A new tetrazole-containing 2-amino-4,6-di(aziridin-1-yl)-1,3,5-triazine derivative

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

In: Russian Chemical Bulletin, Vol. 71, No. 5, 05.2022, p. 1050-1056.

Research output: Contribution to journal › Article › peer-review

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@article{a845470629c144ea959e8a9d43ebde5d,

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

abstract = "({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-2H-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 (9.65·108 L mol−1, UV spectrophotometry; 4.08·108 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 IC50 22.2 mmol L−1) and T98G human glioblastoma cells (IC50 44.9 mmol L−1).",

keywords = "калориметрия, антибиотики, триазин, днк",

author = "Mikolaichuk, {O. V.} and Sharoyko, {V. V.} and Popova, {E. A.} and Protas, {A. V.} and Fonin, {A. V.} and Anufrikov, {Yu A.} and Malkova, {A. M.} and Shmaneva, {N. T.} and Ostrovskii, {V. A.} and Molchanov, {O. E.} and Maistrenko, {D. N.} and Semenov, {K. N.}",

note = "Mikolaichuk, O.V., Sharoyko, V.V., Popova, E.A. et al. A new tetrazole-containing 2-amino-4,6-di(aziridin-1-yl)-1,3,5-triazine derivative: synthesis, interaction with DNA, and antitumor activity. Russ Chem Bull 71, 1050–1056 (2022). https://doi.org/10.1007/s11172-022-3507-1",

year = "2022",

month = may,

doi = "10.1007/s11172-022-3507-1",

language = "English",

volume = "71",

pages = "1050--1056",

journal = "Russian Chemical Bulletin",

issn = "1066-5285",

publisher = "Springer Nature",

number = "5",

}

RIS

TY - JOUR

T1 - A new tetrazole-containing 2-amino-4,6-di(aziridin-1-yl)-1,3,5-triazine derivative

T2 - synthesis, interaction with DNA, and antitumor activity

AU - Mikolaichuk, O. V.

AU - Sharoyko, V. V.

AU - Popova, E. A.

AU - Protas, A. V.

AU - Fonin, A. V.

AU - Anufrikov, Yu A.

AU - Malkova, A. M.

AU - Shmaneva, N. T.

AU - Ostrovskii, V. A.

AU - Molchanov, O. E.

AU - Maistrenko, D. N.

AU - Semenov, K. N.

N1 - Mikolaichuk, O.V., Sharoyko, V.V., Popova, E.A. et al. A new tetrazole-containing 2-amino-4,6-di(aziridin-1-yl)-1,3,5-triazine derivative: synthesis, interaction with DNA, and antitumor activity. Russ Chem Bull 71, 1050–1056 (2022). https://doi.org/10.1007/s11172-022-3507-1

PY - 2022/5

Y1 - 2022/5

N2 - ({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-2H-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 (9.65·108 L mol−1, UV spectrophotometry; 4.08·108 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 IC50 22.2 mmol L−1) and T98G human glioblastoma cells (IC50 44.9 mmol L−1).

AB - ({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-2H-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 (9.65·108 L mol−1, UV spectrophotometry; 4.08·108 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 IC50 22.2 mmol L−1) and T98G human glioblastoma cells (IC50 44.9 mmol L−1).

KW - калориметрия

KW - антибиотики

KW - триазин

KW - днк

UR - http://www.scopus.com/inward/record.url?scp=85130378497&partnerID=8YFLogxK

U2 - 10.1007/s11172-022-3507-1

DO - 10.1007/s11172-022-3507-1

M3 - Article

AN - SCOPUS:85130378497

VL - 71

SP - 1050

EP - 1056

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 5

ER -

ID: 100130803

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

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