Binding of pyrene to DNA, base squence specificity and its implication
Open Access
- 1 January 1983
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 11 (20) , 7231-7250
- https://doi.org/10.1093/nar/11.20.7231
Abstract
Solubilization as well as spectral studies of pyrene in natural DNA and synthetic deoxypolynucleotlde solutions at neutral pH reveal at least two binding modes. Sites I are predominant in native DNA and in poly(dA-dT): poly(dA-dT) whereas sites II are found with denatured DNA and other polynucleotides such as poly(dA): poly(dT) and three different types of guanine containing copolymers which solubilize pyrene to a lesser extent. Spectral comparison with the covalent adducts of trans-7, 8-dihydroxy-anti-9, 10-epoxy-7, 8, 9, 10- tetrahydro-benzo(a)pyrene (anti-BPDE) and the physical complexes of its tetraols lead to the suggestion of a base sequence specific binding model for this carcinogenic retabolite to account for the puzzling fact that although its physical binding is predominantly Intercalative, the covalent adducts appear not to be Intercalated. It is speculated that in neutral solutions, Intercalation may have little, if any, to do with the chemical lesion of this metabolite to the guanine base of the DNA and may, on the contrary, provide an efficient pathway for detoxification.Keywords
This publication has 24 references indexed in Scilit:
- Kinetics of hydrolysis to tetraols and binding of benzo(a)pyrene-7,8-dihydrodiol-9,10-oxide and its tetraol derivatives to DNA. Conformation of adductsBiochemical and Biophysical Research Communications, 1980
- Computer-generated graphic models of the N2-substituted deoxyguanosine adducts of 2-acetylaminofluorene and benzo[a]pyrene and the O6-substituted deoxyguanosine adduct of 1-naphthylamine in the DNA double helixChemico-Biological Interactions, 1978
- COVALENT INTERCALATIVE BINDING TO DNA IN RELATION TO MUTAGENICITY OF HYDROCARBON EPOXIDES AND N-ACETOXY-2-ACETYLAMINOFLUORENE1978
- Structures of benzo(a)pyrene–nucleic acid adducts formed in human and bovine bronchial explantsNature, 1977
- Properties of benzopyrene-DNA complexes investigated by fluorescence and triplet flash photolysis techniquesJournal of the American Chemical Society, 1976
- Benzo[ a ]pyrene Diol Epoxides as Intermediates in Nucleic Acid Binding in Vitro and in VivoScience, 1976
- (+/-)-7alpha,8beta-dihydroxy-9beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo(a)-pyrene is an intermediate in the metabolism and binding to DNA of benzo(a)pyrene.Proceedings of the National Academy of Sciences, 1976
- Cellular binding of benzo(a)pyrene to DNA characterized by low temperature fluorescenceBiochemical and Biophysical Research Communications, 1976
- Fluorescence spectral evidence that benzo(a)pyrene‐DNA products in mouse skin arise from diol‐epoxidesFEBS Letters, 1975
- Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxideNature, 1974