Photosensitized decomposition of S-nitrosothiols and 2-methyl-2-nitrosopropane. Possible use for site-directed nitric oxide production.
Irradiation of S-nitrosoglutathione (GSNO) with light (lambda = 550 nm) resulted in the homolytic decomposition of GSNO to generate glutathionyl radical (GS.) and nitric oxide (.NO), which were monitored by ESR spectrometry. Inclusion of Rose Bengal (RB) resulted in a 9-fold increase in the quantum yield for .NO production and also an increase in the rate of thiyl radical formation. The bimolecular rate constant for the interaction of triplet RB with GSNO has been estimated to be approximately 1.2 x 10(9) M-1s-1 by competition with oxygen. Hematoporphyrin (HP) also enhanced the rate of .NO production by 2-3-fold. 2-Methyl-2-nitrosopropane (MNP) decomposed on irradiation (lambda = 660 nm) to form .NO and tert-butyl radical. Aluminum phthalocyanine tetrasulphonate enhanced the rate of decomposition of MNP by 10-fold. These studies show that photosensitizers enhance the release of .NO from donor compounds.
Singh
R J
RJ
Biophysics Research Institute, Medical College of Wisconsin, Milwaukee 53226.
Hogg
N
N
Joseph
J
J
Kalyanaraman
B
B
D004578:Electron Spin Resonance Spectroscopy; D005609:Free Radicals; D007211:Indoles / Q000737:chemistry; D007700:Kinetics; D009569:Nitric Oxide / Q000096:biosynthesis*; D009603:Nitroso Compounds / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D017319:Photosensitizing Agents / Q000737:chemistry*; D012395:Rose Bengal / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D005609:Free Radicals; D007211:Indoles; D009603:Nitroso Compounds; D009942:Organometallic Compounds; D017319:Photosensitizing Agents; D013438:Sulfhydryl Compounds; C048577:aluminum tetrasulfophthalocyanine; D012395:Rose Bengal; D009569:Nitric Oxide; C034526:tert-nitrosobutane