Cell Targeting by Glycosidic Telomers. Specific Recognition of the Kb CWL1 Lectin by Galactosylated Telomers

Abstract

This work deals with the synthesis and lectinic recognition ability of galactosylated telomers. To investigate if telomeric carriers could exhibit cellular recognition properties, we have synthesized mono- and polygalactosylated tris(hydroxymethyl)acrylamidomethane (THAM) telomers. The affinity of such macromolecular drug carriers toward a receptor, the yeast Kb CWL1 lectin, was defined, and the influence of mono- or polygalactosylation of THAM units on the recognition phenomenon was assessed. The lectinic affinity of the compounds was estimated by measuring the inhibition of yeast aggregation. The average degree of polymerization as well as the hydrophilic-lipophilic balance of such galactosylated telomers affects their recognition ability for the lectin.

Interaction of wheat germ agglutinin with an N-acetylglucosamine-carrying telomer brush accumulated on a colloidal gold monolayer

“…MHGlcNAc had a ␤-structure. [53][54][55][56] An amphiphile with many pendent GlcNAc residues was prepared from DODA-501 and MHGlcNAc as described in detail in Supplementary Materials (DODA-PMHGlcNAc, Table 1). The The total M n of the prepared telomer was twice this value.…”

“…Furthermore, the liposome containing DHDG-GlcNAc (lipid with one GlcNAc moiety) did not show any turbidity change at all, probably due to the steric hindrance preventing the gigantic WGA molecule from approaching the GlcNAc residues on the liposome surface. Recently, Coulon et al [53] reported that the affinity of polygalactosylated tris(hydroxymethyl)acrylamidomethane telomers toward a receptor (yeast Kb CWL1 lectin) was dependent on the DP value. The present result is consistent with their results.…”

Amphiphilic perfluoroalkyl carbohydrates as new tools for liver imaging

“…Glycolipids received considerable attention for their involvement in a variety of physiological events (Hakomori and Handa, 2000) as well as their surfactant properties which have led to numerous industrial applications (Von Rybinski and Hill, 1998). Moreover, thanks to their polar head group, carbohydrate amphiphiles are likely to bind membrane lectins: in this case, their lipid moiety is expected to provide a cluster effect through selfassociation (Arya et al, 1999;Coulon et al, 1998;Sliedregt et al, 1999). Many synthetic efforts have been devoted to the preparation of sophisticated polar headgroups or lipidic tails conferring to the amphiphile optimised binding properties (Chabaud et al, 1998) or absence of detergency toward cell membranes (Maurizis et al, 1993).…”

Dehydration Effect on the Recognition of Amphiphiles with Many Pendent Mannose Residues by Concanavalin A†

“…Taking account of the fact that the presence of many sugar residues in lipid molecules and proteins is quite effective on the recognition by lectins and sugar receptors on cell surfaces, − we have been interested in preparation of lipid molecules which have many pendent sugar residues in the head group using the lipophilic initiator − or phospholipid iniferter (a reagent which pursues ini tiation, chain trans fer and ter mination) . With a similar strategy, Coulon et al recently prepared polygalactosylated tris(hydroxymethyl)acrylamidomethane telomers and examined their affinity toward a galactose receptor (yeast Kb CWL1 lectin) …”