Mutagenicity of aromatic glycidyl ethers with Salmonella

Mutat Res. 1988 Sep;206(1):115-25. doi: 10.1016/0165-1218(88)90147-4.

Abstract

6 aromatic glycidyl ethers containing naphthyl, biphenyl or benzylphenyl substituents were synthesized. These epoxides together with the commercially available compounds 2-biphenylyl glycidyl ether were examined for dose-mutagenicity relationships using the plate incorporation Ames test with Salmonella typhimurium strains TA100 and TA1535. Structure-mutagenicity relationships were further examined for these compounds and 3 phenyl glycidyl ethers by concurrent testing at a single dose with strain TA100. Meaningful correlations could not be established for the mutagenicity of these epoxides to their molecular volumes, partition values, nor to their reactivities with the model nucleophile, 4-(4-nitrobenzyl) pyridine. However, it was noted that increased conjugated aromatic unsaturation with its resulting planarity led to increased mutagenicity and that this effect decreased when it was further removed from the epoxide moiety.

Publication types

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

MeSH terms

  • Alkylation
  • Chemical Phenomena
  • Chemistry, Physical
  • Epoxy Compounds / toxicity*
  • Ethers, Cyclic / toxicity*
  • Mutagenicity Tests
  • Mutagens*
  • Salmonella typhimurium / drug effects
  • Structure-Activity Relationship

Substances

  • Epoxy Compounds
  • Ethers, Cyclic
  • Mutagens
  • glycidyl ethers