Email this article Supramolecular Catalysts for the Radical Destruction of Hydroperoxides Based on Choline Derivatives
- Authors: Potapova N.V.1, Kasaikina O.T.1, Berezin M.P.2, Plashchina I.G.3, Gulin A.A.1
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Affiliations:
- Semenov Federal Research Center for Chemical Physics RAS
- Institute of Problems of Chemical Physics, Chernogolovka Branch, Russian Academy of Sciences
- Emanuel Institute of Biochemical Physics, Russian Academy of Sciences
- Issue: Vol 64, No 1 (2023)
- Pages: 78-85
- Section: ARTICLES
- URL: https://journals.rcsi.science/0453-8811/article/view/137027
- DOI: https://doi.org/10.31857/S0453881123010057
- EDN: https://elibrary.ru/KHDOZU
- ID: 137027
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Abstract
The effect of natural quaternary ammonium compounds (QAC) of choline (Ch) and its derivatives, acetylcholine (AСh) and L-carnitine (LCh), containing the tetraalkylammonium cation (CH3)3RN+, on the radical decomposition of hydroperoxides (ROOH) was studied. In mixtures of ACh and Ch with ROOH in chlorobenzene, mixed supramolecular nanoaggregates are formed, and accelerated decomposition of ROOH into radicals takes place; the rates of radical formation measured by the inhibitor method decrease in the series ACh > Ch \( \gg \) LCh. ACh and Ch immobilized on microcrystalline cellulose retain the ability to catalyze the radical decomposition of ROOH and initiate the polymerization of styrene containing ROOH from the surface. LСh adsorbed on cellulose does not affect the decomposition of ROOH and the rate of polymerization. Scanning electron microscopy (SEM) showed that ACh and Ch adsorbed on a silicon plate accelerate the radical decomposition of ROOH and initiate oxidative condensation of egg phosphatidylcholine on the surface of the plate, while adsorbed LCh does not affect the decomposition of ROOH. LCh, unlike ACh and Ch, is an internal salt in which the R4N+ cation is neutralized by its own carboxy anion, i.e., LCh has no external counterion and, probably, for this reason, it differs from ACh and Ch in the mechanism of adsorption and interaction with ROOH.
About the authors
N. V. Potapova
Semenov Federal Research Center for Chemical Physics RAS
Author for correspondence.
Email: pot.natalia2010@yandex.ru
Russian Federation, 119991, Moscow, 4 Kosygina Street, Building 1
O. T. Kasaikina
Semenov Federal Research Center for Chemical Physics RAS
Email: pot.natalia2010@yandex.ru
Russian Federation, 119991, Moscow, 4 Kosygina Street, Building 1
M. P. Berezin
Institute of Problems of Chemical Physics, Chernogolovka Branch, Russian Academy of Sciences
Email: pot.natalia2010@yandex.ru
Russian Federation, 142432, Moscow Region, Chernogolovka, Prosp. Akad. Semenova 1
I. G. Plashchina
Emanuel Institute of Biochemical Physics, Russian Academy of Sciences
Email: pot.natalia2010@yandex.ru
Russian Federation, 119934, Moscow, 4 Kosygina Street
A. A. Gulin
Semenov Federal Research Center for Chemical Physics RAS
Email: pot.natalia2010@yandex.ru
Russian Federation, 119991, Moscow, 4 Kosygina Street, Building 1
References
- Paulson D.S. // American Chemical Society: Washington, DC, USA, 2007. V. 967. P. 124.
- Gerba C.P. // Appl. Env. Microbiol. 2015. V. 81. P. 464.
- Jia Y., Niu L., MaS., Li J., Tay F.R., Chen J. // Progr. Polymer Sci. 2017. V. 71. P. 53. https://doi.org/10.1016/j.progpolymsci.2017.03.0013
- Vereshchagin A.N., Frolov N.A., Egorova K.S., Seitkalieva M.M., Ananikov V.P. // Int. J. Mol. Sci. 2021. V. 22. P. 6793. https://doi.org/10.3390/ijms22136793
- Карташева З.С., Максимова Т.В., Сирота Т.В., Коверзанова Е.В., Касаикина О.Т. // Нефтехимия. 1997. Т. 37. № 3. С. 249.
- Касаикина О.Т., Карташева З.С., Писаренко Л.М. // Общая химия. 2008. Т. 8. С. 1298.
- Касаикина О.Т., Круговов Д.А., Менгеле Е.А., Березин М.П., Фокин Д.А. // Нефтехимия. 2015. Т. 55. № 6. С. 535.
- Круговов Д.А., Менгеле Е.А, Касаикина О.Т. // Изв. АН. Сер. Хим. 2014. № 8. С. 1837.
- Касаикина О.Т., Потапова Н.В., Круговов Д.А., Березин М.П. // ВМС. Сер. В. 2017. Т. 59. № 3. С. 181.
- Касаикина О.Т., Потапова Н.В., Круговов Д.А., Писаренко Л.М. // Кинетика и катализ. 2017. Т. 58. № 5. С. 567.
- Потапова Н.В., Касаикина О.Т., Березин М.П., Плащина И.Г. // Кинетика и катализ 2020. Т. 61. № 5. С. 700. https://doi.org/10.1134/S0023158420050079
- Al-Shareeda Z.A., Abramovich R.A., Potanina O.G., Alhejoj H. // Int. J. Pharm. Qual. Ass. 2020. V. 11. P. 361. https://doi.org/10.25258/ijpqa.11.3.10
- Organization for Economic Co-operation and Development (OECD), SIDS Initial Assessment Reports: Choline Chloride, 2004.
- Hall J.M., Savage L.M. // Exp. Neurol. 2016. V. 278. P. 62. https://doi.org/10.1016/j.expneurol.2016.01.018
- Cox M.A., Bassi C., Saunders M.E., Nechanitzky R., Morgado-Palacin I., Zheng C., Mak T.W. // J. Intern. Med. 2020. V. 287. P. 120. https://doi.org/10.1111/joim.13006
- Yonei Y., Takahashi Y., Hibino S., Watanabe M., Yoshioka T. // J. Clin. Biochem. Nutr. 2008. V. 42. P. 89.
- Ferreira G.C., McKenna M.C. // Neurochem. Res. 2017. V. 42. P. 1661. https://doi.org/10.1007/s11064-017-2288-7
- Wang M., Maki C.R., Deng Y., Tian Y., Phillips T.D. // Chem. Res. Toxicol. 2017. V. 30. P. 1694. https://doi.org/10.1021/acs.chemrestox.7b00154
- Kobayashi S., Makino A. // Chem. Rev. 2009. V. 109. P. 5288.
- Denisov E.T., Denisova T.G. Handbook of Antioxidants: Bond Dissociation Energies, Rate Constants, Activation Energies and Enthalpies of Reactions. Boca Raton: CRC press, 2000.
- Dougherty D.A. // Acc. Chem. Res. 2013. V. 46. P. 885.
- Van Arnam E.B., Dougherty D.A. // J. Med. Chem. 2014. V. 57. P. 6289.
- Davis M.R., Dougherty D.A. // Phys. Chem. 2015. V. 17. P. 29262.
- Иванчев С.С. Радикальная полимеризация. Ленинград: Химия, 1985.
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