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Basic Characteristics of Mutations
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Mutation Site
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M423T |
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Mutation Site Sentence
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We also tested PSI-353661 against replicons containing amino acid alterations that confer resistance to non-nucleoside inhibitors of NS5B: these included C316Y, which confers resistance to HCV-796; M414T, which confers resistance to benzothiadiazine compounds; M423T, which confers resistance to thiophene compounds; and P495L, which confers resistance to 2-phenol indol compounds. |
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Mutation Level
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Amino acid level |
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Mutation Type
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Nonsynonymous substitution |
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Gene/Protein/Region
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NS5B |
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Standardized Encoding Gene
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NS5B
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Genotype/Subtype
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1a;1b;2a |
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Viral Reference
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AJ238799.1;AF177036;AB047639
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Functional Impact and Mechanisms
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Disease
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HCV Infection
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Immune
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- |
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Target Gene
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-
|
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Clinical and Epidemiological Correlations
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Clinical Information
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- |
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Treatment
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- |
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Location
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- |
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Literature Information
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PMID
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21600932
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Title
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Activity and the metabolic activation pathway of the potent and selective hepatitis C virus pronucleotide inhibitor PSI-353661
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Author
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Furman PA,Murakami E,Niu C,Lam AM,Espiritu C,Bansal S,Bao H,Tolstykh T,Micolochick Steuer H,Keilman M,Zennou V,Bourne N,Veselenak RL,Chang W,Ross BS,Du J,Otto MJ,Sofia MJ
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Journal
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Antiviral research
|
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Journal Info
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2011 Aug;91(2):120-32
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Abstract
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PSI-353661, a phosphoramidate prodrug of 2'-deoxy-2'-fluoro-2'-C-methylguanosine-5'-monophosphate, is a highly active inhibitor of genotype 1a, 1b, and 2a HCV RNA replication in the replicon assay and of genotype 1a and 2a infectious virus replication. PSI-353661 is active against replicons harboring the NS5B S282T or S96T/N142T amino acid alterations that confer decreased susceptibility to nucleoside/tide analogs as well as mutations that confer resistance to non-nucleoside inhibitors of NS5B. Replicon clearance studies show that PSI-353661 was able to clear cells of HCV replicon RNA and prevent a rebound in replicon RNA. PSI-353661 showed no toxicity toward bone marrow stem cells or mitochondrial toxicity. The metabolism to the active 5'-triphosphate involves hydrolysis of the carboxyl ester by cathepsin A (Cat A) and carboxylesterase 1 (CES1) followed by a putative nucleophilic attack on the phosphorus by the carboxyl group resulting in the elimination of phenol and the alaninyl phosphate metabolite, PSI-353131. Histidine triad nucleotide-binding protein 1 (Hint 1) then removes the amino acid moiety, which is followed by hydrolysis of the methoxyl group at the O(6)-position of the guanine base by adenosine deaminase-like protein 1 (ADAL1) to give 2'-deoxy-2'-fluoro-2'-C-methylguanosine-5'-monophosphate. The monophosphate is phosphorylated to the diphosphate by guanylate kinase. Nucleoside diphosphate kinase is the primary enzyme involved in phosphorylation of the diphosphate to the active triphosphate, PSI-352666. PSI-352666 is equally active against wild-type NS5B and NS5B containing the S282T amino acid alteration.
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Sequence Data
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-
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