Liposome-like fucopeptides as sialyl lewis X mimetics

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 IC50 value (50 μM) 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 μM.