Synthesis, Characterization, and Preliminary Biological Study of Glycoconjugates of Poly(styrene-co-maleic acid)
详细信息 查看全文
- 作者：Ivan Donati ; Amelia Gamini ; Amedeo Vetere ; Cristiana Campa ; and Sergio Paoletti
- 刊名：Biomacromolecules
- 出版年：2002
- 出版时间：July 2002
- 年：2002
- 卷：3
- 期：4
- 页码：805 - 812
- 全文大小：87K
- 年卷期：v.3,no.4(July 2002)
- ISSN：1526-4602
文摘
Three derivatives of the biocompatible polymer poly(styrene-co-maleic anhydride) (SMA) were obtainedwith 1-amino-1-deoxy-
-D-galactose, 1-amino-1-deoxy--D-glucose, and 1-amino-1-deoxy--D-lactose,respectively. The amino sugars were chemically conjugated via formation of an amide bond between theanomeric amino group of the sugar residue and the anhydride of the copolymer, giving the correspondingglycoconjugate derivatives. Colorimetric assay of the unreacted amino groups and elemental analysis wereused to determine the degree of substitution. About 56%, 54%, and 94% of the available anhydride groupsreacted 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 transforminfrared spectroscopy, gel permeation chromatography, circular dichroism, and UV and fluorescencespectroscopy. 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. Biologicalactivity tests showed that both SMA-Gal and SMA-Lac allow adhesion of HepG2 hepatic cells about fivetimes larger than that of hydrolyzed, underivatized SMA.
-D-galactose, 1-amino-1-deoxy--D-glucose, and 1-amino-1-deoxy--D-lactose,respectively. The amino sugars were chemically conjugated via formation of an amide bond between theanomeric amino group of the sugar residue and the anhydride of the copolymer, giving the correspondingglycoconjugate derivatives. Colorimetric assay of the unreacted amino groups and elemental analysis wereused to determine the degree of substitution. About 56%, 54%, and 94% of the available anhydride groupsreacted 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 transforminfrared spectroscopy, gel permeation chromatography, circular dichroism, and UV and fluorescencespectroscopy. 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. Biologicalactivity tests showed that both SMA-Gal and SMA-Lac allow adhesion of HepG2 hepatic cells about fivetimes larger than that of hydrolyzed, underivatized SMA.