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 and Reubi, Jean-Claude

ISSN:

0022-2623

ISBN:

19067538

Publisher:

American Chemical Society

Language:

English

Submitter:

Factscience Import

Date Deposited:

04 Oct 2013 15:08

Last Modified:

06 Dec 2013 13:56

Publisher DOI:

10.1021/jm801205x

PubMed ID:

19067538

Web of Science ID:

000262171500011

URI:

https://boris.unibe.ch/id/eprint/29979 (FactScience: 165578)

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