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RESEARCH PRODUCT
Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: New multivalent galectin-3 ligands
Alessandro CasnatiStefania E. SestitoPaola FezzardiFrancesco PeriGabriele RispoliFrancesco SansoneSilvia Bernardisubject
chemistry.chemical_classificationChemistrySpecific lectinStereochemistryClick chemistryOrganic ChemistryAlkyneglycocalixarenesFull Research Paperlcsh:QD241-441Chemistrychemistry.chemical_compoundlcsh:Organic chemistrySurface plasmon resonanceCalixareneClick chemistryMultivalencyCluster glycoside effectlcsh:QSurface plasmon resonancelcsh:ScienceEthylene glycolGlycocalixarenedescription
Four novel calix[4]arene-based glycoclusters were synthesized by conjugating the saccharide units to the macrocyclic scaffold using the CuAAC reaction and using long and hydrophilic ethylene glycol spacers. Initially, two galactosylcalix[4]arenes were prepared starting from saccharide units and calixarene cores which differ in the relative dispositions of the alkyne and azido groups. Once the most convenient synthetic pathway was selected, two further lactosylcalix[4]arenes were obtained, one in the cone, the other one in the 1,3-alternate structure. Preliminary studies of the interactions of these novel glycocalixarenes with galectin-3 were carried out by using a lectin-functionalized chip and surface plasmon resonance. These studies indicate a higher affinity of lactosylover galactosylcalixarenes. Furthermore, we confirmed that in case of this specific lectin binding the presentation of lactose units on a cone calixarene is highly preferred with respect to its isomeric form in the 1,3-alternate structure. © 2014 Bernardi et al.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-03-05 |