Steroid structure and function VII. Remarkable estrogenicity of 3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione

Albert Segaloff; R. Bruce Gabbard; Albert Flores; Ronald F. Borne; John K. Baker; William L. Duax; Phyllis D. Strong; Douglas C. Rohrer

doi:10.1016/0039-128X(80)90046-X

Steroid structure and function VII. Remarkable estrogenicity of 3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione

Albert Segaloff
, R. Bruce Gabbard
, Albert Flores
, Ronald F. Borne
, John K. Baker
, William L. Duax
, Phyllis D. Strong
, Douglas C. Rohrer

Department of Structural Biology

Ochsner Health System
University of Mississippi
Hauptman-Woodward Medical Research Institute, Inc.

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

Remarkably high estrogenic activity was observed for 3-hydroxy93-estra-1,3,5 (10)-triene-ll,17-dione despite its unusual bent conformation. The 9α epimer of this compound has markedly less activity despite the fact that its overall shape is nearly identical to that of estrone. The potency of these compounds in enhancing uterine weight in Fischer rats and reducing ovarian weight in parabiosed rats was compared with that of estrone, and the structures were unambiguously identified by X-ray crystallographic study. The results underscore the importance of the phenolic ring A to estrogenic activity, and suggest a tolerance of the putative estrogenic receptor to flexibility in overall molecular shape.

Original language	English
Pages (from-to)	335-349
Number of pages	15
Journal	Steroids
Volume	35
Issue number	3
DOIs	https://doi.org/10.1016/0039-128X(80)90046-X
State	Published - Mar 1980

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title = "Steroid structure and function VII. Remarkable estrogenicity of 3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione",

abstract = "Remarkably high estrogenic activity was observed for 3-hydroxy93-estra-1,3,5 (10)-triene-ll,17-dione despite its unusual bent conformation. The 9α epimer of this compound has markedly less activity despite the fact that its overall shape is nearly identical to that of estrone. The potency of these compounds in enhancing uterine weight in Fischer rats and reducing ovarian weight in parabiosed rats was compared with that of estrone, and the structures were unambiguously identified by X-ray crystallographic study. The results underscore the importance of the phenolic ring A to estrogenic activity, and suggest a tolerance of the putative estrogenic receptor to flexibility in overall molecular shape.",

author = "Albert Segaloff and Gabbard, \{R. Bruce\} and Albert Flores and Borne, \{Ronald F.\} and Baker, \{John K.\} and Duax, \{William L.\} and Strong, \{Phyllis D.\} and Rohrer, \{Douglas C.\}",

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doi = "10.1016/0039-128X(80)90046-X",

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T1 - Steroid structure and function VII. Remarkable estrogenicity of 3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione

AU - Segaloff, Albert

AU - Gabbard, R. Bruce

AU - Flores, Albert

AU - Borne, Ronald F.

AU - Baker, John K.

AU - Duax, William L.

AU - Strong, Phyllis D.

AU - Rohrer, Douglas C.

PY - 1980/3

Y1 - 1980/3

N2 - Remarkably high estrogenic activity was observed for 3-hydroxy93-estra-1,3,5 (10)-triene-ll,17-dione despite its unusual bent conformation. The 9α epimer of this compound has markedly less activity despite the fact that its overall shape is nearly identical to that of estrone. The potency of these compounds in enhancing uterine weight in Fischer rats and reducing ovarian weight in parabiosed rats was compared with that of estrone, and the structures were unambiguously identified by X-ray crystallographic study. The results underscore the importance of the phenolic ring A to estrogenic activity, and suggest a tolerance of the putative estrogenic receptor to flexibility in overall molecular shape.

AB - Remarkably high estrogenic activity was observed for 3-hydroxy93-estra-1,3,5 (10)-triene-ll,17-dione despite its unusual bent conformation. The 9α epimer of this compound has markedly less activity despite the fact that its overall shape is nearly identical to that of estrone. The potency of these compounds in enhancing uterine weight in Fischer rats and reducing ovarian weight in parabiosed rats was compared with that of estrone, and the structures were unambiguously identified by X-ray crystallographic study. The results underscore the importance of the phenolic ring A to estrogenic activity, and suggest a tolerance of the putative estrogenic receptor to flexibility in overall molecular shape.

UR - https://www.scopus.com/pages/publications/0018859591

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DO - 10.1016/0039-128X(80)90046-X

M3 - Article

C2 - 7376224

AN - SCOPUS:0018859591

SN - 0039-128X

VL - 35

SP - 335

EP - 349

JO - Steroids

JF - Steroids

IS - 3

ER -

Steroid structure and function VII. Remarkable estrogenicity of 3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione

Abstract

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