Title: Synthesis, spectroscopic properties and interaction with a liposomal membrane of a novel iodinated magnesium phthalocyanine
Abstract: Phthalocyanines are applied as effective photosensitizers in photodynamic therapy of cancer and some other diseases. In this study, the synthesis of magnesium 2,9(10),16(17),23(24)-tetraiodophthalocyanine (2) is described. The spectroscopic, photophysical and photochemical parameters of phthalocyanine 2 are discussed, including the ability of this novel photosensitizer to generate singlet oxygen (1O2). The quantum yield of singlet oxygen formation (ΦΔ) was determined by two methods, viz. by measuring time-resolved phosphorescence at 1270 nm and by using 1,3-diphenylisobenzofuran and 9,10-dimethylanthracene, the well-known chemical acceptors. Applying the first method, the value of ΦΔ in N,N-dimethylformamide was found to be 0.70 ± 0.02, while using the second method the quantum yield of singlet oxygen formation was found to be 0.95 ± 0.01. This discrepancy lead to the conclusion that the photooxidation process with phthalocyanine 2 as the photosensitizer proceeds via a mixed mechanism, viz. Type II and Type I and/or Type III. The fluorescence quantum yield of 2 in N,N-dimethylformamide is 0.063 ± 0.004. The interaction between photosensitizer 2 and liposomes in an aqueous suspension was studied using a laser scanning confocal microscopy and the fluorescence technique. It was found that the binding constant of phthalocyanine 2 to liposomes was equal Kb = 40.5 ± 6.4 (mg/mL)−1. This implies, that the studied photosensitizer can readily penetrate cell or lipid membranes.
Publication Year: 2014
Publication Date: 2014-07-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 22
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