Synthesis of polymeric neoglycoconjugates based onN-substituted polyacrylamides

Abstract

Several types of polymeric glycoconjugates, N-substituted polyacrylamides, have been synthesized by the reaction of activated polymers with omega-aminoalkylglycosides: (i) (carbohydrate-spacer)n-polyacrylamide, 'pseudopolysaccharides'; (ii) (carbohydrate-spacer)n-phosphatidylethanolaminem-polyacrylamide, neoglycolipids, derivatives of phosphatidylethanolamine; (iii) (carbohydrate-spacer)n-biotin-polyacrylamide, biotinylated probes; (iv) (carbohydrate-spacer)n-polyacrylamide-(macroporous glass), affinity sorbents based on macroporous glass, covalently coated with polyacrylamide. An almost quantitative yield in the conjunction reaction makes it possible to insert in the conjugate a predetermined quantity of the ligand(s). Pseudopolysaccharides proved to be a suitable form of antigen for activation of polystyrene and poly(vinyl chloride) plates (ELISA) and nitrocellulose membranes (dot blot), being advantageous over traditional neoglycoproteins. Polyvalent glycolipids insert well in biological membranes: their physical properties, particularly solubility, can be changed in a desired direction. Biotinylated derivatives were used as probes for detection and analysis of lectins.

Salivary MUC5B-Mediated Adherence (Ex Vivo) of Helicobacter pylori During Acute Stress

“…MUC5B was isolated from saliva by ultracentrifugation (100,000g, 24 hours) under dissociative conditions, followed by gel filtration (Sephacryl HR-500, Pharmacia, Uppsala, Sweden) in 50 mM Tris/HCl/4 M guanidine chloride, pH 7.4 (60). The mucincontaining fractions were pooled, dialyzed against double-distilled water, and stored as aliquots at Ϫ20°C.…”

Saccharide‐assisted delivery of cytotoxic liposomes to human malignant cells

“…the potent drug delivery system, lipophilic carbohydrate conjugates, Sug-PAA-PE [12] (Fig. 1) were synthesized.…”

“…DL<x-Tocopherol and sodium cholate were purchased from Serva Feinbiochemica (Heidelberg, Germany), cholesterol (Chol) -from Calbiochem-Behring (La Jolla, CA). Syntheses of glycosylated fluorescein-labeled polyacrylamide (Sug-PAA-Flu), fluorescein-labeled polyacrylamide bearing Tris-residues (Tris-PAA-FIu) and sugar conjugates with phosphatidylethanolamine-derivatized polyacrylamide (Sug-PAA-PE) [12], DG-sarcolysine (DGmerphalan) [13], fluorescent lipid dye Rhodaminel01-diglyceride (Rh-DG) [14], anthrylvinyl-(APC) [ 15] and perylenoyl-(PPC) [16] labeled phosphatidylcholines are described elsewhere. Preparation ofliposomes.…”

Carbohydrate Affinity PAGE for the Study of Carbohydrate-Binding Proteins

“…Saccharide-polyacrylamide (PAA) conjugates or neoglycoconjugates ( Figure 1A) were prepared by addition of the saccharide, of >95% purity as a 3-aminopropyl glycoside (4,13) triethylamine, to a solution of poly(4-nitrophenylacrylate) and kept at 25°C for 16 h. Allylamine was added to the solution and kept at 40°C for 24 h. Subsequent concentration of allyl and sugar groups on the neoglycoconjugate was 5 and 20 mol percent, respectively. Thus 5% of available amide groups on the PAA were substituted with allyl, while 20% were substituted with sugar.…”

“…Some of these studies have used the inert properties of the acrylamide polymer. A variety of approaches have been described for the synthesis of sugar-acrylamide copolymers (4,6,9,10,13,24), wherein the acrylamide provides an inert backbone for the presentation of the sugar. These principles have been used in affinity chromatography (21) and cell-adhesion assays (19).…”