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Possible molecular basis for antiviral activity of certain 5-substituted deoxyuridines.

By I S Sim, J Goodchild, D M Meredith, R A Porter, R H Raper, J Viney and H J Wadsworth


The antiviral activity of five structurally related pyrimidine nucleosides, E-5-propenyl-2'-deoxyuridine, 5-allyl-2'-deoxyuridine, E-5-(1-butenyl)-2'-deoxyuridine, 5-(2-butenyl)-2'-deoxyuridine, and 5-butyl-2'-deoxyuridine, in cell culture against herpes simplex virus type 1 was examined. Analogs in which the C-C double bond of the 5-substituent was in conjugation with the pyrimidine ring were more potent antiviral drugs than were the corresponding nonconjugated and alkyl-substituted analogs. Differences in antiviral activity similar to those observed in cell culture occurred in virus-infected mice. The molecular basis for the greater antiviral activity of the conjugated isomers was investigated. It was observed that the conjugated isomer E-5-propenyl-2'-deoxyuridine had a greater affinity for virus thymidine kinase and, as the 5'-triphosphate, for virus DNA polymerase than did the nonconjugated isomer 5-allyl-2'-deoxyuridine. The results are discussed in relation to other data in the literature

Topics: Research Article
Year: 1983
DOI identifier: 10.1128/aac.23.3.416
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Provided by: PubMed Central
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