Syntheses and antiproliferative effects of D-homo- and D-secoestrones

被引：18

作者：

Mernyak, Erzsebet ^{[1
]}

Szabo, Johanna ^{[1
]}

Bacsa, Ildiko ^{[1
]}

Huber, Judit ^{[1
]}

Schneider, Gyula ^{[1
]}

Minorics, Renata ^{[2
]}

Bozsity, Noemi ^{[2
]}

Zupko, Istvan ^{[2
]}

Varga, Monika ^{[3
]}

Bikadi, Zsolt ^{[4
]}

Hazai, Eszter ^{[4
]}

Woelfling, Janos ^{[1
]}

机构：

[1] Univ Szeged, Dept Organ Chem, H-6720 Szeged, Hungary

[2] Univ Szeged, Dept Pharmacodynam & Biopharm, H-6720 Szeged, Hungary

[3] Cereal Res Nonprofit LTD, H-6701 Szeged, Hungary

[4] Virtua Drug Ltd, H-1015 Budapest, Hungary

来源：

STEROIDS | 2014年 / 87卷

基金：

匈牙利科学研究基金会;

关键词：

Homoestrone; Secoestrone; Antiproliferative effect; MTT assay; Tubulin polymerization; ORAL; 2-METHOXYESTRADIOL; TUBULIN POLYMERIZATION; BIOLOGICAL-ACTIVITY; ANTICANCER AGENTS; 3-METHYL ETHERS; DERIVATIVES; CANCER; ESTRONE; DOCKING; ANALOGS;

D O I：

10.1016/j.steroids.2014.05.015

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Substituted and/or heterocyclic D-homoestrone derivatives were synthetized via the intramolecular cyclization of a delta-alkenyl-D-secoaldehyde, -D-secoalcohol or -D-secocarboxylic acid of estrone 3-benzyl ether. The D-secoalcohol was modified at three sites in the molecule. The in vitro antiproliferative activities of the new D-homo- and D-secoestrone derivatives were determined on HeLa, MCF-7, A431 and A2780 cells through use of MU assay. D-Homoalcohols 3 and 5 displayed cell line-selective cytostatic effects against ovarian and cervical cell lines, respectively. Two D-secoestrones (6 and 12c) proved to be effective, with IC50 values comparable with those of the reference agent cisplatin. A selected compound (6) was tested by tubulin polymerization assay and its cancer specificity was additionally determined by using noncancerous human fibroblast cells. (C) 2014 Elsevier Inc. All rights reserved.

引用

页码：128 / 136

页数：9

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