Increasing the water solubility of N-acyl-substituted amino acid esters as inhibitors of the replication of modern influenza A virus strains in vitro due to zinc(II) complexation
- Autores: Garaev Т.М.1, Yudin I.I.1, Breslav N.V.1, Savochkina Т.Е.1, Krepkaya А.S.1, Grebennikova Т.V.1, Nikiforova S.Е.2, Myshletsov I.I.2, Avdeeva V.V.2, Malinina Е.А.2
-
Afiliações:
- National Research Center for Epidemiology and Microbiology named after Honorary Academician N.F. Gamaleya, Ministry of Health of the Russian Federation
- Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
- Edição: Volume 69, Nº 5 (2024)
- Páginas: 736-742
- Seção: КООРДИНАЦИОННЫЕ СОЕДИНЕНИЯ
- URL: https://kazanmedjournal.ru/0044-457X/article/view/666540
- DOI: https://doi.org/10.31857/S0044457X24050113
- EDN: https://elibrary.ru/YEWODX
- ID: 666540
Citar
Resumo
This article proposes carbocyclic derivatives of N-acylated esters of L-amino acids with aromatic carboxylic acids as antiviral low-molecular agents. To increase the water solubility of inhibitors that are insoluble in aqueous solutions, the target compounds were used in the form of zinc(II) complexes. It has been shown that hydrophobic organic compounds in the form of zinc(II)-coordinated ligands are capable of suppressing the replication of an influenza A virus strain resistant to adamantane-type drugs. Zinc(II) chloride at the concentration used does not have antiviral or toxic effects in experiments in vitro.
Palavras-chave
Sobre autores
Т. Garaev
National Research Center for Epidemiology and Microbiology named after Honorary Academician N.F. Gamaleya, Ministry of Health of the Russian Federation
Email: avdeeva.varvara@mail.ru
Rússia, Moscow
I. Yudin
National Research Center for Epidemiology and Microbiology named after Honorary Academician N.F. Gamaleya, Ministry of Health of the Russian Federation
Email: avdeeva.varvara@mail.ru
Rússia, Moscow
N. Breslav
National Research Center for Epidemiology and Microbiology named after Honorary Academician N.F. Gamaleya, Ministry of Health of the Russian Federation
Email: avdeeva.varvara@mail.ru
Rússia, Moscow
Т. Savochkina
National Research Center for Epidemiology and Microbiology named after Honorary Academician N.F. Gamaleya, Ministry of Health of the Russian Federation
Email: avdeeva.varvara@mail.ru
Rússia, Moscow
А. Krepkaya
National Research Center for Epidemiology and Microbiology named after Honorary Academician N.F. Gamaleya, Ministry of Health of the Russian Federation
Email: avdeeva.varvara@mail.ru
Rússia, Moscow
Т. Grebennikova
National Research Center for Epidemiology and Microbiology named after Honorary Academician N.F. Gamaleya, Ministry of Health of the Russian Federation
Email: avdeeva.varvara@mail.ru
Rússia, Moscow
S. Nikiforova
Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Email: avdeeva.varvara@mail.ru
Rússia, Moscow
I. Myshletsov
Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Email: avdeeva.varvara@mail.ru
Rússia, Moscow
V. Avdeeva
Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Autor responsável pela correspondência
Email: avdeeva.varvara@mail.ru
Rússia, Moscow
Е. Malinina
Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Email: avdeeva.varvara@mail.ru
Rússia, Moscow
Bibliografia
- Sarkar A., Mandal K. // Angew. Chem. Int. Ed. Engl. 2021. V. 60. P. 23492. https://doi.org/10.1002/anie.202107481
- Davies W.L., Grunnert R.R., Haff R.F. et al. // Science. 1964. V. 44. P. 862.
- Togo Y., Hornick R.B., Dawkins A.T. // J. Am. Med. Assoc. 1968. V. 203. P. 1089.
- Wendel H.A., Snyder M.T., Pell S. // Clin. Pharmacol. Ther. 1966. V. 7. P. 38.
- Okada A., Miura T., Takeuchi H. // Biochemistry. 2001. V. 40. P. 6053.
- Avdeeva V.V., Garaev T.M., Malinina E.A. et al. // Russ. J. Inorg. Chem. 2022. V. 67. P. 28. https://doi.org/10.1134/S0036023622010028
- Shibnev V.A., Deryabin P.G., Garaev T.M. et al. // Russ. J. Bioorg. Chem. 2017. V. 43. P. 517.
- Garaev T.M., Odnovorov A.I., Grebennikova T.V. et al. // Adv. Pharm. Bull. 2021. V. 11. P. 700.
- Shibnev V.A., Garaev T.M., Finogenova M.P. et al. // Pharm. Chem. J. 2012. V. 46. P. 36.
- Шибнев В.А., Гараев Т.М., Финогенова М.П. и др. Пат. RU 2461544 С1. 2012.
- Климочкин Ю.Н., Леонова М.В., Ширяев А.К. Пат. RU 2553991 С1. 2008.
- Шибнев В.А., Дерябин П.Г., Бурцева Е.И. Пат. RU 2572102 С1. 2014.
- Caetano-Silva M.E., Cilla A., Bertoldo-Pacheco M.T. et al. // J. Food Comp. Anal. 2018. V. 68. P. 95. https://doi.org/10.1016/j.jfca.2017.03.010
- Lebedeva N.S., Mal’kova E.A., Pavlycheva N.A. et al. // Russ. J. Coord. Chem. 2004. V. 30. P. 864. https://doi.org/10.1007/s11173-005-0006-5
- Zhdanova K.A., Savel’eva I.O., Usanev A.Yu. et al. // Russ. J. Inorg. Chem. 2022. V. 67. P. 1756. https://doi.org/10.1134/S0036023622601209
- Dojer B., Golobič A., Babič N. et al. // J. Mol. Struct. 2022. V. 1265. P. 133393. https://doi.org/10.1016/j.molstruc.2022.133393
- Chuprin A.S., Dudkin S.V., Vologzhanina A.V. et al. // Russ. J. Inorg. Chem. 2023. V. 68. P. 713. https://doi.org/10.1134/S003602362360065X
- Jacob W., Mukherjee R. // Inorg. Chim. Acta. 2006. V. 359. P. 4565. https://doi.org/10.1016/j.ica.2006.07.003
- Leite S.M.G., Lima L.M.P., Gama S. et al. // Inorg. Chem. 2016. V. 55. P. 11801. https://doi.org/10.1021/acs.inorgchem.6b01884
- Wei Liao, Ziwei Zhu, Chenglian Feng et al. // J. Environ. Sci. 2023. V. 127. P. 495. https://doi.org/10.1016/j.jes.2022.06.002
- Gur’eva Y.A., Zalevskaya O.A., Kuchin A.V. // Russ. J. Coord. Chem. 2023. V. 49. P. 631. https://doi.org/10.1134/S1070328423700665
- Uvarova M.A., Novikova M.V., Eliseenkova V.A. et al. // Russ. J. Coord. Chem. 2023. V. 49. P. 680. https://doi.org/10.1134/S1070328423600419
- Betancourth J.G., Sánchez-Rodríguez N.E., Giraldo-Dávila D. et al. // Russ. J. Inorg. Chem. 2022. V. 67. P. 2200. https://doi.org/10.1134/S0036023622600782
- Ivanova I.S., Tsebrikova G.S., Ilyukhin A.B. et al. // Russ. J. Inorg. Chem. 2023. https://doi.org/10.1134/S0036023623601393
- Ermakova E.A., Golubeva Y.A., Smirnova K.S. et al. // Russ. J. Coord. Chem. 2023. V. 49. P. 593. https://doi.org/10.1134/S1070328423600158
- Garaev T.M., Yudin I.I., Breslav N.V. et al. // Tetrahedron. 2023. V. 151. № 133785.
- Garaev T., Breslav N., Grebennikova T. et al. // Proc. 9th Int. Electron. Conf. Med. Chem., 1–30 November 2023, MDPI: Basel, Switzerland. https://doi.org/10.3390/ECMC2023–15805
- Garaev T.M., Yudin I.I., Breslav N.V. et al. // Curr. Pharm. Res. 2023 (in press).
- Shibnev V.A., Garaev T.M., Finogenova M.P. et al. // Pharm. Chem. J. 2012. V. 46. P. 1.
- Бурцева Е.И., Шевченко Е.С., Ленева И.А. и др. // Вопр. вирусологии. 2007. № 2. С. 24.
- Лeнeвa И.A., Фaдeeвa Н.И., Фeдякинa И.T. и др. // Хим.-фарм. журн. 1994. № 9. C. 4.
- Шибнев В.А., Дерябин П.Г., Бурцева Е.И. Пат. RU 2624906 С1. 2015.
Arquivos suplementares
