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.
journal_name
Eur J Med Chemjournal_title
European journal of medicinal chemistryauthors
Bellia F,Amorini AM,La Mendola D,Vecchio G,Tavazzi B,Giardina B,Di Pietro V,Lazzarino G,Rizzarelli Edoi
10.1016/j.ejmech.2007.03.038subject
Has Abstractpub_date
2008-02-01 00:00:00pages
373-80issue
2eissn
0223-5234issn
1768-3254pii
S0223-5234(07)00193-6journal_volume
43pub_type
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