TY - JOUR A1 - Bernardi, Silvia A1 - Fezzardi, Paola A1 - Rispoli, Gabriele A1 - Sestito, Stefania E. A1 - Peri, Francesco A1 - Sansone, Francesco A1 - Casnati, Alessandro T1 - Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands JF - Beilstein Journal of Organic Chemistry PY - 2014/// VL - 10 SP - 1672 EP - 1680 SN - 1860-5397 DO - 10.3762/bjoc.10.175 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.10.175 KW - glycocalixarenes KW - cluster glycoside effect KW - multivalency KW - click chemistry KW - surface plasmon resonance N2 - 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 lactosyl- over 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. ER -