Characterization of the oestrogenic activity of non-aromatic steroids: Are there male-specific endogenous oestrogen receptor modulators?

British Journal of Pharmacology

Volumn 158, Issue 7, 2009, Pages 1796-1807

  Wang, Pan ^a   Wen, Yujing ^a   Han, Gui Zhen ^a   Sidhu, Pritam Kaur ^a   Zhu, Bao Ting ^a  

^a UNIVERSITY OF KANSAS SCHOOL OF MEDICINE   (United States)

Author keywords

Molecular modelling; Non aromatic steroids; Oestrogen receptor; Oestrogenic activity

Indexed keywords

3BETA ANDROSTANEDIOL; 4 ESTROGEN 3BETA,17BETA DIOL; 5(10) ESTROGEN 3ALPHA,17BETA DIOL; 5(10) ESTROGEN 3BETA,17BETA DIOL; 5ALPHA ESTRAN 3BETA,17BETA DIOL; ANDROSTENEDIOL; ESTRADIOL; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; SELECTIVE ESTROGEN RECEPTOR MODULATOR; STEROID; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CELL STRAIN LNCAP; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG EFFICACY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; FEMALE; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IN VITRO STUDY; MALE; MOLECULAR DOCKING; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

BREAST NEOPLASMS; CELL LINE, TUMOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FEMALE; HUMANS; LIGANDS; MALE; PROSTATIC NEOPLASMS; PROTEIN BINDING; SEX CHARACTERISTICS; STEROIDS; TRANSCRIPTION, GENETIC;

EID: 71249086833     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2009.00467.x     Document Type: Article

References (25)

1. Adams JY, Leav I, Lau KM, Ho SM, Pflueger SM (2002). Expression of estrogen receptor beta in the fetal, neonatal, and prepubertal human prostate. Prostate 52 : 69 81.
2. Alexander SPH, Mathie A, Peters JA (2008). Guide to receptors and channels (GRAC), 3rd edn. Br J Pharmacol 153 (Suppl. 2 S1 S209.
3. Bosland MC (2006). Sex steroids and prostate carcinogenesis integrated, multifactorial working hypothesis. Ann N Y Acad Sci 1089 : 168 176.
4. Brzozowski AM, Pike AC, Dauter Z, Hubbard RE, Bonn T, Engström O et al. (1997). Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 389 : 753 758.
5. Ellem SJ, Risbridger GP (2007). Treating prostate cancer: A rationale for targeting local oestrogens. Nat Rev Cancer 7 : 621 627.
6. Grosse J, Anielski P, Hemmersbachb P, Lundb H, Mueller RK, Rautenberg C et al. (2005). Formation of 19-norsteroids by in situ demethylation of endogenous steroids in stored urine samples. Steroids 70 : 499 506.
7. Gruber CJ, Tschugguel W, Schneeberger C, Huber JC (2002). Production and actions of estrogens. N Engl J Med 346 : 340 352.
8. Lee AJ, Cai MX, Thomas PE, Conney AH, Zhu BT (2003). Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology 144 (8 3382 3398.
9. Lindzey J, Wetsel WC, Couse JF, Stoker T, Cooper R, Korach KS (1998). Effects of castration and chronic steroid treatments on hypothalamic gonadotropin-releasing hormone content and pituitary gonadotropins in male wild type and estrogen receptor α knockout mice. Endocrinology 139 : 4092 4101.
10. Liu ZJ, Zhu BT (2004). Concentration-dependent mitogenic and antiproliferative actions of 2-methoxyestradiol in estrogen receptor-positive human breast cancer cells. J Steroid Biochem Mol Biol 88 : 265 275.
11. Liu ZJ, Lee WJ, Zhu BT (2005). Selective insensitivity of ZR-75-1 human breast cancer cells to 2-methoxyestradiol: Evidence for type II 17β-hydroxysteroid dehydrogenase as the underlying cause. Cancer Res 65 : 5802 5811.
12. Makridakis NM, di Salle E, Reichardt JKV (2000). Biochemical and pharmacogenetic dissection of human steroid 5[alpha]-reductase type II. Pharmacogenetics 10 : 407 413.
13. Manas ES, Unwalla RJ, Xu ZB, Malamas MS, Miller CP, Harris HA et al. (2004). Structure-based design of estrogen receptor-beta selective ligands. J Am Chem Soc 126 : 15106 15119.
14. Nilsson S, Gustafsson JÅ (2002). Biological role of estrogen and estrogen receptors. Crit Rev Biochem Mol Biol 37 : 1 28.
15. Peltoketo H, Luu-The V, Simard J, Adamski J (1999). 17β- Hydroxysteroid dehydrogenase (HSD)/17-ketosteroid reductase (KSR) family; nomenclature and main characteristics of the 17HSD/KSR enzymes. J Mol Endocrinol 23 : 1 11.
16. Peterson TJ, Karmakar S, Pace MC, Gao T, Smith CL (2007). The silencing mediator of retinoic acid and thyroid hormone receptor (SMRT) corepressor is required for full estrogen receptor alpha transcriptional activity. Mol Cell Biol 27 : 3933 3948.
17. Prins GS, Birch L, Couse JF, Choi I, Katzenellenbogen B, Korach KS (2001). Estrogen imprinting of the developing prostate gland is mediated through stromal estrogen receptor alpha: Studies with alphaERKO and betaERKO mice. Cancer Res 61 : 6089 6097.
18. Rochira V, Balestrieri A, Madeo B, Baraldi E, Faustini-Fustini M, Granata AR et al. (2001). Congenital estrogen deficiency: In search of the estrogen role in human male reproduction. Mol Cell Endocrinol 178 : 107 115. (Pubitemid 32515355)
19. de Ronde W, Pols HA, van Leeuwen JP, de Jong FH (2003). The importance of oestrogens in males. Clin Endocrinol (Oxf) 58 : 529 542.
20. 4 isomerase gene family. Endocr Rev 26 : 525 582.
21. Simpson ER, Davis SR (2001). Mini-review: Aromatase and the regulation of estrogen biosynthesis-some new perspectives. Endocrinology 142 : 4589 4594.
22. Weihua Z, Makela S, Andersson LC, Salmi S, Saji S, Webster JI et al. (2001). A role for estrogen receptor beta in the regulation of growth of the ventral prostate. Proc Natl Acad Sci USA 98 : 6330 6335.
23. Weihua Z, Lathe R, Warner M, JÅ G (2002). An endocrine pathway in the prostate, ERb, AR, 5α-androstane-3β,17β-diol, and CYP7B1, regulates prostate growth. Proc Natl Acad Sci USA 99 : 13589 13594.
24. Zhu BT, Conney AH (1998). Functional role of estrogen metabolism in target cells: Review and perspectives. Carcinogenesis 19 : 1 27.
25. Zhu BT, Han GZ, Shim JY, Wen Y, Jiang XR (2006). Quantitative structure-activity relationship of various endogenous estrogen metabolites for human estrogen receptor α and β subtypes: Insights into the structural determinants favoring a differential subtype binding. Endocrinology 147 : 4132 4150.