Hybrid immobilization of galactosyl lactose and cellobiose on a gold substrate to modulate biological responses

Takuya Kitaoka, Chiharu Yoshiyama, Fumi Uemura

Research output: Contribution to journalArticle

3 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)374-379
Number of pages6
JournalCarbohydrate Polymers
Volume92
Issue number1
DOIs
Publication statusPublished - Jan 30 2013

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

Fingerprint Dive into the research topics of 'Hybrid immobilization of galactosyl lactose and cellobiose on a gold substrate to modulate biological responses'. Together they form a unique fingerprint.

  • Cite this