Fluorescence and photoelectron studies of the intercalative binding of benz(a)anthracene metabolite models to DNA

Biochem Biophys Res Commun. 1983 Apr 15;112(1):1-7. doi: 10.1016/0006-291x(83)91788-6.

Abstract

DNA binding of nonreactive metabolite models derived from benz(a)anthracene was studied. The molecules investigated include 1,2,3,4-tetrahydrobenz(a)anthracene (1), 5,6-dihydrobenz(a)anthracene (2), and 8,9,10,11-tetrahydrobenz(a)anthracene (3), as well as anthracene and phenanthrene. Measurements of the effects of DNA binding upon fluorescence intensities and fluorescence lifetimes indicate that molecules 1 and 3 (KA = 1.5 - 2.5 x 10(3) M-1) bind more strongly to native DNA than does molecule 2 (KA congruent to 0.5 x 10(3) M-1). Furthermore, molecules 1 and 3 bind to DNA much more effectively than do the two less sterically hindered pi electron metabolite models, anthracene and phenanthrene. Photoelectron data suggests that the enhanced binding of molecules 1 and 3 is due to increases in polarizability. Experiments carried out with denatured DNA indicate that the binding of molecule 1 entails the greatest intercalation.

Publication types

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

MeSH terms

  • Benz(a)Anthracenes / metabolism*
  • Binding Sites
  • DNA / metabolism*
  • Electrons
  • Photochemistry
  • Spectrometry, Fluorescence

Substances

  • Benz(a)Anthracenes
  • DNA