An internal fluorene model for iodo-N-2-acetylaminofluorene modified DNA

S. Broyde, B. Hingerty

Research output: Contribution to journalArticle

Abstract

Minimized conformational potential energy calculations have been performed for the 7-iodo (AAIF) and 7-fluoro (AAFF) derivatives of N-2-acetylaminofluorene (AAF), linked covalently to guanine C-8 in dCpdG. Both the iodo and the fluoro derivatives are carcinogenic and mutagenic. The lowest energy forms on the dinucleoside monophosphate level have syn guanine and fluorene-cytidine stacking. However, the iodo adduct cannot adopt this conformation in larger polymers, according to earlier experimental studies (Fuchs et al., Biochemistry, 15 (1976) 3347) and model building, because of iodine's large Van der Waal's radius. Therefore, a model consistent with all the experimental evidence, incorporating the second lowest energy conformation in B form duplex (dCdG)3 was constructed. In this model the modified guanine is syn, yet still stacked with the adjacent cytidine in one direction, the fluorene is located primarily at the helix interior between the base pairing sites, rupturing two base pairs, and the iodine atom and its adjoining ring protrude to the helix exterior.

Original languageEnglish (US)
Pages (from-to)69-78
Number of pages10
JournalChemico-Biological Interactions
Volume47
Issue number1
DOIs
StatePublished - Oct 15 1983

Keywords

  • Conformation
  • Iodo-N-2-acetylaminofluorene
  • Modified DNA

ASJC Scopus subject areas

  • Toxicology

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