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

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Photochemical characteristics and substrate properties of four newly synthesized dCTP analogues: N4-[2-(2-nitro-5-azidobenzoylamino)ethyl]-, N4-[2-(4-azidotetrafluorobenzylideneaminooxymethylcarba-moyl)ethyl]-, N 4-[4-(4-azidotetrafluorobenzylidenehydrazinocarbonyl)butylcarbainoyl] -, 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)-l-pro-penyl)]-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)531-539
Number of pages9
JournalRussian Journal of Bioorganic Chemistry
Volume23
Issue number7
StatePublished - Jul 1 1997
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

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