Preparation of branched cyclomaltoheptaose with 3-O-α-l-fucopyranosyl-α-d-mannopyranose and changes in fucosylation of HCT116 cells treated with the fucose-modified cyclomaltoheptaose Original Research Article

From a mixture of 4-nitrophenyl α-l-fucopyranoside and d-mannopyranose, 3-O-α-l-fucopyranosyl-d-mannopyranose was synthesised through the transferring action of α-fucosidase (Sumizyme PHY). 6I,6IV-Di-O-(3-O-α-l-fucopyranosyl-α-d-mannopyranosyl)-cyclomaltoheptaose {8, 6I,6IV-di-O-[α-l-Fuc-(1→3)-α-d-Man]-βCD} was chemically synthesised using the trichloroacetimidate method. The structures were confirmed by MS and NMR spectroscopy. A cell-based assay using the fucosyl βCD derivatives, including the newly synthesised 8, showed that derivatives with two branches of the α-l-Fuc or α-l-Fuc-(1→3)-α-d-Man residues possessed slight growth-promoting effects and lower toxicity in HCT116 cells compared to those with one branch. These compounds may be useful as drug carriers in targeted drug delivery systems.