PMID: 2506585Sep 1, 1989Paper

Fluorescence spectroscopy of benzo[a]pyrene diol epoxide-DNA adducts. Conformation-specific emission spectra

Photochemistry and Photobiology
S K KimN E Geacintov

Abstract

The fluorescence characteristics of adducts derived from the covalent binding of the highly tumorigenic (+) and the non-tumorigenic (-) enantiomers of trans-7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (BPDE) to native calf thymus DNA are significantly different from one another both at room temperature and at 77 K. The ratio R of fluorescence intensities of the (0,0) band I (situated near 380 nm) and vibronic band V (near 400 nm) of the pyrene ring system in the BPDE-DNA adducts and of the tetraol (BPT) hydrolysis product of BPDE is very sensitive to the polarity of the solvent, thus mimicking the well known behavior of pyrene itself (A. Nakajima, 1971, Bull. Chem. Soc. Jpn. 44, 3272). The fluorescence excitation and emission spectra of the (+)-BPDE-DNA adducts are relatively sharp and only slightly red-shifted (2-3 nm) with respect to those of BPT in aqueous buffer solution, and R = 1.07 when the fluorescence is excited at the maximum of the absorption spectrum; this compares with R = 1.17 for BPT in water, R = 0.75 in ether, and R = 0.84 for noncovalently intercalated BPT. These results suggest that the pyrene ring system in the covalent (+)-BPDE-DNA adducts is located in an environment which is relatively...Continue Reading

References

Jun 21, 1976·Biochemical and Biophysical Research Communications·V IvanovicI B Weinstein
Apr 1, 1987·Photochemistry and Photobiology·N E Geacintov
Jun 1, 1984·Journal of Biomolecular Structure & Dynamics·N E GeacintovR G Harvey
Jan 1, 1982·Carcinogenesis·M C MacLeodJ K Selkirk
Aug 1, 1981·Archives of Biochemistry and Biophysics·V GlushkoC D Karp

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