Guanyl-C8-arylamination of DNA by the ultimate carcinogen of 4-nitroquinoline-1-oxide: a spectrophotometric titration

Anal Biochem. 1984 May 1;138(2):454-7. doi: 10.1016/0003-2697(84)90839-x.

Abstract

Native and denatured DNAs and polynucleotides were modified by 4-acetoxyaminoquinoline-1-oxide, the ultimate carcinogen of 4-nitroquinoline-1-oxide (4 NQO). The N-( deoxyguanosin -C8-yl)-4-aminoquinoline-1-oxide adduct, the so-called "dG III," was quantified on the DNA and on poly(dG-dC) in absorption spectroscopy, by using a spectral property of dG III, i.e., the variation of the absorption spectrum as a function of the pH. Using the "free-dG III" absorption reference spectra, a simple graphic determination of the percentage of dG III was established by recording the absorption spectra of the 4-acetoxyaminoquinoline-1-oxide-modified polymers. It was found that the dG III adduct accounts for about 30% of the total modification in the case of native modified DNA and poly(dG-dC) and for about 70% in the case of denatured modified DNA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Nitroquinoline-1-oxide / metabolism*
  • Aminoquinolines / analysis*
  • Aminoquinolines / metabolism*
  • Carcinogens / metabolism*
  • DNA / analysis*
  • Deoxyguanosine / analogs & derivatives*
  • Deoxyguanosine / analysis
  • Hydrogen-Ion Concentration
  • Nitroquinolines / metabolism*
  • Polydeoxyribonucleotides / analysis
  • Spectrophotometry
  • Spectrophotometry, Ultraviolet

Substances

  • Aminoquinolines
  • Carcinogens
  • Nitroquinolines
  • Polydeoxyribonucleotides
  • poly(dC-dG)
  • 4-Nitroquinoline-1-oxide
  • 4-acetoxyaminoquinoline 1-oxide
  • N-(deoxyguanosin-C(8)-yl)-4-aminoquinoline 1-oxide
  • DNA
  • Deoxyguanosine