Journal ArticleDOI
Benzo(a)pyrene diol epoxides as intermediates in nucleic acid binding in vitro and in vivo.
I. B. Weinstein,Alan M. Jeffrey,K. W. Jennette,S. H. Blobstein,Ronald G. Harvey,Chris Harris,Herman Autrup,Hiroshi Kasai,Koji Nakanishi +8 more
TLDR
Evidence has been obtained that a specific isomer of a diol epoxide derivative of benzo(a)pyrene, (+/-)-7 beta,8alpha-dihydroxy-9alpha, 10alpha-epoxy-7,8,9,10-tetrahydrobenzo( a)pyene, is an intermediate in the binding of benzos(a).pyrene to RNA in cultured bovine bronchial mucosa.Abstract:
Evidence has been obtained that a specific isomer of a diol epoxide derivative of benzo(a)pyrene, (+/-)-7 beta,8alpha-dihydroxy-9alpha, 10alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene, is an intermediate in the binding of benzo(a)pyrene to RNA in cultured bovine bronchial mucosa. An adduct is formed between position 10 of this derivative and the 2-amino group of guanine.read more
Citations
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Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules
TL;DR: Current data are consistent with the idea that the initiation step of chemical carcinogenesis is a mutagenic event and is caused by alteration of DNA by the ultimate carcinogens and there appears to be no requirement that they be electrophilic.
Journal ArticleDOI
Fifty years of benzo( a )pyrene
TL;DR: It is fifty years since the publication of the report on the isolation, from coal tar, and identification of the potent chemical carcinogen benzo(a)pyrene, the culmination of over 10 years of research instigated and directed by E.L. Kennaway.
Journal ArticleDOI
Structural identification of the major DNA adduct formed by aflatoxin B1 in vitro
John M. Essigmann,Robert G. Croy,A M Nadzan,W F Busby,V N Reinhold,G.H. Büchi,Gerald N. Wogan +6 more
TL;DR: Analysis of spectral and chemical data indicates that the major product of the interaction of metabolically activated aflatoxin B1 and DNA is 2,3-dihydro-2-(N7-guanyl)-3-hydroxyaflatoxin B 1 with the guanine and hydroxyl functions possessing a trans configuration.
Journal ArticleDOI
Molecular electrostatic potential of the nucleic acids.
Alberte Pullman,Bernard Pullman +1 more
TL;DR: The aim of this review is to demonstrate the significance of macromolecular electronic effects of the recently much developed concept of ‘molecular electrostatic potential’ (MEP) (Scrocco & Tomasi, 1973, 1978).
Journal ArticleDOI
Structures of benzo(a)pyrene–nucleic acid adducts formed in human and bovine bronchial explants
Alan M. Jeffrey,I. B. Weinstein,K. W. Jennette,K. Grzeskowiak,Koji Nakanishi,Ronald G. Harvey,Herman Autrup,Curtis C. Harris +7 more
TL;DR: Studies on RNA and DNA adducts formed by human bronchial explants are described and evidence that the structures of the majorAdducts are similar to those formed in the analogous bovine system is provided.
References
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Journal Article
Carcinogenesis by chemicals: an overview--G. H. A. Clowes memorial lecture.
Journal ArticleDOI
Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide
TL;DR: It is suggested that epoxides are the important reactive metabolites responsible for the biological effects of these carcinogens4.
Journal ArticleDOI
Evidence for the binding of polynuclear aromatic hydrocarbons to the nucleic acids of mouse skin: relation between carcinogenic power of hydrocarbons and their binding to deoxyribonucleic acid.
Peter Brookes,P. D. Lawley +1 more
TL;DR: Evidence for the Binding of Polynuclear Aromatic Hydrocarbons to the Nucleic Acids of Mouse Skin : Relation between Carcinogenic Power of hydrocarbons and their Binding to Deoxyribonucleic Acid is presented.
Identification of mutagenic metabolites of benzo(a)pyrene in mammalian cells (diol- and K-region epoxides/cell-mediated mutagenesis/8-azaguanine and ouabain resistance/high pressure liquid
TL;DR: The mutagenicity of benzo(a)pyrene and 15 of its derivatives, which included phenols, the K-region epoxide, dihydrodiols, two isomeric 7,8-diol-9,10-epoxides, a 6-methyl derivative, and a 6hydroxymethyl derivative, were tested with Chinese ham- ster V79 cells in order to identify the mutagenic metabolites.
Journal ArticleDOI
Identification of mutagenic metabolites of benzo(a)pyrene in mammalian cells.
TL;DR: High-pressure liquid chromatography analysis indicated that the major metabolite of trans-7,8-diol is 7alpha,8beta-dihydroxy-9beta,10beta-epoxy- 7,8,9,10-tetrahydrobenzo[a]pyrene, and the results indicate that the latter compound is metabolically formed and the major mutagenic intermediate of benzo[ a]yrene metabolism.