title: New sst4/5-selective somatostatin peptidomimetics based on a constrained tryptophan scaffold.
abstract: The synthesis and biological evaluation of four peptidomimetic analogs of somatostatin based on a constrained Trp residue, 3-amino-indolo[2,3-c]azepin-2-one (Aia), are reported. It is shown that dipeptidomimetics with a D-Aia-Lys sequence, functionalized with N- and C-terminal aromatic substituents, display a good selectivity for both sst4 and sst5. This study allowed us to identify a new highly potent sst5 agonist with good selectivity over the other receptors, except versus sst4.
authors.affiliation: Department of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050, Brussels, Belgium.
authors.forename: Debby
authors.initials: D
authors.lastname: Feytens
authors.forename: Renzo
authors.initials: R
authors.lastname: Cescato
authors.forename: Jean Claude
authors.initials: JC
authors.lastname: Reubi
authors.forename: Dirk
authors.initials: D
authors.lastname: Tourwé
mesh_terms: D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D000242:Cyclic AMP / Q000096:biosynthesis; D008968:Molecular Conformation; D018716:Molecular Mimicry; D019906:Nuclear Magnetic Resonance, Biomolecular; D013004:Somatostatin / Q000737:chemistry*; D014364:Tryptophan / Q000737:chemistry*
chemical_list: D013004:Somatostatin; D014364:Tryptophan; D000242:Cyclic AMP