Chemiluminescence singlet oxygen generation

Oosthuizen M M, Engelbrecht M E, Lambrechts H, Greyling D, Levy R D. The effect of pH on chemiluminescence of different probes exposed to superoxide and singlet oxygen generators. J Biolumin Chemilumin 1997 12 277-84. 

Spontaneous Chemituminescence of Urine. There are a large number of potentially chemiluminescent metabolic products excreted in urine. Reaction of a 1 ml aliquot of a urine sample in the singlet oxygen generating system... 

Since the chemiluminescence is an assay for phagocytizing cells and Eq. (56) represents a singlet oxygen generating system it is possible to use the Lumlnol chemiluminescence reaction to enhance the (Eq. (A)) and therefore to increase the sensitivity of the assay. Trush et al. (1978) report a maximum chemiluminescent intensity of 3.3 x lO count s PMN from normal PMN measured in the liquid scintillation counter. 

Also, potassium superoxide (KO2) decomposes DMD in acetone solution to release singlet oxygen, as has been detected by the characteristic infrared chemiluminescence . Furthermore, a catalytic amount of n-Bu4NI decomposes TFD into oxygen gas and triflu-oroacetone in high yield . Analogous to the Caroate decomposition by ketones, also the catalytic decomposition of peroxynitrite by ketones, e.g. methyl pyruvate, is rationahzed in terms of peroxynitrite oxidation by in-situ-generated dioxirane. ... 

Figure 8.14 Sensitized emission from suitable acceptor in chemiluminescence reaction between H4Oj-t-.OCl- generating singlet oxygen and singlet oxygen pair states.

However, the chemiluminescent reaction in the autoxidation of (31) is not inhibited by radical scavengers 208 it may proceed via a 1,2-dioxete (62). The proposed 211) thermal generation of singlet oxygen in the presence of (31) could not be confirmed in various experiments 208). 

Cyclic peroxides may serve as a source of singlet oxygen. Wasserman et reacted 9,10-diphenylanthracene peroxide (238, conveniently prepared as in Nilsson and Kearns ) with 138 to give 140 rubrene peroxide proved to be considerably less efficient. Decomposition of anthracene peroxide alone takes another course. When 13 is treated with phthaloyl peroxide (239), 140 is isolated in 59% yield the reaction is accompanied by a weak chemiluminescence. A bright yellow chemiluminescence has been observed when a solution of 240 in 1,2,4-trichlorobenzene is treated with dibenzoyl peroxide at about 210°C. The generation of visible light from 138 under conditions where peroxides may present has been described. 

Yokawa K, Suzuki N, Kawano T. Ethanol-enhanced singlet oxygen-dependent chemiluminescence interferes with the monitoring of biochemical superoxide generation with a chemiluminescence probe. Cypridina luciferin analog. ITE Lett Batter New Technol Medic 2004 5 49-52. 

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