Yura H, Goto M, Okazaki H, Kobayashi K, Akaike T
Kanagawa Academy of Science and Technology, Japan.
J Biomed Mater Res. 1995 Dec;29(12):1557-65. doi: 10.1002/jbm.820291212.
N-p-Vinylbenzyl-O-beta-D-galactopyranosyl-(1,4)-D-gluconamide++ + (PVLA) has been used as an asialoglycoprotein model polymer. Rat hepatocytes expressing asialoglycoprotein receptors are capable of binding to hydrophobic plastic dishes coated with PVLA. PVLA, water-soluble polystyrene derivatives bearing galactose residues preferentially adsorb to plastic plates made of polystyrene rather than those of poly(methyl methacrylate). Hence, we modified chitosan beads with linear chains composed of a long alkyl or phenyl moiety to study the effect of structural variations of adsorbed PVLA, and investigated the extent of hepatocyte attachment to the hydrophobic beads coated with PVLA. The attachment was independent of the amount of immobilized PVLA; rather, it was dependent on the hydrophobicity of the beads with PVLA. To simplify the surface of the hydrophobic beads with PVLA, galactopyranoses were covalently linked to chitosan beads via hydrophobic spacer arms, and hepatocyte attachment was compared among the prepared beads. The beads with spacer arms containing phenylalanine and a phthalic moiety showed increased hepatocyte attachment, which was elicited by galactose residues on the beads. These results suggest that rotational restriction or stiffness and hydrophobicity due to the phenyl moiety are essential to enhance the specificity of terminal galactose in PVLA. This analysis contributes to the design and optimization of an artificial ligand for cellular receptors recognizing sugar moieties.
N-对乙烯基苄基-O-β-D-吡喃半乳糖基-(1,4)-D-葡糖酰胺（PVLA）已被用作去唾液酸糖蛋白模型聚合物。表达去唾液酸糖蛋白受体的大鼠肝细胞能够与涂有PVLA的疏水塑料培养皿结合。PVLA是带有半乳糖残基的水溶性聚苯乙烯衍生物，优先吸附到由聚苯乙烯制成的塑料板上，而不是聚甲基丙烯酸甲酯制成的塑料板上。因此，我们用由长烷基或苯基部分组成的线性链修饰壳聚糖珠，以研究吸附的PVLA结构变化的影响，并研究肝细胞附着到涂有PVLA的疏水珠上的程度。这种附着与固定化PVLA的量无关；相反，它取决于带有PVLA的珠的疏水性。为了简化带有PVLA的疏水珠的表面，通过疏水间隔臂将吡喃半乳糖共价连接到壳聚糖珠上，并比较制备的珠之间的肝细胞附着情况。含有苯丙氨酸和邻苯二甲酸部分的间隔臂的珠显示肝细胞附着增加，这是由珠上的半乳糖残基引起的。这些结果表明，由于苯基部分导致的旋转限制或刚性以及疏水性对于增强PVLA中末端半乳糖的特异性至关重要。该分析有助于设计和优化用于识别糖部分的细胞受体的人工配体。
