A new nonconjugated naphthalene derivative of meso-tetra-(3-hydroxy)-phenyl-porphyrin as a potential sensitizer for photodynamic therapy.
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 6.80μg mL(-1) for a 24h incubation. In addition to the potential of this compound, the synthetic route used provides possibilities of extension to a wide range of new sensitizers.
Silva
Pedro
P
Departamento de Química, FCTUC, Universidade de Coimbra, Coimbra, Portugal.
Fonseca
Sofia M
SM
Arranja
Cláudia T
CT
Burrows
Hugh D
HD
Urbano
Ana M
AM
Sobral
Abilio J F N
AJ
D002470:Cell Survival / Q000187:drug effects / Q000528:radiation effects; D019073:HT29 Cells; D006801:Humans; D015394:Molecular Structure; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
C556998:5,10,15,20-tetra-(phenoxy-3-carbonyl-1-aminonaphthyl)porphyrin; D017319:Photosensitizing Agents; D011166:Porphyrins