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The covalent binding of benzo[a]pyrene 4,5-oxide and benzo[a]pyrene-7,8-dihydrodiol 9,10-oxide isomer I and isomer II to nucleic acids in aqueous acetone solution has been investigated. Benzo[a]pyrene 4,5-oxide reacted preferentially with guanosine residues. On the other hand, benzo[a]pyrene-7,8-dihydrodiol 9,10-oxide isomer I and II reacted extensively with guanosine, adenosine, and cytidine residues. Time course studies showed that the reactivity of isomer I or isomer II with homopolyribonucleotides followed the order poly(G) greater than poly(A) greater than poly(C). Alkaline or enzymatic hydrolysis of the modified nucleic acids and subsequent chromatography on Sephadex LH-20 columns yielded benzo[a]pyrene-nucleotide adducts. These were enzymatically converted to the corresponding nucleosides which were resolved into several distinct components by high-pressure liquid chromatography. Evidence was obtained for the presence of multiple nucleoside adducts of guanosine, adenosine, cytidine, deoxyguanosine, deoxyadenosine, and deoxycytidine. The HPLC profiles of adducts formed with isomer I were different from the corresponding profiles of adducts formed with isomer II. Structural aspects of these nucleoside adducts are discussed.
K W Jennette, and
A M Jeffrey, and
S H Blobstein, and
F A Beland, and
R G Harvey, and
I B Weinstein
December 1979,
Science (New York, N.Y.),
K W Jennette, and
A M Jeffrey, and
S H Blobstein, and
F A Beland, and
R G Harvey, and
I B Weinstein
January 1983,
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K W Jennette, and
A M Jeffrey, and
S H Blobstein, and
F A Beland, and
R G Harvey, and
I B Weinstein
May 2003,
The Journal of biological chemistry,
K W Jennette, and
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S H Blobstein, and
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K W Jennette, and
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K W Jennette, and
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K W Jennette, and
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K W Jennette, and
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I B Weinstein
April 1978,
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K W Jennette, and
A M Jeffrey, and
S H Blobstein, and
F A Beland, and
R G Harvey, and
I B Weinstein
September 1979,
FEBS letters,
