Keywords: Biotin, Carnosinase, Copper, Nanoparticles, Avidin Chemistry, Biotin Chemistry, Carnosine Chemical Synthesis Chemistry, Dipeptidases Blood Metabolism, Gold Chemistry, Humans, Metal Nanoparticles Chemistry, Molecular Structure, Spectrophotometry, Ultraviolet, Streptavidin Chemistry, Bio Nhs, Cupric Ion, Gold Nanoparticle, Unclassified Drug, Binding Assay, Drug Bioavailability, Drug Synthesis, Mass Spectrometry, Proton Nuclear Magnetic Resonance,
Affiliations: *** IBB - CNR ***
Institute of Biostructure and Bioimaging, CNR, viale A. Doria 6, 95125 Catania, Italy. Electronic address: fbellia@unict.it.
Department of Chemical Sciences, University of Catania, viale A. Doria 6, 95125 Catania, Italy
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New derivative of carnosine for nanoparticle assemblies
Carnosine (beta-alanyl-l-histidine) is an endogenous dipeptide, extensively studied owing to its multifunctional activity exhibited in tissues of several animal species. This natural compound may act as a physiological buffer, ion-chelating agent (especially for copper(II) and zinc(II)), antioxidant and antiglycating agent. The main limit for the therapeutical uses of carnosine is the rapid hydrolysis mostly in human plasma by carnosinase. The chemical derivatization of carnosine is a promising strategy to improve the bioavailability of the dipeptide and facilitating the site-specific transport to different tissues. On this basis, a new carnosine derivative with biotin was synthesized and structurally characterized by NMR and MS measurements, with aim of exploiting the avidin-biotin technology that offers a universal system for selective delivery of any biotinylated agent. The stability of the new carnosine derivative towards the hydrolytic action of serum carnosinase as well as the copper(II) binding ability of the carnosine-biotin conjugate were also assessed. The binding affinity of the new molecular entity to avidin and streptavidin, investigated by a spectrophotometric assay, was exploited to functionalize avidin- and streptavidin-gold nanoparticles with the carnosine-biotin conjugate. Copyright 2013 Elsevier Masson SAS. All rights reserved.
New derivative of carnosine for nanoparticle assemblies
Malvindi MA, Greco A, Conversano F, Figuerola A, Corti M, Bonora M, Lascialfari A, Doumari HA, Moscardini M, Cingolani R, Gigli G, Casciaro S, Pellegrino T, Ragusa A * MR Contrast Agents(292 views) Small Animal Imaging, 2011 Jul 8; 21(13): 2548-2555. Impact Factor:1.784 ViewExport to BibTeXExport to EndNote