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'''2-Hidroksiestron''' ('''2-OHE1'''), poznat i kao '''estra-1,3,5 (10) -trien-2,3-diol-17-on''', je [[endogen]]i, koji se [[prirodni proizvod |prirodno javlja]] kao [[katehol-estrogen]] i glavni [[metabolit]] [[estron]]a i [[estradiol]]a.<ref name="OettelSchillinger2012">{{cite book| first1 = Michael | last1 = Oettel | first2 = Ekkehard | last2 = Schillinger|title=Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens|url=https://books.google.com/books?id=0BfrCAAAQBAJ&pg=PA235|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-58616-3|pages=227}}</ref><ref name="Rakel2012">{{cite book|first = David | last = Rakel|title=Integrative Medicine|url=https://books.google.com/books?id=jlVtJzBwAcEC&pg=PA338|year=2012|publisher=Elsevier Health Sciences|isbn=1-4377-1793-4|pages=338–}}</ref><ref name="Buchsbaum2012">{{cite book| vauthors = Buchsbaum HJ |title=The Menopause|url=https://books.google.com/books?id=z0LuBwAAQBAJ&pg=PA65|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4612-5525-3|pages=64–65}}</ref> Nastaje [[nepovratna reakcija|nepovratno]] od estrona u [[jetra|jetri]] i u manjoj mjeri od drugih [[Tkivo|tkiva]] putem 2-[[hidroksilacija|hidroksilacije]] posredovane [[enzim]]ima [[citohrom P450|citohroma P450]], uglavnom potporodica [[CYP3A]] i [[CYP1A]].<ref name="OettelSchillinger2012"/><ref name="Buchsbaum2012" />
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'''2-Hidroksiestron''' ('''2-OHE1'''), poznat i kao '''estra-1,3,5 (10) -trien-2,3-diol-17-on''', je [[endogen]]i, koji se [[prirodni proizvod |prirodno javlja]] kao [[katehol-estrogen]] i glavni [[metabolit]] [[estron]]a i [[estradiol]]a.<ref name="OettelSchillinger2012">{{cite book| first1 = Michael | last1 = Oettel | first2 = Ekkehard | last2 = Schillinger|title=Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens|url=https://books.google.com/books?id=0BfrCAAAQBAJ&pg=PA235|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-58616-3|pages=227}}</ref><ref name="Rakel2012">{{cite book|first = David | last = Rakel|title=Integrative Medicine|url=https://books.google.com/books?id=jlVtJzBwAcEC&pg=PA338|year=2012|publisher=Elsevier Health Sciences|isbn=1-4377-1793-4|pages=338–}}</ref><ref name="Buchsbaum2012">{{cite book| vauthors = Buchsbaum HJ |title=The Menopause|url=https://books.google.com/books?id=z0LuBwAAQBAJ&pg=PA65|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4612-5525-3|pages=64–65}}</ref> Nastaje [[nepovratna reakcija|nepovratno]] od estrona u [[jetra|jetri]] i u manjoj mjeri od drugih [[tkiva| tkivo]] putem 2-[[hidroksilacija|hidroksilacije]] posredovane [[enzim]]ima [[citohrom P450|citohroma P450]], uglavnom potporodica [[CYP3A]] i [[CYP1A]].<ref name="OettelSchillinger2012"/><ref name="Buchsbaum2012" /> 2-OHE1 is the most abundant catechol estrogen in the body.<ref name="Buchsbaum2012" />


2-Hidroksiestron nije značajno [[uterotrof]]an u biotestovima, dok drugi hidroksilirani [[metabolit]]i estrogena, uključujući [[2-hidroksistradiol]], [[16α-hidroksiestron]], [[estriol]] (16α-hidroksistestradiol) , [[4-hidroksistradiol]] i [[4-hidroksiestron]] svi jesu.<ref name="OettelSchillinger2012" /><ref name="pmid10865186">{{cite journal | vauthors = Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK | title = Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women | journal = Journal of the Society for Gynecologic Investigation | volume = 7 | issue = 3 | pages = 175–83 | year = 2000 | pmid = 10865186 | doi = 10.1016/s1071-5576(00)00049-6}}</ref> I Pored toga, iako nije [[antiestrogen]]i u [[maternica|maternici]],<ref name="pmid590186">{{cite journal | vauthors = Martucci C, Fishman J | title = Direction of estradiol metabolism as a control of its hormonal action--uterotrophic activity of estradiol metabolites | journal = Endocrinology | volume = 101 | issue = 6 | pages = 1709–15 | date = December 1977 | pmid = 590186 | doi = 10.1210/endo-101-6-1709 }}</ref><ref name="pmid7460827">{{cite journal | vauthors = Kono S, Brandon DD, Merriam GR, Loriaux DL, Lipsett MB | title = Metabolic clearance rate and uterotropic activity of 2-hydroxyestrone in rats | journal = Endocrinology | volume = 108 | issue = 1 | pages = 40–3 | date = January 1981 | pmid = 7460827 | doi = 10.1210/endo-108-1-40 }}</ref>2-hidroksiestron pokazuje antiestrogene efekte na nivoe [[luteinizirajući hormon|luteinizirajućeg hormona]] i [[prolaktin]]a.<ref name="pmid499073">{{cite journal | vauthors = Martucci CP, Fishman J | title = Impact of continuously administered catechol estrogens on uterine growth and luteinizing hormone secretion | journal = Endocrinology | volume = 105 | issue = 6 | pages = 1288–92 | date = December 1979 | pmid = 499073 | doi = 10.1210/endo-105-6-1288 }}</ref><ref name="pmid7199421">{{cite journal | vauthors = Katayama S, Fishman J | title = 2-Hydroxyestrone suppresses and 2-methoxyestrone augments the preovulatory prolactin surge in the cycling rat | journal = Endocrinology | volume = 110 | issue = 4 | pages = 1448–50 | date = April 1982 | pmid = 7199421 | doi = 10.1210/endo-110-4-1448 }}</ref><ref name="pmid6378602">{{cite journal | vauthors = Okatani Y, Fishman J | title = Suppression of the preovulatory luteinizing hormone surge in the rat by 2-hydroxyestrone: relationship to endogenous estradiol levels | journal = Endocrinology | volume = 115 | issue = 3 | pages = 1082–9 | date = September 1984 | pmid = 6378602 | doi = 10.1210/endo-115-3-1082 }}</ref><ref name="pmid3013588">{{cite journal | vauthors = Okatani Y, Fishman J | title = Inhibition of the preovulatory prolactin surge in the rat by catechol estrogens: functional and temporal specificity | journal = Endocrinology | volume = 119 | issue = 1 | pages = 261–7 | date = July 1986 | pmid = 3013588 | doi = 10.1210/endo-119-1-261 }}</ref> Nedostatak estrogene ili antiestrogene aktivnosti 2-hidroksiestrona u maternici može se pripisati izuzetno visokom [[metabolički klirens|metaboličkom klirensu]].<ref name="pmid7460827" /><ref name="pmid6279963">{{cite journal | vauthors = MacLusky NJ, Naftolin F, Krey LC, Franks S | title = The catechol estrogens | journal = J. Steroid Biochem. | volume = 15 | pages = 111–24 | date = December 1981 | pmid = 6279963 | doi = 10.1016/0022-4731(81)90265-x }}</ref> Kada se inkubira u vrlo visokim koncentracijama ili u kombinaciji sa [[katehol O-metiltransferaza]]ma (COMT) [[COMT inhibitor| inhibitora]], kako bi se spriječio njegov metabolizam, 2-hidroksiestron pokazuje antiestrogene pozitivni efekte na [[estrogeni receptor]] ljudskih ćelija [[rak dojke|raka dojke]].<ref name="GuptaMcDougal1998">{{cite journal|last1=Gupta|first1=Mona|last2=McDougal|first2=Andrew|last3=Safe|first3=Stephen|title=Estrogenic and antiestrogenic activities of 16α- and 2-hydroxy metabolites of 17β-estradiol in MCF-7 and T47D human breast cancer cells|journal=The Journal of Steroid Biochemistry and Molecular Biology|volume=67|issue=5-6|year=1998|pages=413–419|issn=09600760|doi=10.1016/S0960-0760(98)00135-6}}</ref><ref name="pmid6325410">{{cite journal | vauthors = Schneider J, Huh MM, Bradlow HL, Fishman J | title = Antiestrogen action of 2-hydroxyestrone on MCF-7 human breast cancer cells | journal = J. Biol. Chem. | volume = 259 | issue = 8 | pages = 4840–5 | date = April 1984 | pmid = 6325410 }}</ref>
2-Hidroksiestron nije značajno [[uterotrof]]an u biotestovima, dok drugi hidroksilirani [[metabolit]]i estrogena, uključujući [[2-hidroksistradiol]], [[16α-hidroksiestron]], [[estriol]] (16α-hidroksistestradiol) , [[4-hidroksistradiol]] i [[4-hidroksiestron]] svi jesu.<ref name="OettelSchillinger2012" /><ref name="pmid10865186">{{cite journal | vauthors = Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK | title = Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women | journal = Journal of the Society for Gynecologic Investigation | volume = 7 | issue = 3 | pages = 175–83 | year = 2000 | pmid = 10865186 | doi = 10.1016/s1071-5576(00)00049-6}}</ref> I Pored toga, iako nije [[antiestrogen]]i u [[maternica|maternici]],<ref name="pmid590186">{{cite journal | vauthors = Martucci C, Fishman J | title = Direction of estradiol metabolism as a control of its hormonal action--uterotrophic activity of estradiol metabolites | journal = Endocrinology | volume = 101 | issue = 6 | pages = 1709–15 | date = December 1977 | pmid = 590186 | doi = 10.1210/endo-101-6-1709 }}</ref><ref name="pmid7460827">{{cite journal | vauthors = Kono S, Brandon DD, Merriam GR, Loriaux DL, Lipsett MB | title = Metabolic clearance rate and uterotropic activity of 2-hydroxyestrone in rats | journal = Endocrinology | volume = 108 | issue = 1 | pages = 40–3 | date = January 1981 | pmid = 7460827 | doi = 10.1210/endo-108-1-40 }}</ref> 2-hidroksiestron pokazuje antiestrogene efekte na nivoe [[luteinizirajući hormon|luteinizirajućeg hormona]] i [[prolaktin]]a.<ref name="pmid499073">{{cite journal | vauthors = Martucci CP, Fishman J | title = Impact of continuously administered catechol estrogens on uterine growth and luteinizing hormone secretion | journal = Endocrinology | volume = 105 | issue = 6 | pages = 1288–92 | date = December 1979 | pmid = 499073 | doi = 10.1210/endo-105-6-1288 }}</ref><ref name="pmid7199421">{{cite journal | vauthors = Katayama S, Fishman J | title = 2-Hydroxyestrone suppresses and 2-methoxyestrone augments the preovulatory prolactin surge in the cycling rat | journal = Endocrinology | volume = 110 | issue = 4 | pages = 1448–50 | date = April 1982 | pmid = 7199421 | doi = 10.1210/endo-110-4-1448 }}</ref><ref name="pmid6378602">{{cite journal | vauthors = Okatani Y, Fishman J | title = Suppression of the preovulatory luteinizing hormone surge in the rat by 2-hydroxyestrone: relationship to endogenous estradiol levels | journal = Endocrinology | volume = 115 | issue = 3 | pages = 1082–9 | date = September 1984 | pmid = 6378602 | doi = 10.1210/endo-115-3-1082 }}</ref><ref name="pmid3013588">{{cite journal | vauthors = Okatani Y, Fishman J | title = Inhibition of the preovulatory prolactin surge in the rat by catechol estrogens: functional and temporal specificity | journal = Endocrinology | volume = 119 | issue = 1 | pages = 261–7 | date = July 1986 | pmid = 3013588 | doi = 10.1210/endo-119-1-261 }}</ref> Nedostatak estrogene ili antiestrogene aktivnosti 2-hidroksiestrona u maternici može se pripisati izuzetno visokom [[metabolički klirens|metaboličkom klirensu]].<ref name="pmid7460827" /><ref name="pmid6279963">{{cite journal | vauthors = MacLusky NJ, Naftolin F, Krey LC, Franks S | title = The catechol estrogens | journal = J. Steroid Biochem. | volume = 15 | pages = 111–24 | date = December 1981 | pmid = 6279963 | doi = 10.1016/0022-4731(81)90265-x }}</ref> Kada se inkubira u vrlo visokim koncentracijama ili u kombinaciji sa [[katehol O-metiltransferaza]]ma (COMT) [[COMT inhibitor|inhibitora]], kako bi se spriječio njegov metabolizam, 2-hidroksiestron pokazuje antiestrogene pozitivne efekte na [[estrogeni receptor]] ljudskih ćelija [[rak dojke|raka dojke]].<ref name="GuptaMcDougal1998">{{cite journal|last1=Gupta|first1=Mona|last2=McDougal|first2=Andrew|last3=Safe|first3=Stephen|title=Estrogenic and antiestrogenic activities of 16α- and 2-hydroxy metabolites of 17β-estradiol in MCF-7 and T47D human breast cancer cells|journal=The Journal of Steroid Biochemistry and Molecular Biology|volume=67|issue=5-6|year=1998|pages=413–419|issn=09600760|doi=10.1016/S0960-0760(98)00135-6}}</ref><ref name="pmid6325410">{{cite journal | vauthors = Schneider J, Huh MM, Bradlow HL, Fishman J | title = Antiestrogen action of 2-hydroxyestrone on MCF-7 human breast cancer cells | journal = J. Biol. Chem. | volume = 259 | issue = 8 | pages = 4840–5 | date = April 1984 | pmid = 6325410 }}</ref>


2-Hidroksiestron se disocira od estrogenskih receptora mnogo brže od estradiola.<ref name="pmid6658896">{{cite journal | vauthors = Barnea ER, MacLusky NJ, Naftolin F | title = Kinetics of catechol estrogen-estrogen receptor dissociation: a possible factor underlying differences in catechol estrogen biological activity | journal = Steroids | volume = 41 | issue = 5 | pages = 643–56 | date = May 1983 | pmid = 6658896 | doi = 10.1016/0039-128x(83)90030-2 }}</ref>
2-Hidroksiestron se disocira od estrogenskih receptora mnogo brže od estradiola.<ref name="pmid6658896">{{cite journal | vauthors = Barnea ER, MacLusky NJ, Naftolin F | title = Kinetics of catechol estrogen-estrogen receptor dissociation: a possible factor underlying differences in catechol estrogen biological activity | journal = Steroids | volume = 41 | issue = 5 | pages = 643–56 | date = May 1983 | pmid = 6658896 | doi = 10.1016/0039-128x(83)90030-2 }}</ref>
Red 36: Red 35:
==Vanjski linkovi==
==Vanjski linkovi==
* [http://www.hmdb.ca/metabolites/HMDB00343 Metabocard for 2-Hydroxyestrone (HMDB12623) - Human Metabolome Database]
* [http://www.hmdb.ca/metabolites/HMDB00343 Metabocard for 2-Hydroxyestrone (HMDB12623) - Human Metabolome Database]

{{Endogeni steroidi}}


{{DEFAULTSORT:Hydroxyestrone, 2-}}
{{DEFAULTSORT:Hydroxyestrone, 2-}}

Verzija na dan 20 juli 2021 u 18:22

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

Reference

  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.

Vanjski linkovi

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