| Tartalom: |
http://dx.doi.org/10.1016/j.jsbmb.2015.04.001 |
| Archívum: |
MTA Könyvtár |
| Gyűjtemény: |
Status = Published
Type = Article
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| Cím: |
Synthesis of trans-16-triazolyl-13?-methyl-17-estradiol diastereomers and the effects of structural modifications on their in vitro antiproliferative activities
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| Létrehozó: |
Mernyák, Erzsébet
Kovács, Ida
Minorics, Renáta
Sere, Péter
Czégány, Dóra
Wölfling, János
Schneider, Gyula
Újfaludi, Zsuzsanna
Boros, Imre Miklós
Zupkó, István
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| Dátum: |
2015
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| Téma: |
QH3011 Biochemistry / biokémia
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| Tartalmi leírás: |
Abstract Novel 16-triazoles in the 13?-estrone series were synthesized via Cu(I)-catalyzed azide?alkyne cycloaddition of the two diastereomeric (on C-16 and on C-17) 16-azido-13?-estra-1,3,5(10)-trien-17-ol 3-benzyl ethers with substituted phenylacetylenes. The new heterocyclic derivatives were evaluated in vitro by means of MTT assays for antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, MCF-7, A431, A2780, T47D, MDA-MB-231 and MDA-MB-361). The inversion of the configurations at C-16 and C-17 selectively affected the growth-inhibitory properties of the tested compounds. The 16?,17? isomers generally proved to be potent on all cell lines, with IC50 values comparable to those of the reference agent cisplatin. Change of the substitution pattern of the phenyl group of the acetylene led to great differences in antiproliferative properties. Exclusively the p-phenyl-substituted triazoles exerted high cytostatic effects. One of the most potent compounds activated caspase-3 and caspase-9 without influencing caspase-8, confirming the induction of apoptosis via the intrinsic pathway.
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| Típus: |
Article
PeerReviewed
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| Formátum: |
text
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| Azonosító: |
Mernyák, Erzsébet and Kovács, Ida and Minorics, Renáta and Sere, Péter and Czégány, Dóra and Wölfling, János and Schneider, Gyula and Újfaludi, Zsuzsanna and Boros, Imre Miklós and Zupkó, István (2015) Synthesis of trans-16-triazolyl-13?-methyl-17-estradiol diastereomers and the effects of structural modifications on their in vitro antiproliferative activities. JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 150. pp. 123-134. ISSN 0960-0760
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