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- W79580701 abstract "Protein-carbohydrate interactions are at the heart of many important biological processes as theadesion of bacteria and viruses to the cell surfaces. It is widely accepted that nature compensates forthe low intrinsic affinity of carbohydrate for proteins through the cooperative binding betweenmultiple copies of ligands and receptors so that a strong adhesion results. This important concept,termed cluster effect, has stimulated the search for the construction of highly glycosylated ligandsto inhibit polyvalent processes as well as probe for cell-surfaces-binding events. The aim of thisPhD research work was the synthesis of calix[4]arene-based glycoclusters via Cu(I)-catalyzedazide-alkyne coupling reaction (CuAAC), as well as the investigation of their biological proprieties.The first research conducted dealt with the synthesis of sialoside clusters as potential inhibitors ofviruses infectivity. Tetra- and octavalent sialoside clusters were prepared exploiting the multiplecopper-catalyzed cycloaddition of a propargyl thiosialoside with calix[4]arene polyazides. It wasdemonstrated that these unnatural motifs did not hamper the desired biological activity of thesialoclusters. In fact, they were able to inhibit, at submillimolar concentrations, thehemagglutination and the viral infectivity mediated both by BK and influenza A viruses.Then, this thesis focused on the possibility to support C-glycoside clusters on microarrays to studytheir affinity against lectins. To this aim C-glycosylated calix[4]arenes have been synthesized inwhich four galactose residues are linked through a triazole tether to the upper rim of the macrocyclecavity while an azido group is present on the opposite side. Next the calixsugars were graftedthrough CuAAC on mono or dipropargyloxymethyl-propanediol moieties allowing the synthesis ofoligonucleotides bearing one or two calixarene glycoclusters, respectively. Finally, their affinity forlectins PA-IL and RCA 120, galactose specific lectins from Pseudomonas aeruginosa and Ricinuscommunis, respectively, were compared to that displayed by linear and antenna-type glycoclusters.During the last period of the PhD work it was performed the immobilization of calix[4]arenebasedglycoclusters on TiO2 nanoparticles via Cu(I)-catalyzed azide-alkyne coupling reaction. Thestrategy that has been followed involved first the grafting of bis-functionalized calix[4]arenes(azido groups at upper rim and fenolic or carboxylic groups at the lower rim) onto TiO2 and thenmultiple click copper(I)-catalyzed cycloadditionto propargil glycosides. The glyconanoparticlesobtained were characterized by thermogravimetric analysis (TGA) and infrared spectroscopy. Thisconstitutes the first example of TiO2 nanoparticles coated by a monolayer of calix[4]arene-basedglycoclusters." @default.
- W79580701 created "2016-06-24" @default.
- W79580701 creator A5083188841 @default.
- W79580701 date "2009-03-13" @default.
- W79580701 modified "2023-09-24" @default.
- W79580701 title "SINTESI E PROPRIETA’ BIOLOGICHEDI LIGANDI GLICOSIDICI MULTIVALENTI" @default.
- W79580701 hasPublicationYear "2009" @default.
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