Ring size of somatostatin analogues (ODT-8) modulates receptor selectivity and binding affinity

Erchegyi, Judit; Grace, Christy Rani R; Samant, Manoj; Cescato, Renzo; Piccand, Veronique; Riek, Roland; Reubi, Jean Claude; Rivier, Jean E (2008). Ring size of somatostatin analogues (ODT-8) modulates receptor selectivity and binding affinity. Journal of medicinal chemistry, 51(9), pp. 2668-75. Easton, Pa.: American Chemical Society 10.1021/jm701444y

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The synthesis, biological testing, and NMR studies of several analogues of H-c[Cys (3)-Phe (6)-Phe (7)-DTrp (8)-Lys (9)-Thr (10)-Phe (11)-Cys (14)]-OH (ODT-8, a pan-somatostatin analogue, 1) have been performed to assess the effect of changing the stereochemistry and the number of atoms in the disulfide bridge on binding affinity. Cysteine at positions 3 and/or 14 (somatostatin numbering) were/was substituted with d-cysteine, norcysteine, D-norcysteine, homocysteine, and/or D-homocysteine. The 3D structure analysis of selected partially selective, bioactive analogues (3, 18, 19, and 21) was carried out in dimethylsulfoxide. Interestingly and not unexpectedly, the 3D structures of these analogues comprised the pharmacophore for which the analogues had the highest binding affinities (i.e., sst 4 in all cases).

Item Type:	Journal Article (Original Article)
Division/Institute:	04 Faculty of Medicine > Service Sector > Institute of Pathology 04 Faculty of Medicine > Service Sector > Institute of Pathology > Tumour Pathology
UniBE Contributor:	Cescato, Renzo, Piccand, Véronique, Reubi-Kattenbusch, Jean-Claude
Subjects:	500 Science > 570 Life sciences; biology 600 Technology > 610 Medicine & health
ISSN:	0022-2623
ISBN:	18410084
Publisher:	American Chemical Society
Language:	English
Submitter:	Factscience Import
Date Deposited:	04 Oct 2013 15:02
Last Modified:	05 Dec 2022 14:19
Publisher DOI:	10.1021/jm701444y
PubMed ID:	18410084
Web of Science ID:	000255500000012
URI:	https://boris.unibe.ch/id/eprint/27064 (FactScience: 101625)