Effects of ortho-methyl substituents on the mutagenicity of aminobiphenyls and aminonaphthalenes

Mutat Res. 1981 Dec;90(4):345-54. doi: 10.1016/0165-1218(81)90057-4.

Abstract

A series of aminobiphenyls and aminonaphthalenes were assayed for mutagenicity toward S. typhimurium, in the presence of rat liver 9000 g supernatant, to investigate the effects of positional isomerism and ortho-methyl substitution. Among the 3 possible aminobiphenyl isomers, only 4-aminobiphenyl was a potent mutagen, showing activity in S. typhimurium TA1538 and TA100, but not TA1535. 4-Amino-3-methylbiphenyl was a more potent mutagen in S. typhimurium TA1538 than was 4-aminobiphenyl, whereas both 3-amino-4-methylbiphenyl and 3-aminobiphenyl were inactive in this strain. 3-Amino-4-methylbiphenyl was mutagenic in S. typhimurium TA100, in contrast to 3-aminobiphenyl. These results demonstrate the enhancing effect of an ortho-methyl group on mutagenicity in the aminobiphenyls, which contrasts to the inhibitory effect of methyl substitution frequently observed in the 4-nitrobiphenyl system. Among the 2-aminonaphthalenes, 2-amino-3-methylnaphthalene was the most mutagenic compound in S. typhimurium TA1538, followed by 2-amino-1-methylnaphthalene and 2-aminonaphthalene. In S. typhimurium TA1535, however, 2-aminonaphthalene was a more potent mutagen than either of the ortho-methyl substituted derivatives. No significant mutagenic activity was observed for either 1-aminonaphthalene or 1-amino-2-methylnaphthalene in S. typhimurium TA1538 and TA1535. However, 1-aminoanaphthalene was weakly mutagenic in S. typhimurium TA 100.

Publication types

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

MeSH terms

  • 1-Naphthylamine / analogs & derivatives
  • 1-Naphthylamine / pharmacology*
  • 2-Naphthylamine / analogs & derivatives
  • 2-Naphthylamine / pharmacology*
  • Aminobiphenyl Compounds / pharmacology*
  • Animals
  • Biotransformation
  • Male
  • Microsomes, Liver / metabolism
  • Mutagenicity Tests
  • Mutagens*
  • Mutation*
  • Naphthalenes / pharmacology*
  • Rats
  • Rats, Inbred F344
  • Salmonella typhimurium / drug effects
  • Structure-Activity Relationship

Substances

  • Aminobiphenyl Compounds
  • Mutagens
  • Naphthalenes
  • 1-Naphthylamine
  • 2-Naphthylamine