Skip to main content
SpringerLink
Log in
Book cover

Estrogens and Antiestrogens I pp 223–242Cite as

Estrogen Transforming Enzymes

  • Chapter

  • 252 Accesses

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 135 / 1))

Abstract

Estrogens are synthesized in glandular and extraglandular tissues and exert their biological effects by interacting with the estrogen receptor (ER) which is located mainly within the cell nucleus. Estradiol, the estrogen that binds to the ER with highest affinity, therefore, has to cross the cell membrane and cytoplasm in order to reach the nucleus. The biochemical and molecular events that govern this process remain obscure. However, there is a growing awareness that the enzymes involved in the cellular synthesis and metabolism of estrogens may have a crucial role in regulating the availability of estradiol to interact with the ER (Stewart and Sheppard 1992). Thus, estrogen metabolism, rather than just being viewed as a process which ultimately renders estrogens water soluble prior to their excretion, is now considered to be an important mechanism which contributes to the regulation of cellular estrogen concentrations. It has been postulated that the cytochrome P450 monooxygenases and other steroid metabolizing enzymes act to regulate the steady-state concentrations of ligands, such as estrogens, which are important in growth and development (Nebert 1991). In keeping with this concept, it is now apparent that the formation of estrogen sulphates and lipoidal estrogens, rather than being end products of metabolism, results in the formation of storage forms of estrogens, which can be activated by the appropriate enzymes. The major pathways of estrogen metabolism are shown in Fig. 1.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Abul-Hajj Y, Nurieddin A (1983) Significance of lipoidal estradiol in human mammary tumours. Steroids 42:417–426.

    Article  PubMed  CAS  Google Scholar 

  • Adams JB, Hall RT, Nott S (1986) Esterification-deesterification of estradiol by human mammary cancer cells in culture. J Steroid Biochem 24:1159–1162.

    Article  PubMed  CAS  Google Scholar 

  • Adams JB, Phillips NS, Hall RS (1988) Metabolic fate of estradiol in human mammary cancer cells in culture: estrogen sulfate formation and cooperativity exhibited by estrogen sulfotransferase. Molec Cell Endocrinol 58:231–242.

    Article  PubMed  CAS  Google Scholar 

  • Adlercreutz H, Gorback SL, Goldin BR, Woods MN, Dwyer JT, Hamalainen E (1994) Estrogen metabolism and excretion in Oriental and Caucasian women. J Natl Cancer Inst 86:1076–1082.

    Article  PubMed  CAS  Google Scholar 

  • Adlercreutz H, Luukainen T (1967) Biochemical and clinical aspects of the enterohepatic circulation of estrogens. Acta Endocrinol Copenh (Suppl 124):101-140.

    Google Scholar 

  • Akinola LA, Poutanen M, Vihko R, Vihko P (1997) Expression of 17β-hydroxysteroid dehydrogenase type 1 and Type 2, P450 aromatase, and 20α-hydroxysteroid dehydrogenase enzymes in immature, mature and pregnant rats. Endocrinology 138:2886–2892.

    Article  PubMed  CAS  Google Scholar 

  • Anderson EA, Howell A (1995) Estrogen sulphotransferases in malignant and normal human breast tissue. Endocr-Rel Cancer 2:227–233.

    Article  CAS  Google Scholar 

  • Anderson E, Roebuck Q, Oojageer A, Howell A (1996) Estrogen inactivation by human breast epithelial cells. Breast Cancer Res Treat 41:(Abstr 323).

    Google Scholar 

  • Anderson KE, Kappas A, Conney AH, Bradlow HL, Fishman J (1984) The influence of dietary protein and carbohydrate on the principal oxidative biotransformations of estradiol in normal subjects. J Clin Endocrinol Metab 59:103–107.

    Article  PubMed  CAS  Google Scholar 

  • Andersson S (1995) 17β-Hydroxysteroid dehydrogenase: isoenzymes and mutations. J Endocrinol 146:197–200.

    Article  PubMed  CAS  Google Scholar 

  • Ardevol A, Virili J, Sanchis D, Adan C, Fernandez-Real JM, Fernandez-Lopez JA, Remesar X, Alemany M (1997) A method for the measurement of plasma estrone fatty ester levels. Analyt Biochem 249:247–250.

    Article  PubMed  CAS  Google Scholar 

  • Back DJ, Stevenson P, Tjia JF (1989) Comparative effects of two antimycotic agents ketoconazole and terbinafine on metabolism of tolbutamide, ethinyloestradiol and ethoxycoumarin by human liver microsomes in vitro. Br J Clin Pharmac 28:166–170.

    Article  CAS  Google Scholar 

  • Ball P, Knuppen R (1990) Formation, metabolism and physiologic importance of catechol estrogens. Am J Obstet Gynec 163:2163–2170.

    PubMed  CAS  Google Scholar 

  • Borg W, Shackleton CHL, Pahuja SL, Hochberg RB (1995) Long-lived testosterone esters in the rat. Proc Natl Acad Sci USA 92:1545–1549.

    Article  PubMed  CAS  Google Scholar 

  • Bradlow HL, Davis DL, Lin G, Sepkovic D, Tiwari R (1995) Effects of pesticides on the ratio of 16α/2-hydroxyestrone: a biological marker of breast cancer risk. Environ Health Perspect (Suppl 103):147-150.

    Google Scholar 

  • Bradlow HL, Michnovicz JJ, Telang NT, Osborne MP (1991) Effect of dietary indole-3-carbinol on estradiol metabolism and spontaneous tumours in mice. Carcinogenesis 12:1571–1574.

    Article  PubMed  CAS  Google Scholar 

  • Bradlow HL, Spkovic DW, Telang NT, Osborne MP (1995) Indole-3-carbinol: a novel approach to breast cancer prevention. Ann NY Acad Sci 728:180–200.

    Article  Google Scholar 

  • Bradlow HL, Telang NT, Sepkovic DW, Osborne MP (1996) 2-Hydroxyestrone: the ‘good’ estrogen. J Endocrinol 150:S259–S265.

    PubMed  CAS  Google Scholar 

  • Buirchell BJ, Hahnel R (1975) Metabolism of estradiol-17β in human endometrium during the menstrual cycle. J Steroid Biochem 6:1489–1494.

    Article  PubMed  CAS  Google Scholar 

  • Bush TL, Barrett-Conner E (1985) Noncontraceptive estrogen use and cardiovascular disease. Epidemiol Rev 7:80–104.

    Google Scholar 

  • Casey ML, MacDonald PC, Andersson S (1994) 17β-Hydroxysteroid dehydrogenase type 2: chromosomal assignment and progestin regulation of gene expression in human endometrium. J Clin Invest 94:2135–2141.

    Article  PubMed  CAS  Google Scholar 

  • Cassidenti DL, Vrjod AG, Vijod MA, Stanczyk FZ, Lobo RA (1990) Short-term effects of smoking on the pharmacokinetic profiles of micronized estradiol in postmenopausal women. Am J Obstet Gynecol 163:1953–1960.

    PubMed  CAS  Google Scholar 

  • Clarke CL, Adams JB, Wren BG (1982) Induction of estrogen sulphotransferase activity in the human endometrium by progesterone in organ culture. J Clin Endocrinol Metab 55:70–75.

    Article  PubMed  CAS  Google Scholar 

  • Coker AL, Coker MM, Sticca RP, Sepkovic DW (1997) Re: Ethnic differences in estrogen metabolism in healthy women. J Natl Cancer Inst 89:89.

    Article  PubMed  CAS  Google Scholar 

  • Falany JL, Falany CN (1996) Expression of cytosolic sulfotransferases in normal mammary epithelial cells and breast cancer cell lines. Cancer Res 56:1551–1555.

    PubMed  CAS  Google Scholar 

  • Fishman J, Boyar RM, Hellman L (1975) Influence of body weight on estradiol metabolism in young women. J Clin Endocrinol Metab 41:989–991.

    Article  PubMed  CAS  Google Scholar 

  • Fishman J, Hellman L, Zumoff B, Gallagher TF (1965) Effect of thyroid on hydroxylation of estrogen in man. J Clin Endocrinol Metab 25:365–368.

    Article  PubMed  CAS  Google Scholar 

  • Goebelsmann U, Chen L-C, Saga M, Nakamura RM, Jaffe RB (1973) Plasma concentrations and protein binding of oestriol and its conjugates in pregnancy. Acta Endocrinol Copenh 74:592–604.

    PubMed  CAS  Google Scholar 

  • Gurpide E, Tseng L, Gusberg SB (1977) Estrogen metabolism in normal and neoplastic endometrium. Am J Obstet Gynecol 129:809–816.

    PubMed  CAS  Google Scholar 

  • Hayes CL, Spink DC, Spink BC, Cao JQ, Walker NJ, Sutter TR (1996) 17β-Estradiol hydroxylation catalysed by human cytochrome P450 1B1. Proc Natl Acad Sci USA 93:9776–9781.

    Article  PubMed  CAS  Google Scholar 

  • Hobkirk R, Green RN, Nilsen M, Jennings BA (1974) Direct conversion of 17β-estradiol-3-glucosiduronate and 17β-estradiol-3-sulfate to their keto forms by human kidney homogenates. Can J Biocem 52:15–20.

    Article  CAS  Google Scholar 

  • Hobkirk R, Nilsen M (1970) Metabolism of estrone-3-glucosiduronate and 17β-estra-diol-3-glucosiduronate on the human female. Steroids 15:649–667.

    Article  PubMed  CAS  Google Scholar 

  • Hobkirk R, Mellor JD, Nilsen M (1975) In vitro metabolism of 17β-estradiol by human liver tissue. Can J Biochem 53:903–906.

    Article  PubMed  CAS  Google Scholar 

  • Hochberg RB, Bandy L, Ponticorvo L, Welch M, Leiberman S (1979) Naturally occurring lipoidal derivatives of 3β-hydroxy-5-pregnen-20-one; 3β,17β-dihydroxy-5-pregnen-20-one and 3β-hydroxy-5-androsten-17-one. J Steroid Biochem 11:333–340.

    Article  Google Scholar 

  • James VHT, Reed MJ (1980) Steroid hormones and human cancer. Prog Cancer Res Ther 14:471–487.

    CAS  Google Scholar 

  • Kerlan V, Dreano Y, Bercovici JP, Beaunne PH, Floch HH, Berthou F (1992) Nature of cytochromes P450 involved in the 2-/4-hydroxylations of estradiol in human liver microsomes. Biochem Pharmacol 44:1745–1756.

    Article  PubMed  CAS  Google Scholar 

  • Krozowski Z (1992) 11β-Hydroxysteroid dehydrogenase and the short-chain alcohol dehydrogenase (SCAD) superfamily. Molec Cell Endocrinol 84:C25–C31.

    Article  PubMed  CAS  Google Scholar 

  • Krozowski Z (1994) The short-chain alcohol dehydrogenase superfamily: variations on a common theme. J Steroid Biochem Molec Biol 51:125–130.

    Article  PubMed  CAS  Google Scholar 

  • Lesko SM, Rosenberg L, Kaufman DW, Helmrich SP, Miller DR, Strom B, Schottenfeld D, Rosenshein NB, Knapp RC, Lewis J, et al. (1985) Cigarette smoking and the risk of endometrial cancer. N Engl J Med 313:593–596.

    Article  PubMed  CAS  Google Scholar 

  • Liehr JG (1990) Genotoxic effects of estrogens. Mutat Res 238:269–276.

    Article  PubMed  CAS  Google Scholar 

  • Liehr JC, Ricci MJ, Jefcoate CR, Hannigan EV, Hokanson JA, Zhu BT (1995) 4-Hydroxylation of estradiol by human uterine myometrium and myoma microsomes: implications for the mechanism of uterine tumourigenesis. Proc Natl Acad Sci USA 92:9220–9224.

    Article  PubMed  CAS  Google Scholar 

  • Lim SK, Won YJ, Lee JH, Kwon SH, Lee EJ, Kim KR, Lee HC, Huh KB, Chung BC (1997) Altered hydroxylation of estrogen in patients with postmenopausal osteoporosis. J Clin Endocrinol Metab 82:1001–1006.

    Article  PubMed  CAS  Google Scholar 

  • Larner JM, Hochberg RB (1985b) The clearance and metabolism of estradiol-17-esters in the rat. Endocrinology 117:1209–1214.

    Article  PubMed  CAS  Google Scholar 

  • Larner JM, Pahuja SL, Brown VM, Hochberg RB (1992) Aromatase and testosterone fatty acid esters: the search for a cryptic biosynthetic pathway of estradiol esters. Steroids 57:475–479.

    Article  PubMed  CAS  Google Scholar 

  • Larner JM, Pahuja SL, Shackleton CH, McMurray WJ, Giordano G, Hochberg RB (1993) The isolation and characterization of estradiol — fatty acid esters in human ovarian follicular fluid. J Biol Chem 268:13893–13899.

    PubMed  CAS  Google Scholar 

  • Larner JM, MacLusky NJ, Hochberg RB (1985a) The naturally occurring C-17 fatty acid esters of estradiol are long-acting estrogens. J Steroid Biochem 22:407–413.

    Article  PubMed  CAS  Google Scholar 

  • Larner JM, Shackleton CHL, Roitman E, Schwartz PE, Hochberg RB (1992) Measurement of estradiol-17-fatty acid esters in human tissues. J Clin Endocrinol Metab 75:195–200.

    Article  PubMed  CAS  Google Scholar 

  • Longcope C (1990) Relationship of estrogen to breast cancer, of diet to breast cancer, and of diet to estradiol metabolism. J Natl Cancer Inst 82:896–897.

    Article  PubMed  CAS  Google Scholar 

  • Longcope C, Johnston CC (1988) Androgen and estrogen dynamics in pre-and postmenopausal women: a comparison between smokers and non-smokers. J Clin Endocrinol Metab 67:379–383.

    Article  PubMed  CAS  Google Scholar 

  • Longcope C, Gorbach S, Goldin B, Woods M, Dwyer J, Morrill A, Warram J (1987) The effect of a low fat diet on estrogen metabolism. J Clin Endocrinol Metab 64:1246–1250.

    Article  PubMed  CAS  Google Scholar 

  • Mancini MA, Song CS, Rao TR, Chatterjee B, Roy AK (1992) Spatio-temporal expression of estrogen sulfotransferase within the hepatic lobule of male rats: implications for in situ inactivation. Endocrinology 131:1541–1546.

    Article  PubMed  CAS  Google Scholar 

  • Martel C, Rheaume E, Takahashi M, Trudel C, Couet J, Luu-The V, Simard J Labrie F (1992) Distribution of 17β-hydroxysteroid dehydrogenase gene expression and activity in rat and human tissue. J Steroid Biochem Molec Biol 41:597–603.

    Article  PubMed  CAS  Google Scholar 

  • Martucci C, Fishman J (1977) Direction of estradiol metabolism as a control of its hormonal action: uterotropic activity of estradiol metabolites. Endocrinology 101:1709–1715.

    Article  PubMed  CAS  Google Scholar 

  • Martucci C, Fishman J (1979) Impact of continuously administered catechol estrogens in uterine growth and luteinizing hormone secretion. Endocrinology 105:1288–1292.

    Article  PubMed  CAS  Google Scholar 

  • Martucci CP, Fishman J (1993) P450 enzymes of estrogen metabolism. Pharmac Ther 57:237–257.

    Article  CAS  Google Scholar 

  • Matsui M, Homma H (1994) Biochemistry and molecular biology of drugmetabolizing sulfotransferase. Int J Biochem 26:1237–1247.

    Article  PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Adlercreutz H, Bradlow HL (1997) Changes in levels of urinary estrogen metabolites after oral indole-3-carbinol treatment in humans. J Natl Cancer Inst 89:718–723.

    Article  PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Bradlow HL (1990) Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst 82:947–949.

    Article  PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Bradlow HL (1991) Altered estrogen metabolism and excretion in humans following consumption of indole-3-carbinol. Nutr Cancer 16:59–66.

    Article  PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Galbraith RA (1991) Cimetidine inhibits catechol estrogen metabolism in women. Metab 40:170–174.

    Article  CAS  Google Scholar 

  • Michnovicz JJ, Herscopf RJ, Haley NJ, Bradlow HL, Fishman J (1989) Cigarette smoking alters hepatic estrogen metabolism in men: implications for atherosclerosis. Metab 38:537–541.

    Article  CAS  Google Scholar 

  • Michnovicz JJ, Hershcopf RJ, Naganuma H, Bradlow HL, Fishman J (1986) Increased 2-hydroxylation of estradiol as a possible mechanism for the anti-estrogenic effect of cigarette smoking. N Engl J Med 315:1305–1309.

    Article  PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Naganuma H, Hershcopf RJ, Bradlow HL, Fishman J (1988) Increased urinary catechol estrogen excretion in female smokers. Steroids 52:69–83.

    Article  PubMed  CAS  Google Scholar 

  • Nebert DW (1991) Proposed role of drug-metabolizing enzymes: regulation of steady state levels of the ligands that effect growth, homeostasis, differentiation and neuroendocrine function. Molec Endocrinol 5:1203–1214.

    Article  CAS  Google Scholar 

  • Niwa T, Swaneck G, Bradlow HL (1994) Alterations in estradiol metabolism in MCF-7 cells by treatment with indole-3-carbinol and related compounds. Steroids 59:523–527.

    Article  PubMed  CAS  Google Scholar 

  • Noel CT, Reed MJ, Jacobs HS, James VHT (1981) The plasma concentrations of oestrone sulphate in postmenopausal women: lack of diurnal variation, effect of ovariectomy, age and weight. J Steroid Biochem 14:1101–1105.

    Article  PubMed  CAS  Google Scholar 

  • Numazawa M, Satoh S (1989) Kinetic studies of inhibition of estradiol 2-and 16α-hydroxylases with 17α-ethynyl and 17β-cyanosteroids: preferential inhibition of the 16α-hydroxylase. J Steroid Biochem 32:85–90.

    Article  PubMed  CAS  Google Scholar 

  • Osawa Y, Higashiyama T, Shimizu Y, Yarborough C (1993) Multiple functions of aromatase and the active site structure; aromatase is the placental 2-hydroxylase. J Steroid Biochem Molec Biol 44:469–480.

    Article  PubMed  CAS  Google Scholar 

  • Osborne MP, Bradlow HL, Wong GYC, Telang NT (1993) Upregulation of estradiol C16α-hydroxylation in human breast tissue: a potential marker of breast cancer risk. J Natl Cancer Inst 85:1917–1920.

    Article  PubMed  CAS  Google Scholar 

  • Pasqualini JR, Gelly C, Nguyen B-L, Vella C (1989) Importance of estrogen sulfates in breast cancer. J Steroid Biochem 34:155–163.

    Article  PubMed  CAS  Google Scholar 

  • Poutanen M, Moncharmont B, Vihko R (1992) 17β-Hydroxysteroid dehydrogenase gene expression in human breast cancer: regulation of expression by a progestin. Cancer Res 45:897–900.

    Google Scholar 

  • Purba HS, King EJ, Richert P, Bhatnagar AS (1994) Effect of aromatase inhibitors on estrogen 2-hydroxylase in rat liver. J Steroid Biochem Molec Biol 48:215–219.

    Article  PubMed  CAS  Google Scholar 

  • Purohit A, De Giovanni CV, Reed MJ (1999) The regulation of estrone sulfate formation in breast cancer cells. J Steroid Biochem Molec Biol 68:129–135.

    Article  PubMed  CAS  Google Scholar 

  • Reed MJ, Murray MAF (1979) The estrogens. In: Gray CH, James VHT (eds) Hormones in Blood Vol 3, Academic Press, London, pp 263–353.

    Google Scholar 

  • Reed MJ, Purohit A (1993) Sulphatase inhibitors: the rationale for the development of a new endocrine therapy. Rev Endocr-Rel Cancer 45:51–62.

    Google Scholar 

  • Reed MJ, Purohit A (1997) Breast cancer and the role of cytokines in regulating estrogen synthesis: an emerging hypothesis. Endocrine Reviews 18:701–715.

    Article  PubMed  CAS  Google Scholar 

  • Roy AK (1992) Regulation of steroid hormone action in target cells by specific hormone-inactivating enzymes. Proc Soc Exp Biol Med 199:265–272.

    PubMed  CAS  Google Scholar 

  • Roy D, Weisz J, Liehr JG (1990) The O-methylation of 4-hydroxy estradiol is inhibited by 2-hydroxy estradiol: implications for estrogen-induced carcinogenesis. Carcinogenesis 11:459–462.

    Article  PubMed  CAS  Google Scholar 

  • Ruder HJ, Loriaux DL, Lipsett MB (1972) Estrone sulphate: production rates and metabolism in man. J Clin Invest 51:1020–1023.

    Article  PubMed  CAS  Google Scholar 

  • Sanchis D, Balada F, Del Mar Grasa M, Virgili J, Peinado J, Monserrat C, Fernandez-Lopez J-A, Remesar X, Alemany M (1996) Oleoyl-estrone induces the loss of body fat in rats. Int J Obesity 20:588–594.

    CAS  Google Scholar 

  • Schatz F, Hochberg RB (1981) Lipoidal derivatives of estradiol: the biosynthesis of a non-polar estrogen metabolite. Endocrinology 109:697–703.

    Article  PubMed  CAS  Google Scholar 

  • Singh A, Reed MJ (1991) Insulin-like growth factor I and insulin-like growth factor II stimulate oestradiol 17β-hydroxysteroid dehydrogenase (reductive) activity in breast cancer cells. J Endocrinol 129:R5–R8.

    Article  PubMed  Google Scholar 

  • Snow RC, Barbieri RL, Frisch RE (1989) Estrogen 2-hydroxylase oxidation and menstrual function among elite oarswomen. J Clin Endocrinol Metab 69:369–376.

    Article  PubMed  CAS  Google Scholar 

  • Stewart PM, Sheppard MC (1992) Novel aspects of hormone action: intracellular ligand supply and its control by a series of tissue specific enzymes. Molec Cell Endocrinol 83:C13–C18.

    Article  PubMed  CAS  Google Scholar 

  • Strott CA (1996) Steroid sulfotransferases. Endocrine Reviews 17:670–697.

    PubMed  CAS  Google Scholar 

  • Swaneck GE, Fishman J (1988) Covalent binding of endogenous 16α-hydroxyestrone to estradiol receptor in human breast cancer cells: characterization and intra nuclear location. Proc Natl Acad Sci USA 85:7831–7835.

    Article  PubMed  CAS  Google Scholar 

  • Taioli E, Garte SJ, Trachman J, Garbers S, Sepkovic DW, Osborne MP, Mehl S, Bradlow HL (1996) Ethnic differences in estrogen metabolism in healthy women. J Natl Cancer Inst 88:617.

    Article  PubMed  CAS  Google Scholar 

  • Telang NT, Axelrod DM, Wong GY, Bradlow HL, Osborne MP (1991b) Biotransformation of estradiol by explant culture of human mammary tissue. Steroids 56:37–43.

    Article  PubMed  CAS  Google Scholar 

  • Telang NT, Narayanan R, Bradlow HL, Osborne MP (1991a) Coordinated expression of intermediate biomarkers for tumorigenic transformation in RAS transfected mouse mammary epithelial cells. Breast Cancer Res Treat 13:155–163.

    Article  Google Scholar 

  • Telang NT, Suto A, Wong GY, Osborne MP, Bradlow HL (1992) Induction by estrogen metabolite 16 α-hydroxyestrone of genotoxic damage and aberrant proliferation in mouse mammary epithelial cells. J Natl Cancer Inst 84:634–638.

    Article  PubMed  CAS  Google Scholar 

  • Tiwari RK, Guo L, Bradlow HL, Telang NT, Osborne MP (1994) Selective responsiveness of human breast cancer cells to indole-3-carbinol, a chemopreventive agent. J Natl Cancer Inst 86:126–131.

    Article  PubMed  CAS  Google Scholar 

  • Tseng L, Gurpide E (1979) Stimulation of various 17β-and 20α-hydroxysteroid dehydrogenase activities by progestins in human endometrium. Endocrinology 104:1745–1748.

    Article  PubMed  CAS  Google Scholar 

  • Weisz J, Bui QD, Roy D, Leihr J (1992) Elevated 4-hydroxylation of estradiol by hamster kidney microsomes: a potential pathway of metabolic activation of estrogens. Endocrinology 131:655–661.

    Article  PubMed  CAS  Google Scholar 

  • Whitnall MH, Driscoll WJ, Lee YC, Strott CA (1993) Estrogen and hydroxysteroid sulfotransferases in guinea pig adrenal cortex: cellular and subcellular distribution. Endocrinology 133:2284–2291.

    Article  PubMed  CAS  Google Scholar 

  • Wild MJ, Rudland PS, Back DJ (1991) Metabolism of the oral contraceptive steroids ethynylestradiol and norgestimate by normal (Huma7) and malignant (MCF-7 and ZR75-1) human breast cancer cells in culture. J Steroid Biochem Molec Biol 39:535–543.

    Article  PubMed  CAS  Google Scholar 

  • Wu L, Einstein M, Geissler WM, Chan HK, Elliston KO, Andersson S (1993) Expression cloning and characterization of human 17β-hydroxysteroid dehydrogenase Type 2, a microsomal enzyme possessing 20α-hydroxysteroid dehydrogenase activity. J Biol Chem 268:12964–12969.

    PubMed  CAS  Google Scholar 

  • Yamazoe Y, Nagata K, Osawa S, Kato R (1994) Structural similarity and diversity of sulfotransferases. Chemico-Biol Interactions 92:107–117.

    Article  CAS  Google Scholar 

  • Young BK, Jirku H, Kadner S, Levitz M (1976) Renal clearances of estriol conjugates in normal human pregnancy at term. Am J Obstet Gynecol 126:38–42.

    PubMed  CAS  Google Scholar 

  • Young TB, Wolf DA (1988) Case-control study of proximal and distal colon cancer and diet in Wisconsin. Int J Cancer 42:167–175.

    Article  PubMed  CAS  Google Scholar 

  • Zhu BT, Bui QD, Weisz J, Leihr JG (1994) Conversion of estrone to 2-and 4-hydroxyestrone by Hamster kidney and liver microsomes: implications for the mechanisms of estrogen-induced carcinogenesis. Endocrinology 135:1772–1779.

    Article  PubMed  CAS  Google Scholar 

  • Zhu BT, Liehr JG (1993) Inhibition of the catechol-O-methyl-transferase-catalyzed O-methylation of 2-and 4-hydroxyestradiol by catecholamines: implications for the mechanism of estrogen-induced carcinogenesis. Arch Biochem Biophys 304:248–256.

    Article  PubMed  CAS  Google Scholar 

Download references

Authors
  1. M. J. Reed
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Purohit
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Leiter Forschung und Entwicklung Jenapharm GmbH & Co. KG, Otto-Schott-Str. 15, D-07745, Jena, Germany

    Michael Oettel

  2. Leiter Forschung, Fertilitätskontrolle und Hormontherapie, Schering Aktiengesellschaft, D-13342, Berlin, Germany

    Ekkehard Schillinger

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Reed, M.J., Purohit, A. (1999). Estrogen Transforming Enzymes. In: Oettel, M., Schillinger, E. (eds) Estrogens and Antiestrogens I. Handbook of Experimental Pharmacology, vol 135 / 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-58616-3_11

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-58616-3_11

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-63667-7

  • Online ISBN: 978-3-642-58616-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation