, Chung Yi" uniqKey="Wu C" first="Chung-Yi" last="Wu">Chung-Yi Wu</name></region><name sortKey="Wong, Chi Huey" sort="Wong, Chi Huey" uniqKey="Wong C" first="Chi-Huey" last="Wong">Chi-Huey Wong</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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