eISSN: 2353-9461
ISSN: 0860-7796
BioTechnologia
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1/2019
vol. 100
 
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abstract:
RESEARCH PAPERS

Synthesis and in vitro anticancer activity of N-alkyl phosphoramidate monoesters of 3’-azido-3’-deoxythymidine (AZT)

Ewa Czajkowska-Wojciechowska
1
,
Aleksandra Singh
1
,
Roksana Trznadel
1
,
Piotr Ruszkowski
2
,
Lech Celewicz
1

  1. Faculty of Chemistry, Adam Mickiewicz University, Poznań, Poland
  2. Department of Pharmacology, Poznań University of Medical Sciences, Poznań, Poland
BioTechnologia vol. 100 (1) C pp. 81–88 C 2019
DOI: https://doi.org/10.5114/bta.2019.83214
Online publish date: 2019/03/27
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In this study, a series of novel N-alkyl phosphoramidate monoesters of 3’-azido-3’-deoxythymidine (AZT) were synthesized using two methods. The synthesized phosphoramidates 7a–e were evaluated for their cytotoxic activity in three human cancer cell lines (cervical cancer (HeLa), nasopharyngeal cancer (KB), and breast cancer (MCF-7)) and a normal dermal fibroblast cell line (HDF) using sulforhodamine B assay. Among the synthesized phosphoramidates, the highest cytotoxic activity was demonstrated by phosphoramidate 7d with the N-n-propyl substituent in all the examined cancer cell lines, and its activity was found to be about two fold higher than that of the parent nucleoside (AZT). Phosphoramidate 7d showed not only a high cytotoxic activity against cancer cell lines but also a low toxicity against normal fibroblast cells; its selectivity index was >3 for all the investigated cancer cell lines. A slightly lower cytotoxic activity was shown by phosphoramidates 7a, 7b, and 7e, whereas phosphoramidate 7c with the N-(2,2,2-trifluoroethyl) substituent exhibited the least cytotoxic activity in all the cell lines used.
keywords:

N-alkyl phosphoramidate monoesters of 3’-azido-3’-deoxythymidine, cytotoxic activity, human cancer cell lines – HeLa, KB, MCF-7, normal human cell line – HDF


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