Structural effect of galactose residue in synthetic glycoconjugates on interaction with rat hepatocytes

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Abstract
N-p-Vinylbenzyl-O-β-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 surgar moieties. © 1995 John Wiley & Sons, Inc.