Peptide folding induces high and selective affinity of a linear and small β-peptide to the human somatostatin receptor 4

Journal of Medicinal Chemistry

Volumn 44, Issue 15, 2001, Pages 2460-2468

  Gademann, K ^a,c   Kimmerlin, T ^a   Hoyer, D ^b   Seebach, D ^a  

^a ETH ZURICH   (Switzerland)

^b NOVARTIS PHARMA AG   (Switzerland)

^c HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL BETA3 HYDROXYTHREONYL BETA2 HYDROXYLYSYL BETA3 HYDROXYTRYPTOPHYL BETA3 HYDROXYPHENYLALANINAMIDE; BETA AMINO ACID; OCTREOTIDE; SOMATOSTATIN DERIVATIVE; SOMATOSTATIN RECEPTOR; SOMATOSTATIN RECEPTOR 4; TETRAPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG MECHANISM; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; PROTEIN FOLDING; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

CELL LINE; CIRCULAR DICHROISM; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MEMBRANE PROTEINS; MOLECULAR MIMICRY; OCTREOTIDE; OLIGOPEPTIDES; PROTEIN FOLDING; PROTEIN STRUCTURE, SECONDARY; RADIOLIGAND ASSAY; RECEPTORS, SOMATOSTATIN; RECOMBINANT PROTEINS; SOMATOSTATIN;

EID: 0035913057     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010816q     Document Type: Article

References (41)

1. Foldamers: A manifesto
2. β-Peptides: A surprise at every turn
3. Biological and pharmacokinetic studies with β-Peptides
4. Synthesis and biological evaluation of a Cyclo-β-tetrapeptide as a somatostatin analogue
5. The Cyclo-β-tetrapeptide (β-HPhe-β-Hthr-β-Hlys-β-Htrp) - Synthesis, NMR-Structure in methanol solution and affinity for human somatostatin receptors
6. β-Peptides as inhibitors of small-intestinal cholesterol and fat absorption
7. Antibiotics - non haemolytic beta-amino-acids oligomers
8. De novo design of antibacterial β-Peptides
9. Hypothalamic polypeptide that inhibits the secretion of immunoreactive pituitary growth hormone
10. Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics
11. Peptidomimetics - Tailored enzyme inhibitors
12. A refined model for the somatostatin pharmacophore: Conformational analysis of lanthionine-sandostatin analogs
13. Pleated sheets and turns β-Peptides with proteinogenic side chains
14. 3-Amino acids and their use as building blocks for the solid-phase synthesis β-peptides
15. A useful modification of the evans auxilliary: 4-Isopropyl-5,5-diphenyloxazolidin-2-one
16. A valine-derived lithiated 3-Methylthiomethyl-1,3-oxazolidin-2-one for enantioselective nucleophilic hydroxymethylation, formylation, and alkoxycarbonylation of aldehydes
17. Synthesis of phtaloyl amino-acids under mild conditions
18. 3-Peptides with proteinaceous side chains: Synthesis and solution structures of constitutional isomers, a novel helical secondary structure and the influence of solvation and hydrophobic interactions on folding
19. Enantioselective synthesis of α-Substituted and α-α-Disubstituted β-Amino Acids via chiral derivatives of 3-Aminopropionic acid
20. Synthesis of a β-Hexapeptide from (R)-2-Aminomethyl-alkanoic Acids and structural investigations
21. 'Mixed' β-Peptides: A unique helical secondary structure in solution
22. Solid-phase synthesis of protected peptide-fragments using a trialkoxy-diphenyl-methylester resin
23. Preparation of protected peptide amide using the fmoc chemical protocol - Comparison of resins for solid-phase synthesis
24. Conformation of two somatostatin analogues in aqueous solution. Study by NMR methods and circular dichroism
25. Inferences about the conformation of somatostatin at a biologic receptor based on NMR studies
26. [I-125]Tyr(3) octreotide labels human somatostatin sst(2) and sst(5) receptors expressed in CCL39 cells
27. Discovery of a novel non-peptide somatostatin agonist with SST4 selectivity
28. Nonpeptide somatostatin agonists with SST4 selectivity: Synthesis and structure-activity relationships of Thioureas
29. Modulation of Receptor and Receptor Subtype Affinities Using Diastereomeric and Enantiomeric Monosaccharide Scaffolds as a Means to Structural and Biological Diversity. A New Route to Ether Synthesis
30. Rapid identification of subtype-selective agonists of the somatostatin receptor through combinatorial chemistry
31. Identification of a potent heterocyclic ligand to somatostatin receptor subtype 5 by the synthesis and screening of β-turn mimetic libraries
32. Optimization of a somatostatin mimetic via constrained amino acid and backbone incorporation
33. Rapid, safe and convenient procedure for the preparation and the use of Diazomethane
34. Diazomethane and safety
35. 3,3-amino acids: A turn motif for β-Peptides
36. Solid phase synthesis without repetitive acidolysis
37. A new micro-test for the detection of incomplete coupling reaction in solid-phase peptide synthesis using 2,4,6-trinitrobenzenesulphonic acid