Nucleoside adducts from the in vitro reaction of benzo[a]pyrene-7,8-dihydrodiol 9,10-oxide or benzo[a]pyrene 4,5-oxide with nucleic acids
| Autor: | I. B. Weinstein, K. W. Jennette, Alan M. Jeffrey, F. A. Beland, S. H. Blobstein, Ronald G. Harvey |
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| Rok vydání: | 1977 |
| Předmět: |
Binding Sites
Stereochemistry Deoxyribonucleotides Polynucleotides Guanosine Oxides Cytidine DNA Biochemistry Guanine Nucleotides Adduct Structure-Activity Relationship chemistry.chemical_compound Isomerism chemistry Deoxyadenosine Benzo(a)pyrene Alcohols polycyclic compounds Pyrene Deoxyguanosine Organic chemistry Spectrophotometry Ultraviolet Benzopyrenes Nucleoside |
| Zdroj: | Biochemistry. 16:932-938 |
| ISSN: | 1520-4995 0006-2960 |
| DOI: | 10.1021/bi00624a019 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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