Synthetic Studies on Selectin Ligands/Inhibitors: Synthesis and Inhibitory Activity of 2-O-Fucosyl Sulfatides Containing 2-Branched Fatty Alkyl Residues in Place of Ceramide |
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Authors: | Takao Ikami Takuji Kakigami Kunihisa Baba Hitoshi Hamajima Takahito Jomori Toshinao Usui |
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Affiliation: | Drug Discovery Research Department , Sanwa Kagaku Kenkyusho Co., Ltd. , 363 Shiosaki, Hokusei-cho, Mie, 511-04, Japan |
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Abstract: | Abstract To investigate the biological selectin-ligand interactions, four sulfated 2-O-α-L-fucopyranosyl β-D-galactopyranosides containing 2-branched fatty-alkyl residues in place of ceramide have been systematically synthesized. The target glycolipids were assayed for their ability to block the adhesion of HL-60 cells to immobilized P-, L- and E-selectin. Among them, 2-O-α-L-fucopyranosyl sulfatide, which is anchored with 2-(tetradecyl) hexadecyl residue showed significantly more potency of the blocking adhesion to P- and L-selectins. |
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