Mutagenicity of substituted phenanthrenes in Salmonella typhimurium

Mutat Res. 1983 Feb;116(2):91-102. doi: 10.1016/0165-1218(83)90100-3.

Abstract

An extensive series of alkylated phenanthrenes was assayed for mutagenic activity in Salmonella typhimurium TA98 and TA100. Among the alkylated phenanthrenes assayed, 1-methylphenanthrene, 9-methylphenanthrene, 1,4-dimethylphenanthrene and 4,10-dimethylphenanthrene were active as mutagens. These studies suggest that the structural requirements favoring mutagenic activity among alkylated phenanthrenes are inhibition of 9,10-dihydrodiol formation and the presence of an unsubstituted angular ring adjacent to a free peri position. The mutagenic activities of 9-fluoro-, 9-chloro-, and 9-bromo-phenanthrene were also evaluated. The positive mutagenic response of these halogenated phenanthrenes further supports the observation that inhibition of 9,10-dihydrodiol formation among substituted phenanthrenes favors mutagenic activity.

Publication types

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

MeSH terms

  • Mutagenicity Tests
  • Mutagens*
  • Mutation*
  • Phenanthrenes / pharmacology*
  • Salmonella typhimurium / drug effects
  • Structure-Activity Relationship

Substances

  • Mutagens
  • Phenanthrenes