苯并[a]芘代谢物二醇环氧化物r-7,t-8-二羟基-t-9,10-环氧-7,8,9,10-四氢苯并[a]芘对DNA的修饰作用
Modification of DNA by the benzo[a]pyrene metabolite diol-epoxide r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene.
作者信息
Kakefuda T, Yamamoto H
出版信息
Proc Natl Acad Sci U S A. 1978 Jan;75(1):415-9. doi: 10.1073/pnas.75.1.415.
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.
摘要
研究了通过r-7,t-8-二羟基-t-9,10-氧代-7,8,9,10-四氢苯并[a]芘的体外结合对猴病毒40和质粒ColE1的双链环状DNA进行的结构修饰。用核酸酶S1和脱氧核糖核酸酶进行逐步水解，然后通过薄层色谱法进行DNA碱基分析，结果表明与腺嘌呤的结合导致了DNA的局部变性，而与鸟嘌呤的结合量比与腺嘌呤的结合量多10倍以上却没有产生这种局部变性。在两种合成双链聚合物聚（dA-dT）·聚（dA-dT）和聚（dG-dC）·聚（dG-dC）中，与二醇环氧化物结合后，只有前者在核酸酶S1处理后显示出明显的水解，而后者的结合量是前者的24倍。
相似文献
1
Modification of DNA by the benzo[a]pyrene metabolite diol-epoxide r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene.
Proc Natl Acad Sci U S A. 1978 Jan;75(1):415-9. doi: 10.1073/pnas.75.1.415.
2
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):2594-8. doi: 10.1073/pnas.73.8.2594.
3
Sequence specific binding of tetraols of benzo[a]pyrene-diol-epoxide to DNA in neutral and acidic solutions.
Carcinogenesis. 1984 Jun;5(6):753-8. doi: 10.1093/carcin/5.6.753.
4
Identification of the major adducts formed by reaction of benzo(a)pyrene diol epoxide with DNA in vitro.
Proc Natl Acad Sci U S A. 1977 Dec;74(12):5285-9. doi: 10.1073/pnas.74.12.5285.
5
Mutagenicity and cytotoxicity of benzo(a)pyrene benzo-ring epoxides.
Cancer Res. 1976 Sep;36(9 pt.1):3358-66.
6
Mechanism of benzo[a]pyrene diol epoxide induced deoxyribonucleic acid strand scission.
Biochemistry. 1980 Aug 19;19(17):3948-56. doi: 10.1021/bi00558a009.
7
Repair of daughter strand gaps in nascent DNA from mouse epidermal cells treated with dihydrodiol epoxide derivatives of benzo[a]pyrene.
Biochim Biophys Acta. 1979 Nov 22;565(1):67-83. doi: 10.1016/0005-2787(79)90083-2.
8
Effect of deoxyribonuclease on adriamycin-polynucleotide complexes.
Cancer Res. 1976 Sep;36(9 pt.1):3367-73.
9
Excision repair by human fibroblasts of DNA damaged by r-7, t-8-dihyroxy-t-9,10-oxy-7,8,9,10- tetrahydrobenzo(a)pyrene.
Mutat Res. 1978 Jun;50(3):383-94. doi: 10.1016/0027-5107(78)90043-x.
10
Metabolic activation of benzo(a)pyrene and binding to DNA in cultured human bronchus.
Cancer Res. 1977 Apr;37(4):1210-5.
引用本文的文献
1
Error-free excision of the cytotoxic,mutagenic N2-deoxyguanosine DNA adduct formed in human fibroblasts by (+/-)-7 beta, 8 alpha-dihydroxy-9 alpha, 10 alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene.
Proc Natl Acad Sci U S A. 1980 Oct;77(10):5933-7. doi: 10.1073/pnas.77.10.5933.
2
Nucleic acid adducts of chemical carcinogens and mutagens.
Arch Toxicol. 1983 Apr;52(4):249-85. doi: 10.1007/BF00316495.
3
Base insertion and deletion mutations induced in an Escherichia coli plasmid by benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide.
Proc Natl Acad Sci U S A. 1981 Nov;78(11):6817-20. doi: 10.1073/pnas.78.11.6817.
4
Formation and persistence of benzo(a)pyrene metabolite-DNA adducts.
Environ Health Perspect. 1985 Oct;62:31-9. doi: 10.1289/ehp.856231.
5
Selective alkylation of carcinogenic 9-anthryloxirane at the N-3 position of adenine in DNA.
Proc Natl Acad Sci U S A. 1985 Aug;82(16):5250-4. doi: 10.1073/pnas.82.16.5250.
6
Effect of carcinogenic adducts on transcription by T7 RNA polymerase.
Nucleic Acids Res. 1987 May 26;15(10):4257-71. doi: 10.1093/nar/15.10.4257.
7
Differences in unwinding of supercoiled DNA induced by the two enantiomers of anti-benzo[a]pyrene diol epoxide.
Nucleic Acids Res. 1992 Dec 11;20(23):6167-76. doi: 10.1093/nar/20.23.6167.
8
Tumorigenicity of the optical enantiomers of the diastereomeric benzo[a]pyrene 7,8-diol-9,10-epoxides in newborn mice: exceptional activity of (+)-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene.
Proc Natl Acad Sci U S A. 1978 Nov;75(11):5358-61. doi: 10.1073/pnas.75.11.5358.
本文引用的文献
1
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;202:781-4. doi: 10.1038/202781a0.
2
3
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.
4
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):2260-4. doi: 10.1073/pnas.71.6.2260.
5
Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide.
Nature. 1974 Nov 22;252(5481):326-8. doi: 10.1038/252326a0.
6
Role of molecular conformation in determining the electrophoretic properties of polynucleotides in agarose-acrylamide gels. II.
Biochemistry. 1972 Mar 28;11(7):1242-50. doi: 10.1021/bi00757a020.
7
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.
8
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):343-8. doi: 10.1016/0009-2797(76)90086-7.
9
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):6881-3. doi: 10.1021/ja00856a057.
10
Fluorescence spectral evidence that benzo(a)pyrene-DNA products in mouse skin arise from diol-epoxides.
FEBS Lett. 1975 Oct 1;57(3):250-3. doi: 10.1016/0014-5793(75)80310-3.
Zotero 插件