Synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin scaffold.
A novel synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin (DMJ) scaffold has been developed. This involved development of a route suitable for the strategic grafting of pharmacophoric tryptophan and lysine side chains to the nitrogen atom of the piperidine ring and to the primary hydroxyl group of DMJ, respectively. The novel peptidomimetics were found to bind with higher affinity to sst4 receptors than to sst5 receptors.
Gouin
Sebastien G
SG
Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland.
Murphy
Paul V
PV
D017485:1-Deoxynojirimycin / Q000737:chemistry*; D001667:Binding, Competitive / Q000187:drug effects; D032701:Biomimetics; D002460:Cell Line; D004353:Drug Evaluation, Preclinical; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D017481:Receptors, Somatostatin / Q000037:antagonists & inhibitors / Q000378:metabolism*; D013004:Somatostatin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology
D004791:Enzyme Inhibitors; D017481:Receptors, Somatostatin; D017485:1-Deoxynojirimycin; D013004:Somatostatin