Abstract
Twenty-nine 2-acylaminofluorenes were compared in the Salmonella typhymurium TA-1538 test system to determine the effect of structural changes on mutagenic activity. All the 2-acylaminofluorenes require the S-9 liver fraction for mutagenic activity. Mutagenic activity was highest in carbamate esters, ureas, α-haloacetylamides, and straight chain acylamides. Branching on the α-carbon, or addition of unsaturation reduced mutagenic activity. Pretreatment of C57BL 6 N mice with 3-methylcholanthrene increased (6–20 fold) the mutagenic activity of all the analogs in the S-9 liver fraction. No increase in mutagenic activity is observed in S-9 liver fraction from 3-methylcholanthrene treated DBA 2 N mice, indicating that mutagenic activity correlates with inducible aromatic hydrocarbon (benzo[a]pyrene) hydroxylase activity and N-hydroxylase activity. α-Naphthoflavone, an inhibitor of N-hydroxylation of 2-acetylaminofluorene in vitro , inhibits mutagenic activity of these analogs indicating that N-hydroxylation is the first step in activation of N-acylaminofluorenes into mutagens.
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