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. 2022 Dec 19;71(11):2495–2504. doi: 10.1007/s11172-022-3679-8

Synthesis of water-soluble porphyrin with tyrosine fragments and study of its interaction with S-protein of SARS-CoV-2

S A Syrbu 1, A S Semeikin 2, N Sh Lebedeva 1, Yu A Gubarev 1,✉, E S Yurina 1, S S Guseinov 1, O I Koifman 1,2
PMCID: PMC9762635  PMID: 36569660

Abstract

The multistage purposeful synthesis of 5,15-bis(4′-l-N-tyrosinylamidophenyl)-10,20-bis(N-methylpyridin-3′-yl)porphine diiodide was carried out, and the optimum synthesis conditions were determined. 5,15-Bis(4′-nitrophenyl)-10,20-bis(pyridin-3′-yl)porphine served as the starting porphyrin. The structure, individual character, and purity of the target compound were proved by electron spectroscopy, 1H NMR spectroscopy, mass spectrometry (MALDI TOF), and TLC. Specific features of the interaction of the synthesized porphyrin with S-protein of SARS-CoV-2 were studied using spectral and thermochemical methods, including conditions of photoirradiation. The photoirradiation of the synthesized porphyrin in a complex with the SARS-CoV-2 S-protein can result in the partial oxidation of amino acid residues of the protein and distort its primary and secondary structures. The photoirradiation of the S-protein complex with the porphyrin decreases its thermal resistance to melting by 15 °C compared to the free S-protein and causes porphyrin release.

Key words: synthesis, water-soluble porphyrin, S-protein, SARS-CoV-2, virucidal effect, photoinactivation

Footnotes

Based on the materials of the V Russian Conference on Medicinal Chemistry with international participation “MedChem-Russia 2021” (May 16–19, 2022, Volgograd, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2495–2504, November, 2022.

This work was financially supported by the Russian Foundation for Basic Research (Project No. 20-04-60067). Some research works was carried out using resources of the Upper Volga Regional Center of Physicochemical Research at the G. A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences and the Center for Collective Use at the Ivanovo State University of Chemistry and Technology.

No human or animal subjects were used in this research.

The authors declare no competing interests.

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