Molecular mechanics and dynamics of DNA-furocoumarin complexes: effect of the aromatization of the pyrone ring on the intercalation geometry

J Photochem Photobiol B. 1990 Jun;6(1-2):207-20. doi: 10.1016/1011-1344(90)85091-a.

Abstract

Results of molecular mechanics and dynamics calculations on intercalation complexes of DNA with various furocoumarins (psoralen, angelicin, 7-methylpyrido[3,4-c]psoralen and 7-methylpyrido[4,3-c]psoralen) and their corresponding aromatized derivatives are presented. These calculations were undertaken with the aim to elucidate the roles of the pyrone and pyridine moieties in the interactions which tend to orient the furocoumarins and pyridopsoralens between DNA base pairs. It appears that the intercalation geometries are very similar for the furocoumarins and related aromatized compounds. Therefore the oxygen and nitrogen atoms of the pyrone and pyridine moieties are not important in the orientation of the drug within the oligonucleotide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Composition
  • Base Sequence
  • Computer Graphics
  • DNA*
  • Furocoumarins*
  • Intercalating Agents*
  • Models, Molecular
  • Molecular Conformation
  • Molecular Sequence Data
  • Molecular Structure
  • Nucleic Acid Conformation
  • Oligodeoxyribonucleotides*
  • Structure-Activity Relationship

Substances

  • Furocoumarins
  • Intercalating Agents
  • Oligodeoxyribonucleotides
  • DNA