Synthesis, Characterization, and Preliminary Biological Study of Glycoconjugates of Poly(styrene-co-maleic acid)

Abstract

Three derivatives of the biocompatible polymer poly(styrene-co-maleic anhydride) (SMA) were obtained with 1-amino-1-deoxy-beta-D-galactose, 1-amino-1-deoxy-beta-D-glucose, and 1-amino-1-deoxy-beta-D-lactose, respectively. The amino sugars were chemically conjugated via formation of an amide bond between the anomeric amino group of the sugar residue and the anhydride of the copolymer, giving the corresponding glycoconjugate derivatives. Colorimetric assay of the unreacted amino groups and elemental analysis were used to determine the degree of substitution. About 56%, 54%, and 94% of the available anhydride groups reacted to give galactosyl-amide (SMA-Gal), glucosyl-amide (SMA-Gluc), and lactosyl-amide (SMA-Lac) branched polymers, respectively. The synthesized glycopolymers were characterized by Fourier transform infrared spectroscopy, gel permeation chromatography, circular dichroism, and UV and fluorescence spectroscopy. The release of glucosylamine from the glucosyl-amide branched polymer, by basic hydrolysis, was monitored by high-performance anion-exchange chromatography and by capillary electrophoresis, providing for an additional check of the degree of substitution of this specific polymer derivative. Biological activity tests showed that both SMA-Gal and SMA-Lac allow adhesion of HepG2 hepatic cells about five times larger than that of hydrolyzed, underivatized SMA.

Synthesis of Functional Polymers by Post‐Polymerization Modification

“…A particularly interesting case is the copolymerization of maleic anhydride with MVI, which results in alternating copolymers with two chemical handles for further modification (1 in Scheme 3). [17] Amines have been reported to react with anhydride groups of poly(styrene-co-maleic anhydride) up to near quantitative conversion in mixed DMSO/0.5 m NaHCO 3 buffer in 3 h. [79] Isocyanates can react with both alcohols and amines, but under very different conditions. Primary and secondary amines react with polymeric isocyanates quantitatively in a few minutes at 60 8C under stoichiometric conditions.…”

Efficacy and safety of nanohybrids comprising silver nanoparticles and silicate clay for controlling Salmonella infection

“…24,25 In addition, the SMA will probably not affect antibacterial tests due to its high biocompatibility and weak bactericidal effect. 16,26 The SMA-AgNPs, designated AgNPs in the following text and graphs, were prepared chemically by reducing Ag nitrate with NaBH 4 into NPs ( Figure 1C). The particle size was estimated to be 8.6 ± 0.2 nm ( Figure 1G), similar to the AgNP size of AgNP/NSP.…”

Porphyrin and Galactosyl Conjugated Micelles for Targeting Photodynamic Therapy

“…Gal-APP-PAEMA-PCL, bearing hepatic targeting moieties, exhibits the highest phototoxicity for HepG2 cells. It was reported that asialoglycoprotein (ASGP) receptors were expressed plentifully on the surface of hepatoma cells (20,21), and targeting could be accomplished through introduction of galactose residues, such as terminal β-D-galactose and N-acetylgalactosamine residues, which could bind specifically to the ASGP receptors. In our study, the internalization of Gal-APP-PAEMA-PCL for HepG2 cells is higher compared with the polymers without targeting groups.…”

“…It was reported that Electronic supplementary material The online version of this article (doi:10.1007/s11095-009-9998-8) contains supplementary material, which is available to authorized users. asialoglycoprotein (ASGP) receptors were expressed plentifully on the surface of hepatoma cells and mammalian hepatocytes, and targeting could be accomplished through introduction of galactose residues, which can bind specifically to the ASGP receptors on the cells (20)(21)(22)(23).…”