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

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

Research output: Contribution to journalArticle

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
StatePublished - Aug 1998

Fingerprint

strands
adducts
cleavage
electron transfer
Bearings (structural)
deoxyribonucleic acid
Electrons
DNA
Quantum yield
Oligonucleotides
Nucleic Acids
oligonucleotides
Fluorescence
nucleic acids
damage
fluorescence
probes

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Geacintov, N., Solntsev, K., Johnson, L. W., Chen, J., Kolbanovskiy, A. D., Liu, T., & Shafirovich, V. Y. (1998). Photoinduced electron transfer and strand cleavage in pyrenyl-DNA complexes and adducts. Journal of Physical Organic Chemistry, 11(8-9), 561-565.

Photoinduced electron transfer and strand cleavage in pyrenyl-DNA complexes and adducts. / Geacintov, Nicholas; Solntsev, Kyril; Johnson, Lawrence W.; Chen, Junxin; Kolbanovskiy, Alexander D.; Liu, Tongming; Shafirovich, Vladimir Ya.

In: Journal of Physical Organic Chemistry, Vol. 11, No. 8-9, 08.1998, p. 561-565.

Research output: Contribution to journalArticle

Geacintov, N, Solntsev, K, Johnson, LW, Chen, J, Kolbanovskiy, AD, Liu, T & Shafirovich, VY 1998, 'Photoinduced electron transfer and strand cleavage in pyrenyl-DNA complexes and adducts', Journal of Physical Organic Chemistry, vol. 11, no. 8-9, pp. 561-565.
Geacintov N, Solntsev K, Johnson LW, Chen J, Kolbanovskiy AD, Liu T et al. Photoinduced electron transfer and strand cleavage in pyrenyl-DNA complexes and adducts. Journal of Physical Organic Chemistry. 1998 Aug;11(8-9):561-565.
Geacintov, Nicholas ; Solntsev, Kyril ; Johnson, Lawrence W. ; Chen, Junxin ; Kolbanovskiy, Alexander D. ; Liu, Tongming ; Shafirovich, Vladimir Ya. / Photoinduced electron transfer and strand cleavage in pyrenyl-DNA complexes and adducts. In: Journal of Physical Organic Chemistry. 1998 ; Vol. 11, No. 8-9. pp. 561-565.
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