[New photoreactive N(4)-substituted dCTP analogues:synthesis, photochemical characteristics, and substrate properties in HIV-1 reverse transcriptase catalyzed DNA synthesis]

Bioorg Khim. 1997 Jul;23(7):576-85.
[Article in Russian]


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 N4-[4-(4-azidotetrafluorobenzylideneaminooxy)butyloxy]-2'-de oxycytidine 5'-triphosphates as well as those of the earlier described N4-[2-(4-azidotetrafluorobenzoylamino)ethyl]- and 5-[E-3-(4-azidotetrafluorobenzoylamino)-1-propenyl)]-2'-deoxycytid ine 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.

Publication types

  • Comparative Study
  • English Abstract

MeSH terms

  • Catalysis
  • DNA / biosynthesis*
  • DNA Primers
  • Deoxycytosine Nucleotides / chemical synthesis
  • Deoxycytosine Nucleotides / chemistry*
  • Deoxycytosine Nucleotides / metabolism
  • Deoxycytosine Nucleotides / radiation effects
  • HIV Reverse Transcriptase / metabolism*
  • Photochemistry
  • Structure-Activity Relationship
  • Substrate Specificity
  • Ultraviolet Rays


  • DNA Primers
  • Deoxycytosine Nucleotides
  • 2'-deoxycytidine 5'-triphosphate
  • DNA
  • HIV Reverse Transcriptase