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 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 52nM over A375 cells.
Chymiotechnon, Departamento de Química, Universidade de Coimbra, 3004-535 Coimbra, Portugal.
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Serra
Chymiotechnon, Departamento de Química, Universidade de Coimbra, 3004-535 Coimbra, Portugal.
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Pineiro
Chymiotechnon, Departamento de Química, Universidade de Coimbra, 3004-535 Coimbra, Portugal.
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Rocha Gonsalves
Instituto de Biofísica/Biomatemática, CIMAGO, IBILI, Faculdade de Medicina de Coimbra, 3000-354 Coimbra, Portugal.
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Abrantes
Instituto de Biofísica/Biomatemática, CIMAGO, IBILI, Faculdade de Medicina de Coimbra, 3000-354 Coimbra, Portugal.
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Laranjo
Instituto de Biofísica/Biomatemática, CIMAGO, IBILI, Faculdade de Medicina de Coimbra, 3000-354 Coimbra, Portugal.
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Santos
Instituto de Biofísica/Biomatemática, CIMAGO, IBILI, Faculdade de Medicina de Coimbra, 3000-354 Coimbra, Portugal.
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Botelho
D001966:Bromine / Q000737:chemistry*; D045744:Cell Line, Tumor; D006801:Humans; D007455:Iodine / Q000737:chemistry*; D038761:Photobleaching; D010777:Photochemistry; D010782:Photolysis; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D026082:Singlet Oxygen / Q000378:metabolism
D011166:Porphyrins; D026082:Singlet Oxygen; D007455:Iodine; D001966:Bromine