Feytens, DebbyDebbyFeytensDe Vlaeminck, MagaliMagaliDe VlaeminckCescato, RenzoRenzoCescatoTourwé, DirkDirkTourwéReubi-Kattenbusch, Jean-ClaudeJean-ClaudeReubi-Kattenbusch2024-10-132024-10-132009https://boris-portal.unibe.ch/handle/20.500.12422/103357The synthesis, biological evaluation, and conformational analysis of 4-amino-indolo[2,3-c]azepin-3-one (Aia)-containing SRIF mimetics are reported. Different subtype selectivities are observed depending on the N- and C-terminal substituents of the D-Aia-Lys dipeptide mimetic. An sst(5)-selective analogue with subnanomolar binding affinity was obtained that is the most potent agonist reported to date. A nonselective mimetic with high potency was also identified. This study allows a better definition of the bioactive conformation of the essential D-Trp side chain in the somatostatin pharmacophore.en500 - Science::570 - Life sciences; biology600 - Technology::610 - Medicine & healtharticle1906753800026217150001110.1021/jm801205x