title: Coelenterazine: a two-stage antioxidant in lipid micelles.
abstract: Coelenterazine is a luciferin found in many marine bioluminescent organisms. This luciferin also possesses high antioxidant properties and an exceptional ability to protect cells exposed to oxidative stress. It has been suggested that coelenterazine's antioxidative mechanisms include the formation of an oxidation product, coelenteramine, also endowed with chain-breaking properties. In this work, coelenterazine analogs were shown to delay the onset of lipid peroxidation in a linoleate micellar solution exposed to free radical initiators. Their consumption was accompanied by the concomitant formation of coelenteramine. This was followed by a reduction in the peroxidation rate coinciding with the consumption of coelenterazine's oxidation product coelenteramine. The addition of coelenteramine to micelles reduced the propagation rate of the oxidative process. When coelenterazine analogs oxidizing into an inactive analog of coelenteramine were applied, the delaying effect but not the reduced peroxidation rate nor the consumption of the aminopyrazine was observed. These results demonstrate the role of the oxidation product coelenteramine in the chain-breaking properties of coelenterazine and analogs.
authors.affiliation: Animal Biology Unit, I.S.V., Biology Department, Université Catholique de Louvain, 1348 Louvain-la-Neuve, Belgium.
authors.forename: Bertrand
authors.initials: B
authors.lastname: de Wergifosse
authors.forename: Marlène
authors.initials: M
authors.lastname: Dubuisson
authors.forename: Jacqueline
authors.initials: J
authors.lastname: Marchand-Brynaert
authors.forename: André
authors.initials: A
authors.lastname: Trouet
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Rees
mesh_terms: D000578:Amidines / Q000494:pharmacology; D000975:Antioxidants / Q000494:pharmacology*; D005609:Free Radicals / Q000494:pharmacology; D007093:Imidazoles / Q000737:chemistry; D019787:Linoleic Acid / Q000737:chemistry; D050356:Lipid Metabolism; D015227:Lipid Peroxidation / Q000187:drug effects*; D008823:Micelles; D015394:Molecular Structure; D009570:Nitriles / Q000494:pharmacology; D010084:Oxidation-Reduction / Q000187:drug effects; D011719:Pyrazines / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013997:Time Factors
chemical_list: D000578:Amidines; D000975:Antioxidants; D005609:Free Radicals; D007093:Imidazoles; D008823:Micelles; D009570:Nitriles; D011719:Pyrazines; C017144:coelenterazine; C046728:2,2'-azobis(2-amidinopropane); D019787:Linoleic Acid; C004526:azobis(isobutyronitrile)