New Photoreactive N4-Substituted dCTP Analogues: Preparation, Photochemical Characteristics, and Substrate Properties in HIV-1 Reverse Transcriptase-Catalyzed DNA Synthesis

I. V. Safronov, N. V. Shcherbik, S. N. Khodyreva, V. A. Vlasov, M. I. Dobrikov, G. V. Shishkin, O. I. Lavrik

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Abstract

Photochemical characteristics and substrate properties of four newly synthesized dCTP analogues: N4-[2-(2-nitro-5-azidobenzoylamino)ethyl]-, N4-[2-(4-azidotetrafluorobenzylideneaminooxymethylcarbamoyl)ethyl]-, N4-[4-(4-azidotetrafluorobenzylideneaminooxy)butyloxy]-, and N4-[4-(4-azidotetrafluorobenzylidene hydrazinocarbonyl)butylcarbamoyl]-, and N 4-[4-(4-azidotetrafluorobenzylideneaminooxy)butyloxy]-2′- deoxycytidine 5′-triphosphates as well as those of the earlier described N4-[2-(4-azidotetrafluorobenzoylamino)ethyl]- and 5-[E-3-(4-azidotetrafluorobenzoylamino)-1-propenyl)]-2′-deoxycytidine 5′-triphosphates were compared. When being irradiated with UV light at a wavelength of 303-313 nm, the new analogues demonstrated greater than 10-fold higher photoactivity as compared with the old compounds. The first three new compounds were utilized by HIV-1 reverse transcriptase as dCTP and dTTP, while the last derivative was recognized only as dTTP. Once incorporated into the primer 3′-terminus, none of the analogues synthesized terminated further primer elongation with natural triphosphates.

Original languageEnglish (US)
Pages (from-to)584-585
Number of pages2
JournalBioorganicheskaya Khimiya
Volume23
Issue number7
StatePublished - Nov 1997

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All Science Journal Classification (ASJC) codes

  • Medicine(all)

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