Polyhedral Oligomeric Silsesquioxane (POSS) Bearing Glyoxylic Aldehyde as Clickable Platform Towards Multivalent Conjugates

Abstract

The straightforward access to octafunctional "cubic" silsesquioxane platform grafter with pendant glyoxylic aldehydes is described. This clickable hybrid platform readily reacts with oxyamine or hydrazide compounds to provide, respectively, oxime and acylhydrazone conjugates, thereby offering a new and effective access from which one can elaborate multivalent systems for the targeting of biomolecules of interest.

Multivalent Fucosides with Nanomolar Affinity for the Aspergillus fumigatus Lectin FleA Prevent Spore Adhesion to Pneumocytes

“…αCD was chosen for the possibility to easily design a fucoside that matches FleA valency with all six sugars presented on the primary face. Polyhedral silsesquioxanes are emerging as versatile platforms for the design of multivalent compounds; furthermore, pharmaceutical studies suggest that the organosilica core has low intrinsic toxicity . Here, COSS functionalization should allow for a homogeneous distribution of the grafted sugars.…”

Multivalent Carbonic Anhydrases Inhibitors

“…Nanoparticles coated with CAIs revealed to be particularly effective in targeting selectively the hCA isoforms expressed extracellularly, such as the tumor-associated IX [11,12,13,14]. Since nanomaterial usually possesses the size and physicochemical features which do not allow them to bypass the cellular membranes, and thus to access into the intracellular lumen, they represent ideal platforms to address target selectivity and multivalent effect.…”

“…In the continuity of our work on nanoparticle-type platforms, we reported in 2015, the design and the synthesis of multivalent nanometer-sized fluorescent hybrid silica (NFHS) decorated with sulfonamide carbonic anhydrase inhibitors. [14] They were prepared by grafting silylated inhibitor ligand 11 , on the fluorescent silica nanoparticle 13 previously obtained by co-hydrolysis and polycondensation of the fluorescent silylated precursor 12 and tetramethoxysilane under basic catalysis (Scheme 3) [14]. NFHS 14 with a diameter of about (3.5 ± 0.8) nm were characterized as non-porous, and the evaluation of the number of sulfonamide ligands was estimated between 12 and 14.…”

Monitoring glycosidase activity for clustered sugar substrates, a study on β-glucuronidase

“…35 Compound 6 was designed from a cubic octameric silsequioxane (COSS) scaffold. COSS are emerging as versatile core for the design of multivalent sugar ligands, [36][37][38] the cubic geometry allowing an homogeneous spatial distribution of the graed ligands.…”