Impact of site-specific benzo[a]pyrene diol epoxide-dg lesions at or near single/double-strand DNA junctions on DNA bending

Hong Tsao, Olga Rechkoblit, Shantu Amin, Nicholas E. Geacintov

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1 Scopus citations

Abstract

Adducts derived from the binding of the (+)-7R,8S,9S,10R and (-)-7S,8R,9R,10S enantiomers of r7,t8-dihydrodiol-t9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (anti-BPDE) to 2′-deoxyguanosine residues in DNA are known to induce mutations due to error-prone DNA replication. Because the conformational properties of these lesions may be important in these phenomena, we have examined the effects of the stereoisomeric (+)- and (-)-trans-anti-[BP]-N 2-dG lesions positioned site-specifically at or near primer/template oligonucleotide junctions on DNA bending using high resolution gel electrophoresis. Remarkable differences in electrophoretic mobilities μ are observed in the two adducts derived from the tumorigenic (+)-anti-BPDE, and the non-tumorigenic (-)-anti-BPDE enantiomer. With the (+)-trans lesion positioned on the template strand adjacent to the 3′-end of the primer strand, a remarkable decrease in μ is observed. This suggests the existence of a bend at the single strand-double strand junction. Only modest decreases in μ are observed hi the case of the (-)-trans lesion, or when the 3′-end is opposite to, or more distant from the lesion site. These observations are discussed in terms of the known NMR solution structures of these lesions in the same sequence context, and the properties of primer/template DNA in polymerases.

Original languageEnglish (US)
Pages (from-to)1-10
Number of pages10
JournalPolycyclic Aromatic Compounds
Volume21
Issue number1-4
DOIs
StatePublished - Jan 1 2000

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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