Halogen atom effect on photophysical and photodynamic characteristics of derivatives of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin

Brominated and iodinated derivatives of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin were synthesised directly from the corresponding aldehydes. Photophysical and photochemical properties, singlet oxygen formation quantum yields, photobleaching and log P were measured. Cellular uptake measurements...

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Bibliographic Details
Published in:Journal of photochemistry and photobiology. B, Biology Biology, 2008-07, Vol.92 (1), p.59-65
Main Authors: Serra, A.C., Pineiro, M., Rocha Gonsalves, A.M.d’A., Abrantes, M., Laranjo, M., Santos, A.C., Botelho, M.F.
Format: Article
Language:English
Subjects:
Bromine - chemistry
Cell Line, Tumor
Halogenated porphyrins
Heavy atom effect
Humans
Iodine - chemistry
Photobleaching
Photochemistry
Photodynamic therapy
Photolysis
Porphyrins - chemical synthesis
Porphyrins - chemistry
Porphyrins - metabolism
Porphyrins - pharmacology
Singlet Oxygen - metabolism
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Summary:Brominated and iodinated derivatives of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin were synthesised directly from the corresponding aldehydes. Photophysical and photochemical properties, singlet oxygen formation quantum yields, photobleaching and log P were measured. Cellular uptake measurements and cytotoxicity assays on WiDr and A375 tumour cell lines were performed. 5,10,15,20-Tetrakis(2-bromo-5-hydroxyphenyl)porphyrin showed the best cytotoxicity with values of IC 50 of 113 nM over WiDr cells and 52 nM over A375 cells.
ISSN:1011-1344
1873-2682
DOI:10.1016/j.jphotobiol.2008.04.006