Photosensitizing properties of a boronated phthalocyanine: studies at the molecular and cellular level.
A synthetic procedure has been developed for the preparation of a Zn-phthalocyanine peripherally substituted with a dodecaborane. The absorption spectrum of the derivative is typical of the phthalocyanine chromophore. Moreover, the boronated phthalocyanine exhibits a high photosensitizing efficiency against a model biological substrate, such as N-acetyl-L-tryptophanamide, and a singlet oxygen quantum yield of 0.53 in dimethylformamide. Even though the presence of the dodecaborane moiety appears to decrease the affinity of the phthalocyanine for HT-1080 transformed human fibroblasts, the boronated phthalocyanine causes an essentially complete loss of cell viability upon irradiation with 600-700 nm light under mild conditions (1 microM concentration, 5-min irradiation at 10 mW/cm(2)).
Fabris
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Molteni Farmaceutici, S.S 67 Loc. Granatieri - 50018 Scandicci, Florence, Italy. jorilab1@civ.bio.unipd.it
Jori
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Giuntini
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Roncucci
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D001896:Boron Compounds / Q000737:chemistry* / Q000494:pharmacology; D002461:Cell Line, Transformed; D002470:Cell Survival / Q000187:drug effects; D004126:Dimethylformamide; D005347:Fibroblasts / Q000187:drug effects; D006801:Humans; D007211:Indoles / Q000737:chemistry* / Q000494:pharmacology; D054833:Isoindoles; D008027:Light; D017319:Photosensitizing Agents / Q000737:chemistry* / Q000494:pharmacology; D026082:Singlet Oxygen
D001896:Boron Compounds; D007211:Indoles; D054833:Isoindoles; D017319:Photosensitizing Agents; D026082:Singlet Oxygen; D004126:Dimethylformamide; C013647:phthalocyanine