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In Vitro Photodynamic Activity of 5,15‐bis(3‐Hydroxyphenyl)porphyrin and Its Halogenated Derivatives Against Cancer Cells
Author(s) -
Serra Arménio,
Pineiro Marta,
Santos Catarina Isabel,
Rocha Gonsalves António Manuel d’A.,
Abrantes Margarida,
Laranjo Mafalda,
Botelho Maria Filomena
Publication year - 2010
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.2009.00622.x
Subject(s) - porphyrin , phototoxicity , chemistry , singlet oxygen , quantum yield , photochemistry , yield (engineering) , fluorescence , halogen , in vitro , photodynamic therapy , medicinal chemistry , oxygen , organic chemistry , biochemistry , materials science , physics , alkyl , metallurgy , quantum mechanics
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 n m level for WiDr cells and 25 n m 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.