SYNTHESIS OF HYDROGENATED  MESO -TETRAPYRIDYLPORPHYRINS WITH A CONTROLLED COMPOSITION

A. V. Lyubimtsev; Любимцев А. В.; A. S. Semeikin; Семейкин А. С.; M. O. Koifman; Койфман М. О.; O. I. Koifman; Койфман О. И.

doi:10.31857/S2686953522600465

SYNTHESIS OF HYDROGENATED MESO-TETRAPYRIDYLPORPHYRINS WITH A CONTROLLED COMPOSITION

Authors: Lyubimtsev A.V.¹, Semeikin A.S.¹, Koifman M.O.¹, Koifman O.I.¹
Affiliations:
1. Ivanovo State University of Chemistry and Technology
Issue: Vol 508, No 1 (2023)
Pages: 39-49
Section: CHEMISTRY
URL: https://journals.rcsi.science/2686-9535/article/view/135958
DOI: https://doi.org/10.31857/S2686953522600465
EDN: https://elibrary.ru/EVXGPT
ID: 135958

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Abstract
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Abstract

The work is devoted to the development of a method for obtaining a highly sensitive composition of a controlled composition containing cationic water-soluble 5,10,15,20-tetrakis(N-Me-pyridin-3-yl)chlorine and 5,10,15,20-tetrakis(N-Me-pyridin-3-yl)bacteriochlorin. The process of diimide reduction of 5,10,15,20-tetrakis(pyridin-3-yl)porphine in pyridine and in the absence of a solvent has been studied. It is shown that the reduction in the alloy significantly reduces the reaction time (from 12 to 1.5 h) and allows to obtain compositions with a yield of up to 90%.

Keywords

porphyrin, chloride, bacteriochlorin, diimide reduction

References

Koifman O.I., Ageeva T.A., Beletskaya I.P., Averin A.D., Yakushev A.A., Tomilova L.G., Dubinina T.V., Tsiva-dze A.Yu., Gorbunova Yu.G., Martynov A.G., Konarev D.V., Khasanov S.S., Lyubovskaya R.N., Lomova T.N., Korolev V.V., Zenkevich E.I., Blaudeck T., von Borczyskowski Ch., Zahn D.R.T., Mironov A.F., Bragina N.A., Ezhov A.V., Zhdanova K.A., Stuzhin P.A., Pakhomov G.L., Rusakova N.V., Semenishyn N.N., Smola S.S., Parfenyuk V.I., Vashurin A.S., Makarov S.V., Dereven’kov I.A., Mamardashvili N.Zh., Kurtikyan T.S., Martirosyan G.G., Burmistrov V.A., Aleksandriiskii V.V., Novikov I.V., Pritmov D.A., Grin M.A., Suvorov N.V., Tsigankov A.A., Fedorov A.Yu., Kuzmina N.S., Nyu-chev A.V., Otvagin V.F., Kustov A.V., Belykh D.V., Bere-zin D.B., Solovieva A.B., Timashev P.S., Milaeva E.R., Gracheva Yu.A., Dodokhova M.A., Safronenko A.V., Shpakovsky D.B., Syrbu S.A., Gubarev Yu.A., Kiselev A.N., Koifman M.O., Lebedeva N.Sh., Yurina E.S. // Macroheterocycles. 2020. № 13. P. 311–467. https://doi.org/10.6060/mhc200814k
Shastak S., Shulga A., Berr F., Wiedemann P. Porphyrins and their use as photosensitizer. Patent US 6410568 B1. 2002.
Oertel M., Shastak S., Tannapfel A., Hermann R., Sack U., Moessner J., Berr F. // J. Photochem. Photobiol., B. 2003. V. 71. P. 1–10. https://doi.org/10.1016/S1011-1344(03)00091-5
Shastak S., Jean B., Handzel R., Kostenich G., Hermann R., Sack U., Orenstein A., Wang Yu., Wiedemann P. // J. Photochem. Photobiol., B. 2005. V. 78. P. 203–213. https://doi.org/10.1016/j.jphotobiol.2004.11.006
Койфман О.И., Пономарев Г.В., Сырбу С.А., Жаров Е.В., Сергеева Т.В., Луковкин А.В. Фотосенсибилизатор и способ его получения. Патент РФ № 2535097 C1. 2014.
Berndt-Paetz M., Weimann A., Sieger N., Shastak S., Riyad Y., Griebel J., Arthanareeswaran V., Stolzenburg J-U., Neuhaus J. // Photodiagnostics Photodyn. Ther. 2017. V. 18. P. 244–251. https://doi.org/10.1016/j.pdpdt.2017.02.017
Hambsch P., Istomin Yu., Tzerkovsky D., Patties I., Neuhaus J., Kortmann R.-D., Shastack S., Glasow A. // Oncotarget. 2017. V. 8. № 42. P. 72411–72423. https://doi.org/10.18632/oncotarget.20403
Тиганова И.Г., Макарова Е.А., Меерович Г.А., Алексеева Н.В., Толордава Э.Р., Жижимова Ю.С., Лукьянец Е.А., Романова Ю.М. // Biomed. Photonics. 2017. Т. 6. № 4. С. 27–36. https://doi.org/10.24931/2413-9432-2017-6-4-27-36
Морозова Н.Б., Плотникова Е.А., Плютинская А.Д., Страмова В.О., Воронцова М.С., Панкратов А.А., Якубовская Р.И., Макарова Е.А., Лукъянец Е.А., Каприн А.Д. // Российский Биотерапевтический Журнал. 2018. Т. 17. № 3. С. 55–64. https://doi.org/10.17650/1726-9784-2018-17-3-55-64
Макарова Е.А., Меерович Г.А., Лукьянец Е.А., Тиганова И.Г., Романова Ю.М., Лощенов В.Б., Алексее-ва Н.В., Ахлюстина Е.В. Фотосенсибилизаторы для фотодинамической инактивации бактерий, в том числе в биопленках. Патент РФ № 2670201. 2018.
Меерович Г.А., Ахлюстина Е.В., Тиганова И.Г., Макарова Е.А., Филипова Н.И., Романишкин И.Д., Алексеева Н.В., Лукьянец Е.А., Романова Ю.М., Лощенов В.Б. // Вестник РГМУ. 2018. № 6. С. 80–85. https://doi.org/10.24075/brsmu.2018.087
Meerovich G.A., Akhlyustina E.V., Tiganova I.G., Lukyanets E.A., Makarova E.A., Tolordava E.R., Yuzhako-va O.A., Romanishkin I.D., Philipova N.I., Zhizhimo-va Yu.S., Romanova Yu.M., Loschenov V.B., Gintsburg A.L. // Adv. Exp. Med. Biol. 2019. P. 1–19. https://doi.org/10.1007/5584_2019_431
Meerovich G.A., Akhlyustina E.V., Tiganova I.G., Lukyanets E.A., Makarova E.A., Tolordava E.R., Yuzhako-va O.A., Romanishkin I.D., Philipova N.V., Zhizhimo-va Yu.S., Gonchukov S.A., Romanova Yu.M., Losche-nov V.B. // Laser Phys. Lett. 2019. V. 16. P. 115603. https://doi.org/10.1088/1612-202X/ab4806
Tiganova I.G., Zhizhimova Yu.S., Philipova N.I., Tolordava E.R., Alekseeva N.V., Makarova E.A., Lukyanets E.A., Meerovich G.A., Romanova Yu.M., Gintsburg A.L. // Mol. Gen. Microbiol. Virol. 2020. V. 35. № 4. P. 248–256. https://doi.org/10.3103/S0891416820040096
Kogan E.A., Meerovich G.A., Karshieva S.Sh., Akhlyustina E.V., Makarova E.A., Dalina A.A., Romanishkin I.D., Zharkov N.V., Gonchukov S.A., Angelov I.P., Losche-nov V.B. // Laser Phys. Lett. 2022. V. 19. № 3. P. 035601. https://doi.org/10.1088/1612-202X/ac4e96
Семейкин А.С., Койфман О.И., Березин Б.Д. // ХГС. 1986. № 6. С. 798–801.
Whitlock H., Hanauer J., Oester M., Bower B. // J. Am. Chem. Soc. 1969. P. 7485–7489. https://doi.org/10.1021/ja01054a044
Dudkin S., Makarova E., Slivka L., Lukyanets E. // J. Porphyrins Phthalocyanines. 2014. V. 18. P. 107–114. https://doi.org/10.1142/S1088424613501162
Burns D., Li Yu., Shi D., Delaney M. // Chem. Commun. 1998. P. 1677–1678. https://doi.org/10.1039/A802165A
Laville I., Pigaglio S., Blais J.-C., Loock B., Maillard Ph., Grierson D., Blais J. // Bioorg. Med. Chem. 2004. V. 12. P. 3673–3682. https://doi.org/10.1016/j.bmc.2004.04.022
Hirohara S., Obata M., Ogata S., Ohtsuki S., Higashida S., Ogura S., Okura I., Takenaka M., Ono H., Sugai Y., Mikata Y., Tanihara M., Yano M. // J. Photochem. Photobiol., B. 2005. V. 78. P 7–15. https://doi.org/10.1016/j.jphotobiol.2004.09.003
Bonnett R., White R., Winfield U-J., Berenbaum M. // Biochem. J. 1989. V. 261. P. 277–280. https://doi.org/10.1042/bj2610277
Laville I., Figueiredo T., Loock B., Pigaglio S., Mail-lard Ph., Grierson D., Carrez A., Blais J. // Bioorg. Med. Chem. 2003. V. 11. P. 1643–1652. 10.1016/S0968-0896(03)00050-6' target='_blank'>https://doi.org/doi: 10.1016/S0968-0896(03)00050-6
Pereira M., Abreu A., Goncalves N., Calvete M., Simões A., Monteiro C., Arnaut L., Eusébio M., Canotilho J. // Green Chem. 2012. V. 14. P. 1666–1672. https://doi.org/10.1039/C2GC35126A
Dabrowski J., Arnaut L., Pereira M., Monteiro C., Urbanska K., Sims S., Stochel G. // Chem. Med. Chem. 2010. V. 5. P. 1770–1780. https://doi.org/10.1002/cmdc.201000223