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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.

作者信息

Yagi H, Hernandez O, Jerina D M

出版信息

J Am Chem Soc. 1975 Nov 12;97(23):6881-3. doi: 10.1021/ja00856a057.

DOI:10.1021/ja00856a057
PMID:1184887
Abstract
摘要

相似文献

1
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.信函:(±)-7β,8α-二羟基-9β,10β-环氧-7,8,-9,10-四氢苯并(a)芘的合成,苯并(a)芘的一种潜在代谢产物,其立体化学与抗白血病雷公藤内酯醇相关 。
J Am Chem Soc. 1975 Nov 12;97(23):6881-3. doi: 10.1021/ja00856a057.
2
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.
3
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.
4
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.
5
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.
6
Carcinogenicity of benzo-ring derivatives of benzo(a)pyrene on mouse skin.苯并(a)芘的苯环衍生物对小鼠皮肤的致癌性。
Cancer Res. 1977 Sep;37(9):3356-61.
7
(+/-)-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.
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.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.
9
Epoxy derivatives of aromatic polycyclic hydrocarbons. The preparation and metabolism of epoxides related to benzo(a)pyrene and to 7,8- and 9,10-dihydrobenzo(a)pyrene.芳香多环烃的环氧衍生物。与苯并(a)芘以及7,8-和9,10-二氢苯并(a)芘相关的环氧化物的制备与代谢。
Biochem J. 1972 Jun;128(2):265-77. doi: 10.1042/bj1280265.
10
Synthesis of anti-7,8-dihydroxy-9,10-epoxy-7,8,9, 10-tetrahydro-11-methylbenzo[a]pyrene and its reaction with DNA.抗7,8 - 二羟基 - 9,10 - 环氧 - 7,8,9,10 - 四氢 - 11 - 甲基苯并[a]芘的合成及其与DNA的反应
Chem Res Toxicol. 1999 Apr;12(4):341-6. doi: 10.1021/tx980178n.

引用本文的文献

1
Establishing Linkages Among DNA Damage, Mutagenesis, and Genetic Diseases.建立 DNA 损伤、突变和遗传疾病之间的联系。
Chem Res Toxicol. 2022 Oct 17;35(10):1655-1675. doi: 10.1021/acs.chemrestox.2c00155. Epub 2022 Jul 26.
2
Crystal and molecular structure of a benzo[a]pyrene 7,8-diol 9,10-epoxide N2-deoxyguanosine adduct: absolute configuration and conformation.苯并[a]芘7,8-二醇9,10-环氧化物N2-脱氧鸟苷加合物的晶体和分子结构:绝对构型和构象
Proc Natl Acad Sci U S A. 2004 Feb 10;101(6):1433-8. doi: 10.1073/pnas.0307305101. Epub 2004 Feb 2.
3
Mechanism of the inhibition of mutagenicity of a benzo[a]pyrene 7,8-diol 9,10-epoxide by riboflavin 5'-phosphate.
核黄素5'-磷酸酯对苯并[a]芘7,8-二醇9,10-环氧化物诱变性的抑制机制。
Proc Natl Acad Sci U S A. 1982 Sep;79(17):5122-6. doi: 10.1073/pnas.79.17.5122.
4
Inhibition of the mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: exceptional activity of ellagic acid.天然存在的植物酚类对多环芳烃湾区二醇环氧化物致突变性的抑制作用:鞣花酸的卓越活性。
Proc Natl Acad Sci U S A. 1982 Sep;79(18):5513-7. doi: 10.1073/pnas.79.18.5513.
5
Epoxidation of (+/-)-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene during (bi)sulfite autoxidation: activation of a procarcinogen by a cocarcinogen.(±)-7,8-二羟基-7,8-二氢苯并[a]芘在(亚)硫酸盐自氧化过程中的环氧化:一种辅致癌物对一种前致癌物的激活作用。
Proc Natl Acad Sci U S A. 1986 Oct;83(19):7499-502. doi: 10.1073/pnas.83.19.7499.
6
(+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo (a)pyrene: a potent skin carcinogen when applied topically to mice.(±)-反式-7,8-二羟基-7,8-二氢苯并(a)芘:局部应用于小鼠时是一种强效皮肤致癌物。
Proc Natl Acad Sci U S A. 1976 Nov;73(11):3867-71. doi: 10.1073/pnas.73.11.3867.
7
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.苯并[a]芘的代谢:(±)-反式-7,8-二羟基-7,8-二氢苯并[a]芘向高致突变性的7,8-二羟基-9,10-环氧化物的转化。
Proc Natl Acad Sci U S A. 1976 Oct;73(10):3381-5. doi: 10.1073/pnas.73.10.3381.
8
(+/-)-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.
9
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.苯并(a)芘的酶促转化主要通过单一异构体的r-7,t-8-二羟基-7,8-二氢苯并(a)芘生成二醇环氧化物r-7,t-8-二羟基-t-9,10-氧基-7,8,9,10-四氢苯并(a)芘。
Proc Natl Acad Sci U S A. 1976 Aug;73(8):2594-8. doi: 10.1073/pnas.73.8.2594.
10
Elucidation of hydrocarbon structure in an enzyme-catalyzed benzo[a]pyrene-poly (G) covalent complex.酶催化的苯并[a]芘-聚(G)共价复合物中烃结构的解析
Proc Natl Acad Sci U S A. 1976 May;73(5):1437-41. doi: 10.1073/pnas.73.5.1437.