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SPECTROSCOPY AND PHOTOSENSITIZATION OF SAPPHYRINS IN SOLUTIONS AND BIOLOGICAL MEMBRANES
Author(s) -
Roitman Leonid,
Ehrenberg Benjamin,
Nitzan Yeshayahu,
Kral Vladimir,
Sessler Jonathan L.
Publication year - 1994
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.1751-1097.1994.tb05127.x
Subject(s) - chemistry , moiety , photochemistry , singlet oxygen , absorption spectroscopy , absorption (acoustics) , fluorescence , molecule , membrane , liposome , oxygen , organic chemistry , materials science , biochemistry , physics , quantum mechanics , composite material
A spectroscopic and photophysical study of three new sapphyrin molecules is presented. The sapphyrin backbone that was derivatized to make them water soluble possesses an absorption band around 700 nm, a desired property for biological photosensitization. We studied the absorption and fluorescence spectra, from which evidence for aggregation in solvents of different polarities was obtained. The extent of aggregation is correlated with the nature of the attached moiety. The absolute quantum yields of singlet oxygen production were measured, with 1,3‐diphenyl isobenzofuran as a model target, and were 0.13–0.18 in ethanol. The binding constants to liposomes and to cells were determined spectroscopically and were found to correspond to the hydrophobicities of the compounds, with an additional effect, ascribed to the sugar moiety, which was found in the case of one of the sapphyrins. The efficiency of photodamage to Staphylococcus aureus by sapphyrins and hematoporphyrin was equivalent, on the basis of cells killed per microgram of sensitizer in the incubation mixture.