A new tetrazole-containing 2-amino-4,6-di(aziridin-1-yl)-1,3,5-triazine derivative: synthesis, interaction with DNA, and antitumor activity

({5-[4,6-Di(aziridin-1-yl)-1,3,5-triazin-2-yl]amino}-2,2-dimethyl-1,3-dioxan-5-yl)-methyl 2-(5-phenyl-2 H -tetrazol-2-yl)acetate was synthesized and characterized. The interaction of the obtained tetrazole-containing 2-amino-4,6-di(aziridin-1-yl)-1,3,5-triazine derivative with DNA was studied by UV...

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Veröffentlicht in:Russian chemical bulletin 2022-05, Vol.71 (5), p.1050-1056
Hauptverfasser: Mikolaichuk, O. V., Sharoyko, V. V., Popova, E. A., Protas, A. V., Fonin, A. V., Anufrikov, Yu. A., Malkova, A. M., Shmaneva, N. T., Ostrovskii, V. A., Molchanov, O. E., Maistrenko, D. N., Semenov, K. N.
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Sprache:eng
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Zusammenfassung:({5-[4,6-Di(aziridin-1-yl)-1,3,5-triazin-2-yl]amino}-2,2-dimethyl-1,3-dioxan-5-yl)-methyl 2-(5-phenyl-2 H -tetrazol-2-yl)acetate was synthesized and characterized. The interaction of the obtained tetrazole-containing 2-amino-4,6-di(aziridin-1-yl)-1,3,5-triazine derivative with DNA was studied by UV spectrophotometry, circular dichroism spectroscopy, and isothermal calorimetry. The values of binding constants (9.65·10 8 L mol −1 , UV spectrophotometry; 4.08·10 8 L mol −1 , isothermal calorimetry) of the 1,3,5-triazine derivative to DNA attests to efficient binding and formation of stable associates with the biopolymer. The addition of the tetrazole-containing 1,3,5-triazine derivative to a DNA solution has virtually no effect on the DNA melting point. The tetrazole-containing 1,3,5-triazine derivative exhibits a cytostatic effect on SK-HEP-1 human hepatic adenocarcinoma cells (half-maximal inhibitory concentration IC 50 22.2 mmol L −1 ) and T98G human glioblastoma cells (IC 50 44.9 mmol L −1 ).
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-022-3507-1