Abstract
The structural modification of double-stranded circular DNA of simian virus 40 and plasmid ColE1 by in vitro binding of r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene was studied. Stepwise hydrolysis with endonuclease S1 and DNase followed by DNA base analysis by thin-layer chromatography provided evidence that binding to adenine caused the local denaturation of DNA, whereas the more than 10-fold greater binding to guanine did not create such local denaturation. Of the two synthetic double-stranded polymers, poly(dA-dT).poly(dA-dT) and poly(dG-dC).poly(dG-dC), bound to the diol-epoxide, only the former showed a marked hydrolysis after endonuclease S1 treatment, whereas binding occurred 24-fold more on the latter.
Full text
PDFImages in this article
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- BROOKES P., LAWLEY P. D. 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. Nature. 1964 May 23;202:781–784. doi: 10.1038/202781a0. [DOI] [PubMed] [Google Scholar]
- Baird W. M., Brookes P. Isolation of the hydrocarbon-deoxyribonucleoside products from the DNA of mouse embryo cells treated in culture with 7-methylbenz(a)anthracene-3H. Cancer Res. 1973 Oct;33(10):2378–2385. [PubMed] [Google Scholar]
- Crawford L. V., Waring M. J. Supercoiling of polyoma virus DNA measured by its interaction with ethidium bromide. J Mol Biol. 1967 Apr 14;25(1):23–30. doi: 10.1016/0022-2836(67)90276-8. [DOI] [PubMed] [Google Scholar]
- Daudel P., Duquesne M., Vigny P., Grover P. L., Sims P. Fluorescence spectral evidence that benzo(a)pyrene-DNA products in mouse skin arise from diol-epoxides. FEBS Lett. 1975 Oct 1;57(3):250–253. doi: 10.1016/0014-5793(75)80310-3. [DOI] [PubMed] [Google Scholar]
- Dingman C. W., Fisher M. P., Kakefuda T. Role of molecular conformation in determining the electrophoretic properties of polynucleotides in agarose-acrylamide gels. II. Biochemistry. 1972 Mar 28;11(7):1242–1250. doi: 10.1021/bi00757a020. [DOI] [PubMed] [Google Scholar]
- Gamper H. B., Tung A. S., Straub K., Bartholomew J. C., Calvin M. DNA strand scission by benzo[a]pyrene diol epoxides. Science. 1977 Aug 12;197(4304):671–674. doi: 10.1126/science.877583. [DOI] [PubMed] [Google Scholar]
- Huberman E., Sachs L., Yang S. K., Gelboin V. Identification of mutagenic metabolites of benzo(a)pyrene in mammalian cells. Proc Natl Acad Sci U S A. 1976 Feb;73(2):607–611. doi: 10.1073/pnas.73.2.607. [DOI] [PMC free article] [PubMed] [Google Scholar]
- King H. W., Thompson M. H., Tarmy E. M., Brookes P., Harvey R. G. On the nature of the product which results when 7,8-dihydro-7,8-dihydroxybenzo(a)pyrene is metabolised in vitro and bound to DNA. Chem Biol Interact. 1976 Jun;13(3-4):349–352. doi: 10.1016/0009-2797(76)90087-9. [DOI] [PubMed] [Google Scholar]
- Marquardt H., Grover P. L., Sims P. In vitro malignant transformation of mouse fibroblasts by non-K-region dihydrodiols derived from 7-methylbenz(a)anthracene, 7,12-dimethylbenz(a)anthracene, and benzo(a)pyrene. Cancer Res. 1976 Jun;36(6):2059–2064. [PubMed] [Google Scholar]
- Musso R., Di Lauro R., Rosenberg M., de Crombrugghe B. Nucleotide sequence of the operator-promoter region of the galactose operon of Escherichia coli. Proc Natl Acad Sci U S A. 1977 Jan;74(1):106–110. doi: 10.1073/pnas.74.1.106. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Osborne M. R., Thompson M. H., Tarmy E. M., Beland F. A., Harvey R. G., Brookes P. The reaction of 7,8-dihydro-7,8-dihydroxybenzo (a) pyrene-9,10-oxide with DNA in relation to the benzo (a) pyrene-DNA products isolated from cells. Chem Biol Interact. 1976 Jun;13(3-4):343–348. doi: 10.1016/0009-2797(76)90086-7. [DOI] [PubMed] [Google Scholar]
- Sims P., Grover P. L., Swaisland A., Pal K., Hewer A. Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide. Nature. 1974 Nov 22;252(5481):326–328. doi: 10.1038/252326a0. [DOI] [PubMed] [Google Scholar]
- Thakker D. R., Yagi H., Lu A. Y., Levin W., Conney A. H. Metabolism of benzo[a]pyrene: conversion of (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene to highly mutagenic 7,8-diol-9,10-epoxides. Proc Natl Acad Sci U S A. 1976 Oct;73(10):3381–3385. doi: 10.1073/pnas.73.10.3381. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Tomizawa J. I., Ohmori H., Bird R. E. Origin of replication of colicin E1 plasmid DNA. Proc Natl Acad Sci U S A. 1977 May;74(5):1865–1869. doi: 10.1073/pnas.74.5.1865. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Tomizawa J., Sakakibara Y., Kakefuda T. Replication of colicin E1 plasmid DNA in cell extracts. Origin and direction of replication. Proc Natl Acad Sci U S A. 1974 Jun;71(6):2260–2264. doi: 10.1073/pnas.71.6.2260. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Vogt V. M. Purification and further properties of single-strand-specific nuclease from Aspergillus oryzae. Eur J Biochem. 1973 Feb 15;33(1):192–200. doi: 10.1111/j.1432-1033.1973.tb02669.x. [DOI] [PubMed] [Google Scholar]
- Weinstein I. B., Jeffrey A. M., Jennette K. W., Blobstein S. H., Harvey R. G., Harris C., Autrup H., Kasai H., Nakanishi K. Benzo(a)pyrene diol epoxides as intermediates in nucleic acid binding in vitro and in vivo. Science. 1976 Aug 13;193(4253):592–595. doi: 10.1126/science.959820. [DOI] [PubMed] [Google Scholar]
- Yagi H., Hernandez O., Jerina D. M. Letter: Synthesis of (+/-)-7 beta,8alpha-dihydroxy-9 beta,10beta-epoxy-7,8,-9,10-tetrahydrobenzo(a)pyrene, a potential metabolite of the carcinogen benzo(a)pyrene with stereochemistry related to the antileukemic triptolides. J Am Chem Soc. 1975 Nov 12;97(23):6881–6883. doi: 10.1021/ja00856a057. [DOI] [PubMed] [Google Scholar]
- Yang S. K., McCourt D. W., Roller P. P., Gelboin H. V. Enzymatic conversion of benzo(a)pyrene leading predominantly to the diol-epoxide r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene through a single enantiomer of r-7, t-8-dihydroxy-7,8-dihydrobenzo(a)pyrene. Proc Natl Acad Sci U S A. 1976 Aug;73(8):2594–2598. doi: 10.1073/pnas.73.8.2594. [DOI] [PMC free article] [PubMed] [Google Scholar]