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doi:10.1016/j.ejmech.2006.12.036 
Copyright © 2007 Elsevier Masson SAS All rights reserved.
Original article
Synthesis and antioxidant activity of new homocarnosine β-cyclodextrin conjugates
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Angela Maria Amorinia, Francesco Belliaa, Valentina Di Pietrob, Bruno Giardinab, Diego La Mendolac, Giuseppe Lazzarinoa, Salvatore Sortinoa, Barbara Tavazzib, Enrico Rizzarellia, 
, 
and Graziella Vecchioa
Received 5 December 2006;
Abstract
Several in vitro and in vivo studies have suggested that carnosine (β-alanil-l-histidine) and homocarnosine (β-aminobutyril-l-histidine) can act as scavengers of reactive oxygen species. β-Cyclodextrin was functionalized with homocarnosine, obtaining the following new bioconjugate isomers: 6A-[(4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}-4-oxobutyl)amino]-6A-deoxy-β-cyclodextrin and (2AS,3AR)-3A-[(4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}-4-oxobutyl)amino]-3A-deoxy-β-cyclodextrin. Pulse radiolysis investigations show that the β-cyclodextrin homocarnosine bioconjugates are scavengers of OH radicals because of the formation of stable imidazole-centered radicals and the scavenger ability of glucose molecules of the macrocycle. The ability of these new β-cyclodextrin derivatives to inhibit the copper(II) driven LDL oxidation was determined in comparison with that displayed by the analogous carnosine derivatives. Both the β-cyclodextrin carnosine isomers show a higher protective effect than that of free dipeptide and homocarnosine derivatives, bringing into light the role of the β-CD cavity.
The ability of these new β-cyclodextrin derivatives to inhibit the copper(II) driven LDL oxidation was determined in comparison with that displayed by the analogous carnosine derivatives. Both the β-cyclodextrin carnosine isomers show a higher protective effect than that of free dipeptide and homocarnosine derivatives, bringing into light the role of the β-CD cavity.
Graphical abstract
The ability of new β-cyclodextrin homocarnosine conjugates to scavenger hydroxyl radicals and to inhibit LDL oxidation makes them promising agents against harmful oxygen species.
Keywords: β-Cylodextrin; Homocarnosine; Carnosine; Low density lipoprotein; Pulse radiolysis
Article Outline
- 1. Introduction
- 2. Experimental procedures
- 2.1. Chemicals
- 2.1.1. Synthesis of 6A-[(4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}-4-oxobutyl)amino]-6A-deoxy-β-cyclodextrin (CDHC6)
- 2.1.2. Synthesis of (2AS,3AR)-3A-[(4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}-4-oxobutyl)amino]-3A-deoxy-β-cyclodextrin CDHC3
- 2.2. Pulse radiolysis
- 2.3. Oxidation of human LDL
- 2.4. HPLC analysis of MDA
- 3. Results and discussion
- 3.1. Synthesis and NMR characterization
- 3.1.1. NMR spectra of CDHC6
- 3.1.2. NMR spectra of CDHC3
- 3.2. Pulse radiolysis
- 3.3. LDL oxidation
- 4. Conclusions
- Acknowledgements
- References
) on 40 μM copper-induced lipid peroxidation of human LDL. Peroxidation was evaluated by the HPLC determination of MDA. Control LDL were incubated in presence of 40 μM Cu2+ and buffer only, with no added antioxidant (0% protection). Each point represents the mean of four different experiments. Standard deviations are represented by vertical bars.
