Synthesis and photophysical properties of a chlorin conjugate with a photoswitchable local anesthetic.
| Title: | Synthesis and photophysical properties of a chlorin conjugate with a photoswitchable local anesthetic. |
|---|---|
| Authors: | Minakov DA; Federal State Budgetary Educational Institution of Higher Education MIREA - Russian Technological University, M.V. Lomonosov Institute of Fine Chemical Technologies, Russia, 86 Vernadsky Avenue, 119571 Moscow, Russian Federation. Electronic address: d-m2020@yandex.ru.; Egorov AE; Emanuel Institute of Biochemical Physics, Russian Academy of Science, 4 Kosygin st., 119334 Moscow, Russian Federation.; Noev AN; Federal State Budgetary Educational Institution of Higher Education MIREA - Russian Technological University, M.V. Lomonosov Institute of Fine Chemical Technologies, Russia, 86 Vernadsky Avenue, 119571 Moscow, Russian Federation; Radiological Centre of the Ministry of Health of the Russian Federation, P. Hertsen Moscow Oncology Research Institute-Branch of the National Medical Research, Moscow, Russian Federation, 2nd Botkinsky proezd, 3, Moscow 125284, Russian Federation.; Ostroverkhov PV; Federal State Budgetary Educational Institution of Higher Education MIREA - Russian Technological University, M.V. Lomonosov Institute of Fine Chemical Technologies, Russia, 86 Vernadsky Avenue, 119571 Moscow, Russian Federation.; Suvorov NV; Federal State Budgetary Educational Institution of Higher Education MIREA - Russian Technological University, M.V. Lomonosov Institute of Fine Chemical Technologies, Russia, 86 Vernadsky Avenue, 119571 Moscow, Russian Federation.; Usachev MN; Federal State Budgetary Educational Institution of Higher Education MIREA - Russian Technological University, M.V. Lomonosov Institute of Fine Chemical Technologies, Russia, 86 Vernadsky Avenue, 119571 Moscow, Russian Federation.; Cheshkov DA; Federal State Budgetary Educational Institution of Higher Education MIREA - Russian Technological University, M.V. Lomonosov Institute of Fine Chemical Technologies, Russia, 86 Vernadsky Avenue, 119571 Moscow, Russian Federation.; Kostyukov AA; Emanuel Institute of Biochemical Physics, Russian Academy of Science, 4 Kosygin st., 119334 Moscow, Russian Federation.; Nekipelova TD; Emanuel Institute of Biochemical Physics, Russian Academy of Science, 4 Kosygin st., 119334 Moscow, Russian Federation.; Zevakin EA; Vernadsky Institute of Geochemistry and Analytical Chemistry, Russian Academy of Sciences, 19 Kosygin St., Moscow 119991, Russian Federation.; Kuzmin VA; Emanuel Institute of Biochemical Physics, Russian Academy of Science, 4 Kosygin st., 119334 Moscow, Russian Federation; National Research Nuclear University 'MEPhI', 31 Kashirskoe Highway, Moscow 115409, Russian Federation.; Filonenko EV; Federal State Budgetary Educational Institution of Higher Education MIREA - Russian Technological University, M.V. Lomonosov Institute of Fine Chemical Technologies, Russia, 86 Vernadsky Avenue, 119571 Moscow, Russian Federation; Radiological Centre of the Ministry of Health of the Russian Federation, P. Hertsen Moscow Oncology Research Institute-Branch of the National Medical Research, Moscow, Russian Federation, 2nd Botkinsky proezd, 3, Moscow 125284, Russian Federation.; Grin MA; Federal State Budgetary Educational Institution of Higher Education MIREA - Russian Technological University, M.V. Lomonosov Institute of Fine Chemical Technologies, Russia, 86 Vernadsky Avenue, 119571 Moscow, Russian Federation. |
| Source: | Journal of photochemistry and photobiology. B, Biology [J Photochem Photobiol B] 2025 Oct; Vol. 271, pp. 113238. Date of Electronic Publication: 2025 Aug 08. |
| Publication Type: | Journal Article |
| Language: | English |
| Journal Info: | Publisher: Elsevier Sequoia Country of Publication: Switzerland NLM ID: 8804966 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-2682 (Electronic) Linking ISSN: 10111344 NLM ISO Abbreviation: J Photochem Photobiol B Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: Lausanne : Elsevier Sequoia, 1987- |
| MeSH Terms: | Porphyrins*/chemistry ; Porphyrins*/chemical synthesis ; Photosensitizing Agents*/chemistry ; Photosensitizing Agents*/chemical synthesis ; Anesthetics, Local*/chemistry ; Anesthetics, Local*/chemical synthesis; Singlet Oxygen/chemistry ; Azo Compounds/chemistry ; Light ; Isomerism ; Energy Transfer |
| Abstract: | A conjugate of natural chlorin and azobenzene bound via a linker was synthesized, its stability and photophysical properties were studied. This conjugate can be proposed as a prototype of a dual-action photopharmacological agent, which acts as a photosensitizer for photodynamic therapy and as a local anesthetic agent with light-controlled activity. Conjugate irradiation by red light (660 nm), results in the triplet state formation (kT = 2.0 × 103 s-1) that leads to singlet oxygen generation. Simultaneously endothermic intramolecular triplet-triplet energy transfer (kTET = 3.3 × 105 s-1) from the triplet chlorin chromophore to the azobenzene fragment take place, which led to isomerization of the latter. Singlet oxygen reacts with the conjugate linker, which leads to the formation of various cleavage products.; (Copyright © 2025 Elsevier B.V. All rights reserved.) |
| Competing Interests: | Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. |
| Contributed Indexing: | Keywords: Azobenzenes; Cleavable linkers; Local anesthesia; Natural chlorins; Photodynamic therapy; Photosensitizers; Photoswitchable anesthetics |
| Substance Nomenclature: | 2683-84-3 (chlorin); 0 (Porphyrins); 0 (Photosensitizing Agents); 17778-80-2 (Singlet Oxygen); F0U1H6UG5C (azobenzene); 0 (Anesthetics, Local); 0 (Azo Compounds) |
| Entry Date(s): | Date Created: 20250817 Date Completed: 20250908 Latest Revision: 20250908 |
| Update Code: | 20260130 |
| DOI: | 10.1016/j.jphotobiol.2025.113238 |
| PMID: | 40819409 |
| Database: | MEDLINE |
Journal Article