2-Hidroksiestron

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2-Hidroksiestron
Općenito
Hemijski spoj2-Hidroksiestron
Druga imena2-OHE1; 2,3-Dihidroksiestra-1,3,5(10)-trien-17-on; Estra-1,3,5(10)-trien-2,3-diol-17-on
Molekularna formulaC18H22O3
CAS registarski broj362-06-1
SMILESC[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=C(C=C34)O)O
Osobine1
Molarna masa286,371 g/mol
Dipolni moment
PubChem: 440623
Rizičnost
NFPA 704
 
 
 
 
1 Gdje god je moguće korištene su SI jedinice. Ako nije drugačije naznačeno, dati podaci vrijede pri standardnim uslovima.

2-Hidroksiestron (2-OHE1), poznat i kao estra-1,3,5 (10) -trien-2,3-diol-17-on, je endogeni, koji se prirodno javlja kao katehol-estrogen i glavni metabolit estrona i estradiola.[1][2][3] Nastaje nepovratno od estrona u jetri i u manjoj mjeri od drugih tkiva putem 2-hidroksilacije posredovane enzimima citohroma P450, uglavnom potporodica CYP3A i CYP1A.[1][3]

2-Hidroksiestron nije značajno uterotrofan u biotestovima, dok drugi hidroksilirani metaboliti estrogena, uključujući 2-hidroksistradiol, 16α-hidroksiestron, estriol (16α-hidroksistestradiol) , 4-hidroksistradiol i 4-hidroksiestron svi jesu.[1][4] I Pored toga, iako nije antiestrogeni u maternici,[5][6] 2-hidroksiestron pokazuje antiestrogene efekte na nivoe luteinizirajućeg hormona i prolaktina.[7][8][9][10] Nedostatak estrogene ili antiestrogene aktivnosti 2-hidroksiestrona u maternici može se pripisati izuzetno visokom metaboličkom klirensu.[6][11] Kada se inkubira u vrlo visokim koncentracijama ili u kombinaciji sa katehol O-metiltransferazama (COMT) inhibitora, kako bi se spriječio njegov metabolizam, 2-hidroksiestron pokazuje antiestrogene pozitivne efekte na estrogeni receptor ljudskih ćelija raka dojke.[12][13]

2-Hidroksiestron se disocira od estrogenskih receptora mnogo brže od estradiola.[14]

Također pogledajte[uredi | uredi izvor]

Reference[uredi | uredi izvor]

  1. ^ a b c Oettel, Michael; Schillinger, Ekkehard (6 December 2012). Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens. Springer Science & Business Media. str. 227. ISBN 978-3-642-58616-3.
  2. ^ Rakel, David (2012). Integrative Medicine. Elsevier Health Sciences. str. 338–. ISBN 1-4377-1793-4.
  3. ^ a b Buchsbaum HJ (6 December 2012). The Menopause. Springer Science & Business Media. str. 64–65. ISBN 978-1-4612-5525-3.
  4. ^ Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK (2000). "Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women". Journal of the Society for Gynecologic Investigation. 7 (3): 175–83. doi:10.1016/s1071-5576(00)00049-6. PMID 10865186.
  5. ^ Martucci C, Fishman J (December 1977). "Direction of estradiol metabolism as a control of its hormonal action--uterotrophic activity of estradiol metabolites". Endocrinology. 101 (6): 1709–15. doi:10.1210/endo-101-6-1709. PMID 590186.
  6. ^ a b Kono S, Brandon DD, Merriam GR, Loriaux DL, Lipsett MB (January 1981). "Metabolic clearance rate and uterotropic activity of 2-hydroxyestrone in rats". Endocrinology. 108 (1): 40–3. doi:10.1210/endo-108-1-40. PMID 7460827.
  7. ^ Martucci CP, Fishman J (December 1979). "Impact of continuously administered catechol estrogens on uterine growth and luteinizing hormone secretion". Endocrinology. 105 (6): 1288–92. doi:10.1210/endo-105-6-1288. PMID 499073.
  8. ^ Katayama S, Fishman J (April 1982). "2-Hydroxyestrone suppresses and 2-methoxyestrone augments the preovulatory prolactin surge in the cycling rat". Endocrinology. 110 (4): 1448–50. doi:10.1210/endo-110-4-1448. PMID 7199421.
  9. ^ Okatani Y, Fishman J (September 1984). "Suppression of the preovulatory luteinizing hormone surge in the rat by 2-hydroxyestrone: relationship to endogenous estradiol levels". Endocrinology. 115 (3): 1082–9. doi:10.1210/endo-115-3-1082. PMID 6378602.
  10. ^ Okatani Y, Fishman J (July 1986). "Inhibition of the preovulatory prolactin surge in the rat by catechol estrogens: functional and temporal specificity". Endocrinology. 119 (1): 261–7. doi:10.1210/endo-119-1-261. PMID 3013588.
  11. ^ MacLusky NJ, Naftolin F, Krey LC, Franks S (December 1981). "The catechol estrogens". J. Steroid Biochem. 15: 111–24. doi:10.1016/0022-4731(81)90265-x. PMID 6279963.
  12. ^ Gupta, Mona; McDougal, Andrew; Safe, Stephen (1998). "Estrogenic and antiestrogenic activities of 16α- and 2-hydroxy metabolites of 17β-estradiol in MCF-7 and T47D human breast cancer cells". The Journal of Steroid Biochemistry and Molecular Biology. 67 (5–6): 413–419. doi:10.1016/S0960-0760(98)00135-6. ISSN 0960-0760.
  13. ^ Schneider J, Huh MM, Bradlow HL, Fishman J (April 1984). "Antiestrogen action of 2-hydroxyestrone on MCF-7 human breast cancer cells". J. Biol. Chem. 259 (8): 4840–5. PMID 6325410.
  14. ^ Barnea ER, MacLusky NJ, Naftolin F (May 1983). "Kinetics of catechol estrogen-estrogen receptor dissociation: a possible factor underlying differences in catechol estrogen biological activity". Steroids. 41 (5): 643–56. doi:10.1016/0039-128x(83)90030-2. PMID 6658896.

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