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SPECTROSCOPIC STUDIES OF CUTANEOUS PHOTOSENSITIZING AGENTS–XVI. ISPERSE BLUE 35
Author(s) -
Dabestani Reza,
Reszka Krzysztof J.,
Davis Donald G.,
Sik Robert H.,
Chignell Colin F.
Publication year - 1991
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.1751-1097.1991.tb01982.x
Subject(s) - chemistry , biophysics , combinatorial chemistry , photochemistry , stereochemistry , biology
The photochemistry (Type I and II) of the phototoxic textile dye Disperse Blue 35 (DB‐35) and its purified components has been studied using electron spin resonance in conjunction with spin trapping technique and the direct detection of singlet oxygen ( 1 O 2 ) luminescence. The main components of DB‐35 (which is synthesized by the successive nitration, reduction and methylation of 1,8‐dihydroxy‐anthraquinone) were separated by HPLC and identified by mass spectrometry and 2‐D NMR as 4,5‐diamino‐1,8‐dihydroxyanthraquinone (4,5‐DDHAQ; 62% of total dye) and 2,7‐diamino‐1,8‐dihydroxyanthraquinone (2,7‐DDHAQ; 31% of total dye). Minor components included 2,5‐diamino‐1,8‐dihydroxyanthraquinone (2,5‐DDHAQ) and a monomethylated derivative of either 4,5‐DDHAQ or 2,7‐DDHAQ. Irradiation (624 nm) of 4,5‐DDHAQ and 2,7‐DDHAQ in dimethylsulfoxide resulted in the generation of superoxide which was trapped by 5,5‐dimethyl‐l‐pyrroline‐ N ‐oxide (DMPO). Visible light irradiation of the components in ethanol generated 1 O 2 with the yields decreasing in the following order: 4,5‐DDHAQ > 2,5‐DDHAQ > 2,7‐DDHAQ. These findings indicate that upon irradiation by visible light DB‐35 can generate active oxygen species which may be responsible for the photocontact dermatitis caused by this dye.