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Chemical Compound Review

AG-H-95688     (8R,9S,13S,14S)-3,16- dihydroxy-13-methyl-7...

Synonyms: SureCN2310466, CTK5H8826, AR-1E8146, AC1L3G2Q, AC1Q6O9W, ...
 
 
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Disease relevance of Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-

 

High impact information on Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-

  • PURPOSE: The newly established mammary epithelial cell line C57/MG, derived from the C57BL mouse strain, was used to examine whether E2 or its metabolites, 16-hydroxyestrone (16 alpha-OHE1) and estriol (E3), function as initiators of mammary cell transformation [3].
  • Given the recent findings that human CYP3A7 is a polymorphic isoform also expressed in adult liver and certain extrahepatic tissues (in addition to fetal tissues), our data raise the possibility that CYP3A7 may be an important catalyst for the local and/or systemic formation of the procarcinogenic 16alpha-hydroxyestrone in women [4].
  • It is tempting to suggest that the fatty acid esters of the endogenous estrogens and their bioactive metabolites (e.g., 4-hydroxyestradiol and 16alpha-hydroxyestrone) may be of unique importance for stimulating cell growth and possibly also for inducing tumor formation in the fat-rich mammary tissues as compared with the uterus [5].
  • The human fetal osteoblastic cell line, hFOB/ER9, which expresses high levels of the estrogen receptor (ER) alpha, was used to examine the direct effects of 16alpha-hydroxyestrone (16alpha-OHE1) and 2-hydroxyestrone (2-OHE1) on osteoblast differentiation [6].
  • This would suggest that the human intestine (or intestinal contents) has the ability to carry out the transformation, 16alpha-hydroxyestrone leads to 15alpha-hydroxyestrone [7].
 

Chemical compound and disease context of Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-

 

Biological context of Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-

 

Anatomical context of Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-

 

Associations of Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy- with other chemical compounds

 

Gene context of Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-

 

Analytical, diagnostic and therapeutic context of Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-

References

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  2. Urinary estrogen metabolites and prostate cancer: a case-control study in the United States. Muti, P., Westerlind, K., Wu, T., Grimaldi, T., De Berry, J., Schünemann, H., Freudenheim, J.L., Hill, H., Carruba, G., Bradlow, L. Cancer Causes Control (2002) [Pubmed]
  3. Induction by estrogen metabolite 16 alpha-hydroxyestrone of genotoxic damage and aberrant proliferation in mouse mammary epithelial cells. Telang, N.T., Suto, A., Wong, G.Y., Osborne, M.P., Bradlow, H.L. J. Natl. Cancer Inst. (1992) [Pubmed]
  4. Human cytochrome P450 3A7 has a distinct high catalytic activity for the 16alpha-hydroxylation of estrone but not 17beta-estradiol. Lee, A.J., Conney, A.H., Zhu, B.T. Cancer Res. (2003) [Pubmed]
  5. Preferential growth stimulation of mammary glands over uterine endometrium in female rats by a naturally occurring estradiol-17beta-fatty acid ester. Mills, L.H., Lee, A.J., Parlow, A.F., Zhu, B.T. Cancer Res. (2001) [Pubmed]
  6. Direct action of naturally occurring estrogen metabolites on human osteoblastic cells. Robinson, J.A., Waters, K.M., Turner, R.T., Spelsberg, T.C. J. Bone Miner. Res. (2000) [Pubmed]
  7. Intestinal metabolism of estrogens. Adlercreutz, H., Martin, F., Pulkkinen, M., Dencker, H., Rimér, U., Sjöberg, N.O., Tikkanen, M.J. J. Clin. Endocrinol. Metab. (1976) [Pubmed]
  8. Is there an association between exposure to environmental estrogens and breast cancer? Safe, S.H. Environ. Health Perspect. (1997) [Pubmed]
  9. Estrogen metabolism and the malignant potential of human papillomavirus immortalized keratinocytes. Newfield, L., Bradlow, H.L., Sepkovic, D.W., Auborn, K. Proc. Soc. Exp. Biol. Med. (1998) [Pubmed]
  10. Regulation of cell cycle and cyclins by 16alpha-hydroxyestrone in MCF-7 breast cancer cells. Lewis, J.S., Thomas, T.J., Klinge, C.M., Gallo, M.A., Thomas, T. J. Mol. Endocrinol. (2001) [Pubmed]
  11. Association of CYP17, CYP19, CYP1B1, and COMT polymorphisms with serum and urinary sex hormone concentrations in postmenopausal women. Tworoger, S.S., Chubak, J., Aiello, E.J., Ulrich, C.M., Atkinson, C., Potter, J.D., Yasui, Y., Stapleton, P.L., Lampe, J.W., Farin, F.M., Stanczyk, F.Z., McTiernan, A. Cancer Epidemiol. Biomarkers Prev. (2004) [Pubmed]
  12. In vitro pro- and antioxidant properties of estrogens. Thibodeau, P.A., Kachadourian, R., Lemay, R., Bisson, M., Day, B.J., Paquette, B. J. Steroid Biochem. Mol. Biol. (2002) [Pubmed]
  13. Endocrine characteristics of human breast epithelial cells, MCF-10F. Singhal, H., Guo, L., Bradlow, H.L., Mittelman, A., Tiwari, R.K. Horm. Res. (1999) [Pubmed]
  14. Induction by estrogens of methotrexate resistance in MCF-7 breast cancer cells. Thibodeau, P.A., Bissonnette, N., Bédard, S.K., Hunting, D., Paquette, B. Carcinogenesis (1998) [Pubmed]
  15. Estrogens and autoimmune diseases. Cutolo, M., Capellino, S., Sulli, A., Serioli, B., Secchi, M.E., Villaggio, B., Straub, R.H. Ann. N. Y. Acad. Sci. (2006) [Pubmed]
  16. A hormonal association between estrogen metabolism and proliferative thyroid disease. Chan, E.K., Sepkovic, D.W., Yoo Bowne, H.J., Yu, G.P., Schantz, S.P. Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery. (2006) [Pubmed]
  17. Supplementation with flaxseed alters estrogen metabolism in postmenopausal women to a greater extent than does supplementation with an equal amount of soy. Brooks, J.D., Ward, W.E., Lewis, J.E., Hilditch, J., Nickell, L., Wong, E., Thompson, L.U. Am. J. Clin. Nutr. (2004) [Pubmed]
  18. Effects of dietary broccoli on human drug metabolising activity. Kall, M.A., Vang, O., Clausen, J. Cancer Lett. (1997) [Pubmed]
  19. CYP1A1 and CYP1B1 polymorphisms and their association with estradiol and estrogen metabolites in women who are premenopausal and perimenopausal. Sowers, M.R., Wilson, A.L., Kardia, S.R., Chu, J., McConnell, D.S. Am. J. Med. (2006) [Pubmed]
  20. Differential effects of 16alpha-hydroxyestrone and 2-methoxyestradiol on cyclin D1 involving the transcription factor ATF-2 in MCF-7 breast cancer cells. Lewis, J.S., Thomas, T.J., Pestell, R.G., Albanese, C., Gallo, M.A., Thomas, T. J. Mol. Endocrinol. (2005) [Pubmed]
  21. Epidemiological study of urinary 6beta-hydroxycortisol to cortisol ratios and breast cancer risk. Zheng, W., Jin, F., Dunning, L.A., Shu, X.O., Dai, Q., Wen, W.Q., Gao, Y.T., Holtzman, J.L. Cancer Epidemiol. Biomarkers Prev. (2001) [Pubmed]
  22. The effect of flaxseed and wheat bran consumption on urinary estrogen metabolites in premenopausal women. Haggans, C.J., Travelli, E.J., Thomas, W., Martini, M.C., Slavin, J.L. Cancer Epidemiol. Biomarkers Prev. (2000) [Pubmed]
  23. A new ELISA kit for measuring urinary 2-hydroxyestrone, 16alpha-hydroxyestrone, and their ratio: reproducibility, validity, and assay performance after freeze-thaw cycling and preservation by boric acid. Falk, R.T., Rossi, S.C., Fears, T.R., Sepkovic, D.W., Migella, A., Adlercreutz, H., Donaldson, J., Bradlow, H.L., Ziegler, R.G. Cancer Epidemiol. Biomarkers Prev. (2000) [Pubmed]
 
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