A. Kichler et F. Schuber, VERSATILE SYNTHESIS OF BI-ANTENNARY AND TRI-ANTENNARY GALACTOSE LIGANDS - INTERACTION WITH THE GAL GALNAC RECEPTOR OF HUMAN HEPATOMA-CELLS/, Glycoconjugate journal, 12(3), 1995, pp. 275-281
We have synthesized bi- and tri-antennary galactose ligands by couplin
g 1-thio-beta-D-galactose derivatives to the alpha- and epsilon-amino
groups of L-lysine and L-lysyl-L-lysine via highly flexible hydrophili
c spacer arms that allow variation of their intergalactose distances.
The interaction of these ligands with the Gal/GalNAc receptor of HepG2
cells showed a binding affinity that was: (i) in agreement with the c
lustering effect known to occur with more complex oligomeric structure
s, i.e. tri- > bi-antennary; ii) dependent on the intergalactose dista
nces (optimal interactions were observed for the tri-antennary structu
res with distances > 2 nm). These ligands, that can be easily conjugat
ed to bioactive (macro) molecule carrier systems, could be useful for
their targeting to hepatocytes.