Synthesis and biological evaluation of 4-(Hydroxyalkyl)estradiols and related compounds

Journal of Medicinal Chemistry

Volumn 40, Issue 23, 1997, Pages 3756-3764

  Lovely, Carl J ^a,b   Bhat, Abhijit S ^a   Coughenour, Holly D ^a   Gilbert, Nancy E ^a   Brueggemeier, Kobert W ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYESTRADIOL; ESTRADIOL DERIVATIVE; ESTRADIOL RECEPTOR;

ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG OXIDATION; DRUG SYNTHESIS; ESTROGEN ACTIVITY; HORMONE RECEPTOR INTERACTION; HUMAN; HUMAN CELL; RECEPTOR AFFINITY; RECEPTOR DENSITY; STRUCTURE ANALYSIS;

ADENOCARCINOMA; BREAST NEOPLASMS; CELL DIVISION; ESTRADIOL; ESTROGENS, CATECHOL; HUMANS; KINETICS; NEOPLASMS, HORMONE-DEPENDENT; RECEPTORS, ESTROGEN; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0030730055     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9701684     Document Type: Article

References (25)

1. Cancer Facts and Figures; American Cancer Society: 1996.
2. Henderson, B. E.; Ross, R. K.; Pike, M. C. Toward the primary prevention of cancer. Science 1991, 254, 1131-1138.
3. American Cancer Society Textbook of Clinical Oncology; The American Cancer Society: Atlanta, GA, 1991; pp 177-194.
4. Newbold, R. R.; Bullock, B. C.; McLachlan, J. A. Uterine adenocarcinoma in mice following developmental treatment with estrogens: a model for hormonal carcinogenesis. Cancer Res. 1990, 50, 7677-7681.
5. Fishman, J. A. Aromatic Hydroxylation of Estrogens. Ann. Rev. Physiol. 1983, 45, 61-72.
6. Liehr, J. G.; Roy, D. Free radical generation by redox cycling of estrogens. Free Radical Biol. Med. 1990, 8, 415-423.
7. Kalyanaraman, B.; Sealy, R. C.; Liehr, J. G. Characterization of semiquinone free radicals formed from stilbene catechol estrogens. An ESR spin stabilization and spin trapping study. J. Biol. Chem. 1989,264, 11014-11019.
8. Gladek, A.; Liehr, J. G. Mechanism of genotoxicity of diethylstilbestrol in vivo. J. Biol. Chem. 1989, 264, 16847-16852.
9. Epe, B.; Harttig, U.; Stopper, H.; Metzler, M. Covalent binding of reactive estrogen metabolites to microtubular protein as a possible mechanism of aneuploidy induction and neoplastic cell transformation. Environ. Health Perspect. 1990, 88, 123-127.
10. Roy, D.; Floyd, R. A.; Liehr, J. G. Elevated 8-hydroxydeoxyguanosine levels in DNA of diethylstilbestrol-treated Syrian hamsters: covalent DNA damage by free radicals generated by redox cycling of diethylstilbestrol. Cancer Res. 1991, 51, 3882-3885.
11. Nutter, L. M.; Zhou, B.; Sierra, E. E.; Wu, Y. Y.; Rummel, AI. AI.; Gutierrez, P.; Abul-Hajj, Y. Cellular biochemical determinants modulating the metabolism of estrone 3,4-quinone. Chem. Res. Toxicol. 1994, 7, 609-613.
12. Han, X.; Lichr, J. G. Microsome-mediated 8-hydroxylation of guanine bases of DNA by steroid estrogens: correlation of DNA damage by free radicals with metabolic activation to quinones. Carcinogenesis 1995, 16, 2571-2574.
13. Li, Y.; Trush, M. A.; Yager, J. D. DNA damage caused by reactive oxygen species originating from a copper-dependent oxidation of the 2-hydroxy catechol of estradiol. Carcinogenesis 1994,15, 1421-1427.
14. Toyokuni, S.; Okamoto, K.; Yodoi, J.; Hiai, H. Persistent oxidative stress in cancer. FEES Lett. 1995, 358, 1-3.
15. Liehr, J. G.; Ricci, M. J. 4-HydroxyIation of estrogens as marker of human mammary tumors. Proc. Natl. Acad. Sci. U.SA. 1996, 93, 3294-3296.
16. Li J. J.; Li, S. A. Estrogen Carcinogenesis in hamster tissues: a critical review. Endocrine Hev. 1990, 11, 524-531.
17. Paria, B. C.; Chakraborty, C.; Dey, S. K. Catechol estrogen formation in mouse uterus and its role in implantation. Mol. Cell. Endocrinol. 1990, 69, 25-32.
18. Weisz, J.; Bui, Q. D.; Roy, D.; Liehr, J. G. Elevate 4-hydroxylation of estradiol by hamster kidney microsomes: a potential pathway of metabolic activation of estrogens. Endocrinology 1992, 131, 655-661.
19. Li, Y.; Trush, M. A. Reactive oxygen-dependent DNA damage resulting from the oxidation of phenolic compounds by a copper-redox cycle mechanism. Cancer Res. 1994, 54, 1895s-1898s.
20. Lovely, C. J.; Gilbert, N. E.; Liberto, M. M.; Sharp, D. W.; Lin, Y. C.; Brueggemeier, R. W. 2-(Hydroxyalkyl)estradiols: synthesis and biological evaluation. J. Med. Chem. 1996,39, 1917-1923.
21. Lovely, C. J.; Brueggemeier, R. W. Synthesis of 2-substituted hydroxyalkyl and amino alkylestradiols. Tetrahedron Lett. 1994, 35, 8735-8738.
22. Pert, D. J.; Ridley, D. D. Formylation of Oestrogens. Aust. J. Chem. 1989, 42, 405-419.
23. Stille, J. K. The Palladium catalyzed coupling reactions of organotin reagents with organic electrophiles. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
24. Brown, A. M. C.; Jeltsch, J.-M.; Roberts, M.; Chambon, P. Activation of pS2 gene transcription is a primary response to estrogen in the human breast cancer cell line MCF-7. Proc. Nail. Acad. Sci. U.SA. 1984, 81, 6344-6348.
25. Gilbert, N. E.; O'Reilly, J. E.; Chang, C. J. G.; Lin, Y. C.; Brueggemeier, R. W. Antiproliferative activity of gossypol and gossypolone on human' breast cancer cells. Life Sci. 1995, 57, 61-67.