Chymiotechnon, Departamento de Química, Universidade de Coimbra, 3049-535, Coimbra, Portugal.
Photochem Photobiol. 2010 Jan-Feb;86(1):206-12. doi: 10.1111/j.1751-1097.2009.00622.x. Epub 2009 Nov 10.
5,15-Diarylporphyrins (1-5) with hydroxyl groups and halogens as substituents were prepared by condensation between unsubstituted dipyrromethane and halogenated m-hydroxybenzaldehydes. Photophysical properties show that the nonhalogenated porphyrin 1 has higher fluorescence yield but lower singlet oxygen formation quantum yield than the halogenated derivatives due to the heavy atom effect. The in vitro activity of these derivatives was tested against WiDr colorectal adenocarcinoma and A375 melanoma cancer cells. All porphyrins present a much higher phototoxicity than Photofrin with IC(50) values lower than the 50 nM level for WiDr cells and 25 nM level for A375 cancer cells. The most photoactive compound is the nonhalogenated porphyrin 1 which also presents the highest uptake. Halogenated derivatives present much lower uptakes than 1. However, their photoactivity is similar to compound 1 showing that their intrinsic photoactivity (ISP) is very high. Iodinated compound 4 presents the highest ISP. The greater ability of these porphyrins to destroy cancer cells could be related to their photophysical and photochemical properties.
5,15-二芳基卟啉（1-5）具有羟基和卤素取代基，通过未取代的二吡咯甲烷与卤代间羟基苯甲醛缩合制备。光物理性质表明，由于重原子效应，未卤代卟啉 1 的荧光产率高于卤代衍生物，但单线态氧生成量子产率较低。这些衍生物的体外活性测试了对 WiDr 结直肠腺癌细胞和 A375 黑色素瘤细胞的抑制作用。所有卟啉的光毒性都明显高于 Photofrin，IC50 值对于 WiDr 细胞低于 50 nM，对于 A375 癌细胞低于 25 nM。最具光活性的化合物是未卤代卟啉 1，其摄取率也最高。卤代衍生物的摄取率远低于 1。然而，它们的光活性与化合物 1 相似，表明它们的固有光活性（ISP）非常高。碘化化合物 4 具有最高的 ISP。这些卟啉破坏癌细胞的能力可能与它们的光物理和光化学性质有关。
