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Original Articles

Possible role of 4′,4′′‐diethylstilbestrol quinone in diethylstilbestrol carcinogenesis

Pages 693-701 | Published online: 20 Oct 2009

References

  • Bachur , N. R. , Gordon , S. L. and Gee , M. V. 1978 . A general mechanism for microsomal activation of quinone anticancer agents to free radicals . Cancer Res. , 38 : 1745 – 1750 .
  • Chesis , P. L. , Levin , D. E. , Smith , M. T. , Ernster , L. and Ames , B. N. 1984 . Mutagenicity of quiñones: Pathways of metabolic activation and detoxification . Proc. Natl. Acad. Sci. U.S.A. , 81 : 1696 – 1700 .
  • Cohen , P. , Chiu , R. C. and Kidson , C. 1969 . Interactions of hormonal steroids with nucleic acids. II. Structural and thermodynamic aspects of binding . Biochemistry , 8 : 3603 – 3609 .
  • Corcoran , G. B. and Mitchell , J. R. 1982 . “ Evidence for redox cycling of acetaminophen and its reactive metabolite by endogenous microsomal systems ” . In Biological Reactive Intermediates, Part B, Chemical Mechanisms and Biological Effects , Edited by: Snyder , R. , Jollow , D. J. , Parke , D. V. , Gibson , G. G. , Kocsis , J. J. and Witmer , C. M. Vol. II , 1085 – 1097 . New York : Plenum .
  • Engel , L. L. , Weidenfeld , J. and Merriam , G. R. 1976 . Metabolism of diethylstilbestrol by rat liver: A preliminary report . J. Toxicol. Environ. Health, Suppl. , 1 : 37 – 44 .
  • Euler , H. and von Adler , E. 1944 . “ Überαß‐Dialkylstilbenchinone, neue synthetische Östrogene ” . In The Svedberg Memorial Volume 246 – 260 . Uppsala, , Sweden
  • Greenberg , E. R. , Barnes , A. B. , Resseguie , L. , Barrett , J. A. , Burnside , S. , Lanza , L. L. , Neff , R. K. , Stevens , M. , Young , R. H. and Colton , T. 1984 . Breast cancer in mothers given diethylstilbestrol in pregnancy . N. Engl. J. Med. , 311 : 1393 – 1398 .
  • Herbst , A. L. and Bern , H. A. , eds. 1981 . Developmental Effects of Diethylstilbestrol (DES) in Pregnancy , New York : Thieme‐Stratton .
  • Horning , E. C. , Thenot , J. P. and Helton , E. D. 1978 . Toxic agents resulting from the oxidative metabolism of steroid hormones and drugs . J. Toxicol. Environ. Health , 4 : 341 – 361 .
  • Hospital , M. , Busetta , B. , Bucourt , R. , Weintraub , H. and Baulieu , E. E. 1972 . X‐ray crystallography of estrogens and their binding to receptor sites . Mol. Pharmacol. , 8 : 438 – 445 .
  • Hospital , M. , Busetta , B. , Courseille , C and Precigoux , G. 1975 . X‐ray conformation of some estrogens and their binding to uterine receptors . J. Steroid Biochem. , 6 : 221 – 225 .
  • Irons , R. D. , Pfeifer , R. W. , Aune , T. M. and Pierce , C. W. 1984 . Soluble immune response suppressor (SIRS) inhibits microtubule function in vivo and microtubule assembly in vitro . J. Immunol. , 133 : 2032 – 2036 .
  • Keller , G. M. and Jefcoate , C. R. 1983 . Modulation of microsomal benzo(a)pyrene metabolism by DNA . Mol. Pharmacol. , 23 : 735 – 742 .
  • Kidson , C , Thomas , A. and Cohen , P. 1970 . Interactions of hormonal steroids with nucleic acids. III. Role of polymer structure . Biochemistry , 9 : 1571 – 1576 .
  • Kirkman , H. 1959 . Estrogen‐induced tumors of the kidney. III. Growth characteristics in the Syrian hamster . Natl. Cancer Inst. Monogr. , 1 : 1 – 57 .
  • Korach , K. S. , Sarver , P. J. , McLachlan , J. A. and Liehr , J. G. Receptor binding and hormonal activity of the catechols of diethylstilbestrol (DES) and other active metabolites . 7th Int. Cong. Endocrinol. July 1–7 1984 , Quebec City, Canada. pp. 785 Abstr.
  • Li , J. J. and Li , S. A. 1984 . Estrogen‐induced tumorigenesis in hamsters: Roles for hormonal and carcinogenic activities . Arch. Toxicol. , 55 : 110 – 118 .
  • Liehr , J. G. 1983 . 2‐Fluoroestradiol. Separation of estrogenicity from carcinogenicity . Mol. Pharmacol. , 23 : 278 – 281 .
  • Liehr , J. G. 1984 . Modulation of estrogen‐induced carcinogenesis by chemical modifications . Arch. Toxicol. , 55 : 119 – 122 .
  • Liehr , J. G. , DaGue , B. B. , Ballatore , A. M. and Sirbasku , D. A. 1982 . “ Multiple roles of estrogen in estrogen‐dependent renal clear‐cell carcinoma of Syrian hamster ” . In Cold Spring Harbor Conferences in Cell Proliferation , Edited by: Sato , G. H. , Pardee , A. B. and Sirbasku , D. A. 445 – 458 . Cold Spring Harbor, N.Y. : Cold Spring Harbor Laboratory .
  • Liehr , J. G. , DaGue , B. B. , Ballatore , A. M. and Henkin , J. 1983 . Diethylstilbestrol (DES) quinone: A reactive intermediate in DES metabolism . Biochem. Pharmacol. , 32 : 3711 – 3718 .
  • Liehr , J. G. , DaGue , B. B. and Ballatore , A. M. 1985a . Reactivity of 4’,4"‐diethylstilbestrol . Carcinogenesis , 6 : 829 – 836 .
  • Liehr , J. C. , Randerath , K. and Randerath , E. 1985b . Target organ‐specific covalent DNA damage preceding diethylstilbestrol‐induced carcinogenesis . Carcinogenesis , 6 : 1067 – 1069 .
  • Liehr , J. G. , Randerath , K. and Randerath , E. 1985c . Organ‐specific estrogen‐induced covalent DNA adducts preceding renal carcinogenesis in the Syrian hamster . Proc. Am. Assoc. Cancer Res. , 26 : 85
  • Lillehaug , J. R. and Djurhuus , R. 1982 . Effect of diethylstilbestrol on the transformable mouse embryo fibroblast C3H/10TV2 CI 8 cells. Tumor promotion, cell growth, DNA synthesis, and ornithine decarboxylase . Carcinogenesis , 3 : 797 – 799 .
  • Lown , J. W. 1983 . The mechanism of action of quinone antibiotics . Mol. Cell. Biochem. , 55 : 17 – 40 .
  • Metzler , M. 1982 . Diethylstilbestrol: Hormonal or chemical carcinogen . Trends Pharmacol. Sci. , 3 : 174 – 175 .
  • Metzler , M. and McLachlan , J. A. 1978a . “ Oxidative metabolism of diethylstilbestrol and steroidal estrogens as a potential factor in their fetotoxicity ” . In Role of Pharmacokinetic in Prenatal and Perinatal Toxicology , Edited by: Neubert , D. , Merker , H. J. , Nau , H. and Langman , J. 157 – 164 . Stuttgart : George Thieme .
  • Metzler , M. and McLachlan , J. A. 1978b . Peroxidase‐mediated oxidation, a possible pathway for metabolic activation of diethylstilbestrol . Biochem. Biophys. Res. Commun. , 85 : 874 – 884 .
  • Metzler , M. and McLachlan , J. A. 1979 . Diethylstilbestrol metabolic transformation in relation to organ specific tumor manifestation . Arch. Toxicol. , 2 ( [Suppl.] ) : 275 – 280 .
  • Miller , E. C. 1978 . Some current perspectives on chemical carcinogenesis in humans and experimental animals: Presidential address . Cancer Res. , 38 : 1479 – 1496 .
  • Murakami , M. and Fukami , J. 1983 . The binding of steroid hormones and diethylstilbestrol to proteins of human cells in culture . Arch. Toxicol. , 53 : 245 – 248 .
  • Neumann , H. G. 1976 . Dose‐dependent kinetics of diethylstilbestrol in the rat . J. Toxicol. Environ. Health , 1 ( [Suppl] ) : 61 – 76 .
  • Seiglie , C. A. , Liehr , J. G. and Albright , T. A. 1984 . The structure of 4’,4"‐diethylstilbestrol (DES) quinone . Steroids , 43 : 529 – 543 .
  • Siegfried , J. M. , Nelson , K. G. , Martin , J. L. and Kaufman , D. G. 1984 . Promotional effect of diethylstilbestrol on human endometrial stromal cells pretreated with a direct‐acting carcinogen . Carcinogenesis , 5 : 641 – 646 .
  • Slaga , T. J. , Klein‐Szanto , A. J. P. , Triplett , L. L. , Yotti , L. P. and Trosko , J. E. 1981 . Skin tumor promoting activity of benzoyl peroxide, a widely used free radical generating compound . Science , 213 : 1023 – 1025 .
  • Thor , H. , Smith , M. T. , Hartzell , P. , Bellomo , G. , Jewell , S. A. and Orrenius , S. 1982 . The metabolism of menadione (2‐methyl‐1,4‐naphthoquinone) by isolated hepatocytes. A study of the implications of oxidative stress in intact cells . J. Biol. Chem. , 257 : 12419 – 12425 .
  • Ts'o , P. O. P. and Lu , P. 1964 . Interaction of nucleic acids. I. Physical binding of thymine, adenine, steroids, and aromatic hydrocarbons to nucleic acids . Proc. Natl. Acad. Sci. U.S.A. , 51 : 17 – 24 .
  • Tsutsui , T. , Maizumi , H. , McLachlan , J. A. and Barrett , J. C. 1983 . Aneuploidy induction and cell transformation by diethylstilbestrol: A possible chromosomal mechanism in carcinogenesis . Cancer Res. , 43 : 3814 – 3821 .

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