11
Views
33
CrossRef citations to date
0
Altmetric
Session: Steroids: Mechanisms, metabolism, and resulting toxicities

Toxic agents resulting from the oxidative metabolism of steroid hormones and drugs

, &
Pages 341-361 | Published online: 19 Oct 2009

References

  • Auterhoff , H. and Riethmüller , H‐J. 1972 . Die Farbreaction des Diäthylsilbostrols mit Vanillin . Arch. Pharm. (Weinheim) , 305 : 386 – 392 .
  • Beland , F. A. and Harvey , R. G. 1976 . The isomeric 9,10‐oxides of trans‐7,8‐dihydroxy‐7,8‐dihydrobenzo[a] pyrene . Chem. Commun. , : 84 – 85 .
  • Blackburn , M. G. , Thompson , M. H. and King , H. W. S. 1976 . Binding of diethylstilbestrol to deoxyribonucleic acid by rat liver microsomal fractions in vitro and in mouse foetal cells in culture . Biochem. J. , 158 : 643 – 646 .
  • Blackburn , M. G. , Orgee , L. and Williams , G. M. 1977 . Oxidative bonding of natural oestrogens to DNA by chemical and metabolic means . Chem. Commun. , 11 : 386 – 387 .
  • Bolt , H. M. , Kappus , H. and Remmer , H. 1973 . Studies on the metabolism of ethynylestradiol in vitro and in vivo: The significance of 2‐hydroxylation and the formation of polar products . Xenobiotica , 3 : 773 – 785 .
  • Bolt , H. M. , Kappus , H. and Kasbohrer , R. 1974 . Metabolism of 17α‐ethynylestradiol by human liver microsomes in vitro: Aromatic hydroxylation and irreversible protein binding of metabolites . J. Clin. Endocrinol. , 39 : 1072 – 1080 .
  • Brookes , P. and Lawley , P. D. 1964 . 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 (Lond) , 202 : 781 – 784 .
  • Chang , T. , Savory , A. and Glazko , A. J. 1970 . A new metabolite of 5,5‐diphenylhydantoin (Dilantin) . Biochem. Biophys. Res. Commun. , 38 : 444 – 449 .
  • Clayson , D. B. and Garner , R. C. 1976 . “ Carcinogenic aromatic amines ” . In Chemical Carcinogens , Edited by: Searle , C. E. 366 – 461 . Washington, D.C. : American Chemical Society .
  • Davies , I. J. , Naftolin , R. , Ryan , K. , Fishman , J. and Siu , J. 1975 . The affinity of catechol estrogens for estrogen receptors in the pituitary and anterior hypothalamus of the rat . Endocrinology , 97 : 554 – 557 .
  • Dipple , A. 1976 . “ Polynuclear aromatic carcinogens ” . In Chemical Carcinogens , Edited by: Searle , C. E. 245 – 314 . Washington, D.C. : American Chemical Society .
  • Dzidic , I. , Carroll , D. I. , Stillwell , R. N. and Horning , E. C. 1975 . Atmospheric pressure ionization (API) mass spectrometry: Formation of phenoxide ions from chlorinated aromatic compounds . Anal. Chem. , 47 : 1308 – 1312 .
  • Elce , J. S. 1972 . Metabolism of a glutathione conjugate of 2‐hydroxyestradiol‐17β in the adult male rat . Biochem. J. , 126 : 1067 – 1071 .
  • Elce , J. S. and Harris , J. 1971 . Conjugation of 2‐hydroxyestradiol‐17 β‐(i,3,5(10)‐estratriene‐ 2,3,17 β‐triol) with glutathione in the rat . Steroids , 18 : 584 – 591 .
  • Felton , J. S. , Nebert , D. W. and Thorgeirsson , S. S. 1976 . Genetic differences in 2‐acetylamino‐fluorene mutagenicity in vitro associated with mouse hepatic aryl hydrocarbon hydroxylase activity induced by polycyclic aromatic compounds . Mol. Pharmacol. , 12 : 225 – 233 .
  • Gelboin , H. V. 1969 . A microsome‐dependent binding of benzo [a] pyrene to DNA . Cancer Res. , 29 : 1272 – 1276 .
  • Hecker , E. and Marks , F. 1965 . Zum Stoffwechsel und Wirkungsmechanismus der Oestrogene. VII.Die o‐Hydroxylierung von Oestron in Rattenleber und ihre Beziehung zur Proteinbindung sowie zur p‐Hydroxylierung und zu Hydroxylierungen in aliphatischen Positionen . Blochem. Z. , 343 : 211 – 226 .
  • Helton , E. D. and Goldzieher , J. W. 1977 . Metabolism of ethynyl estrogens . J. Toxicol. Environ. Health , 3 : 231 – 242 .
  • Helton , E. D. , Williams , M. C. and Goldzieher , J. W. 1976 . Human urinary and liver conjugates of 17α‐ethynylestradiol . Steroids , 27 : 851 – 867 .
  • Helton , E. D. , Williams , M. C. and Goldzieher , J. W. 1977 . Oxidative metabolism and deethynylation of 17α‐ethynylestradiol by baboon liver microsomes . Steroids , 30 : 71 – 83 .
  • Herbst , A. L. and Scully , R. E. 1970 . Adenocarcinoma of the vagina in adolescence . Cancer , 25 : 745 – 757 .
  • Herbst , A. L. , Ulfelder , H. and Poskanzer , D. C. 1971 . Adenocarcinoma of the vagina: Association of maternal stilbestrol therapy with tumor appearance in young women . N. Engl. J. Med. , 284 : 878 – 881 .
  • Herbst , A. L. , Kurman , R. J. , Scully , R. E. and Poskanzer , D. C. 1972 . Clear‐cell adenocarcinoma of the genital tract in females. Registry report . N. Engl. J. Med. , 287 : 1259 – 1264 .
  • Herbst , A. L. , Robboy , S. J. , Scully , R. E. and Poskanzer , D. C. 1974 . Clear‐cell adenocarcinoma of the vagina and cervix in girls . Am. J. Obstet. Gynecol. , 119 : 713 – 724 .
  • Horning , M. G. , Stratton , C. , Wilson , A. , Horning , E. C. and Hill , R. M. 1971 . Detection of 5‐(3,4‐dihydroxy‐1,5‐cyclohexadien‐1‐yl)‐5‐phenylhydantoin as a major metabolite of 5,5‐diphenyl‐hydantoin (Dilantin) in the new born human . Anal. Lett. , 4 : 537 – 545 .
  • Horning , M. G. , Butler , C. M. , Stafford , M. , Stillwell , R. N. , Hill , R. M. , Zion , T. E. , Harvey , D. J. and Stillwell , W. G. 1976 . “ Metabolism of drugs by the epoxide‐diol pathway ” . In Advances in Mass Spectrometry in Biochemistry and Medicine , Edited by: Frigerio , A. and Castagnoli , N. vol. 1 , 91 – 108 . Holliswood, N.Y. : Spectrum .
  • Huberman , E. , Sachs , L. , Yang , S. K. and Gelboin , H. V. 1976 . Identification of mutagenic metabolites of benzo [a] pyrene in mammalian cells . Proc. Natl. Acad. Sci. U.S.A. , 73 : 607 – 611 .
  • Hulbert , P. B. 1975 . Carbonium ion as ultimate carcinogen of polycyclic aromatic hydrocarbons . Nature (Land) , 256 : 146 – 148 .
  • Ishikawa , K. and Griffin , G. W. 1977 . A complimentary route to anti‐1,2:3,4‐naphthalene diepoxide. Direct oxidation of arenes with m‐chloroperbenzoic acid . Angew. Chem. [Engl] , 16 : 171 – 172 .
  • Jeffrey , A. M. , Jennette , K. W. , Blobstein , S. H. , Weinstein , I. B. , Beland , F. A. , Harvey , R. G. , Kasai , H. , Miura , I. and Nakanishi , K. 1976 . Benzo [a] pyrene‐nucleic acid derivative found in vivo: Structure of a benzo [a] pyrene tetrahydrodiol epoxide‐guanosine adduct . J. Am. Chem. Soc. , 98 : 5714 – 5715 .
  • Jeffrey , A. M. , Weinstein , I. B. , Jennette , K. W. , Greskowiak , K. , Nakanishi , K. , Harvey , R. G. , Antrup , H. and Harris , C. 1977 . Structures of benzo [a] pyrene‐nucleic acid adducts formed in human and bronchial explants . Nature (Lond) , 269 : 348 – 350 .
  • Jellinck , P. H. and Fletcher , R. 1970 . Peroxidase‐catalyzed conjugation of [4–14 C]estradiol with albumin and thiols . Can. J. Biochem. , 48 : 1192 – 1198 .
  • Jellinck , P. H. and McNabb , T. 1977 . Metabolism of estradiol by uterine peroxidase: Nature of the water‐soluble products . Steroids , 29 : 525 – 537 .
  • Kappus , H. and Bolt , B. M. 1974 . Irreversible binding of ethynylestradiol to proteins and nucleic acids . Acta Endocrinol. (Kbh) , 75 : 184 – 185 .
  • King , H. W. S. , Thompson , M. H. and Brookes , P. 1975 . The benzo [a] pyrene deoxyribonucleoside products isolated from DNA after metabolism of benzo [a] pyrene by rat liver microsomes in the presence of DNA . Cancer Res. , 35 : 1263
  • King , H. W. S. , Osborne , M. R. , Beland , F. A. , Harvey , R. G. and Brookes , P. 1976 . (±)‐7α8β‐Dihydroxy‐9 β10β‐epoxy‐7,8,9,10‐tetrahydrobenzo [a] pyrene as an intermediate in the metabolism and binding to DNA of benzo[a] pyrene . Proc. Natl. Acad. Sci. U.S.A. , 73 : 2679 – 2681 .
  • Koreeda , M. , Moore , P. D. , Yagi , H. , Yeh , H. J. and Jerina , D. M. 1976 . Alkylation of polyguanylic acid at the 2‐amino group and phosphate by the potent mutagen (±)‐7β8α‐dihydroxy‐9β10β‐epoxy‐7,8,9,10‐tetrahydrobenzo [a] pyrene . J. Am. Chem. Soc. , 98 : 6720 – 6722 .
  • Kuss , E. 1971 . Microsomale Oxidation des Östradiols‐17β . Z. Physiol. Chem. , 352 : 817 – 836 .
  • Lawley , P. D. 1976 . “ Carcinogenesis by alkylating agents ” . In Chemical Carcinogens , Edited by: Searle , C. E. 83 – 244 . Washington, D.C. : American Chemical Society .
  • Marks , F. and Hecker , E. 1969 . Metabolism and mechanism of action of oestrogens. XII. Structure and mechanism of formation of water‐soluble and protein‐bound metabolites of oestrone in rat‐liver microsomes in vitro and in vivo . Biochim. Biophys. Acta , 187 : 250 – 265 .
  • Martucci , C. and Fishman , J. 1976 . Uterine estrogen receptor binding of catecholestrogens and estetrol (1,3,5(10)‐estratriene‐3,15α,16α,17β‐tetrol) . Steroids , 27 : 325 – 333 .
  • McCaustland , D. J. and Engel , J. F. 1975 . Metabolites of polycyclic aromatic hydrocarbons. II. Synthesis of 7,8‐dihydrobenzo [a] pyrene‐7,8‐diol and 7,8‐dihydrobenzo [a] pyrene‐7/8‐epoxide . Tetrahedron Lett. , 30 : 2549 – 2552 .
  • Meehan , T. , Straub , K. and Calvin , M. 1976 . Elucidation of hydrocarbon structure in an enzyme‐catalyzed benzo [a] pyrene‐poly (G) covalent complex . Proc. Natl. Acad. Sci. U.S.A. , 73 : 1437 – 1441 .
  • Meehan , T. , Straub , K. and Calvin , M. 1977 . Benzo [a] pyrene diol epoxide covalently binds to deoxyguanosine and deoxyadenosine in DNA . Nature (Lond) , 269 : 725 – 727 .
  • Metzler , M. 1975 . Metabolic activation of diethylstilbestrol: Indirect evidence for the formation of a stilbene oxide intermediate in hamster and rat . Biochem. Pharmacol. , 24 : 1449 – 1453 .
  • Metzler , M. 1976 . Metabolic activation of carcinogenic diethylstilbestrol in rodents and man . J. Toxicol. Environ. Health Suppl. , 1 : 21 – 35 .
  • Metzler , M. and McLachlan , J. A. Diethylstilbestrol: Its metabolism in fetal, neonatal and adult mice and the electrophilic reactivity of metabolites . Proceedings, 1st Annual International Congress on Toxicology . pp. 16
  • Miller , E. C. and Miller , J. A. 1976 . “ The metabolism of chemical carcinogens to reactive electrophiles and their possible mechanism of action in carcinogenesis ” . In Chemical Carcinogens , Edited by: Searle , C. E. 737 – 762 . Washington, D.C. : American Chemical Society .
  • Mitchell , J. R. and Jollow , D. J. 1975 . Metabolic activation of drugs to toxic substances. Progress in hepatology . Gastroenterology , 68 : 392 – 410 .
  • Mitchell , J. R. , Nelson , S. D. , Thorgeirsson , S. S. , McMurtry , R. J. and Dybing , E. 1976 . Metabolic activation: Biochemical basis for many drug‐induced liver injuries . Progr. Liver Dis. , 5 : 259 – 279 .
  • Mitchell , J. R. , McMurtry , R. J. , Statham , C. N. and Nelson , S. D. 1977 . Molecular basis for several drug‐induced nephropathies . Am. J. Med. , 62 : 518 – 526 .
  • Nakanishi , K. , Kasai , H. , Cho , H. , Harvey , R. G. , Jeffrey , A. M. , Jennette , K. W. and Weinstein , I. B. 1977 . Absolute configuration of a ribonucleic acid adduct formed in vivo by metabolism of benzo [a] pyrene . J. Am. Chem. Soc. , 99 : 258 – 260 .
  • Nelson , S. D. , Mitchell , J. R. , Dybing , E. and Sasame , H. A. 1976 . Cytochrome P450 mediated oxidation of 2‐hydroxyestrogens to reactive intermediates . Biochem. Biophys. Res. Commun. , 70 : 1157 – 1165 .
  • Nelson , S. D. , Boyd , M. R. and Mitchell , J. R. 1977 . “ Role of metabolic activation in chemical‐induced tissue injury ” . In Drug Metabolism Concepts , Edited by: Jerina , D. M. 155 – 185 . Washington, D.C. : American Chemical Society . no. 44
  • Oesch , F. 1972 . Mammalian epoxide hydrases: Inducible enzymes catalyzing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds . Xenobiotica , 3 : 305
  • Osborne , M. R. , Thompson , M. H. , Tarmy , E. M. , Beland , F. A. , Harvey , R. G. and Brookes , P. 1976 . The reaction of 7,8‐dihydro‐7,8‐dihydroxybenzo [a] pyrene‐DNA products isolated from cells . Chem. Biol. Interact. , 13 : 343 – 348 .
  • Paul , S. M. and Skolnick , P. 1977 . Catechol oestrogens inhibit oestrogen elicited accumulation of hypothalamic cyclic AMP suggesting role as endogenous anti‐oestrogens . Nature (Lond) , 266 : 559 – 561 .
  • Pott , P. 1775 . Chirurgical observations . Natl. Cancer Inst. Monogr. , 10 : 7 (1963)
  • Riegel , I. L. and Mueller , G. C. 1954 . Formation of protein‐bound metabolite of estradiol‐16‐l4 C by rat liver homogenates . J. Biol. Chem. , 210 : 249 – 257 .
  • Sims , P. , Grover , P. L. , Swaisland , A. , Pal , K. and Hewer , A. 1974 . Metabolic activation of benzo [a] pyrene proceeds by a diol‐epoxide . Nature (Lond) , 252 : 326 – 328 .
  • Stout , D. L. , Baptist , J. N. , Mattney , T. S. and Shaw , C. R. 1976 . N‐Hydroxy‐2‐aminofluorene: The principal mutagen produced from N‐hydroxy‐2‐acetylaminofluorene by a mammalian supernatant enzyme preparation . Cancer Lett. , 1 : 269
  • Szego , C. M. 1953 . The influence of the liver upon estrogen‐protein binding in vitro . Endocrinology , 52 : 669 – 678 .
  • Tsibris , J. C. M. and McGuire , P. M. 1977 . Microsomal activation of estrogens and binding to nucelic acids and proteins . Biochem. Biophys. Res. Commun. , 78 : 411 – 417 .
  • Weinstein , I. B. , Jeffrey , A. M. , Jennette , K. W. , Blobstein , S. H. , Harvey , R. G. , Harris , R. G. , Autrep , H. , Kasai , H. and Nakanishi , K. 1976 . Benzo [a] pyrene diol epoxides as intermediates in nucleic acid binding In vitro and in vivo . Science , 193 : 592 – 595 .
  • Williams , J. G. and Williams , K. I. H. 1975 . Metabolism of 2–3 H and 4–14 C‐17α‐ethynylestradiol 3‐methyl ether (mestranol) by women . Steroids , 26 : 707 – 720 .
  • Williams , M. C. , Helton , E. D. and Goldzieher , J. W. 1975 . The urinary metabolites of 17α‐ethynylestradiol‐9α11–3H in women. Chromatographic profiling and identification of ethynyl and non‐ethynyl compounds . Steroids , 25 : 229 – 245 .
  • Williams , R. T. 1947 1959 . Detoxication Mechanisms. , (1st ed), (2d ed) , London : Chapman and Hill .
  • Yagi , H. , Hernandez , O. and Jerina , D. M. 1975 . Synthesis of (±)‐7β8α‐dihydroxy‐9β10β‐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. , 97 : 6881 – 6883 .
  • Yagi , H. , Thacker , D. R. , Hernandez , O. , Koreeda , M. and Jerina , D. M. 1977 . Synthesis and reactions of the highly mutagenic 7,8‐diol‐9,10‐epoxides of the carcinogen benzo[a]pyrene . J. Am. Chem. Soc. , 99 : 1604 – 1611 .
  • Yang , S. K. and Gelboin , H. V. 1976 . Microsomal mixed‐function oxidases and epoxide hydratase convert benzo [a] pyrene stereospecifically to optically active dihydroxydihydrobenzo [a] pyrenes . Biochem. Pharmacol. , 25 : 2221 – 2225 .
  • Yang , S. K. , McCourt , D. W. , Roller , P. P. and Gelboin , H. V. 1976 . 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. , 73 : 2594 – 2598 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.