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Pure and Applied Chemistry

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Volume 89, Issue 9 (Aug 2017)

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Synthesis and antiproliferative evaluation of novel azido nucleosides and their phosphoramidate derivatives

Nuno M. XavierORCID iD: http://orcid.org/0000-0001-8739-8768 / Rita Gonçalves-PereiraORCID iD: http://orcid.org/0000-0002-8501-1627 / Radek JordaORCID iD: http://orcid.org/0000-0002-4905-7126
  • Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Palacký University and Institute of Experimental Botany AS CR, Šlechtitelů 27, 78371 Olomouc, Czech Republic
  • orcid.org/0000-0002-4905-7126
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Eva ŘezníčkováORCID iD: http://orcid.org/0000-0003-4773-2850
  • Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Palacký University and Institute of Experimental Botany AS CR, Šlechtitelů 27, 78371 Olomouc, Czech Republic
  • orcid.org/0000-0003-4773-2850
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Vladimír KryštofORCID iD: http://orcid.org/0000-0001-5838-2118
  • Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Palacký University and Institute of Experimental Botany AS CR, Šlechtitelů 27, 78371 Olomouc, Czech Republic
  • orcid.org/0000-0001-5838-2118
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ M. Conceição OliveiraORCID iD: http://orcid.org/0000-0002-3068-4920
Published Online: 2017-03-27 | DOI: https://doi.org/10.1515/pac-2016-1218

Abstract:

New xylofuranosyl and glucopyranosyl nucleoside phosphoramidates were synthesized as potential mimetics of nucleoside 5′-monophosphates. Their access involved N-glycosylation of uracil and 2-acetamido-6-chloropurine with 5′/6′-azido-1,2-di-O-acetyl glycosyl donors and subsequent Staudinger-phosphite reaction of the resulting azido nucleosides. The coupling of the purine derivative with the pyranosyl donor furnished N9- and N7-linked nucleosides in 1:1 ratio, whereas with the furanosyl donor, the N9-nucleoside was the major regioisomer formed. When using uracil, only 5′/6′-azido N1-linked nucleosides were obtained. The purine 5′/6′-azido nucleosides were converted into corresponding phosphoramidates in good yields. The antiproliferative effects of the nucleoside phosphoramidates and those of the azido counterparts on cancer cells were evaluated. While the nucleoside phosphoramidates did not show significant activities, the purine 5′/6′-azido nucleosides displayed potent effects against K562, MCF-7 and BT474 cell lines. The 5′-azidofuranosyl N9 and N7-linked purine nucleosides exhibited highest activity towards the chronic myeloid leukemia cell line (K562) with GI50 values of 13.6 and 9.7 μM, respectively. Among pyranosyl nucleosides, the N7-linked nucleoside was the most active compound with efficacy towards all cell lines assayed and a highest effect on K562 cells (GI50=6.8 μM). Cell cycle analysis of K562 and MCF-7 cells showed that the most active compounds cause G2/M arrest.

Keywords: anticancer activity; azido nucleosides; bioactive molecules; ICS-28; nucleoside/nucleotide analogs; nucleoside phosphoramidates; N-glycosylation; Staudinger-phosphite reaction

Article note:

A collection of invited papers based on presentations at the XXVIII International Carbohydrate Symposium (ICS-28), New Orleans, July 17–21 2016.

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About the article

Published Online: 2017-03-27

Published in Print: 2017-08-28


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2016-1218.

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[1]
Nuno M. Xavier, Alexandre Porcheron, Daniela Batista, Radek Jorda, Eva Řezníčková, Vladimír Kryštof, and M. Conceição Oliveira
Org. Biomol. Chem., 2017, Volume 15, Number 21, Page 4667

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