Importance of the orthogonal structure between porphyrin and aniline moieties on the pH-activatable porphyrin derivative for photodynamic therapy
| Autor: | Atsuki Hirabara, Tetsuo Okutsu, Hiroaki Horiuchi |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Singlet oxygen
General Chemical Engineering General Physics and Astronomy 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology Photochemistry 01 natural sciences Fluorescence Porphyrin Acid dissociation constant 0104 chemical sciences chemistry.chemical_compound Aniline chemistry Intramolecular force Moiety Photosensitizer 0210 nano-technology |
| Zdroj: | Journal of Photochemistry and Photobiology A: Chemistry. 365:60-66 |
| ISSN: | 1010-6030 |
| DOI: | 10.1016/j.jphotochem.2018.07.034 |
| Popis: | The photo-induced side effects of photodynamic therapy of cancer can be suppressed using pH-activatable porphyrin derivatives, which have been developed using an aniline moiety as a pH-responsive quencher. The acid dissociation coefficient of a pH-activatable photosensitizer increased by replacing a dimethylamino with a diethylamino group. Based on this diethylamino derivative, we studied the importance of the intramolecular orthogonal structure between porphyrin and aniline moieties on the pH-activatable properties. The character of the S1 state of the non-orthogonal derivative (Por-NEt2) was different from that of the orthogonal derivative (Por-Me-NEt2), but the derivatives possessed the ON/OFF switching functions for both fluorescence and singlet oxygen sensitization. However, the maximum quantum yields of Por-Me-NEt2 were much larger than those of Por-NEt2, and the ON/OFF switching ratio of Por-Me-NEt2 was higher than that of Por-NEt2. This is due to the suppressed rotation of the aniline moiety, indicating that the intramolecular orthogonal structure is important for the high ON/OFF switching performances. |
| Databáze: | OpenAIRE |
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