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Synthesis and study of water-soluble asymmetric cationic porphyrins as potential photoinactivators of pathogens

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Abstract

Water-soluble asymmetrically substituted porphyrins containing the heterocyclic fragments (benzoxazole, N-methylbenzimidazole, and benzothiazole residues) at the periphery of the porphyrin ring were synthesized using the C-H-activation method. The compounds were identified by electron absorption spectroscopy, 1H NMR spectroscopy, and mass spectrometry. The quantum yields of singlet oxygen generation and complexation ability of the synthesized porphyrins with respect to albumin were determined. The affinity of albumin to the porphyrins with the N-methylbenzimidazole and benzoxazole residues was shown to be nearly two times higher than the affinity to the porphyrin with the benzothiazole fragment. The synthesized porphyrins can efficiently interact with proteins. The bactericidal activity of the synthesized porphyrins to archival strains of microorganisms was studied. The lytic activity for gram-positive Staphylococcus spp. bacteria under photoirradiation conditions was revealed.

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Authors and Affiliations

  1. G. A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 1 ul. Akademicheskaya, 153045, Ivanovo, Russian Federation

    A. N. Kiselev, M. A. Lebedev, S. A. Syrbu, E. S. Yurina, Yu. A. Gubarev, N. Sh. Lebedeva & O. I. Koifman

  2. Ivanovo State University of Chemistry and Technology, 7 Sheremetevskii prosp., 153000, Ivanovo, Russian Federation

    A. N. Kiselev, M. A. Lebedev & O. I. Koifman

  3. Research Institute of Prophylactic Medicine, Privolzhsky Research Medical University, Ministry of Health of the Russian Federation, 18/1 Verkhnevolzhskaya nab., 603155, Nizhny Novgorod, Russian Federation

    N. A. Belyanina, I. Yu. Shirokova & O. V. Kovalishena

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  1. A. N. Kiselev
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  2. M. A. Lebedev
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  3. S. A. Syrbu
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  4. E. S. Yurina
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  5. Yu. A. Gubarev
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  6. N. Sh. Lebedeva
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  7. N. A. Belyanina
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  8. I. Yu. Shirokova
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  9. O. V. Kovalishena
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  10. O. I. Koifman
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Corresponding author

Correspondence to E. S. Yurina.

Additional information

Based on the materials of the VI North Caucasus Symposium on Organic Chemistry NCOCS-2022 (April 18–22, 2022, Stavropol, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2691–2700, December, 2022.

A part of research was carried out using resources of the Center for Collective Use “New Materials and Resource Saving Technologies” (Nizhny Novgorod) and equipment of the Center for Collective Use at the Ivanovo State University of Chemistry and Technology (Ivanovo).

This work was financially supported by the Russian Science Foundation (Project No. 21-73-20140).

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Kiselev, A.N., Lebedev, M.A., Syrbu, S.A. et al. Synthesis and study of water-soluble asymmetric cationic porphyrins as potential photoinactivators of pathogens. Russ Chem Bull 71, 2691–2700 (2022). https://doi.org/10.1007/s11172-022-3698-5

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  • DOI: https://doi.org/10.1007/s11172-022-3698-5

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