Dabestani R, Reszka K J, Davis D G, Sik R H, Chignell C F
Laboratory of Molecular Biophysics, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709.
Photochem Photobiol. 1991 Jul;54(1):37-42. doi: 10.1111/j.1751-1097.1991.tb01982.x.
The photochemistry (Type I and II) of the phototoxic textile dye Disperse Blue (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 (1O2) 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-1-pyrroline-N-oxide (DMPO). Visible light irradiation of the components in ethanol generated 1O2 with the yields decreasing in the following order: 4,5-DDHAQ greater than 2,5-DDHAQ greater than 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.
利用电子自旋共振结合自旋捕获技术以及单线态氧（1O2）发光的直接检测，研究了光毒性纺织染料分散蓝（DB - 35）及其纯化成分的光化学（I型和II型）。DB - 35（由1,8 - 二羟基蒽醌经连续硝化、还原和甲基化合成）的主要成分通过高效液相色谱法分离，并通过质谱和二维核磁共振鉴定为4,5 - 二氨基 - 1,8 - 二羟基蒽醌（4,5 - DDHAQ；占总染料的62%）和2,7 - 二氨基 - 1,8 - 二羟基蒽醌（2,7 - DDHAQ；占总染料的31%）。次要成分包括2,5 - 二氨基 - 1,8 - 二羟基蒽醌（2,5 - DDHAQ）以及4,5 - DDHAQ或2,7 - DDHAQ的单甲基化衍生物。在二甲基亚砜中对4,5 - DDHAQ和2,7 - DDHAQ进行624 nm光照会产生超氧化物，该超氧化物被5,5 - 二甲基 - 1 - 吡咯啉 - N - 氧化物（DMPO）捕获。在乙醇中对这些成分进行可见光照射会产生1O2，产率按以下顺序降低：4,5 - DDHAQ大于2,5 - DDHAQ大于2,7 - DDHAQ。这些发现表明，在可见光照射下，DB - 35可产生活性氧物种，这可能是该染料引起光接触性皮炎的原因。
