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Istituto di scienza dell'alimentazione

Torna all'elenco Contributi in rivista anno 2004

Contributo in rivista

Tipo: Articolo in rivista

Titolo: Tetrahydrobiisoquinoline derivatives by reaction of dopamine with glyoxal: a novel potential degenerative pathway of catecholamines under oxidative stress conditions.

Anno di pubblicazione: 2004

Formato: Elettronico Cartaceo

Autori: Manini P; Panzella L; Tedesco I; Petitto F; Russo GL; Napolitano A; Palumbo A; d'Ischia M

Affiliazioni autori: Department of Organic Chemistry and Biochemistry, University of Naples "Federico II", Naples, Italy Institute of Food Sciences, National Research Council, Avellino, Italy Laboratory of Biochemistry and Molecular Biology, Zoological Station "Anton Dohrn", Naples, Italy

Autori CNR:


Lingua: inglese

Abstract: In 0.1 M phosphate buffer, pH 7.4, dopamine reacts with glyoxal, a cytotoxic and genotoxic alpha-oxoaldehyde produced by oxidative degradation of carbohydrates, to give three main products, two of which could be isolated and identified as the isomeric tetrahydrobiisoquinolines 1 and 2 by extensive two-dimensional NMR and mass spectrometric analysis. Time course studies indicated that 1 is the first intermediate in the process and changes slowly to 2 via an unstable species that escaped all efforts at isolation and structural identification. Products 1 and 2 were detected also among the species formed by the interaction of dopamine with oxidized carbohydrates, such as glucose, ribose, and fructose. Mechanistic evidence suggests that the formation of 1 proceeds by an unusual reaction pathway involving intramolecular cyclization of a double Schiff base intermediate followed by glyoxal-induced oxidation of the resulting octahydrobiisoquinoline intermediate (4). Subsequent conversion of 1 to 2 would involve a complex redox mechanism depending on an initial oxidation step. Product 2 was only poorly toxic to PC12 cells, whereas its methylated derivative 3 was as toxic as salsolinol, an established neurotoxin. Overall, these results throw light on a novel pathway of dopamine modification of potential relevance to the mechanisms underlying neurodegenerative changes in Parkinson's disease and other disorders characterized by a prooxidant state.

Lingua abstract: inglese

Pagine da: 1190

Pagine a: 1198


Chemical research in toxicology American Chemical Society,
Paese di pubblicazione: Stati Uniti d'America
Lingua: inglese
ISSN: 0893-228X

Numero volume: 17

Numero fascicolo: 9

DOI: 10.1021/tx034268q

Referee: Sė: Internazionale

Indicizzato da:

  • PubMed [15377152]
  • ISI Web of Science (WOS) [000224048300004]

Strutture CNR:


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