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

被引：5

作者：

Ikami, T

Kakigami, T

Baba, K

Hamajima, H

Jomori, T

Usui, T

Suzuki, Y

Tanaka, H

Ishida, H

Hasegawa, A

Kiso, M

机构：

[1] Sanwa Kagaku Kenkyusho Co Ltd, Drug Discovery Res Dept, Hokusei Cho, Mie 51104, Japan

[2] Univ Shizuoka, Sch Pharmaceut Sci, Dept Biochem, Shizuoka 422, Japan

[3] Gifu Univ, Dept Appl Bioorgan Chem, Gifu 50111, Japan

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1998年 / 17卷 / 03期

关键词：

D O I：

10.1080/07328309808002905

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

To investigate the biological selectin-ligand interactions, four sulfated 2-0-alpha-L-fucopyranosyl beta-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-alpha-L-fucopyranosyl sulfatide, which is anchored with 2-(tetradecyl) hexadecyl residue showed significantly more potency of the blocking adhesion to P- and L-selectins.

引用

页码：453 / 470

页数：18

共 16 条

[1] 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
Drug Discov. Res. Dept. Sanwa K., 363 Shiosaki, Hokusei-cho, Mie 511-04, Japan
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J. Carbohydr. Chem., 3 (453-470):
[2] Synthetic studies on selectin ligands/inhibitors:: Synthesis and biological activity of the sulfated and phosphorylated multivalent β-D-galactopyranosides containing fatty alkyl residues
Ikami, T
Tomiya, N
Morimoto, T
Iwata, N
Yamashita, R
Jomori, T
Usui, T
Suzuki, Y
Tanaka, H
Miyamoto, D
Ishida, H
Hasegawa, A
Kiso, M
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1998, 17 (4-5) : 499 - 518
[3] Synthetic studies on sialoglycoconjugates .88. Synthesis of ganglioside GM(3) and GM(4) analogs containing 2- or 3-branched fatty-alkyl residues in place of ceramide
Hasegawa, A
Suzuki, N
Ishida, H
Kiso, M
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1996, 15 (05) : 623 - 637
[4] Synthetic studies on selectin ligands/inhibitors.: Synthesis and biological evaluation of sulfated and phosphorylated β-D-galacto- and lactopyranosides containing fatty-alkyl residues of different carbon chain lengths
Ikami, T
Tsuruta, N
Inagaki, H
Kakigami, T
Matsumoto, Y
Tomiya, N
Jomori, T
Usui, T
Suzuki, Y
Tanaka, H
Miyamoto, D
Ishida, H
Hasegawa, A
Kiso, M
CHEMICAL & PHARMACEUTICAL BULLETIN, 1998, 46 (05) : 797 - 806
[5] Synthetic studies on selectin ligands/inhibitors: A systematic synthesis of sulfatide and its higher congeners carrying 2-(tetradecyl)hexadecyl group as a ceramide substitute
Tanahashi, E
Murase, K
Shibuya, M
Igarashi, Y
Ishida, H
Hasegawa, A
Kiso, M
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1997, 16 (06) : 831 - 858
[6] Synthetic studies on sialoglycoconjugates 81: Synthesis of positional isomers of sialyl lewis X epitope containing 1-deoxy-D-glucose in place of n-acetylglucosamine, and their inhibitory activity to selectin-mediated adhesion
Dept. of Appl. Bioorganic Chemistry, Gifu University, Gifu 501-11, Japan
J. Carbohydr. Chem., 2 (147-162):
[7] Synthetic studies on sialoglycoconjugates .81. Synthesis of positional isomers of sialyl Lewis X epitope containing 1-deoxy-D-glucose in place of N-acetylglucosamine, and their inhibitory activity to selectin-mediated adhesion
Yoshida, M
Suzuki, T
Ishida, H
Kiso, M
Hasegawa, A
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1996, 15 (02) : 147 - 162
[8] Synthetic Studies on Selectin Ligands/Inhibitors: One-Pot Synthesis of the Mono- and Oligo-Sulfated 2-(Tetradecyl)hexadecyl a-D-Galacto- and Lactopyranosides as the Sulfatide Mimetics
Ikami, T.
Hamajima, H.
Usui, T.
Mitani, T.
Journal of Carbohydrate Chemistry, 16 (06):
[9] SYNTHESIS AND CONFORMATIONAL STUDIES OF BRANCHED OLIGOSACCHARIDES .15. 2,3-DI-O-GLYCOSYLATED METHYL ALPHA-L-RHAMNOPYRANOSIDES CONTAINING 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL RESIDUES
NIFANTEV, NE
SHASHKOV, AS
KHATUNTSEVA, EA
TSVETKOV, YE
SHERMAN, AA
KOCHETKOV, NK
BIOORGANICHESKAYA KHIMIYA, 1994, 20 (8-9): : 1001 - 1012
[10] Synthetic studies on selectin ligands/inhibitors: One-pot synthesis of the mono- and oligo-sulfated 2-(tetradecyl)hexadecyl beta-D-galacto- and lactopyranosides as the sulfatide mimetics
Ikami, T
Hamajima, H
Usui, T
Mitani, T
Ishida, H
Kiso, M
Hasegawa, A
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1997, 16 (06) : 859 - 875

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