Reactions of ‘bay-region’ and non-‘bay-region’ diol-epoxides of benz(a)anthracene with DNA: evidence indicating that the major products are hydrocarbon-N2-guanine adducts

Publisher Website
Google Scholar
Abstract
The rates of reaction and the products formed when two vicinal diol-epoxides derived from benz(a)an-thracene, anti-BA-3, 4-dioI 1, 2-oxide (t-3, r-4-dihydroxy-t-1, 2-oxy-l, 2, 3, 4-tetrahydrobenz(a) anthracene)* and anti-BA-8, 9-diol 10, 11-oxide (r-8, t-9-dihydroxy-t-10, ll-oxy-8, 9, 10, ll-tetrahydro-benz(a)anthracene) reacted with DNA were studied in vitro and the results were compared with those obtained in similar experiments using anti-BP-7, 8-diol 9, 10-oxide (r-7, t-8-dihydroxy-t-9, 10-oxy-7, 8, 9, 10-tetrahydrobenzo(a)pyrene). The reactivities appeared to decrease in the order anti-BP-7, 8-diol 9, 10-oxide > anti-BA-3, 4-diol 1, 2-oxide anti-BA-8, 9-diol 10, 11-oxide. The diol-epoxides reacted to a similar extent with single- and with double-stranded DNA but reactions with dGMP, at equivalent concentrations, were much slower than with DNA. With the diol-epoxides of benz(a)anthracene, two principal adducts were present in DNA hydrolysates and evidence was obtained, based on pK determinations before and after nitrous acid treatment, consistent with their being N2-guanine derivatives, analogous to the known DNA-reaction products of benzo(a)-pyrene 7, 8-diol 9, 10-oxide.

This publication has 29 references indexed in Scilit: