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Molecules 2016, 21(9), 1212; doi:10.3390/molecules21091212

Synthesis and Biological Evaluation of Triazolyl 13α-Estrone–Nucleoside Bioconjugates

1
Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary
2
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary
3
1st Department of Medicine, University of Szeged, Korányi fasor 8-10, H-6720 Szeged, Hungary
4
Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary
*
Authors to whom correspondence should be addressed.
Academic Editor: Gyorgy M. Keseru
Received: 28 July 2016 / Revised: 2 September 2016 / Accepted: 6 September 2016 / Published: 10 September 2016
(This article belongs to the Collection New Frontiers in Nucleic Acid Chemistry)
View Full-Text   |   Download PDF [2934 KB, uploaded 10 September 2016]   |  

Abstract

2′-Deoxynucleoside conjugates of 13α-estrone were synthesized by applying the copper-catalyzed alkyne–azide click reaction (CuAAC). For the introduction of the azido group the 5′-position of the nucleosides and a propargyl ether functional group on the 3-hydroxy group of 13α-estrone were chosen. The best yields were realized in our hands when the 3′-hydroxy groups of the nucleosides were protected by acetyl groups and the 5′-hydroxy groups were modified by the tosyl–azide exchange method. The commonly used conditions for click reaction between the protected-5′-azidonucleosides and the steroid alkyne was slightly modified by using 1.5 equivalent of Cu(I) catalyst. All the prepared conjugates were evaluated in vitro by means of MTT assays for antiproliferative activity against a panel of human adherent cell lines (HeLa, MCF-7 and A2780) and the potential inhibitory activity of the new conjugates on human 17β-hydroxysteroid dehydrogenase 1 (17β-HSD1) was investigated via in vitro radiosubstrate incubation. Some protected conjugates displayed moderate antiproliferative properties against a panel of human adherent cancer cell lines (the protected cytidine conjugate proved to be the most potent with IC50 value of 9 μM). The thymidine conjugate displayed considerable 17β-HSD1 inhibitory activity (IC50 = 19 μM). View Full-Text
Keywords: nucleosides; 13α-estrone; copper-catalyzed alkyne–azide click reaction; triazoles; antiproliferative; 17β-HSD1 nucleosides; 13α-estrone; copper-catalyzed alkyne–azide click reaction; triazoles; antiproliferative; 17β-HSD1
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Bodnár, B.; Mernyák, E.; Wölfling, J.; Schneider, G.; Herman, B.E.; Szécsi, M.; Sinka, I.; Zupkó, I.; Kupihár, Z.; Kovács, L. Synthesis and Biological Evaluation of Triazolyl 13α-Estrone–Nucleoside Bioconjugates. Molecules 2016, 21, 1212.

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