Liposome-like fucopeptides as sialyl lewis X mimetics

✍ Scribed by Chun-Cheng Lin; Teiji Kimura; Shih-Hsiung Wu; Gabriele Weitz-Schmidt; Chi-Huey Wong

• Book ID: 104364655
• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 344 KB
• Volume: 6
• Category: Article
• ISSN: 0960-894X
• DOI: 10.1016/s0960-894x(96)00509-4

✦ Synopsis

Several fucodipeptides and their liposome-like derivatives were prepared and tested as inhibitors of sialyl Lewis X binding to E-selectin. It has been found that trans-hydroxyproline (D or L) can be used to mimic the galactose residue of sialyl Lewis X, and the mimetic containing 3,4-dihydroxy-D-proline is the most active with ICso value (50 I.tM) 10-fold greater than sialyl Lewis X. Derivatization of a hydroxythreonine-containing fucodipeptides into a covalent liposome-like derivative, however, provides a mimetic with only IC50 -30 I.tM.