Effect of aromatic short-chain analogues of ceramide on axonal growth in hippocampal neurons
Van Overmeire, I × Boldin, S A Dumont, F Van Calenbergh, Serge Slegers, G De Keukeleire, Denis Futerman, A H Herdewijn, Piet #
Journal of Medicinal Chemistry vol:42 issue:14 pages:2697-2705
A series of D-erythro- and L-threo-ceramide analogues was synthesized and investigated for their ability to reverse the inhibitory effects of fumonisin B(1) (FB(1)) on axonal growth in hippocampal neurons. The analogues contained either a C(7) side chain or a phenyl group substituted for the C(13) residue present in naturally occurring ceramides, while the N-acyl chain length was reduced from C(16)-C(24) to C(2)-C(8). D-erythro-Ceramide 18a with a C(7) side chain and an N-acetyl residue and D-erythro-ceramide 20c with an aromatic side chain and an N-hexanoyl residue were most active in reversing the inhibitory effects of FB(1) on axonal growth, although the mechanism remains unclear.