Synthesis and Antibacterial Activity of Ethynyl and Azido Derivatives of N4-Dodecylamino-2'-deoxycytidine

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Resumo

Methods for obtaining new derivatives of N4-dodecylamino-2'-deoxycytidine and cytidine have been developed. The new derivatives contain 5-ethynyl, 5-(prop-2-in-1-yl)oxymethyl or 5'-azido groups necessary for the introduction of dyes in vitro using click chemistry methods. The obtained compounds, as well as N4-dodecylamino-2'-deoxycytidine, showed significant antibacterial activity against Gram-positive bacteria. The new nucleosides can be used to visualize their subcellular localization in order to determine the possible mechanism of action of antibacterial agents of this kind.

Sobre autores

D. Makarov

Engelhardt Institute of Molecular Biology Russian Academy of Sciences

Email: dmitmakarov_97@mail.ru
Moscow, Russia

M. Jasko

Engelhardt Institute of Molecular Biology Russian Academy of Sciences

Moscow, Russia

I. Karpenko

Engelhardt Institute of Molecular Biology Russian Academy of Sciences

Moscow, Russia

E. Urbina

Engelhardt Institute of Molecular Biology Russian Academy of Sciences

Moscow, Russia

V. Popenko

Engelhardt Institute of Molecular Biology Russian Academy of Sciences

Moscow, Russia

O. Leonova

Engelhardt Institute of Molecular Biology Russian Academy of Sciences

Moscow, Russia

Y. Tkachev

Engelhardt Institute of Molecular Biology Russian Academy of Sciences

Moscow, Russia

B. Vasilyeva

Gause Institute of New Antibiotics

Moscow, Russia

O. Efremenkova

Gause Institute of New Antibiotics

Moscow, Russia

S. Kochetkov

Engelhardt Institute of Molecular Biology Russian Academy of Sciences

Moscow, Russia

L. Alexandrova

Engelhardt Institute of Molecular Biology Russian Academy of Sciences

Moscow, Russia

Bibliografia

  1. Cañeque T., Müller S., Rodriguez R. // Nat. Rev. Chem. 2018. V. 2. P. 202–215. https://doi.org/10.1038/s41570-018-0030-x
  2. Kaur J., Saxena M., Rishi N. // Bioconjug. Chem. 2021. V. 32. P. 1455–1471. https://doi.org/10.1021/acs.bioconjchem.1c00247
  3. Ustinov A.V., Stepanova I.A., Dubnyakova V.V., Zatsepin T.S., Kochevnikova E.V., Korshun V.A. // Bioorg. Khimia. 2010. V. 36. P. 437–481.
  4. Alexandrova L.A., Jasko M.V., Negrya S.D., Solyev P.N., Shevchenko O.V., Solodinin A.P., Kolonitskaya D.P., Karpenko I.L., Efremenkova O.V., Glukhova A.A., Boykova Y.V., Efimenko T.A., Kost N.V., Avdanina D.A., Nuraeva G.K., Volkov I.A., Kochetkov S.N., Zhgun. A.A. // Eur. J. Med. Chem. 2021. V. 215. P. 113212. https://doi.org/10.1016/j.ejmech.2021.113212
  5. Alexandrova L.A., Shevchenko O.V., Jasko M.V., Solyev P.N., Karpenko I.L., Negrya S.D., Efremenkova O.V., Vasilieva B.F., Efimenko T.A., Avdanina D.A., Nuraeva G.K., Potapov M.P., Kukushkina V.I., Kochetkov S.N., Zhgun A.A. / // New J. Chem. 2022. V. 46. P. 5614–5626. https://doi.org/10.1039/D1NJ04312A
  6. Alexandrova L.A., Oskolsky I.A., Makarov D.A., Jasko M.V., Karpenko I.L., Efremenkova O.V., Vasilieva B.F., Avdanina D.A., Ermolyuk, A.A., Benko, E.E., Kalinin S.G., Kolganova T.V., Berzina M.Y., Konstantinova I.D., Chizhov A.O., Kochevkov S.N., Zhgun A.A. // Int. J. Mol. Sci. 2024. V. 25. P. 3053. https://doi.org/10.3390/ijms25053053
  7. Divakar K.J., Reese C.B. // J. Chem. Soc., Perkin Trans. 1982. P. 1171–1176. https://doi.org/10.1039/P19820001171
  8. Lin T.S., Gao Y.S., Mancini W.R. // J. Med. Chem. 1983. V. 26. P. 1691–1696. https://doi.org/10.1021/jm00366a006
  9. Barwolf D., Langen. P. // Nucleic Acid Chem. 1978, V. 1. P. 359–366.
  10. Wohl A. // Berichte der Dtsch. Chem. Gesellschaft (A B Ser.) 1919. V. 52. P. 51–63.
  11. Ziegler K., Schenck G., Krockow E.W., Siebert A., Wenz A., Weber H. // Justus Liebig's Ann. der Chemie. 1942. V. 551. P. 80–119.
  12. Levina A.S., Tabatadse D.R., Khalimskaya L.M., Prichodko T.A., Shishkin G.V., Alexandrova L.A., Zarytova V.P. // Bioconjug. Chem. 1993. V. 4. P. 319–325.
  13. Zarytova V.F., Komarova N.I., Levina A.S., Lokhov S.G., Tabatadze D.R., Khalimskaya L.M., Alexandrova L.A. // Bioorg. Khim. 1991. V. 17. P. 1059–1065.
  14. Nikš M., Otto M. // J. Immunol. Methods. 1990. V. 130. P. 149–151. https://doi.org/10.1016/0022-1759(90)90309-j
  15. Negrya S.D., Jasko M. V., Solyev P.N., Karpenko I.L., Efremenkova O.V., Vasilyeva B.F., Sumarakova I.G., Kochetkov S.N., Alexandrova L.A. // J. Antibiot. (Tokyo). 2020. V. 73. P. 236–246. https://doi.org/10.1038/s41429-019-0273-x

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