Paquette B, Boyle R W, Ali H, MacLennan A H, Truscott T G, van Lier J E
MRC Group in the Radiation Sciences, Faculty of Medicine, University of Sherbrooke, Québec, Canada.
Photochem Photobiol. 1991 Mar;53(3):323-7. doi: 10.1111/j.1751-1097.1991.tb03635.x.
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.
研究了磺化邻苯二甲酰亚胺甲基铝酞菁的光细胞毒性，与仅被磺酸基团取代的酞菁相比，它是一种疏水性更强的光敏剂。在二磺化铝酞菁中引入1-2个邻苯二甲酰亚胺甲基基团，导致正辛醇与水之间的分配系数增加，对中国仓鼠肺成纤维细胞（V-79系）的细胞摄取和光细胞毒性增加了六倍。减少邻苯二甲酰亚胺甲基基团的数量或增加磺化程度，会导致分配系数、细胞摄取和光毒性降低。该系列中测试的所有染料的单线态氧量子产率相当，表明邻苯二甲酰亚胺甲基化并未导致该光物理参数发生显著变化。这些结果表明，在二磺化铝酞菁中添加1-2个邻苯二甲酰亚胺甲基基团可改善细胞摄取，但由于细胞杀伤的相对效率未受影响，光敏分子的细胞内分布可能未被改变。
