title: Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands.
abstract: 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.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Parma, Parco Area delle Scienze 17/a, 43124 Parma, Italy.
authors.forename: Silvia
authors.initials: S
authors.lastname: Bernardi
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Parma, Parco Area delle Scienze 17/a, 43124 Parma, Italy.
authors.forename: Paola
authors.initials: P
authors.lastname: Fezzardi
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Parma, Parco Area delle Scienze 17/a, 43124 Parma, Italy.
authors.forename: Gabriele
authors.initials: G
authors.lastname: Rispoli
authors.affiliation: Dipartimento di Biotecnologie e Bioscienze, Università degli Studi di Milano-Bicocca, Piazza della Scienza 2, 20126 Milano, Italy.
authors.forename: Stefania E
authors.initials: SE
authors.lastname: Sestito
authors.affiliation: Dipartimento di Biotecnologie e Bioscienze, Università degli Studi di Milano-Bicocca, Piazza della Scienza 2, 20126 Milano, Italy.
authors.forename: Francesco
authors.initials: F
authors.lastname: Peri
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Parma, Parco Area delle Scienze 17/a, 43124 Parma, Italy.
authors.forename: Francesco
authors.initials: F
authors.lastname: Sansone
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Parma, Parco Area delle Scienze 17/a, 43124 Parma, Italy.
authors.forename: Alessandro
authors.initials: A
authors.lastname: Casnati
keywords: click chemistry; cluster glycoside effect; glycocalixarenes; multivalency; surface plasmon resonance