Photoinduced electron transfer and strand cleavage in pyrenyl-DNA complexes and adducts

Nicholas E. Geacintov, Kyril Solntsev, Lawrence W. Johnson, Junxin Chen, Alexander D. Kolbanovskiy, Tongming Liu, Vladimir Ya Shafirovich

Research output: Contribution to journalReview articlepeer-review

Abstract

The fluorescence of pyrenyl residues in complexes with the nucleic acid bases G, C and T, but not A, is strongly quenched by photoinduced electron transfer mechanisms. Site-specifically modified 11-mer oligonucleotide duplexes containing a single modified guanosyl base G* bearing a covalently attached pyrenyl residue were prepared in order to probe for photochemical damage associated with these photoinduced electron transfer reactions. When the pyrenyl residue positioned at G* is photoexcited with 355 nm light, direct strand cleavage is observed at that site with low quantum yield. Frank strand breaks are also observed up to five base pairs away from G*, suggesting that intrastrand migration of a reactive intermediate from base to base is occurring.

Original languageEnglish (US)
Pages (from-to)561-565
Number of pages5
JournalJournal of Physical Organic Chemistry
Volume11
Issue number8-9
DOIs
StatePublished - 1998

Keywords

  • Photoinduced electron transfer
  • Pyrenyl-DNA complexes and adducts
  • Strand cleavage

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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