Synthesis and Antiproliferative Activity of Steroidal Diaryl Ethers

被引：12
作者：
Kovacs, Edua [1 ]
Ali, Hazhmat [2 ]
Minorics, Renata [2 ]
Traj, Peter [1 ]
Resch, Vivien [3 ]
Paragi, Gabor [3 ,4 ,5 ]
Bruszel, Bella [3 ]
Zupko, Istvan [2 ]
Mernyak, Erzsebet [1 ]
机构：
[1] Univ Szeged, Dept Organ Chem, H-6720 Szeged, Hungary
[2] Univ Szeged, Inst Pharmacodynam & Biopharm, H-6720 Szeged, Hungary
[3] Univ Szeged, Dept Med Chem, H-6720 Szeged, Hungary
[4] Univ Pecs, Inst Phys, H-7625 Pecs, Hungary
[5] Univ Szeged, Dept Theoret Phys, H-6720 Szeged, Hungary
来源：
MOLECULES | 2023年 / 28卷 / 03期
关键词：
Chan-Lam reaction; diaryl ether; 13; alpha-estrone; antiproliferative effect; tubulin polymerization; molecular dynamics; 13-ALPHA-ESTRONE DERIVATIVES; ANTICANCER AGENTS; BREAST-CANCER; IN-VITRO; INHIBITORS; DESIGN; DISCOVERY; GROWTH; COPPER; ACIDS;
D O I：
10.3390/molecules28031196
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：
Novel 13 alpha-estrone derivatives have been synthesized via direct arylation of the phenolic hydroxy function. Chan-Lam couplings of arylboronic acids with 13 alpha-estrone as a nucleophilic partner were carried out under copper catalysis. The antiproliferative activities of the newly synthesized diaryl ethers against a panel of human cancer cell lines (A2780, MCF-7, MDA-MB 231, HeLa, SiHa) were investigated by means of MTT assays. The quinoline derivative displayed substantial antiproliferative activity against MCF-7 and HeLa cell lines with low micromolar IC50 values. Disturbance of tubulin polymerization has been confirmed by microplate-based photometric assay. Computational calculations reveal significant interactions of the quinoline derivative with the taxoid binding site of tubulin.
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页数：17
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