二苯并[a,h]蒽（±）反式-1,2-二氢二醇和屈（±）反式-3,4-二氢二醇向邻位二氢二醇环氧化物的代谢转化。
Metabolic conversion of dibenz[a,h]anthracene (+/-)trans-1,2-dihydrodiol and chrysene (+/-)trans-3,4-dihydrodiol to vicinal dihydrodiol epoxides.
作者信息
Chou M W, Fu P P, Yang S K
出版信息
Proc Natl Acad Sci U S A. 1981 Jul;78(7):4270-3. doi: 10.1073/pnas.78.7.4270.
Abstract
The hydroxyl groups of dibenz[a,h]anthracene trans-1,2-dihydrodiol and chrysene trans-3,4-dihydrodiol are known to be predominantly in quasi-axial conformations. These dihydrodiols were metabolized by liver microsomes from 3-methylcholanthrene-pretreated rats to form 1,2,3,4-tetrahydrotetrols as the major products. The major metabolites of the dihydrodiols were isolated by reversed-phase high-performance liquid chromatography and identified by ultraviolet--visible absorption and mass spectral analyses. The results indicate that axial hydroxyl groups of dibenz[a,h]anthracene trans-1,2-dihydrodiol and of chrysene trans-3,4-dihydrodiol do not direct metabolism away from their respective vicinal double bond.
摘要
已知二苯并[a,h]蒽反式-1,2-二氢二醇和屈反式-3,4-二氢二醇的羟基主要处于准轴向构象。这些二氢二醇由经3-甲基胆蒽预处理大鼠的肝微粒体代谢，形成1,2,3,4-四氢四醇作为主要产物。通过反相高效液相色谱法分离二氢二醇的主要代谢产物，并通过紫外-可见吸收和质谱分析进行鉴定。结果表明，二苯并[a,h]蒽反式-1,2-二氢二醇和屈反式-3,4-二氢二醇的轴向羟基不会使代谢偏离其各自的邻位双键。
相似文献
1
Metabolic conversion of dibenz[a,h]anthracene (+/-)trans-1,2-dihydrodiol and chrysene (+/-)trans-3,4-dihydrodiol to vicinal dihydrodiol epoxides.二苯并[a,h]蒽（±）反式-1,2-二氢二醇和屈（±）反式-3,4-二氢二醇向邻位二氢二醇环氧化物的代谢转化。
Proc Natl Acad Sci U S A. 1981 Jul;78(7):4270-3. doi: 10.1073/pnas.78.7.4270.
2
The formation of dihydrodiols in the chemical or enzymic oxidation of dibenz[a,c]anthracene, dibenz[a,h]-anthracene and chrysene.二苯并[a,c]蒽、二苯并[a,h]蒽和芘在化学或酶促氧化过程中形成二氢二醇。
Chem Biol Interact. 1979 Oct;27(2-3):365-79. doi: 10.1016/0009-2797(79)90139-x.
3
The effect of enzyme induction on the stereoselective metabolism of optically pure (-)1R,2R- and (+)1S,2S-dihydroxy-1,2-dihydrobenz-[a]anthracenes to vicinal 1,2-dihydrodiol 3,4-epoxides by rat liver microsomes.酶诱导对大鼠肝微粒体将光学纯的(-)1R,2R-和(+)1S,2S-二羟基-1,2-二氢苯并[a]蒽立体选择性代谢为邻位1,2-二氢二醇3,4-环氧化物的影响。
Carcinogenesis. 1983;4(5):629-38. doi: 10.1093/carcin/4.5.629.
4
Microsomal metabolism of picene.苝的微粒体代谢
Chem Biol Interact. 1988;66(3-4):157-75. doi: 10.1016/0009-2797(88)90069-5.
5
Metabolism of the bay-region trans-1,2-dihydrodiol of benz[a]anthracene in rat liver microsomes occurs primarily at the 3,4-double bond.大鼠肝脏微粒体中苯并[a]蒽的湾区反式-1,2-二氢二醇的代谢主要发生在3,4-双键处。
Carcinogenesis. 1980 Sep;1(9):803-6. doi: 10.1093/carcin/1.9.803.
6
7
Regio- and stereoselective metabolism of dibenz[a,h]anthracene: identification of 12 new microsomal metabolites.二苯并[a,h]蒽的区域和立体选择性代谢：12种新的微粒体代谢产物的鉴定
Mol Pharmacol. 1987 Nov;32(5):710-22.
8
Synthesis of fjord region tetraols and their use in hepatic biotransformation studies of dihydrodiols of benzo[c]chrysene, benzo[g]chrysene and dibenzo[a,l]pyrene.峡湾地区四醇的合成及其在苯并[c]芘、苯并[g]芘和二苯并[a,l]芘二氢二醇肝生物转化研究中的应用。
Carcinogenesis. 1998 Apr;19(4):639-48. doi: 10.1093/carcin/19.4.639.
9
Metabolism of 6-methylbenz[a]anthracene by rat liver microsomes and mutagenicity of metabolites.大鼠肝脏微粒体对6-甲基苯并[a]蒽的代谢及其代谢产物的致突变性
Cancer Res. 1985 Sep;45(9):4006-14.
10
Stereoselective metabolism of chrysene by rat liver microsomes. Direct separation of diol enantiomers by chiral stationary phase h.p.l.c.大鼠肝脏微粒体对chrysene的立体选择性代谢。通过手性固定相高效液相色谱法直接分离二醇对映体。
Carcinogenesis. 1986 Jul;7(7):1221-30. doi: 10.1093/carcin/7.7.1221.
引用本文的文献
1
Urinary and faecal excretion of chrysene and chrysene metabolites by rats after oral, intraperitoneal, intratracheal or intrapulmonary application.
Arch Toxicol. 1988;62(6):401-5. doi: 10.1007/BF00288341.
本文引用的文献
1
Protein measurement with the Folin phenol reagent.使用福林酚试剂进行蛋白质测定。
J Biol Chem. 1951 Nov;193(1):265-75.
2
Metabolism of the bay-region trans-1,2-dihydrodiol of benz[a]anthracene in rat liver microsomes occurs primarily at the 3,4-double bond.大鼠肝脏微粒体中苯并[a]蒽的湾区反式-1,2-二氢二醇的代谢主要发生在3,4-双键处。
Carcinogenesis. 1980 Sep;1(9):803-6. doi: 10.1093/carcin/1.9.803.
3
Metabolism of (-)-trans-(3R, 4R)-dihydroxy-3,4-dihydrochrysene to diol epoxides by liver microsomes.
Biochem Biophys Res Commun. 1981 Feb 27;98(4):961-9. doi: 10.1016/0006-291x(81)91204-3.
4
The metabolism of a series of polycyclic hydrocarbons by mouse skin maintained in short-term organ culture.
Chem Biol Interact. 1980 Feb;29(2):169-88. doi: 10.1016/0009-2797(80)90031-9.
5
Qualitative and quantitative studies on the metabolism of a series of aromatic hydrocarbons by rat-liver preparations.关于大鼠肝脏制剂对一系列芳烃代谢的定性和定量研究。
Biochem Pharmacol. 1970 Mar;19(3):795-818. doi: 10.1016/0006-2952(70)90243-1.
6
Polycyclic hydrocarbon epoxides: the involvement of 8,9-dihydro-8,9-dihydroxybenz (a) anthracene 10,11-oxide in reactions with the DNA of benz (a) anthracene-treated hamster embryo cells.
FEBS Lett. 1974 Oct 1;47(1):34-8. doi: 10.1016/0014-5793(74)80420-5.
7
Substrate-inducible microsomal aryl hydroxylase in mammalian cell culture. I. Assay and properties of induced enzyme.哺乳动物细胞培养中底物诱导的微粒体芳基羟化酶。I. 诱导酶的测定及特性
J Biol Chem. 1968 Dec 10;243(23):6242-9.
8
8,9-Dihydro-8,9-dihydroxybenz(a)anthracene 10,11-oxide: a new type of polycyclic aromatic hydrocarbon metabolite.
FEBS Lett. 1974 Oct 1;47(1):30-3. doi: 10.1016/0014-5793(74)80419-9.
9
Different pathways involved in the metabolism of the 7,8- and 9,10-dohydrodiols of benzo(a)pyrene.
Biochem Pharmacol. 1976 Apr 15;25(8):979-80. doi: 10.1016/0006-2952(76)90326-9.
10
Relationships between carcinogenicity and theoretical reactivity indices in polycyclic aromatic hydrocarbons.
Cancer Res. 1978 Sep;38(9):2968-77.
Zotero 插件