Thiopurine analogues inhibit papain-like protease of severe acute respiratory syndrome coronavirus.
Identifieur interne : 001C00 ( PubMed/Corpus ); précédent : 001B99; suivant : 001C01Thiopurine analogues inhibit papain-like protease of severe acute respiratory syndrome coronavirus.
Auteurs : Chi-Yuan Chou ; Chia-Hui Chien ; Yu-San Han ; Mojca Trstenjak Prebanda ; Hsing-Pang Hsieh ; Boris Turk ; Gu-Gang Chang ; Xin ChenSource :
- Biochemical pharmacology [ 1873-2968 ] ; 2008.
English descriptors
- KwdEn :
- MESH :
- chemical , antagonists & inhibitors : Viral Proteins.
- chemical , chemistry : Cysteine Endopeptidases, Mercaptopurine, Protease Inhibitors, Thioguanine, Viral Proteins.
- enzymology : SARS Virus.
Abstract
The papain-like protease of severe acute respiratory syndrome coronavirus (PLpro) (EC 3.4.22.46) is essential for the viral life cycle and therefore represents an important antiviral target. We have identified 6MP and 6TG as reversible and slow-binding inhibitors of SARS-CoV PLpro, which is the first report about small molecule reversible inhibitors of PLpro. The inhibition mechanism was investigated by kinetic measurements and computer docking. Both compounds are competitive, selective, and reversible inhibitors of the PLpro with K(is) values approximately 10 to 20 microM. A structure-function relationship study has identified the thiocarbonyl moiety of 6MP or 6TG as the active pharmacophore essential for these inhibitions, which has not been reported before. The inhibition is selective because these compounds do not exert significant inhibitory effects against other cysteine proteases, including SARS-CoV 3CLpro and several cathepsins. Thus, our results present the first potential chemical leads against SARS-CoV PLpro, which might be used as lead compounds for further optimization to enhance their potency against SARS-CoV. Both 6MP and 6TG are still used extensively in clinics, especially for children with acute lymphoblastic or myeloblastic leukemia. In light of the possible inhibition against subset of cysteine proteases, our study has emphasized the importance to study in depth these drug actions in vivo.
DOI: 10.1016/j.bcp.2008.01.005
PubMed: 18313035
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pubmed:18313035Le document en format XML
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We have identified 6MP and 6TG as reversible and slow-binding inhibitors of SARS-CoV PLpro, which is the first report about small molecule reversible inhibitors of PLpro. The inhibition mechanism was investigated by kinetic measurements and computer docking. Both compounds are competitive, selective, and reversible inhibitors of the PLpro with K(is) values approximately 10 to 20 microM. A structure-function relationship study has identified the thiocarbonyl moiety of 6MP or 6TG as the active pharmacophore essential for these inhibitions, which has not been reported before. The inhibition is selective because these compounds do not exert significant inhibitory effects against other cysteine proteases, including SARS-CoV 3CLpro and several cathepsins. Thus, our results present the first potential chemical leads against SARS-CoV PLpro, which might be used as lead compounds for further optimization to enhance their potency against SARS-CoV. Both 6MP and 6TG are still used extensively in clinics, especially for children with acute lymphoblastic or myeloblastic leukemia. In light of the possible inhibition against subset of cysteine proteases, our study has emphasized the importance to study in depth these drug actions in vivo.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">18313035</PMID><DateCompleted><Year>2008</Year><Month>04</Month><Day>22</Day></DateCompleted><DateRevised><Year>2020</Year><Month>04</Month><Day>07</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1873-2968</ISSN><JournalIssue CitedMedium="Internet"><Volume>75</Volume><Issue>8</Issue><PubDate><Year>2008</Year><Month>Apr</Month><Day>15</Day></PubDate></JournalIssue><Title>Biochemical pharmacology</Title><ISOAbbreviation>Biochem. Pharmacol.</ISOAbbreviation></Journal><ArticleTitle>Thiopurine analogues inhibit papain-like protease of severe acute respiratory syndrome coronavirus.</ArticleTitle><Pagination><MedlinePgn>1601-9</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bcp.2008.01.005</ELocationID><Abstract><AbstractText>The papain-like protease of severe acute respiratory syndrome coronavirus (PLpro) (EC 3.4.22.46) is essential for the viral life cycle and therefore represents an important antiviral target. We have identified 6MP and 6TG as reversible and slow-binding inhibitors of SARS-CoV PLpro, which is the first report about small molecule reversible inhibitors of PLpro. The inhibition mechanism was investigated by kinetic measurements and computer docking. Both compounds are competitive, selective, and reversible inhibitors of the PLpro with K(is) values approximately 10 to 20 microM. A structure-function relationship study has identified the thiocarbonyl moiety of 6MP or 6TG as the active pharmacophore essential for these inhibitions, which has not been reported before. The inhibition is selective because these compounds do not exert significant inhibitory effects against other cysteine proteases, including SARS-CoV 3CLpro and several cathepsins. Thus, our results present the first potential chemical leads against SARS-CoV PLpro, which might be used as lead compounds for further optimization to enhance their potency against SARS-CoV. Both 6MP and 6TG are still used extensively in clinics, especially for children with acute lymphoblastic or myeloblastic leukemia. In light of the possible inhibition against subset of cysteine proteases, our study has emphasized the importance to study in depth these drug actions in vivo.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Chou</LastName><ForeName>Chi-Yuan</ForeName><Initials>CY</Initials><AffiliationInfo><Affiliation>Department of Life Sciences and Institute of Genome Sciences, National Yang-Ming University, Taipei 112, Taiwan, ROC.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Chien</LastName><ForeName>Chia-Hui</ForeName><Initials>CH</Initials></Author><Author ValidYN="Y"><LastName>Han</LastName><ForeName>Yu-San</ForeName><Initials>YS</Initials></Author><Author ValidYN="Y"><LastName>Prebanda</LastName><ForeName>Mojca Trstenjak</ForeName><Initials>MT</Initials></Author><Author ValidYN="Y"><LastName>Hsieh</LastName><ForeName>Hsing-Pang</ForeName><Initials>HP</Initials></Author><Author ValidYN="Y"><LastName>Turk</LastName><ForeName>Boris</ForeName><Initials>B</Initials></Author><Author ValidYN="Y"><LastName>Chang</LastName><ForeName>Gu-Gang</ForeName><Initials>GG</Initials></Author><Author ValidYN="Y"><LastName>Chen</LastName><ForeName>Xin</ForeName><Initials>X</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2008</Year><Month>01</Month><Day>19</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Biochem Pharmacol</MedlineTA><NlmUniqueID>0101032</NlmUniqueID><ISSNLinking>0006-2952</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011480">Protease 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