Copper(II) сomplexes with 2-hydrохy-5-ethylphenylphosphosphonic acid: synthesis, structure, cytotoxicity, and accumulation in HeLa cells
- Autores: Rogacheva Y.1, Lapshina M.1, Baulin V.1
-
Afiliações:
- Institute of Physiologically Active Substances of the Federal Research Center for Problems of Chemical Physics and Medicinal Chemistry of the Russian Academy of Sciences
- Edição: Volume 93, Nº 6 (2023)
- Páginas: 967-977
- Seção: Articles
- URL: https://journals.rcsi.science/0044-460X/article/view/145073
- DOI: https://doi.org/10.31857/S0044460X23060161
- EDN: https://elibrary.ru/FNJMGL
- ID: 145073
Citar
Resumo
In order to study the physicochemical and biological properties of the coordination compounds of bioactive metal ions with 2-hydroxyphenylphosphonic acid derivatives, the reaction of 2-hydroxy-5-ethylphenylphosphonic acid (Н3L1) with copper(II) perchlorate, sulfate, nitrate, and acetate in water was studied for the first time. It has been established that, regardless of the ratio of reagents, in the case of copper(II) perchlorate, sulfate, and nitrate, a complex of the composition [Cu(H2L1)2(Н2О)2] is formed in high yield, while in the case of using copper(II) acetate a complex [Cu(HL1)(H2O)2] is formed, the composition of which is established on the basis of a combination of elemental analysis data, IR and electronic spectra. Quantum-chemical calculations of the structure of [Cu(H2L1)2(H2O)2] and [Cu(HL1)(H2O)2] complexes were performed for the first time by the density functional theory (DFT) method. The cytotoxic properties of H3L1 acid and copper complexes [Cu(HL1)(H2O)2] and [Cu(H2L1)2(H2O)2] with respect to HeLa tumor cells of human cervical adenocarcinoma were studied. The accumulation of the resulting copper(II) complexes in HeLa cells was proved by laser confocal microscopy.
Sobre autores
Yu. Rogacheva
Institute of Physiologically Active Substances of the Federal Research Center for Problems of Chemical Physics and Medicinal Chemistry of the Russian Academy of Sciences
M. Lapshina
Institute of Physiologically Active Substances of the Federal Research Center for Problems of Chemical Physics and Medicinal Chemistry of the Russian Academy of Sciences
V. Baulin
Institute of Physiologically Active Substances of the Federal Research Center for Problems of Chemical Physics and Medicinal Chemistry of the Russian Academy of Sciences
Email: mager1988@gmail.com
Bibliografia
- Zhang C., Lippard S. // Curr. Opin. Chem. Biol. 2003. Vol. 7. P. 481. doi: 10.1016/s1367-5931(03)00081-4
- Hambley T. // Science. 2007. Vol. 318. P. 1392. doi: 10.1126/science.1150504
- Barry N., Sadler P. // ACS Nano. 2013. Vol. 7. P. 5654. doi: 10.1021/nn403220e.
- Patra M., Gasser G. // Chem. Bioсhem. 2012. Vol. 13. P. 1232. doi: 10.1002/cbic.201200159
- Yu G., Jiang M., Huang F., Chen X. // Curr. Opin. Chem. Biol. 2021. Vol. 61. P. 19. doi: 10.1016/j.cbpa.2020.08.0076
- Pöthig A., Casini A. // Theranostics. 2019. Vol. 9. P. 3150. doi: 10.7150/thno.31828-6
- Mehrotra R., Bohra R., Gaur D. Metal β-diketonates and allied derivatives. London; New York: Academic Press, 1978. P. 382.
- Solomon E., Heppner D., Johnston E., Ginsbach J., Cirera J., Qayyum M., Kieber-Emmons M., Kjaergaard C., Hadt R., Tian L. // Chem. Rev. 2014. Vol. 114. P. 3659. doi: 10.1021/cr400327t
- Hussain A., AlAjmi M., Rehman M., Rehman M., Amir S., Husain F., Alsalme A., Siddiqui M., AlKhedhairy A., Khan R. // Sci. Rep. 2019. Vol. 9. P. 5237. doi: 10.1038/s41598-019-41063-x
- Iakovidis I., Delimaris I., Piperakis S. // Mol. Biol. Int. 2011. P. 594529. doi: 10.4061/2011/594529
- Tabti1 R., Tounsi N., Gaiddon C., Bentouhami E., Désaubry L. // Med. Chem. 2017. Vol. 75. P. 875. doi: 10.4172/2161-0444.1000445
- Dalecki A., Crawford C., Wolschendorf F. // Rev. Adv. Microb. Physiol. 2017. Vol. 70. P. 193. doi: 10.1016/bs.ampbs.2017.01.007
- Arredondo M., Nunez M. // Mol. Aspects Med. 2005. Vol. 26. N 4-5. P. 313. doi: 10.1016/j.mam.2005.07.010
- Uriu-Adams J., Keen C. // Mol. Aspects Med. 2005. Vol. 26. N 4-5. P. 268. doi: 10.1016/j.mam.2005.07.015
- Crisponi G., Nurchi V., Fanni D., Gerosa C., Nemolato S., Faa G. // Coord Chem Rev. 2010. Vol. 254 P. 876. doi: 10.1016/j.ccr.2009.12.018
- Weder J., Dillon C., Hambley T., Kennedy T., Lay B., Biffin P., Regtop J., Davies H. // Coord Chem Rev. 2002. Vol. 232. P. 95. doi: 10.1016/s0010-545(02)00086-3.
- Muñoz C., López M., Olivares M., Pizarro F., Arredondo M., Araya M. // Eur. Cytokine Netw. 2005. Vol. 16. N 4. P. 261.
- Ott I, Gust R. // Arch. Pharm. Chem. Life Sci. 2007. Vol. 340. N 3. P. 117. doi: 10.1002/ardp.200600151
- González-Vílchez F., Vilaplana R. Metallotherapeutic Drugs and Metal-Based Diagnostic Agents. The Use of Metals in Medicine. New York: John Wiley & Sons, Ltd., 2005. P. 219. doi: 10.1002/0470864052.ch12
- Szymański P., Frączek T., Markowicz M., Mikiciuk-Olasik Е. // Biometals. 2012. Vol. 25. P. 1089. doi: 10.1007/s10534-012-9578-y
- Орлов А.П., Трофимова Т.П., Орлова М.А. // Изв. АН. Сер. хим. 2022. № 3. С. 415
- Orlov A.P., Trofimova T.P., Orlova M.A. // Russ. Chem. Bull. 2022. Vol. 71. N 3. Р. 415. doi: 10.1007/s11172-022-3429-y
- Ekinciz D., Senturk M., Kufrevioglu O. // Expert Opin Ther Pat. 2011. Vol. 21. N 12. P. 1831. doi: 10.1517/13543776.2011.636354
- Amann R., Peskar B. // Eur. J. Pharmacol. 2002. Vol. 447. P. 1. doi: 10.1016/s0014-2999(02)01828-9
- Egorova K., Gordeev E., Ananikov V. // Chem. Rev. 2017. Vol. 117. P. 7132. doi: 10.1021/acs.chemrev.6b00562
- Rodriguez-Aller M., Guillarme D., Veuthey J.-L., Gurny R. // J. Drug Deliv. Sci. Technol. 2015. Vol. 30. P. 342. doi: 10.1016/j.jddst.2015.05.009
- Баулин В.Е., Калашникова И.П., Вихарев Ю.Б., Вихарева Е.А., Баулин Д.В., Цивадзе А.Ю. // ЖОХ. 2018. № 9. C. 1438
- Baulin V.Е., Kalashnikova I.Р., Vikharev Yu.В., Vikharevа Е.А., Baulin D.V., Tsivadze A.Yu. // Russ. J. Gen. Chem. 2018. Vol. 88. N 9. P. 1786. doi: 10.1134/S0044460X18090044
- Иванова И.С., Цебрикова Г.С., Лапшина М.А., Рогачева Ю.И., Илюхин А.Б, Соловьев В.П., Пятова Е.Н., Баулин В.Е. // Изв. АН. Сер. хим. 2022. № 11. C. 2365
- Ivanova I.S., Tsebrikova G.S., Lapshina M.А., Rogacheva Yu.I., Ilyukhin A.B., Solov'ev V.P., Pyatova E.N., Baulin V.E. // Russ. Chem. Bulletin. Vol. 71. N 11. Р. 2365. doi: 10.1007/s11172-022-3664-2
- Иванова И.С., Цебрикова Г.С., Рогачева Ю.И., Илюхин А.Б., Соловьев В.П., Пятова Е.Н., Баулин В.Е. // ЖНХ. 2021. Т. 66. № 12. С. 1723
- Ivanova I.S., Tsebrikova G.S., Rogacheva Yu. I., Ilyukhin A.B., Solov'ev V.P., Pyatova E.N., Baulin V.E. // Russ. J. Inorg. Chem. 2021. Vol. 66. N 12. P. 1846. doi: 10.1134/S0036023621120068