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LOCATION OF EXCIMER-FORMING ADDUCTS OF (+)-ANTI-BENZO A PYRENE DIOL EPOXIDE IN DNA

M. Eriksson ; Seog K. Kim (Institutionen för fysikalisk kemi) ; S. Sen ; A. Graslund ; B. Jernstrom ; Bengt Nordén (Institutionen för fysikalisk kemi)
Journal of the American Chemical Society (0002-7863). Vol. 115 (1993), 5, p. 1639-1644.
[Artikel, refereegranskad vetenskaplig]

Covalent adducts of the carcinogenic polycyclic aromatic hydrocarbon (+)-anti-benzo[a]pyrene 7,8-dihydrodiol 9,10-epoxide ((+)-anti-BPDE) in polynucleotides have been studied by fluorescence spectroscopy. The pyrenyl chromophores of the BPDE adducts, linked by the C10 atom to the exocyclic nitrogen of guanine, interact in the photoexcited state, as evidenced by excimer fluorescence. Strong BPDE excimer fluorescence is observed in the alternating poly(dGdC).poly(dGdC) sequence, whereas it is weak in the homopolymeric poly(dG).poly(dC) and in calf thymus DNA. No excimer fluorescence is observed for the BPDE adducts in poly(dAdC).poly(dGdT) or poly(dAdG).poly(dCdT). It is concluded that the formation of BPDE excimers in polynucleotides requires binding to guanines on different strands on consecutive basepairs. The experimental results are supported by graphics modeling and energy minimization of BPDE adducts in various oligonucleotide sequences. The results show that the most favorable arrangement for excimer formation of the BPDE-dG adducts is in a 5'(dCdG-BPDE).5'(dCdG-BPDE) sequence, where the pyrenyl chromophores interact in the minor groove.

Nyckelord: molecular mechanics, covalent complexes, linear dichroism, benzopyrene, fluorescence, poly(dg-dc), binding



Denna post skapades 2011-08-16.
CPL Pubid: 144364

 

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Institutionen för fysikalisk kemi (1900-2003)

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Kemi

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