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 and Reubi, Jean-Claude

ISSN:

0022-2623

ISBN:

18410084

Publisher:

American Chemical Society

Language:

English

Submitter:

Factscience Import

Date Deposited:

04 Oct 2013 15:02

Last Modified:

04 May 2014 23:19

Publisher DOI:

10.1021/jm701444y

PubMed ID:

18410084

Web of Science ID:

000255500000012

URI:

https://boris.unibe.ch/id/eprint/27064 (FactScience: 101625)

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