In Vitro Photodynamic Activity of 5,15-bis(3-Hydroxyphenyl)porphyrin and Its Halogenated Derivatives Against Cancer Cells

Authors

  • Arménio Serra,

    1. Chymiotechnon, Departamento de Química, Universidade de Coimbra, 3049-535, Coimbra, Portugal
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  • Marta Pineiro,

    1. Chymiotechnon, Departamento de Química, Universidade de Coimbra, 3049-535, Coimbra, Portugal
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  • Catarina Isabel Santos,

    1. Chymiotechnon, Departamento de Química, Universidade de Coimbra, 3049-535, Coimbra, Portugal
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  • António Manuel d’A. Rocha Gonsalves,

    Corresponding author
    1. Chymiotechnon, Departamento de Química, Universidade de Coimbra, 3049-535, Coimbra, Portugal
    2. Centre of Investigation on Environment Genetics and Oncobiology (CIMAGO), Faculty of Medicine, University of Coimbra, Coimbra, Portugal
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  • Margarida Abrantes,

    1. Centre of Investigation on Environment Genetics and Oncobiology (CIMAGO), Faculty of Medicine, University of Coimbra, Coimbra, Portugal
    2. Instituto de Biofísica/Biomatemática, IBILI, Faculdade de Medicina de Coimbra, 3000-354 Coimbra, Portugal
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  • Mafalda Laranjo,

    1. Instituto de Biofísica/Biomatemática, IBILI, Faculdade de Medicina de Coimbra, 3000-354 Coimbra, Portugal
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  • Maria Filomena Botelho

    1. Centre of Investigation on Environment Genetics and Oncobiology (CIMAGO), Faculty of Medicine, University of Coimbra, Coimbra, Portugal
    2. Instituto de Biofísica/Biomatemática, IBILI, Faculdade de Medicina de Coimbra, 3000-354 Coimbra, Portugal
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*Corresponding author email: arg@qui.uc.pt (António M. d’A. Rocha Gonsalves)

Abstract

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 IC50 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.

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