Beilstein J. Org. Chem.2014,10, 1672–1680, doi:10.3762/bjoc.10.175
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.
Keywords: glycocalixarenes; cluster glycoside effect; multivalency; click chemistry; surface
activity [6]. Furthermore, Gal-3 can act as a competitive inhibitor against Gal-1 which, on the other side, induces anoikis of tumor cells [7][8]. Glycocalixarenes [9][10][11][12], calixarenes [13][14][15] adorned with carbohydrates at the upper and/or at the lower rims, have been demonstrated to be
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Graphical Abstract
Figure 1:
Lactosylthioureidocalix[4]arenes I–III used to inhibit Gal-3 [20,21].
Beilstein J. Org. Chem.2012,8, 951–957, doi:10.3762/bjoc.8.107
[14]. Multivalent calixarenes functionalised with carbohydrate units (glycocalixarenes) [15] have been extensively reported in the literature and represent examples of sugar clustering on macrocyclic structures [16][17]. Thanks to the “glycoside cluster effect” [18][19][20], glycocalixarenes can
enhance the avidity of interactions between glycans and lectins [15]. Some glycocalixarenes have shown remarkable inhibition properties towards galectins [21][22] or Pseudomonas Aeruginosa lectin [23], the inhibition ability being dependent on the macrocyclic conformation and presentation of the glycoside
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Graphical Abstract
Figure 1:
First (2) and second (3) generation of dendrimers based on chiral C2-symmetric pyrrolidine 1 and ha...