Electrochemical genotoxicity screening for arylamines bioactivated by N-acetyltransferase

Anal Chem. 2008 Feb 15;80(4):1192-200. doi: 10.1021/ac701781y. Epub 2008 Jan 12.

Abstract

Genotoxicity screening sensors that measure DNA damage from metabolism of arylamines were developed and evaluated. The sensors feature ultrathin films containing DNA and N-acetyltransferase (NAT) on pyrolytic graphite (PG) electrodes. NAT in the film catalyzed the conversion of the arylamine 2-aminofluorene (2-AF) to 2-acetylaminofluorene (2-AAF) by acetyl coenzyme A (AcCoA) dependent N-acetylation, as verified by liquid chromatography. DNA damage in the films from exposure to reactive 2-AF metabolites was measured subsequent to the enzyme reaction using catalytic voltammetric oxidation with Ru(bpy)32+. Square wave voltammetric (SWV) peaks increased with enzyme reaction time, and relative DNA damage rates at pH 5.8 were measured within 2 min. Control incubations of DNA/NAT films without AcCoA gave no significant sensor response. CapLC-MS/MS analysis of 2-AAF/DNA reaction products was consistent with 2-AF-guanine adducts formed in the films. DNA damage occurred more rapidly under weakly acidic conditions (pH 5.5-5.8) than at neutral pH, suggesting that genotoxicity from arylamine metabolism by NAT could be more significant in slightly acidic environments.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • 2-Acetylaminofluorene / toxicity*
  • Acetyl Coenzyme A / metabolism*
  • Acetylation
  • Arylamine N-Acetyltransferase / metabolism*
  • Biosensing Techniques / methods*
  • Catalysis
  • Chromatography, Liquid
  • DNA / drug effects*
  • DNA Damage*
  • Electrochemistry
  • Electrodes
  • Graphite / chemistry
  • Hydrogen-Ion Concentration
  • Kinetics
  • Mass Spectrometry
  • Mutagenicity Tests / methods*

Substances

  • Acetyl Coenzyme A
  • Graphite
  • DNA
  • 2-Acetylaminofluorene
  • Arylamine N-Acetyltransferase