SULFONATED PHTHALIMIDOMETHYL ALUMINUM PHTHALOCYANINE: THE EFFECT OF HYDROPHOBIC SUBSTITUENTS ON THE in vitro PHOTOTOXICITY OF PHTHALOCYANINES
| Autor: | T. George Truscott, Hasrat Ali, Alexander H. Maclennan, Benoit Paquette, Johan E. van Lier, R. W. Boyle |
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| Rok vydání: | 1991 |
| Předmět: |
Radiation-Sensitizing Agents
Indoles Light Cell Survival Singlet oxygen Quantum yield Phthalimides General Medicine Photochemistry Biochemistry Cell Line Partition coefficient Structure-Activity Relationship chemistry.chemical_compound Sulfonate Cell killing chemistry Organometallic Compounds Phthalocyanine Animals Photosensitizer Physical and Theoretical Chemistry Phototoxicity |
| Zdroj: | Photochemistry and Photobiology. 53:323-327 |
| ISSN: | 1751-1097 0031-8655 |
| Popis: | The photocytotoxicity of sulfonated phthalimidomethyl aluminum phthalocyanine, a more hydrophobic photosensitizer as compared to phthalocyanine substituted with sulfonate groups only, was investigated. Inclusion of 1-2 phthalimidomethyl groups into disulfonated aluminum phthalocyanine, resulted in increased partition coefficients between n-octanol and water, and a six-fold increase in both cellular uptake and photocytotoxicity towards Chinese hamster lung fibroblast cells (line V-79). Reducing the number of phthalimidomethyl groups, or increasing the degree of sulfonation, lead to a decrease in the partition coefficient, cellular uptake, and phototoxicity. The quantum yield of singlet oxygen was comparable for all dyes tested in this series, indicating that no significant change in this photophysical parameter resulted from phthalimidomethylation. These results suggest that the addition of 1-2 phthalimidomethyl groups to disulfonated aluminum phthalocyanine improves cellular uptake, but, as the relative efficiency of cell killing was not effected, the intracellular distribution on photosensitive molecules may not be modified. |
| Databáze: | OpenAIRE |
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