title: Hybrid immobilization of galactosyl lactose and cellobiose on a gold substrate to modulate biological responses.
abstract: Bioactive O-β-d-galactopyranosyl-(1→4)-O-β-d-galactopyranosyl-(1→4)-d-glucopyranose (4'-galactosyl lactose) was site-selectively modified at a reducing end with thiosemicarbazide (TSC). As-synthesized 4'-galactosyl lactose-TSC was immobilized on a gold substrate with cellobiose-TSC as a spacer through spontaneous self-assembly chemisorption via SAu bonding. Quartz crystal microbalance analysis suggested the successful formation of self-assembled monolayers (SAMs) of 4'-galactosyl lactose-TSC and/or cellobiose-TSC. Galactose-binding lectin exhibited the highest affinity for hybrid SAMs with an equimolar ratio of the two oligosaccharide-TSCs, while glucose-binding lectin showed decreasing adsorption with a decrease in cellobiose-TSC ratios. Human hepatocellular carcinoma cells, which recognize galactose residues, efficiently adhered to the hybrid SAMs. Higher enzymatic deethoxylation of ethoxyresorufin via cytochrome P450 appeared on hybrid SAMs. These results suggested that clustering of the bioactive sugars was involved in the cellular responses, possibly via biological carbohydrate-protein interactions. This approach to designing carbohydrate-based scaffolds should provide a basis for the functional development of glyco-decorated biointerfaces for cell culture applications.
authors.affiliation: Department of Agro-Environmental Sciences, Graduate School of Bioresource and Bioenvironmental Sciences, and Biotron Application Center, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan. tkitaoka@agr.kyushu-u.ac.jp
authors.forename: Takuya
authors.initials: T
authors.lastname: Kitaoka
authors.forename: Chiharu
authors.initials: C
authors.lastname: Yoshiyama
authors.forename: Fumi
authors.initials: F
authors.lastname: Uemura
mesh_terms: D002475:Cellobiose / Q000138:chemical synthesis / Q000737:chemistry; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry / Q000378:metabolism; D005690:Galactose / Q000737:chemistry; D037161:Galectins / Q000737:chemistry; D006046:Gold / Q000737:chemistry; D056945:Hep G2 Cells; D006801:Humans; D007103:Immobilization; D007785:Lactose / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D012663:Semicarbazides / Q000737:chemistry*
chemical_list: D037161:Galectins; D009844:Oligosaccharides; D012663:Semicarbazides; D002475:Cellobiose; C005151:thiosemicarbazide; D006046:Gold; D003577:Cytochrome P-450 Enzyme System; D007785:Lactose; D005690:Galactose