Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase
Identifieur interne : 00A165 ( Main/Exploration ); précédent : 00A164; suivant : 00A166Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase
Auteurs : Gilles Ferry [France] ; Caroline Ubeaud [France] ; Pierre-Hervé Lambert [France] ; Sophie Bertin [France] ; Francis Cogé [France] ; Pascale Chomarat [France] ; Philippe Delagrange [France] ; Bernard Serkiz [France] ; Jean-Paul Bouchet [France] ; Roger J. W. Truscott [Australie] ; Jean A. Boutin [France]Source :
- Biochemical Journal [ 0264-6021 ] ; 2005.
Abstract
The catabolism of melatonin, whether naturally occurring or ingested, takes place via two pathways: ∼70% can be accounted for by conjugation (sulpho- and glucurono-conjugation), and ∼30% by oxidation. It is commonly thought that the interferon-induced enzyme indoleamine 2,3-dioxygenase (EC 1.13.11.42), which oxidizes tryptophan, is also responsible for the oxidation of 5-hydroxytryptamine (serotonin) and its derivative, melatonin. Using the recombinant enzyme expressed in
Url:
DOI: 10.1042/BJ20042075
PubMed: 15636586
PubMed Central: 1186709
Affiliations:
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G" first="Gilles" last="Ferry">Gilles Ferry</name><affiliation wicri:level="3"><nlm:aff id="A1">*Pharmacologie Moléculaire et Cellulaire, Institut de Recherches SERVIER 125, chemin de Ronde 78290, Croissy-sur-Seine, France</nlm:aff><country xml:lang="fr">France</country><wicri:regionArea>*Pharmacologie Moléculaire et Cellulaire, Institut de Recherches SERVIER 125, chemin de Ronde 78290, Croissy-sur-Seine</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Croissy-sur-Seine</settlement></placeName></affiliation></author><author><name sortKey="Ubeaud, Caroline" sort="Ubeaud, Caroline" uniqKey="Ubeaud C" first="Caroline" last="Ubeaud">Caroline Ubeaud</name><affiliation wicri:level="3"><nlm:aff id="A1">*Pharmacologie Moléculaire et Cellulaire, Institut de Recherches SERVIER 125, chemin de Ronde 78290, Croissy-sur-Seine, France</nlm:aff><country xml:lang="fr">France</country><wicri:regionArea>*Pharmacologie Moléculaire et Cellulaire, 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Bertin</name><affiliation wicri:level="3"><nlm:aff id="A2">†Physico-chimie analytique, Institut de Recherches SERVIER 11, rue des Moulineaux, 92150 Suresnes, France</nlm:aff><country xml:lang="fr">France</country><wicri:regionArea>†Physico-chimie analytique, Institut de Recherches SERVIER 11, rue des Moulineaux, 92150 Suresnes</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Suresnes</settlement></placeName></affiliation></author><author><name sortKey="Coge, Francis" sort="Coge, Francis" uniqKey="Coge F" first="Francis" last="Cogé">Francis Cogé</name><affiliation wicri:level="3"><nlm:aff id="A1">*Pharmacologie Moléculaire et Cellulaire, Institut de Recherches SERVIER 125, chemin de Ronde 78290, Croissy-sur-Seine, France</nlm:aff><country xml:lang="fr">France</country><wicri:regionArea>*Pharmacologie Moléculaire et Cellulaire, Institut de Recherches SERVIER 125, chemin de Ronde 78290, 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Delagrange</name><affiliation wicri:level="3"><nlm:aff id="A1">*Pharmacologie Moléculaire et Cellulaire, Institut de Recherches SERVIER 125, chemin de Ronde 78290, Croissy-sur-Seine, France</nlm:aff><country xml:lang="fr">France</country><wicri:regionArea>*Pharmacologie Moléculaire et Cellulaire, Institut de Recherches SERVIER 125, chemin de Ronde 78290, Croissy-sur-Seine</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Croissy-sur-Seine</settlement></placeName></affiliation></author><author><name sortKey="Serkiz, Bernard" sort="Serkiz, Bernard" uniqKey="Serkiz B" first="Bernard" last="Serkiz">Bernard Serkiz</name><affiliation wicri:level="3"><nlm:aff id="A2">†Physico-chimie analytique, Institut de Recherches SERVIER 11, rue des Moulineaux, 92150 Suresnes, France</nlm:aff><country xml:lang="fr">France</country><wicri:regionArea>†Physico-chimie analytique, Institut de Recherches SERVIER 11, rue des Moulineaux, 92150 Suresnes</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Suresnes</settlement></placeName></affiliation></author><author><name sortKey="Bouchet, Jean Paul" sort="Bouchet, Jean Paul" uniqKey="Bouchet J" first="Jean-Paul" last="Bouchet">Jean-Paul Bouchet</name><affiliation wicri:level="3"><nlm:aff id="A2">†Physico-chimie analytique, Institut de Recherches SERVIER 11, rue des Moulineaux, 92150 Suresnes, France</nlm:aff><country xml:lang="fr">France</country><wicri:regionArea>†Physico-chimie analytique, Institut de Recherches SERVIER 11, rue des Moulineaux, 92150 Suresnes</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Suresnes</settlement></placeName></affiliation></author><author><name sortKey="Truscott, Roger J W" sort="Truscott, Roger J W" uniqKey="Truscott R" first="Roger J. W." last="Truscott">Roger J. W. Truscott</name><affiliation wicri:level="1"><nlm:aff id="A3">‡Australian Cataract Research Foundation and Department of Chemistry, University of Wollongong, New South Wales 2522, Australia</nlm:aff><country xml:lang="fr">Australie</country><wicri:regionArea>‡Australian Cataract Research Foundation and Department of Chemistry, University of Wollongong, New South Wales 2522</wicri:regionArea><wicri:noRegion>New South Wales 2522</wicri:noRegion></affiliation></author><author><name sortKey="Boutin, Jean A" sort="Boutin, Jean A" uniqKey="Boutin J" first="Jean A." last="Boutin">Jean A. Boutin</name><affiliation wicri:level="1"><nlm:aff id="A1">*Pharmacologie Moléculaire et Cellulaire, Institut de Recherches SERVIER 125, chemin de Ronde 78290, Croissy-sur-Seine, France</nlm:aff><country xml:lang="fr">France</country><wicri:regionArea>*Pharmacologie Moléculaire et Cellulaire, Institut de Recherches SERVIER 125, chemin de Ronde 78290, Croissy-sur-Seine</wicri:regionArea><wicri:noRegion>78290, Croissy-sur-Seine</wicri:noRegion><wicri:noRegion>78290, Croissy-sur-Seine</wicri:noRegion></affiliation></author></analytic><series><title level="j">Biochemical Journal</title><idno type="ISSN">0264-6021</idno><idno type="eISSN">1470-8728</idno><imprint><date when="2005">2005</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The catabolism of melatonin, whether naturally occurring or ingested, takes place via two pathways: ∼70% can be accounted for by conjugation (sulpho- and glucurono-conjugation), and ∼30% by oxidation. It is commonly thought that the interferon-induced enzyme indoleamine 2,3-dioxygenase (EC 1.13.11.42), which oxidizes tryptophan, is also responsible for the oxidation of 5-hydroxytryptamine (serotonin) and its derivative, melatonin. Using the recombinant enzyme expressed in <italic>Escherichia coli</italic>, we show in the present work that indoleamine 2,3-dioxygenase indeed cleaves tryptophan; however, under the same conditions, it is incapable of cleaving the two other indoleamines. By contrast, myeloperoxidase (EC 1.11.1.7) is capable of cleaving the indole moiety of melatonin. However, when using the peroxidase conditions of assay – with H<sub>2</sub>O<sub>2</sub> as co-substrate – indoleamine 2,3-dioxygenase is able to cleave melatonin into its main metabolite, a kynurenine derivative. The present work establishes that the oxidative metabolism of melatonin is due, in the presence of H<sub>2</sub>O<sub>2</sub>, to the activities of both myeloperoxidase and indoleamine 2,3-dioxygenase (with lower potency), since both enzymes have <italic>K</italic><sub>m</sub> values for melatonin in the micromolar range. Under these conditions, several indolic compounds can be cleaved by both enzymes, such as tryptamine and 5-hydroxytryptamine. Furthermore, melatonin metabolism results in a kynurenine derivative, the pharmacological action of which remains to be studied, and could amplify the mechanisms of action of melatonin.</p></div></front></TEI><affiliations><list><country><li>Australie</li><li>France</li></country><region><li>Île-de-France</li></region><settlement><li>Croissy-sur-Seine</li><li>Suresnes</li></settlement></list><tree><country name="France"><region name="Île-de-France"><name sortKey="Ferry, Gilles" sort="Ferry, Gilles" uniqKey="Ferry G" first="Gilles" last="Ferry">Gilles Ferry</name></region><name sortKey="Bertin, Sophie" sort="Bertin, Sophie" uniqKey="Bertin S" first="Sophie" last="Bertin">Sophie Bertin</name><name sortKey="Bouchet, Jean Paul" sort="Bouchet, Jean Paul" uniqKey="Bouchet J" first="Jean-Paul" last="Bouchet">Jean-Paul Bouchet</name><name sortKey="Boutin, Jean A" sort="Boutin, Jean A" uniqKey="Boutin J" first="Jean A." last="Boutin">Jean A. Boutin</name><name sortKey="Chomarat, Pascale" sort="Chomarat, Pascale" uniqKey="Chomarat P" first="Pascale" last="Chomarat">Pascale Chomarat</name><name sortKey="Coge, Francis" sort="Coge, Francis" uniqKey="Coge F" first="Francis" last="Cogé">Francis Cogé</name><name sortKey="Delagrange, Philippe" sort="Delagrange, Philippe" uniqKey="Delagrange P" first="Philippe" last="Delagrange">Philippe Delagrange</name><name sortKey="Lambert, Pierre Herve" sort="Lambert, Pierre Herve" uniqKey="Lambert P" first="Pierre-Hervé" last="Lambert">Pierre-Hervé Lambert</name><name sortKey="Serkiz, Bernard" sort="Serkiz, Bernard" uniqKey="Serkiz B" first="Bernard" last="Serkiz">Bernard Serkiz</name><name sortKey="Ubeaud, Caroline" sort="Ubeaud, Caroline" uniqKey="Ubeaud C" first="Caroline" last="Ubeaud">Caroline Ubeaud</name></country><country name="Australie"><noRegion><name sortKey="Truscott, Roger J W" sort="Truscott, Roger J W" uniqKey="Truscott R" first="Roger J. W." last="Truscott">Roger J. W. 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