Crystal structure of a carcinogen:nucleoside adduct

Cancer Res. 1981 Jun;41(6):2230-4.

Abstract

The product of reaction between the carcinogen, 7-bromomethyl-12-methylbenz[a]anthracene, and 2'-deoxyadenosine, i.e., N6-(12-methylbenz[a]anthracenyl-7-methyl)deoxyadenosine, has been prepared and characterized, and its structure has been determined by X-ray crystallographic techniques. The major structural features are: (a) the adenine and polycyclic aromatic hydrocarbon residues lie nearly perpendicular to one another; (b) the conformation about the glycosidic bond is syn, rather than anti, and an internal hydrogen bond between the deoxyribose 5'-hydroxyl group and N(3) of the adenine residue is present; and (c) the more planar anthracene portion of the hydrocarbon is stacked between adenine residues of other molecules throughout the crystal.

Publication types

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

MeSH terms

  • 9,10-Dimethyl-1,2-benzanthracene / analogs & derivatives
  • 9,10-Dimethyl-1,2-benzanthracene / analysis
  • 9,10-Dimethyl-1,2-benzanthracene / chemical synthesis*
  • Benz(a)Anthracenes* / chemical synthesis*
  • Benz(a)Anthracenes* / metabolism
  • Carcinogens
  • Chemical Phenomena
  • Chemistry
  • DNA / metabolism
  • Deoxyadenosines*
  • Isomerism
  • Models, Molecular
  • Molecular Conformation
  • X-Ray Diffraction

Substances

  • Benz(a)Anthracenes
  • Carcinogens
  • Deoxyadenosines
  • 7-bromomethyl-12-methylbenzanthracene
  • 9,10-Dimethyl-1,2-benzanthracene
  • N(6)-(12-methylbenzanthracenyl-7-methyl)deoxyadenosine
  • DNA