The Novel Nucleoside Analog R1479 (4′-Azidocytidine) Is a Potent Inhibitor of NS5B-dependent RNA Synthesis and Hepatitis C Virus Replication in Cell Culture
Hepatitis C virus (HCV) polymerase activity is essential for HCV replication. Targeted screening of nucleoside analogs identified R1479 (4′-azidocytidine) as a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC50 = 1.28 μm) with similar potency compared with 2′-C-methylc...
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| Published in | The Journal of biological chemistry Vol. 281; no. 7; pp. 3793 - 3799 |
|---|---|
| Main Authors | , , , , , , , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
Elsevier Inc
17.02.2006
American Society for Biochemistry and Molecular Biology |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0021-9258 1083-351X |
| DOI | 10.1074/jbc.M510195200 |
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| Abstract | Hepatitis C virus (HCV) polymerase activity is essential for HCV replication. Targeted screening of nucleoside analogs identified R1479 (4′-azidocytidine) as a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC50 = 1.28 μm) with similar potency compared with 2′-C-methylcytidine (IC50 = 1.13 μm). R1479 showed no effect on cell viability or proliferation of HCV replicon or Huh-7 cells at concentrations up to 2 mm. HCV replicon RNA could be fully cleared from replicon cells after prolonged incubation with R1479. The corresponding 5′-triphosphate derivative (R1479-TP) is a potent inhibitor of native HCV replicase isolated from replicon cells and of recombinant HCV polymerase (NS5B)-mediated RNA synthesis activity. R1479-TP inhibited RNA synthesis as a CTP-competitive inhibitor with a Ki of 40 nm. On an HCV RNA-derived template substrate (complementary internal ribosome entry site), R1479-TP showed similar potency of NS5B inhibition compared with 3′-dCTP. R1479-TP was incorporated into nascent RNA by HCV polymerase and reduced further elongation with similar efficiency compared with 3′-dCTP under the reaction conditions. The S282T point mutation in the coding sequence of NS5B confers resistance to inhibition by 2′-C-MeATP and other 2′-methyl-nucleotides. In contrast, the S282T mutation did not confer cross-resistance to R1479. |
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| AbstractList | Hepatitis C virus (HCV) polymerase activity is essential for HCV replication. Targeted screening of nucleoside analogs identified
R1479 (4â²-azidocytidine) as a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC 50 = 1.28 μ m ) with similar potency compared with 2â²- C -methylcytidine (IC 50 = 1.13 μ m ). R1479 showed no effect on cell viability or proliferation of HCV replicon or Huh-7 cells at concentrations up to 2 m m . HCV replicon RNA could be fully cleared from replicon cells after prolonged incubation with R1479. The corresponding 5â²-triphosphate
derivative (R1479-TP) is a potent inhibitor of native HCV replicase isolated from replicon cells and of recombinant HCV polymerase
(NS5B)-mediated RNA synthesis activity. R1479-TP inhibited RNA synthesis as a CTP-competitive inhibitor with a K i of 40 n m . On an HCV RNA-derived template substrate (complementary internal ribosome entry site), R1479-TP showed similar potency of
NS5B inhibition compared with 3â²-dCTP. R1479-TP was incorporated into nascent RNA by HCV polymerase and reduced further elongation
with similar efficiency compared with 3â²-dCTP under the reaction conditions. The S282T point mutation in the coding sequence
of NS5B confers resistance to inhibition by 2â²- C -MeATP and other 2â²-methyl-nucleotides. In contrast, the S282T mutation did not confer cross-resistance to R1479. Hepatitis C virus (HCV) polymerase activity is essential for HCV replication. Targeted screening of nucleoside analogs identified R1479 (4'-azidocytidine) as a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC sub(50) = 1.28 mu M) with similar potency compared with 2'-C-methylcytidine (IC sub(50) = 1.13 mu M). R1479 showed no effect on cell viability or proliferation of HCV replicon or Huh-7 cells at concentrations up to 2 mM. HCV replicon RNA could be fully cleared from replicon cells after prolonged incubation with R1479. The corresponding 5'-triphosphate derivative (R1479-TP) is a potent inhibitor of native HCV replicase isolated from replicon cells and of recombinant HCV polymerase (NS5B)-mediated RNA synthesis activity. R1479-TP inhibited RNA synthesis as a CTP-competitive inhibitor with a K sub(i) of 40 nM. On an HCV RNA-derived template substrate (complementary internal ribosome entry site), R1479-TP showed similar potency of NS5B inhibition compared with 3'-dCTP. R1479-TP was incorporated into nascent RNA by HCV polymerase and reduced further elongation with similar efficiency compared with 3'-dCTP under the reaction conditions. The S282T point mutation in the coding sequence of NS5B confers resistance to inhibition by 2'-C-MeATP and other 2'-methyl-nucleotides. In contrast, the S282T mutation did not confer cross-resistance to R1479. Hepatitis C virus (HCV) polymerase activity is essential for HCV replication. Targeted screening of nucleoside analogs identified R1479 (4′-azidocytidine) as a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC50 = 1.28 μm) with similar potency compared with 2′-C-methylcytidine (IC50 = 1.13 μm). R1479 showed no effect on cell viability or proliferation of HCV replicon or Huh-7 cells at concentrations up to 2 mm. HCV replicon RNA could be fully cleared from replicon cells after prolonged incubation with R1479. The corresponding 5′-triphosphate derivative (R1479-TP) is a potent inhibitor of native HCV replicase isolated from replicon cells and of recombinant HCV polymerase (NS5B)-mediated RNA synthesis activity. R1479-TP inhibited RNA synthesis as a CTP-competitive inhibitor with a Ki of 40 nm. On an HCV RNA-derived template substrate (complementary internal ribosome entry site), R1479-TP showed similar potency of NS5B inhibition compared with 3′-dCTP. R1479-TP was incorporated into nascent RNA by HCV polymerase and reduced further elongation with similar efficiency compared with 3′-dCTP under the reaction conditions. The S282T point mutation in the coding sequence of NS5B confers resistance to inhibition by 2′-C-MeATP and other 2′-methyl-nucleotides. In contrast, the S282T mutation did not confer cross-resistance to R1479. Hepatitis C virus (HCV) polymerase activity is essential for HCV replication. Targeted screening of nucleoside analogs identified R1479 (4'-azidocytidine) as a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC(50) = 1.28 microM) with similar potency compared with 2'-C-methylcytidine (IC(50) = 1.13 microM). R1479 showed no effect on cell viability or proliferation of HCV replicon or Huh-7 cells at concentrations up to 2 mM. HCV replicon RNA could be fully cleared from replicon cells after prolonged incubation with R1479. The corresponding 5'-triphosphate derivative (R1479-TP) is a potent inhibitor of native HCV replicase isolated from replicon cells and of recombinant HCV polymerase (NS5B)-mediated RNA synthesis activity. R1479-TP inhibited RNA synthesis as a CTP-competitive inhibitor with a K(i) of 40 nM. On an HCV RNA-derived template substrate (complementary internal ribosome entry site), R1479-TP showed similar potency of NS5B inhibition compared with 3'-dCTP. R1479-TP was incorporated into nascent RNA by HCV polymerase and reduced further elongation with similar efficiency compared with 3'-dCTP under the reaction conditions. The S282T point mutation in the coding sequence of NS5B confers resistance to inhibition by 2'-C-MeATP and other 2'-methyl-nucleotides. In contrast, the S282T mutation did not confer cross-resistance to R1479.Hepatitis C virus (HCV) polymerase activity is essential for HCV replication. Targeted screening of nucleoside analogs identified R1479 (4'-azidocytidine) as a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC(50) = 1.28 microM) with similar potency compared with 2'-C-methylcytidine (IC(50) = 1.13 microM). R1479 showed no effect on cell viability or proliferation of HCV replicon or Huh-7 cells at concentrations up to 2 mM. HCV replicon RNA could be fully cleared from replicon cells after prolonged incubation with R1479. The corresponding 5'-triphosphate derivative (R1479-TP) is a potent inhibitor of native HCV replicase isolated from replicon cells and of recombinant HCV polymerase (NS5B)-mediated RNA synthesis activity. R1479-TP inhibited RNA synthesis as a CTP-competitive inhibitor with a K(i) of 40 nM. On an HCV RNA-derived template substrate (complementary internal ribosome entry site), R1479-TP showed similar potency of NS5B inhibition compared with 3'-dCTP. R1479-TP was incorporated into nascent RNA by HCV polymerase and reduced further elongation with similar efficiency compared with 3'-dCTP under the reaction conditions. The S282T point mutation in the coding sequence of NS5B confers resistance to inhibition by 2'-C-MeATP and other 2'-methyl-nucleotides. In contrast, the S282T mutation did not confer cross-resistance to R1479. Hepatitis C virus (HCV) polymerase activity is essential for HCV replication. Targeted screening of nucleoside analogs identified R1479 (4'-azidocytidine) as a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC(50) = 1.28 microM) with similar potency compared with 2'-C-methylcytidine (IC(50) = 1.13 microM). R1479 showed no effect on cell viability or proliferation of HCV replicon or Huh-7 cells at concentrations up to 2 mM. HCV replicon RNA could be fully cleared from replicon cells after prolonged incubation with R1479. The corresponding 5'-triphosphate derivative (R1479-TP) is a potent inhibitor of native HCV replicase isolated from replicon cells and of recombinant HCV polymerase (NS5B)-mediated RNA synthesis activity. R1479-TP inhibited RNA synthesis as a CTP-competitive inhibitor with a K(i) of 40 nM. On an HCV RNA-derived template substrate (complementary internal ribosome entry site), R1479-TP showed similar potency of NS5B inhibition compared with 3'-dCTP. R1479-TP was incorporated into nascent RNA by HCV polymerase and reduced further elongation with similar efficiency compared with 3'-dCTP under the reaction conditions. The S282T point mutation in the coding sequence of NS5B confers resistance to inhibition by 2'-C-MeATP and other 2'-methyl-nucleotides. In contrast, the S282T mutation did not confer cross-resistance to R1479. |
| Author | Laxton, Carl Heindl, Dieter Hobbs, Chris J. Symons, Julian Martin, Joseph A. Klumpp, Klaus Devos, Rene Le Pogam, Sophie Lévêque, Vincent Ma, Han Sarma, Keshab Smith, David B. Merrett, John H. Granycome, Caroline Jiang, Wen-Rong Nájera, Isabel Singer, Margaret Cammack, Nick Hang, Julie Qi Kang, Hyunsoon |
| Author_xml | – sequence: 1 givenname: Klaus surname: Klumpp fullname: Klumpp, Klaus email: klaus.klumpp@roche.com organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 2 givenname: Vincent surname: Lévêque fullname: Lévêque, Vincent organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 3 givenname: Sophie surname: Le Pogam fullname: Le Pogam, Sophie organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 4 givenname: Han surname: Ma fullname: Ma, Han organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 5 givenname: Wen-Rong surname: Jiang fullname: Jiang, Wen-Rong organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 6 givenname: Hyunsoon surname: Kang fullname: Kang, Hyunsoon organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 7 givenname: Caroline surname: Granycome fullname: Granycome, Caroline organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 8 givenname: Margaret surname: Singer fullname: Singer, Margaret organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 9 givenname: Carl surname: Laxton fullname: Laxton, Carl organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 10 givenname: Julie Qi surname: Hang fullname: Hang, Julie Qi organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 11 givenname: Keshab surname: Sarma fullname: Sarma, Keshab organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 12 givenname: David B. surname: Smith fullname: Smith, David B. organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 13 givenname: Dieter surname: Heindl fullname: Heindl, Dieter organization: Roche Diagnostics GmbH, 82377 Penzberg, Germany – sequence: 14 givenname: Chris J. surname: Hobbs fullname: Hobbs, Chris J. organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 15 givenname: John H. surname: Merrett fullname: Merrett, John H. organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 16 givenname: Julian surname: Symons fullname: Symons, Julian organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 17 givenname: Nick surname: Cammack fullname: Cammack, Nick organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 18 givenname: Joseph A. surname: Martin fullname: Martin, Joseph A. organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 19 givenname: Rene surname: Devos fullname: Devos, Rene organization: Roche Palo Alto LLC, Palo Alto, California 94304 – sequence: 20 givenname: Isabel surname: Nájera fullname: Nájera, Isabel organization: Roche Palo Alto LLC, Palo Alto, California 94304 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/16316989$$D View this record in MEDLINE/PubMed |
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| Copyright | 2006 © 2006 ASBMB. Currently published by Elsevier Inc; originally published by American Society for Biochemistry and Molecular Biology. |
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| Snippet | Hepatitis C virus (HCV) polymerase activity is essential for HCV replication. Targeted screening of nucleoside analogs identified R1479 (4′-azidocytidine) as a... Hepatitis C virus (HCV) polymerase activity is essential for HCV replication. Targeted screening of nucleoside analogs identified R1479 (4â²-azidocytidine) as... Hepatitis C virus (HCV) polymerase activity is essential for HCV replication. Targeted screening of nucleoside analogs identified R1479 (4'-azidocytidine) as a... |
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| SubjectTerms | Antiviral Agents - pharmacology Cell Line Cytidine - analogs & derivatives Cytidine - pharmacology Hepacivirus - drug effects Hepacivirus - physiology Hepatitis C virus Humans RNA, Viral - biosynthesis RNA-Dependent RNA Polymerase - antagonists & inhibitors Viral Nonstructural Proteins - antagonists & inhibitors Virus Replication - drug effects |
| Title | The Novel Nucleoside Analog R1479 (4′-Azidocytidine) Is a Potent Inhibitor of NS5B-dependent RNA Synthesis and Hepatitis C Virus Replication in Cell Culture |
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