Synthesis of trans-16-triazolyl-13α-methyl-17-estradiol diastereomers and the effects of structural modifications on their in vitro antiproliferative activities
Abstract Novel 16-triazoles in the 13α-estrone series were synthesized via Cu(I)-catalyzed azide–alkyne cycloaddition of the two diastereomeric (on C-16 and on C-17) 16-azido-13α-estra-1,3,5(10)-trien-17-ol 3-benzyl ethers with substituted phenylacetylenes. The new heterocyclic derivatives were eval...
Elmentve itt :
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| Dokumentumtípus: | Cikk |
| Megjelent: |
2015
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| Sorozat: | JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY
150 No. 0 |
| doi: | 10.1016/j.jsbmb.2015.04.001 |
| mtmt: | 2878758 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/6931 |
| LEADER | 02403nab a2200349 i 4500 | ||
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| 005 | 20190311175030.0 | ||
| 008 | 160603s2015 hu o 0|| zxx d | ||
| 022 | |a 0960-0760 | ||
| 024 | 7 | |a 10.1016/j.jsbmb.2015.04.001 |2 doi | |
| 024 | 7 | |a 2878758 |2 mtmt | |
| 040 | |a SZTE Publicatio Repozitórium |b hun | ||
| 041 | |a zxx | ||
| 100 | 1 | |a Mernyák Erzsébet | |
| 245 | 1 | 0 | |a Synthesis of trans-16-triazolyl-13α-methyl-17-estradiol diastereomers and the effects of structural modifications on their in vitro antiproliferative activities |h [elektronikus dokumentum] / |c Mernyák Erzsébet |
| 260 | |c 2015 | ||
| 300 | |a 123-134 | ||
| 490 | 0 | |a JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY |v 150 No. 0 | |
| 520 | 3 | |a Abstract Novel 16-triazoles in the 13α-estrone series were synthesized via Cu(I)-catalyzed azide–alkyne cycloaddition of the two diastereomeric (on C-16 and on C-17) 16-azido-13α-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 16β,17α 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. | |
| 700 | 0 | 1 | |a Kovács Ida |e aut |
| 700 | 0 | 1 | |a Minorics Renáta |e aut |
| 700 | 0 | 1 | |a Sere Péter |e aut |
| 700 | 0 | 1 | |a Czégány Dóra |e aut |
| 700 | 0 | 1 | |a Sinka Izabella |e aut |
| 700 | 0 | 1 | |a Wölfling János |e aut |
| 700 | 0 | 1 | |a Schneider Gyula |e aut |
| 700 | 0 | 1 | |a Újfaludi Zsuzsanna |e aut |
| 700 | 0 | 1 | |a Boros Imre Miklós |e aut |
| 700 | 0 | 1 | |a Ocsovszki Imre |e aut |
| 700 | 0 | 1 | |a Varga Mónika |e aut |
| 700 | 0 | 1 | |a Zupkó István |e aut |
| 856 | 4 | 0 | |u http://publicatio.bibl.u-szeged.hu/6931/1/134_J_Steroid_Biochem_Mol_Biol_2015.pdf |z Dokumentum-elérés |