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2′-Deoxy-2′-azidonucleoside analogs: synthesis and evaluation of antitumor and antimicrobial activity

Mieczkowski, Adam and Wińska, Patrycja and Kaczmarek, Marta and Mroczkowska, Magdalena and Garbicz, Damian and Pilżys, Tomasz and Marcinkowski, Michał and Piwowarski, Jan and Grzesiuk, Elzbieta (2018) 2′-Deoxy-2′-azidonucleoside analogs: synthesis and evaluation of antitumor and antimicrobial activity. Chemical Papers, 72 (4). pp. 981-990.

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Official URL: https://link.springer.com/article/10.1007%2Fs11696...


A series of ten pyrimidine nucleosides modified in 2′ position with azide or amine group was tested for the antibacterial, antifungal and cytotoxic activity. The cytotoxic effect was determined on three cancer (CCRF-CEM, MCF7, HeLa) and one normal (HEK293) cell lines, while antibacterial activity was evaluated on five bacterial strains. Among others, 2′-azido-2′deoxycytidine and 2′-amino-2′-deoxycytidine exhibited the strongest antiproliferative activity at 200 μM concentration, decreasing the viability of CCRF-CEM cells to 33 ± 1 and 36 ± 2%, respectively. Newly synthesized 2′-amino-2′-deoxythymidine exhibited cytotoxic effect exclusively toward HeLa cancer cell line, but not toward the normal HEK293 cells. Also, investigated compounds did not exhibit any antibacterial or antifungal activity at a concentration of 40 mM. The obtained results suggest that the presence of cytosine base is desirable for the appearance of cytotoxic effect, while the structural variations of the sugar ring play a minor role. Future modification of 2′-amino-2′-deoxythymidine could be a promising way to obtain more active anticancer substances.

Item Type:Article
Subjects:Q Science > QD Chemistry
R Medicine > RM Therapeutics. Pharmacology
Divisions:Department of Biophysics
ID Code:1515
Deposited By: Dr Adam Mieczkowski
Deposited On:26 Mar 2018 08:03
Last Modified:16 Nov 2018 23:05

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