title: 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.
abstract: 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). 6(I),6(IV)-Di-O-(3-O-α-L-fucopyranosyl-α-D-mannopyranosyl)-cyclomaltoheptaose {8, 6(I),6(IV)-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.
authors.affiliation: School of Pharmaceutical Sciences, Mukogawa Women's University, Nishinomiya, Japan.
authors.forename: Madoka
authors.initials: M
authors.lastname: Kimura
authors.forename: Yuki
authors.initials: Y
authors.lastname: Masui
authors.forename: Yuko
authors.initials: Y
authors.lastname: Shirai
authors.forename: Chie
authors.initials: C
authors.lastname: Honda
authors.forename: Kenta
authors.initials: K
authors.lastname: Moriwaki
authors.forename: Taku
authors.initials: T
authors.lastname: Imai
authors.forename: Uichiro
authors.initials: U
authors.lastname: Takagi
authors.forename: Takaaki
authors.initials: T
authors.lastname: Kiryu
authors.forename: Taro
authors.initials: T
authors.lastname: Kiso
authors.forename: Hiromi
authors.initials: H
authors.lastname: Murakami
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Nakano
authors.forename: Sumio
authors.initials: S
authors.lastname: Kitahata
authors.forename: Eiji
authors.initials: E
authors.lastname: Miyoshi
authors.forename: Toshiko
authors.initials: T
authors.lastname: Tanimoto
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D002236:Carbohydrate Conformation; D049109:Cell Proliferation / Q000187:drug effects; D004187:Disaccharides / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D005643:Fucose / Q000737:chemistry* / Q000378:metabolism; D045325:HCT116 Cells; D006801:Humans; D013329:Structure-Activity Relationship; D005644:alpha-L-Fucosidase / Q000302:isolation & purification / Q000378:metabolism; D047392:beta-Cyclodextrins / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D004187:Disaccharides; D047392:beta-Cyclodextrins; D005643:Fucose; D005644:alpha-L-Fucosidase; C031215:betadex