Mutagenicity of bay-region amino-substituted cyclopenta[a]phenanthrenes and 2- and 5-aminochrysene

Mutat Res. 2001 May 31;492(1-2):7-11. doi: 10.1016/s1383-5718(01)00144-9.

Abstract

The relative mutagenic potentials of 11-amino-16,17-dihydro-15H-cyclopenta[a]phenanthrene, its 17-keto derivative, and 2- and 5-aminochrysene have been compared in Salmonella typhimurium TA98 and TA100 in the presence of a postmitochondrial liver preparation from Aroclor 1254 induced rats. The 11-amino hydrocarbon is a very weak mutagen (0.27 revertants/nmol), whereas the 11-amino-17-ketone is much more active (129 revertants/nmol). 2-Aminochrysene is the most mutagenic arylamine ( approximately 500 revertants/nmol) among these compounds, but its 5-amino isomer is much less active (0.9 revertants/nmol). Possible reasons for these marked differences are suggested. Use of TA98 with over-expressing O-acetyltransferase (YG 1024) and deficient in this enzyme (TA98/l,8-DNP(6)) with the 11-amino-17-ketone and with 5-aminochrysene clearly indicates the importance of this enzyme in their bioactivation, implying oxidation of the amino group to the hydroxylamine in both these compounds.

MeSH terms

  • Androstenes / toxicity*
  • Animals
  • Bay-Region, Polycyclic Aromatic Hydrocarbon
  • Chrysenes / toxicity*
  • Male
  • Microsomes, Liver / drug effects
  • Microsomes, Liver / metabolism
  • Mutagenicity Tests
  • Mutagens / toxicity*
  • Rats
  • Rats, Wistar
  • Salmonella typhimurium / drug effects
  • Salmonella typhimurium / genetics
  • Structure-Activity Relationship

Substances

  • 11-amino-16,17-dihydro-15H-cyclopenta(a)phenanthrene
  • Androstenes
  • Chrysenes
  • Mutagens
  • 6-chrysenamine
  • 2-aminochrysene