Steroids p. 242 - 246 (1990)
Update date:2022-08-29
Topics:
Kellis, James T.
Vickery, Larry E.
In an early survey of steroids which might serve as estrogen precursors, Gual et al. reported that 6α-fluorotestosterone is not aromatized by human placental microsomes.Subsequently, 6α-fluorotestosterone has been used to distinguish between androgen- and estrogen-mediated physiologic effects.We have reexamined the interaction of 6α-fluorotestosterone with human placental and rat ovarian microsomes and with reconstituted purified aromatase cytochrome P450.Under conditions in which testosterone was readily aromatized, no aromatization of 6α-fluorotestosterone was observed using either fluorescence detection of dansyl-estrogens separated by high-performance liquid chromatography or estrogen radioimmunoassay methods.The lack of aromatization is not due to failure of 6α-fluorotestosterone to bind P450arom, because 6α-fluorotestosterone acts as a competitive inhibitor of the enzyme, and it exhibits a binding affinity similar to that of testosterone.Moreover, the addition of 6α-fluorotestosterone to human placental microsomes elicits a spectral shift indicative of conversion of the heme from a low to a high spin state as observed for androgen substrates, cosistent with its binding to the substrate site.The mechanism by which substitution of a fluorine at the 6α-position interferes with the aromatization reaction remains to be determined, but the inhibitory action on estrogen formation may potentiate the androgenic properties of 6α-fluorotestosterone in vivo due to a lowering of estrogen levels.
View MoreTangshan Wisdom Trading Co.,Ltd
Contact:86 315 2222979
Address:No.41 BeiXinXi Road, Yangguang building 1-1102 , Tangshan, Hebei, China
Jiangsu Hualun Chemical Industry Co., Ltd
website:http://www.hualunchem.com
Contact:+86-0514-86464168 86507985
Address:39# Middle Renmin Road, Dinghuo Town
Beijing Hope Pharmaceutical Co., Ltd.
Contact:86-10-67886402
Address:309,Block 1 District B,No.12 Hongda North Road , Beijing Economic-Technological Development Area, Beijing, China
Shanghai Rainbow Chemistry Co., Ltd.
Contact:+86-21-64968086-5815/5812
Address:3rd floor, Building 7, 251 Faladi Road, Zhangjiang Hi-Tech Park, Pudong District, Shanghai, P.R. China
ZHEJIANG JIANYE CHEMICAL CO.,LTD.
Contact:86-571-64149273,64149234
Address:No. 48, Fuxi Road, Meicheng Town
Doi:10.14233/ajchem.2020.22710
(2020)Doi:10.1246/bcsj.69.1423
(1996)Doi:10.1016/j.tetlet.2005.08.098
(2005)Doi:10.1111/j.1751-1097.2009.00669.x
(2010)Doi:10.1271/bbb.59.1938
(1995)Doi:10.1016/j.tetlet.2009.03.110
(2009)