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Alkylation of polyguanylic acid at the 2-amino group and phosphate by the potent mutagen (+/-)-7beta,8alpha-dihydroxy-9beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene.

作者信息

Koreeda M, Moore P D, Yagi H, Yeh H J, Jerina D M

出版信息

J Am Chem Soc. 1976 Oct 13;98(21):6720-2. doi: 10.1021/ja00437a061.

DOI:10.1021/ja00437a061
PMID:972227
Abstract
摘要

相似文献

1
Alkylation of polyguanylic acid at the 2-amino group and phosphate by the potent mutagen (+/-)-7beta,8alpha-dihydroxy-9beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene.强效诱变剂（±）-7β,8α-二羟基-9β,10β-环氧-7,8,9,10-四氢苯并[a]芘对聚鸟苷酸2-氨基和磷酸基团的烷基化作用
J Am Chem Soc. 1976 Oct 13;98(21):6720-2. doi: 10.1021/ja00437a061.
2
In vitro reaction of radioactive 7beta, 8alpha, --dihydroxy--9alpha, 10alpha-epoxy--7,8,9,10--tetrahydrobenzo (A) pyrene and 7beta,8alpha--dihydroxy--9beta, 10beta--epoxy--7,8,9,10--tetrahydrobenzo (A) pyrene with DNA.放射性7β, 8α - 二羟基 - 9α, 10α - 环氧 - 7,8,9,10 - 四氢苯并(A)芘和7β,8α - 二羟基 - 9β, 10β - 环氧 - 7,8,9,10 - 四氢苯并(A)芘与DNA的体外反应
Biochem Biophys Res Commun. 1977 Feb 7;74(3):934-40. doi: 10.1016/0006-291x(77)91608-4.
3
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.非对映体苯并[a]芘7,8 - 二醇 - 9,10 - 环氧化物光学对映体在新生小鼠中的致瘤性：(+)-7β,8α - 二羟基 - 9α,10α - 环氧 - 7,8,9,10 - 四氢苯并[a]芘的异常活性
Proc Natl Acad Sci U S A. 1978 Nov;75(11):5358-61. doi: 10.1073/pnas.75.11.5358.
4
Comparison of the tumor-initiating activities of benzo(a)pyrene arene oxides and diol-epoxides.苯并(a)芘芳烃氧化物和二醇环氧化物的肿瘤起始活性比较。
Cancer Res. 1977 Nov;37(11):4130-3.
5
Arachidonic acid-dependent metabolism of (+/-)-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene to polyguanylic acid-binding derivatives.（±）-7,8-二羟基-7,8-二氢苯并[a]芘依赖花生四烯酸的代谢生成聚鸟苷酸结合衍生物。
Chem Biol Interact. 1981 Jan;33(2-3):239-52. doi: 10.1016/0009-2797(81)90044-2.
6
Tumorigenicity studies with diol-epoxides of benzo(a)pyrene which indicate that (+/-)-trans-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene is an ultimate carcinogen in newborn mice.苯并(a)芘二醇环氧化物的致癌性研究表明，(±)-反式-7β,8α-二羟基-9α,10α-环氧-7,8,9,10-四氢苯并(a)芘是新生小鼠的一种最终致癌物。
Cancer Res. 1978 Feb;38(2):354-8.
7
Mutagenicity and cytotoxicity of benzo(a)pyrene benzo-ring epoxides.苯并(a)芘苯环环氧化物的致突变性和细胞毒性。
Cancer Res. 1976 Sep;36(9 pt.1):3358-66.
8
Epidermal hyperplasia after topical application of benzo (a) pyrene, benzo (a) pyrene diol epoxides, and other metabolites.局部应用苯并（a）芘、苯并（a）芘二醇环氧化物及其他代谢产物后出现的表皮增生。
Cancer Res. 1977 Apr;37(4):984-90.
9
(+/-)-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.（±）-7α，8β-二羟基-9β，10β-环氧-7,8,9,10-四氢苯并（a）芘是苯并（a）芘代谢及与DNA结合过程中的一种中间体。
Proc Natl Acad Sci U S A. 1976 Aug;73(8):2679-81. doi: 10.1073/pnas.73.8.2679.
10
Base specificity in the binding of benzo[a]pyrene diol epoxide to simian virus 40 DNA.
Cancer Lett. 1978 Sep;5(3):131-7. doi: 10.1016/s0304-3835(78)80029-9.

引用本文的文献

1
Detection of phosphodiester adducts formed by the reaction of benzo[a]pyrene diol epoxide with 2'-deoxynucleotides using collision-induced dissociation electrospray ionization tandem mass spectrometry.使用碰撞诱导解离电喷雾电离串联质谱法检测苯并[a]芘二醇环氧化物与2'-脱氧核苷酸反应形成的磷酸二酯加合物。
Nucleic Acids Res. 2007;35(15):5014-27. doi: 10.1093/nar/gkm526. Epub 2007 Jul 18.
2
Benzo[a]pyrene diol epoxide-DNA cis adduct formation through a trans chlorohydrin intermediate.通过反式氯醇中间体形成苯并[a]芘二醇环氧化物-DNA顺式加合物。
Proc Natl Acad Sci U S A. 1997 Mar 4;94(5):1749-54. doi: 10.1073/pnas.94.5.1749.
3
Chloride ions catalyze the formation of cis adducts in the binding of anti-benzo[a]pyrene diol epoxide to nucleic acids.
氯离子在抗苯并[a]芘二醇环氧化物与核酸的结合中催化顺式加合物的形成。
Proc Natl Acad Sci U S A. 1994 Feb 15;91(4):1371-5. doi: 10.1073/pnas.91.4.1371.
4
Equilibrium binding of carcinogens and antitumor antibiotics to DNA: site selectivity, cooperativity, allosterism.致癌物和抗肿瘤抗生素与DNA的平衡结合：位点选择性、协同性、变构效应
Nucleic Acids Res. 1981 Jul 10;9(13):3175-86. doi: 10.1093/nar/9.13.3175.
5
Hydrolysis of benzo[a]pyrene diol epoxide and its covalent binding to DNA proceed through similar rate-determining steps.苯并[a]芘二氢二醇环氧化物的水解及其与DNA的共价结合通过相似的速率决定步骤进行。
Proc Natl Acad Sci U S A. 1984 May;81(9):2635-9. doi: 10.1073/pnas.81.9.2635.
6
Nucleic acid adducts of chemical carcinogens and mutagens.化学致癌物和诱变剂的核酸加合物
Arch Toxicol. 1983 Apr;52(4):249-85. doi: 10.1007/BF00316495.
7
Metabolism and activation of chemical carcinogens.化学致癌物的代谢与活化
Mol Cell Biochem. 1980 Sep 15;32(2):95-104. doi: 10.1007/BF00227802.
8
Formation and persistence of benzo(a)pyrene metabolite-DNA adducts.苯并(a)芘代谢物-DNA加合物的形成与持久性。
Environ Health Perspect. 1985 Oct;62:31-9. doi: 10.1289/ehp.856231.
9
Immunohistochemical detection of anti-(+/-)-trans-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)p yrene-bound adduct in nuclei of cultured HeLa cells and mouse lung tissue.免疫组织化学检测培养的HeLa细胞核及小鼠肺组织中抗-（+/-）-反式-7,8-二羟基-9,10-环氧-7,8,9,10-四氢苯并（a）芘结合加合物。
J Cancer Res Clin Oncol. 1988;114(3):225-30. doi: 10.1007/BF00405826.
10
Solution conformation of the major adduct between the carcinogen (+)-anti-benzo[a]pyrene diol epoxide and DNA.
Proc Natl Acad Sci U S A. 1992 Mar 1;89(5):1914-8. doi: 10.1073/pnas.89.5.1914.