Dioxolane cytosine nucleosides as anti-hepatitis B agents

Lee, Migyoung; Chu, Chung K.; Pai, S. Balakrishna; Zhu, Yangyang; Cheng, Yung‐Chi; Chun, Moon Woo; Chung, Won Keun

doi:10.1016/0960-894x(95)00343-r

Cited by 6 publications

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“…Nucleosides are found in nature only in the ␤-D configuration, and this compound was the first nucleoside analog with the unnatural ␤-L configuration shown to have biological activity. Subsequently, several other ␤-L-deoxycytidine analogs were found to have similar activities against HBV and HIV (10,11,16,17,29). However, none of these compounds is active against Epstein-Barr virus (EBV).…”

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confidence: 99%

Unique Metabolism of a Novel Antiviral l -Nucleoside Analog, 2′-Fluoro-5-Methyl-β- l -Arabinofuranosyluracil: a Substrate for Both Thymidine Kinase and Deoxycytidine Kinase

Liu

Grove

Cheng

1998

Antimicrob Agents Chemother

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2′-Fluoro-5-methyl-β-l-arabinofuranosyluracil (l-FMAU) is the first l-nucleoside analog with low cytotoxicity discovered to have potent antiviral activities against both hepatitis B virus and Epstein-Barr virus but not human immunodeficiency virus. This spectrum of activity is different from those of the other l-nucleoside analogs examined.l-FMAU enters cells through equilibrative-sensitive and -insensitive nucleoside transport as well as through nonfacilitated passive diffusion. l-FMAU is phosphorylated stepwise in cells to its mono-, di-, and triphosphate forms. In the present study the enzymes responsible for the first step of l-FMAU phosphorylation were identified. This is the first thymidine analog shown to be a substrate not only for cytosolic thymidine kinase and mitochondrial deoxypyrimidine kinase but also for deoxycytidine kinase. This finding suggests that the antiviral activity of l-FMAU will not be limited by the loss or alteration of any of these deoxynucleoside kinases.

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confidence: 99%