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A New Nonconjugated Naphthalene Derivative of Meso ‐tetra‐(3‐hydroxy)‐phenyl‐porphyrin as a Potential Sensitizer for Photodynamic Therapy
Author(s) -
Silva Pedro,
Fonseca Sofia M.,
Arranja Cláudia T.,
Burrows Hugh D.,
Urbano Ana M.,
Sobral Abilio J. F. N.
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.1751-1097.2010.00764.x
Subject(s) - porphyrin , singlet oxygen , tetra , photodynamic therapy , chemistry , photochemistry , photodegradation , photosensitizer , derivative (finance) , medicinal chemistry , organic chemistry , photocatalysis , oxygen , catalysis , financial economics , economics
A new 5,10,15,20‐tetra‐(phenoxy‐3‐carbonyl‐1‐amino‐naphthyl)‐porphyrin was prepared by an isocyanate condensation reaction and its photophysical properties fully evaluated, both in terms of photostability and singlet oxygen production. It shows considerably enhanced photostability when compared with the parent 5,10,15,20‐tetra‐(3‐hydroxy‐phenyl)‐porphyrin, with the photodegradation quantum yields for T(NAF)PP and T(OH)PP being 4.65 × 10 −4 and 5.19 × 10 −3 , respectively. Its photodynamic effect in human carcinoma HT‐29 cells was evaluated. The new porphyrin showed good properties as a sensitizer in photodynamic therapy with an in vitro cytotoxicity IC 50 value of 6.80 μg mL −1 for a 24 h incubation. In addition to the potential of this compound, the synthetic route used provides possibilities of extension to a wide range of new sensitizers.