The catechol estrogens

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Fishman, 1963, Role of 2-hydroxycstrone in estrogen metabolism, J. clin. Endocr. Metab., 23, 207, 10.1210/jcem-23-2-207

Gelbke, 1972, A new method for preventing oxidative decomposition of catechol estrogens during chromatography, J. Chromatogr., 71, 465, 10.1016/S0021-9673(01)91900-4

Westerfield, 1940, The inactivation of oestrone, Biochem. J., 34, 51, 10.1042/bj0340051

Krachy, 1957, 2-methoxyestrone, a new metabolite of estradiol-17β in man, J. biol. Chem., 229, 519, 10.1016/S0021-9258(18)70636-4

Fishman, 1958, 2-methoxyestriol: a new metabolite of estradiol in man, Archs. Biochem. Biophys., 77, 511, 10.1016/0003-9861(58)90097-3

Axelrod, 1958, Enzymatic o-methylation of epinephrine and other catechols, J. biol. Chem., 233, 702, 10.1016/S0021-9258(18)64731-3

Breuer, 1962, Enzymatische methylierung von 2-hydroxy-östradiol-(17β) durch ein S-Adenosyl-methionin: Acceptor-o-methyltransferase der Rattenleber, Hoppe-Seyler's Z. Physiol. Chem., 327, 217, 10.1515/bchm2.1962.327.1.217

King, 1960, Biosynthesis of 2-methoxyoestriol by rat liver preparations, Biochem. J., 74, 22P

King, 1961, Oestriol metabolism by rat and rabbit liver slices. Isolation of 2-methoxyoestriol and 2-hydroxyoestriol, Biochem. J., 79, 355, 10.1042/bj0790355

Fishman, 1960, 2-hydroxyestrone: a new metabolite of estradiol in man, Archs. Biochem. Biophys., 90, 318, 10.1016/0003-9861(60)90586-5

Hecker, 1965, Zum Stoffwechsel und Wirkungsmechanisms der Oestrogene VII. Die o-hydroxylienung von Oestron in Rattenleber und ihre Beziehung zur Protein bindung sowie zur p-Hydroxylierung und zu Hydroxyliening in aliphatischen Positionen, Biochem. Z., 343, 211

Williams, 1974, 4-hydroxyoestrone: A new metabolite of estradiol-17β from humans, Steroids, 24, 687, 10.1016/0039-128X(74)90021-X

Paul, 1977, Catechol estrogen-forming enzyme of brain: Demonstration of a cytochrome p. 450 Monooxygenase, Endocrinology, 101, 1604, 10.1210/endo-101-5-1604

Fishman, 1963, Role of 2-hydroxyestrone in estrogen metabolism, J. clin. Endocr. Metab., 23, 207, 10.1210/jcem-23-2-207

Gelbke, 1975, Excretion of 2-hydroxyestrone in urine throughout human pregnancies, J. clin. Endocr. Metab., 41, 744, 10.1210/jcem-41-4-744

Ball, 1972, Kinetic properties of a soluble catechol-o-methyl transferase of human liver, Eur. J. Biochem., 26, 560, 10.1111/j.1432-1033.1972.tb01799.x

Ball, 1972, Interactions between estrogens and catechol amines III. Studies on the methylation of eatechol estrogens. catecholamines and other catechols by the catechol-omethyltransferase of human liver, J. clin. Endocr. Metab., 34, 736, 10.1210/jcem-34-4-736

Ball, 1976, Comparative studies on the metabolism of estradiol-17β and 2-hydroxy-estradiol-17β in man in vitro and in vivo, J. steroid Biochem., 7, 139, 10.1016/0022-4731(76)90150-3

Ball, 1977, Metabolism of 2-methoxy and 4-methoxyestrone in man in vivo, J. steroid Biochem., 8, 989, 10.1016/0022-4731(77)90198-4

Jellinck, 1967, Further evidence for the formation of an estrogen-peptide conjugate by rat liver in vitro, Steroids, 10, 329, 10.1016/0039-128X(67)90058-X

Kuss, 1967, Wasserlösliche metabolite des Östradiols-17β, Hoppe-Seyler's Z. Physiol. Chem., 348, 1707

Hoppen, 1974, Stoffwechsel von Oestron in der Mikro-somenfraktion der Rattenleber, Hoppe-Seyler's Z. Physiol. Chem., 355, 1305, 10.1515/bchm2.1974.355.2.1305

Ball, 1978, Radioimmunoassay of 2-hydroxyestrone, Steroids, 31, 249, 10.1016/0039-128X(78)90117-4

Emons, 1979, Radioimmunoassay for 2-methoxyoestrone in human plasma, Acta endocr. Copenh., 91, 158

Axelrod, 1971, Methyltransferase enzymes in red blood cells, J. Pharmac. Exp. Ther., 176, 650

Bates, 1977, Metabolism of catechol estrogen by human erythrocytes, J. clin. Endocr. Metab., 45, 1120, 10.1210/jcem-45-5-1120

Merriam, 1980, Rapid metabolic clearance of the eatechol estrogen, 2-hydroxy-estrone, J. clin. Endocr. Metab., 51, 1211, 10.1210/jcem-51-5-1211

Longcope, 1981, H. Metabolism of 3H-2-hydroxyestrone (3H-2-OHE1) in normal men

Fishman, 1970, Aromatic ring hydroxylation of estradiol in man, Biochemistry, 9, 1593, 10.1021/bi00809a018

Fishman, 1975, Catechol estrogen formation in the central nervous system of the rat, Endocrinology, 96, 1054, 10.1210/endo-96-4-1054

Jellinck, 1980, Formation of 3H2O from (2-3H) and (4-3H) estradiol by rat uteri in vitro: possible role of peroxidase, Steroids, 35, 579, 10.1016/S0039-128X(80)80010-9

Merriam, 1976, An assay for catechol estrogens based on their enzymic o-methylation, 494

Eisenfeld, 1980, Estrogen receptor in the mammalian liver, 69

Weinberger, 1978, Effect of metabolism on the amount and identity of receptor-bound estrogen, Biochem. Pharmacol., 27, 2469, 10.1016/0006-2952(78)90364-7

Dickson, 1980, Receptor bound estrogens and their metabolites in the nucleus of the isolated rat liver parenchymal cell, Mol. Pharmacol., 18, 215

Ball, 1978, Comparative studies on the metabolism of oestradiol in the brain, the pituitary and liver of the rat, Acta endocr. Copenh., 87, 1

Barbieri, 1978, Estrogen 2-hydroxylase activity in rat tissues, Steroids, 32, 529, 10.1016/0039-128X(78)90064-8

Hoffman, 1979, Estrogen 2-hydroxylase in the rat: distribution and response to hormonal manipulation, Biochem. Pharmacol., 29, 83, 10.1016/0006-2952(80)90248-8

Ball, 1978, Formation of 2- and 4-hydroxyestrogens by brain, pituitary and liver of the human fetus, J. clin. endocr. Metab., 47, 732, 10.1210/jcem-47-4-732

Fishman, 1976, Catechol estrogen formation by the human fetal brain and pituitary, J. clin. Endocr. Metab., 42, 177, 10.1210/jcem-42-1-177

Smith, 1969, Studies on the metabolism of steroid hormones and their precursors by the human placenta at various stages of gestation I. in vitro metabolism of 1,3,5(10)-estratriene-3,17β-diol, J. clin. Endocr. Metab., 29, 85, 10.1210/jcem-29-1-85

Acevedo, 1965, The metabolism of (14C) estrone by hypertrophic and carcinomatous human prostate tissue, Biochem. biophys. Acta, 97, 571, 10.1016/0304-4165(65)90171-6

Acevedo, 1965, The metabolism of 4-14C estradiol-17β by pheochromocytoma tissue, Steroids, 6, 531, 10.1016/0039-128X(65)90016-4

Hoffman, 1979, Catechol estrogens: synthesis and metabolism by human breast tumors in vitro, Cancer Res., 39, 4584

Fishman, 1980, 2-Hydroxylation in the brain participates in the initiation of the preovulatory LH surge in the rat, Biochem. biophys. Res. Commun., 93, 471, 10.1016/0006-291X(80)91101-8

Fishman, 1962, Influence of thyroid hormone on estrogen metabolism in man, J. clin. Endocr. Metab., 22, 389, 10.1210/jcem-22-4-389

Fishman, 1965, Effect of thyroid on hydroxylation of estrogen in man, J. clin. Endocr. Metab., 25, 356, 10.1210/jcem-25-3-365

Fishman, 1980, Opiate regulation of estradiol 2-hydroxylase in brains of male rats: mechanism for control of pituitary hormone secretion, 77, 120

Zumoff, 1968, Estradiol metabolism in cirrhosis, J. clin. Invest., 47, 20, 10.1172/JCI105709

Fishman, 1975, Influence of body weight on estradiol metabolism in young women, J. clin. Endocr. Metab., 41, 989, 10.1210/jcem-41-5-989

Hellman, 1971, Peripheral metabolism of [3H]estradiol and the excretion of endogenous estrone and estriol glucosiduronate in women with breast cancer, J. clin. Endocr. Metab., 33, 138, 10.1210/jcem-33-1-138

Clark, 1977, Nuclear binding and retention of the receptor estrogen complex: relation to the agonistic and antagonistic properties of estriol, Endocrinology, 100, 91, 10.1210/endo-100-1-91

Martucci, 1977, Direction of estradiol metabolism as a control of its hormonal action—uterotrophic activity of estradiol metabolites, Endocrinology, 101, 1709, 10.1210/endo-101-6-1709

Yoshizawa, 1971, Radioimmunoassay of 2-hydroxyestrone in human plasma, J. clin. Endocr. Metabol., 32, 3, 10.1210/jcem-32-1-3

Lecchini, 1980, Radioimmunoassay of 2-hydroxyestrone in human and rat plasma

Kono, 1981, Radioimmunoassay and metabolism of the catechol estrogen, 2-hydroxyestradiol

Kono, 1980, Low plasma levels of 2-hydroxyestrone are consistent with its rapid metabolic clearance, Steroids, 36, 463, 10.1016/0039-128X(80)90033-1

Paul, 1977, Catechol estrogens: presence in brain and endocrine tissues, Science, 167, 657, 10.1126/science.877577

Kono, 1981, Metabolic clearance rate and uterotrophic activity of 2-hydroxyestrone in rats

Naftolin, 1972, Plasma and pituitary luteinizing hormone and peripheral oestradiol concentrations in the normal oestrous cycle of the rat and after experimental manipulation of the cycle, J. Endocr., 53, 17, 10.1677/joe.0.0530017

Fishman, 1979, Absence of measurable 2-hydroxyestrone in the rat brain: evidence for rapid turnover, J. clin. Endocr. Metab., 49, 940, 10.1210/jcem-49-6-940

Niederl, 1949, Estracatechol, J. Am. Chem. Soc., 71, 2566, 10.1021/ja01175a091

Franks, 1981, In vivo and in vitro uterotrophic actions of catechol estrogens in the immature female rat, J. Endocr., 85, 33P

Franks S., Merriam G. R., Goodyer C. G. and Naftolin F.: Catechol estrogens stimulate LH secretion by dispersed rat pituitary cells in culture. Proc. Endocrine. Soc. 61st Annual Meeting, Abstract No. 919.

Franks, 1980, The role of oestradiol and catechol oestrogens in the control of gonadotrophin and prolactin secretion, 27

Hsueh, 1979, The sensitizing effect of estrogens and catechol estrogen on cultured pituitary cells to luteinizing hormone-releasing hormone: its antagonism by progestins, Endocrinology, 104, 807, 10.1210/endo-104-3-807

Gordon, 1964, Steroids and lipid metabolism. The hypocholeresteremic effect of estrogen metabolites, Steroids, 4, 267, 10.1016/0039-128X(64)90018-2

Patt, 1971, Beeinflussung der Blutlipide bei der Ratte durch 2 oder 4 substitiuerte öestrogen derivative, Arzneim Forsch., 21, 308

Mueller, 1955, In vitro Stimulation of incorporation of formate-14C in surviving uterine segments by hydroxylated oestradiols, Nature, 176, 127, 10.1038/176127a0

Kelly, 1980, Catechol estrogens stimulate and direct prostaglandin synthesis, Prostaglandins, 20, 613, 10.1016/0090-6980(80)90102-1

Naftolin, 1975, 2-Hydroxyesirone induced rise in serum luteinizing hormone in the immature male rat, Biochem. Biophys. Res. Commun., 64, 905, 10.1016/0006-291X(75)90133-3

Franks, 1981, Actions of catechol estrogens on concentrations of serum luteinizing hormone in the adult castrated rat: various effects of 4-hydroxyestradiol and 2-hydroxyestradiol, J. Endocr., 89, 289, 10.1677/joe.0.0890289

Paul, 1977, Catechol estrogens inhibit oestrogen elicited accumulation of hypothalamic cyclic-AMP, suggesting role as endogenous antioestrogens, Nature, 266, 559, 10.1038/266559a0

Emons, 1981, Effects of catecholoestrogens (CE) on LH secretions in immature female rats, Acta Endocr., 97

Jellinck, 1981, Central and peripheral actions of estradiol and catechol estrogens administered at low concentrations at constant infusion, Endocrinology, 108, 1848, 10.1210/endo-108-5-1848

Franks, 1980, Effect of catechol estrogens on induced ovulation in the immature rat, J. Endocr., 86, 263, 10.1677/joe.0.0860263

Rodriguez-Sierra, 1980, Lack of stimulation of phasic LH release by catechol estrogens in the rat, Life Sci., 26, 743, 10.1016/0024-3205(80)90265-9

Morishita, 1975, Elevation of serum gonadotrophins in male rats by catechol estrogens, Acta Obstet. Gynaecol. Jpn Engl. Ed., 23, 421

Merriam, 1980, Effects of catechol estrogen infusions upon gonadotrophin an prolactin levels in men

Barbieri, 1980, Response of serum prolactin to catechol estrogen in the immature rat, Fertil. Steril., 34, 391, 10.1016/S0015-0282(16)45015-6

Adashi, 1979, The effect of acutely administered 2-hydroxyestrone on the release of gonadotropins and prolactin before and after estrogen priming in hypogonadal women, Life Sci., 25, 2051, 10.1016/0024-3205(79)90196-6

Schinfeld, 1980, Suppression of prolactin and gonadotrophin secretion in post-menopausal women by 2-hydroxyestrone, J. Clin. Endocr. Metab., 50, 408, 10.1210/jcem-50-2-408

Fishman, 1980, Suppression of prolactin secretion in normal young women by 2-hydroxyestrone, Science, 210, 73, 10.1126/science.7414322

Franks S., Lightman S. L., MacLusky N. J., Naftolin F., Lynch S. S., Butt W. R. and Jacobs H. S.: Failure of 2-hydroxyoestrone to lower prolactin concentrations in hyperprolactinaemic women. Clin. Endocr. in press.

Merriam, 1981, Does 2-hydroxyestrone suppress prolactin in women?, Acta Endocr., 97

Dunn, 1981, Testosterone-estradiol binding globulin binds to 2-methoxyestradiol with greater affinity than to testosterone, J. Clin. Endocr. Metab., 51, 404, 10.1210/jcem-51-2-404

Fishman, 1978, Differential biological activity of estradiol metabolites, Pediatrics, 62, 1128, 10.1542/peds.62.6.1128

Davies, 1975, The affinity of catechol estrogens for estrogen receptors in the pituitary and anterior hypothalamus of the rat, Endocrinology, 97, 554, 10.1210/endo-97-3-554

Martucci, 1976, Uterine estrogen receptor binding of catechol estrogens and of estetrol (1,3,5,(10)estratriene-3,15α,16α,17β-tetrol), Steroids, 27, 325, 10.1016/0039-128X(76)90054-4

Merriam, 1980, Comparative properties of the catechol estrogens I: rnethylation by catechol-o-methyl transferase and binding to cytosol estrogen receptors, Steroids, 31, 1, 10.1016/0039-128X(80)90062-8

MacLusky N. J., Clark C. R., Paden C. M. and Naftolin F. : End-organ metabolism of estrogens. In Mechanisms of Steroid Action (Edited by G. P. Lewis), MacMillan, in press.

MacLusky N. J., Clark C. R. and Naftolin F.: In vivo and in vitro interactions between catechol estrogens and estrogen receptor sites in the brain, pituitary and uterus of the rat. Endocrinology, submitted.

Lloyd, 1978, Direct inhibition of tyrosine hydroxylase activity by catechol estrogens, J. biol. Chem., 253, 4841, 10.1016/S0021-9258(17)34622-7

Foreman, 1980, Effects of catechol estrogens and catecholamines on hypothalamic and corpus striatal tyrosine hydroxylase activity, J. Neurochem., 34, 1175, 10.1111/j.1471-4159.1980.tb09957.x

Schaeffer, 1979, 2-Hydroxyestradiol interaction with dopamine receptor binding in rat anterior pituitary, J. biol. Chem., 254, 5606, 10.1016/S0021-9258(18)50455-5

Schaeffer, 1980, 2-Hydroxyestradiol (2-OHE2) binding to rat anterior pituitary cell membranes

Emons, 1981, No effects of antibodies to catecholestrogens and catechol estrogen-methyl ethers or pregnant mare's scrum induced ovulation in immature rats

Bardin, 1981, Testosterone: a major determinant of estragenital sexual dimorphism, Science, 211, 1285, 10.1126/science.7010603

MacLusky, 1981, Sexual differentiation of the central nervous system, Science, 211, 1294, 10.1126/science.6163211

Merriam, 1980, 2-Hydroxyestradiol 17α and 4-hydroxyestradiol-17α, catechol estrogen analogs with reduced estrogen receptor affinity, Steroids, 36, 13, 10.1016/0039-128X(80)90063-X

Salmon, 1979, Reference compounds for the study of moxestrol metabolism, Steroids, 34, 381, 10.1016/0039-128X(79)90101-6

Milewich, 1971, Metabolism of [4-14C] testosterone by lypophilized baboon placental microsomes, Endocrinology, 88, 589, 10.1210/endo-88-3-589

Martucci, 1979, Impact of continuously administered catechol estrogens on uterine growth and LH secretion, Endocrinology, 105, 1288, 10.1210/endo-105-6-1288

Gethman, 1976, Effect of 2-hydroxyestrone on lutropin (LH) and follitropin (FSH) secretion in the ovariectomized primed rat, HoppeSeyler's Z. Physiol. Chem., 357, 1011

Parvizi, 1975, 2-Hydroxyestradiol-17β as a possible link in steroid-brain interaction, Nature, Lond., 256, 59, 10.1038/256059a0

Marrone, 1977, Role of catechol estrogens in activation of lordosis in femal rats and guinea pigs, Pharmacol. Biochem. Behav., 7, 13, 10.1016/0091-3057(77)90005-3

Luttge, 1977, Studies on the possible role of 2-OH estradiol in the control of sexual behavior in female rats, Life Sci., 20, 419, 10.1016/0024-3205(77)90382-4

Parvizi, 1977, Effects of cateehol estrogens on sexual differentiation in neonatal female rats, Phychoneuroendocrinology, 2, 409, 10.1016/0306-4530(77)90012-9

McEwen, 1981, Neural gonadal steroid interactions, Science, 211, 1303, 10.1126/science.6259728

Naftolin, 1981, Estrogen actions on developing brain: sexual differentiation and nuclear receptors after exogenous estradiol (E2), 4-hydroxyestradiol (4-OHE2) and 2-hydroxyestradiol (2-OHE2)