The reaction of trans-7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene with DNA involves attack at the N7-position of guanine moieties

Chem Biol Interact. 1978 Jan;20(1):123-30. doi: 10.1016/0009-2797(78)90087-x.

Abstract

The reaction of trans-7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene (anti-BPDE) with DNA prelabelled with [14C] and [3H]-purine precursors has indicated that in addition to the N2-position of guanine previously reported [10--12] reaction also involves the N7-position of guanine. The hydrocarbon-N7-guanine product was not detected earlier because it is lost from the DNA very readily at pH 7. The same N7-product was obtained by reaction of anti-BPDE with guanine in dimethylformamide.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Benzopyrenes / metabolism*
  • Chromatography
  • DNA / metabolism*
  • Epoxy Compounds / metabolism
  • Guanine / metabolism

Substances

  • Benzopyrenes
  • Epoxy Compounds
  • Guanine
  • DNA