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The reaction of (±)‐7α, 8β‐dihydroxy‐9β, 10β‐epoxy‐7,8,9,10‐tetrahydrobenzo(a)pyrene with dna
Author(s) -
Osborne M. R.,
Brookes P.,
Beland F. A.,
Harvey R. G.
Publication year - 1976
Publication title -
international journal of cancer
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.475
H-Index - 234
eISSN - 1097-0215
pISSN - 0020-7136
DOI - 10.1002/ijc.2910180315
Subject(s) - guanine , chemistry , deoxyribonucleoside , deoxyadenosine , epoxide , deoxyguanosine , dna , pyrene , sephadex , purine , tritiated water , diol , organic chemistry , stereochemistry , biochemistry , tritium , nucleotide , enzyme , catalysis , gene , physics , nuclear physics
Abstract The reaction of (±)‐7α,8β‐dihydroxy‐9β,10β‐epoxy‐7,8,9,10‐tetrahydrobenzo( a )pyrene (BP diol epoxide) with DNA, followed by enzymatic hydrolysis and LH 20 Sephadex column chromatography, yielded products containing a purine deoxyribonucleoside linked to a 7,8,9,10‐tetrahydrobenzo( a )pyrene derivative. DNA containing tritiated adenine or pyrimidines gave little or no tritiated products, showing that reaction occurred chiefly with the guanine residues. Results with 8‐( 3 H)‐guanine‐labelled DNA, and studies on the protonation and ionization of the products in acid or alkaline media, led to the formulation of the main product as an N 2 ‐substituted guanine derivative. The reaction of BP diol epoxide with deoxyadenosine and deoxyguanosine gave further nucleoside derivatives which were probably minor products in the reaction with DNA. Treatment with strong acid unexpectedly converted each of the isolated products to free guanine or adenine.