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.

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Journal
Journal of Porphyrins and Phthalocyanines
Published
2025-12-30
DOI
https://doi.org/10.1142/s1088424625501172
Primary Topic
Photodynamic Therapy Research Studies
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article
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article

Photophysical and photobiological properties of natural chlorins with additional heterocyclic fragments

Anton E. Egorov, Alina A. Markova, Alexey A. Kostyukov, Ivan D. Burtsev et al.
Journal of Porphyrins and Phthalocyanines
Photodynamic Therapy Research Studies
article

Photophysical and photobiological properties of natural chlorins with additional heterocyclic fragments

Anton E. Egorov, Alina A. Markova, Alexey A. Kostyukov, Ivan D. Burtsev, Kirill P. Birin, Mikhail A. Grin, Yulia K. Biryukova, Petr Ostroverkhov, Bezborodova Si, Anastasia S. Pukhova, Vladimir Kuzmin, Anna Shibaeva, Nikita Kirin, Alexandra Lelyukhova
article en

Abstract

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.

Journal of Porphyrins and PhthalocyaninesVol. 30(01)
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)
Openalex Percentile: Top 27%
Photodynamic Therapy Research Studies
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