New glycosidic derivatives of histidine-containing dipeptides with antioxidant properties and resistant to carnosinase activity.

Angela Maria Amorini, Bruno Giardina, Valentina Di Pietro, F Bellia, D La Mendola, G Vecchio, B Tavazzi, G Lazzarino, E. Rizzarelli

Risultato della ricerca: Contributo in rivistaArticolo in rivista

41 Citazioni (Scopus)

Abstract

Synthesis, antioxidant properties and resistance to carnosinase hydrolysis of histidine-containing dipeptides are reported in this study. Carnosine (beta-alanyl-l-histidine), homocarnosine (gamma-aminobutyryl-l-histidine) and anserine (beta-alanyl-3-methyl-l-histidine) were covalently derivatized with beta-cyclodextrin to form different OH- or NH-bound conjugates. Mass spectroscopic and (1)H NMR data were used to determine the structure and the purity of the various beta-cyclodextrin derivatives. The inhibitory effect towards oxidation of human LDL induced by Cu(2+) ions, was estimated by measuring malondialdehyde formation as a function of increasing concentrations of these newly synthesized compounds (the beta-cyclodextrin-anserine conjugated in 3 had the highest antioxidant effect). All derivatives had higher antioxidant effects than those of the corresponding free histidine-containing dipeptides. Resistance to rat brain carnosinase hydrolysis of the most active derivatives indicated that these compounds are good candidates for further studies in more complex cellular and animal models. Their possible applications for remedies in neurodegenerative disorders, such as Alzheimer's and Parkinson's diseases, are discussed.
Lingua originaleEnglish
pagine (da-a)373-380
Numero di pagine8
RivistaEuropean Journal of Medicinal Chemistry
Stato di pubblicazionePubblicato - 2008

Keywords

  • carnosinase

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