Abstract
Chemiluminescence associated with oxidation by free radicals was investigated in an alkaline, hemin-catalysed hydrogen peroxide system, using the following tryptophan metabolites as radical scavengers: indole-3-pyruvic, indole-3-propionic, kynurenic, xanthurenic and quinaldic acids and 4-hydroxy-quinoline. Light emission from oxidation of the indolic compounds was only partially inhibited by the hydroxyl-radical scavenger DMSO, but strongly suppressed by the superoxide-anion scavenger Tiron, whereas chemi-luminescence generated from kynurenic acid was strongly inhibited by either of these compounds. Light emission from oxidation of kynurenic acid lasts for a surprisingly long period of time: At 0.4 mM and 20°C, luminescence increased for 5 hours and continued at a high rate for more than a day. Comparison of structural analogues indicated that the 4-hydroxyl and carboxyl groups of kynurenic acid are essential for effective light emission, and that an additional 8-hydroxyl residue leading to an intramolecular hydrogen bond diminishes the reaction rate.
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References
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Hardeland, R., Zsizsik, B.K., Poeggeler, B., Fuhrberg, B., Holst, S., Coto-Montes, A. (1999). Indole-3-Pyruvic and -Propionic Acids, Kynurenic Acid, and Related Metabolites as Luminophores and Free-Radical Scavengers. In: Huether, G., Kochen, W., Simat, T.J., Steinhart, H. (eds) Tryptophan, Serotonin, and Melatonin. Advances in Experimental Medicine and Biology, vol 467. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4709-9_49
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DOI: https://doi.org/10.1007/978-1-4615-4709-9_49
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