Highly potent 4-amino-indolo[2,3-c]azepin-3-one-containing somatostatin mimetics with a range of sst receptor selectivities

Feytens, Debby; De Vlaeminck, Magali; Cescato, Renzo; Tourwé, Dirk; Reubi, Jean-Claude (2009). Highly potent 4-amino-indolo[2,3-c]azepin-3-one-containing somatostatin mimetics with a range of sst receptor selectivities. Journal of medicinal chemistry, 52(1), pp. 95-104. Easton, Pa.: American Chemical Society 10.1021/jm801205x

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The 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.

Item Type:	Journal Article (Original Article)
Division/Institute:	04 Faculty of Medicine > Service Sector > Institute of Pathology
UniBE Contributor:	Cescato, Renzo, Reubi-Kattenbusch, Jean-Claude
Subjects:	500 Science > 570 Life sciences; biology 600 Technology > 610 Medicine & health
ISSN:	0022-2623
ISBN:	19067538
Publisher:	American Chemical Society
Language:	English
Submitter:	Factscience Import
Date Deposited:	04 Oct 2013 15:08
Last Modified:	05 Dec 2022 14:21
Publisher DOI:	10.1021/jm801205x
PubMed ID:	19067538
Web of Science ID:	000262171500011
URI:	https://boris.unibe.ch/id/eprint/29979 (FactScience: 165578)