Photophysical and photobiological properties of natural chlorins with additional heterocyclic fragments
New substituted trimethyl ester chlorin [Formula: see text] derivatives possess pronounced fluorescent ([Formula: see text] [Formula: see text] 0,3) and photosensitizing properties ([Formula: see text] [Formula: see text] 0,6). The dyes are capable of binding with albumin (K[Formula: see text] [Formula: see text] 10 5 M[Formula: see text]. The triplet state of the dye 3 in complex with BSA showed the ability to transfer electron from the electron donor molecule (ascorbic acid). The recombination rate constant for the dye 3 anion radicals was determined (1.8 × 10 8 M[Formula: see text] s[Formula: see text]. These results show that the dye studied can act as a photosensitizer via both Type I and Type II reactions. The synthesized compounds exhibit low dark cytotoxicity at concentrations up to 50 [Formula: see text]M over 24 hours of incubation in HCT116 cells. When cells are photoexcited with a 660 nm laser, chlorins 3 and 4 cause rapid cell death at submicromolar concentrations, higher than that of the drug chlorin [Formula: see text] “Photolon”. The phototoxicity of compound 2, 5 was lower than that of “Photolon”. For the most photodynamically active compound 3, accumulation in the endoplasmic reticulum of cells and the mechanism of death are shown - rapid photo-induced necrosis.
Authors
- Anton E. Egorov (ORCID: https://orcid.org/0000-0001-8259-898X)
- Alina A. Markova (ORCID: https://orcid.org/0000-0002-3867-8760)
- Alexey A. Kostyukov (ORCID: https://orcid.org/0000-0002-4574-8624)
- Ivan D. Burtsev
- Kirill P. Birin (ORCID: https://orcid.org/0000-0001-6951-2440)
- Mikhail A. Grin (ORCID: https://orcid.org/0000-0002-4333-4516)
- Yulia K. Biryukova (ORCID: https://orcid.org/0000-0002-5804-4001)
- Petr Ostroverkhov (ORCID: https://orcid.org/0000-0001-5778-4510)
- Bezborodova Si (ORCID: https://orcid.org/0000-0002-5009-1508)
- Anastasia S. Pukhova
- Vladimir Kuzmin
- Anna Shibaeva
- Nikita Kirin
- Alexandra Lelyukhova
Institutions
- Frumkin Institute of Physical Chemistry and Electrochemistry Russian Academy of Sciences (RU)
- Ministry of Health (ES)
- MIREA - Russian Technological University (RU)
- P.A. Hertzen Moscow Oncology Research Institute (RU)
- Institute of Biochemical Physics NM Emanuel (RU)
- Chumakov Institute of Poliomyelitis and Viral Encephalitides (RU)
- National Research Nuclear University MEPhI (RU)
Publication Details
- Journal
- Journal of Porphyrins and Phthalocyanines
- Published
- 2025-12-30
- DOI
- https://doi.org/10.1142/s1088424625501172
- Primary Topic
- Photodynamic Therapy Research Studies
- Type
- article
- Field-Weighted Citation Impact
- 0.00