Ring size in octreotide amide modulates differently agonist versus antagonist binding affinity and selectivity

Journal of Medicinal Chemistry

Volumn 51, Issue 9, 2008, Pages 2676-2681

  Grace, Christy Rani R ^b   Erchegyi, Judit ^a   Samant, Manoj ^a   Cescato, Renzo ^c   Piccand, Veronique ^c   Riek, Roland ^b   Reubi, Jean Claude ^c   Rivier, Jean E ^a  

^a SALK INSTITUTE FOR BIOLOGICAL STUDIES   (United States)

^b SALK INSTITUTE FOR BIOLOGICAL STUDIES   (United States)

^c UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYL SULFOXIDE; HOMOCYSTEINE; OCTREOTIDE; SOMATOSTATIN DERIVATIVE;

AGONIST; ARTICLE; BINDING AFFINITY; DRUG ANTAGONISM; DRUG SELECTIVITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING; STRUCTURE ANALYSIS; THREE DIMENSIONAL IMAGING;

CELL LINE; CYSTEINE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OCTREOTIDE; RADIOLIGAND ASSAY; RECEPTORS, SOMATOSTATIN; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 42949155714     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701445q     Document Type: Article

References (28)

1. Melacini, G.; Zhu, Q.; Goodman, M. Multiconformational NMR analysis of sandostatin (octreotide): Equilibrium between β-sheet and partially helical structures. Biochemistry 1997, 36, 1233-1241.
2. Osapay, G.; Prokai, L.; Kin, H.-S.; Medzihradszky, K. F.; Coy, D. H.; Liapakis, G.; Reisine, T.; Melacini, G.; Zhu, Q.; Wang, S. H.-H.; Mattern, R.-H.; Goodman, M. Lanthionine-somatostatin analogs: Synthesis, characterization, biological activity, and enzymatic stability studies. J. Med. Chem. 1997, 40, 2241-2251.
3. Melacini, G.; Zhu, Q.; Osapay, G.; Goodman, M. A refined model for the somatostatin pharmacophore: Conformational analysis of lanthionine-sandostatin analogs. J. Med. Chem. 1997, 40, 2252-2258.
4. 2-selective somatostatin agonists. Three-dimensional consensus structure by NMR. J. Med. Chem. 2006, 49, 4487-4496.
5. Bass, R. T.; Buckwalter, B. L.; Patel, B. P.; Pausch, M. H.; Price, L. A.; Strnad, J.; Hadcock, J. R. Identification and characterization of novel somatostatin antagonists. Mol. Pharmacol. 1996, 50, 709-715.
6. Samant, M. P.; Rivier, J. E. Norcystine, a new tool for the study of the structure-activity relationship of peptides. Org. Lett. 2006, 8, 2361-2364.
7. Erchegyi, J.; Grace, C. R. R.; Samant, M.; Cescato, R.; Piccand, V.; Riek, R.; Reubi, J. C.; Rivier, J. E. Ring size of somatostatin analogues (ODT-8) modulates receptor selectivity and binding affinity. J. Med. Chem. 2008, 51, 2668-2675.
8. Erchegyi, J.; Hoeger, C. A.; Low, W.; Hoyer, D.; Waser, B.; Eltschinger, V.; Schaer, J.-C.; Cescato, R.; Reubi, J. C.; Rivier, J. E. Somatostatin receptor 1 selective analogues: 2. N-methylated scan. J. Med. Chem. 2005, 48, 507-514.
9. Miller, C.; Rivier, J. Peptide chemistry: Development of high-performance liquid chromatography and capillary zone electrophoresis. Biopolym. Pept. Sci. 1996, 40, 265-317.
10. Miller, C.; Rivier, J. Analysis of synthetic peptides by capillary zone electrophoresis in organic/aqueous buffers. J. Pept. Res. 1998, 51, 444-451.
11. Reubi, J. C.; Schaer, J. C.; Waser, B.; Wenger, S.; Heppeler, A.; Schmitt, J. S.; Mäcke, H. R. Affinity profiles for human somatostatin receptor sst1-sst5 of somatostatin radiotracers selected for scintigraphic and radiotherapeutic use. Eur. J. Nucl. Med. 2000, 27, 273-282.
12. Reubi, J. C.; Schaer, J. C.; Waser, B.; Hoeger, C.; Rivier, J. A selective analog for the somatostatin sst1-receptor subtype expressed by human tumors. Eur. J. Pharmacol. 1998, 345, 103-110.
13. Güntert, P.; Mumenthaler, C.; Wüthrich, K. Torsion angle dynamics for NMR structure calculation with the new program DYANA. J. Mol. Biol. 1997, 273, 283-298.
14. Hagler, A. T.; Dauber, P.; Osguthorpe, D. J.; Hempel, J. C. Dynamics and conformational energetics of a peptide hormone: Vasopressin. Science 1985, 227, 1309-1315.
15. 2-selective somatostatin antagonists suitable for radio-targeting. J. Med. Chem. 2008, submitted.
16. 5 receptors: Effects of somatostatin agonists and antagonists. J. Nucl. Med. 2006, 47, 502-511.
17. 1H NMR spectra via two-dimensional homonuclear Hartmann-Hahn spectroscopy. J. Am. Chem. Soc. 1985, 107, 2820-2821.
18. Braunschweiler, L.; Ernst, R. R. Coherence transfer by isotropic mixing: Application to proton correlation spectroscopy. J. Magn. Reson. 1983, 53, 521-528.
19. 1H NMR spectra of proteins via double quantum filtering. Biochem. Biophys. Res. Commun. 1983, 117, 479-485.
20. Kumar, A.; Wagner, G.; Ernst, R. R.; Wüthrich, K. Buildup rates of the nuclear Overhauser effect measured by two-dimensional proton magnetic resonance spectroscopy: Implications for studies of protein conformation. J. Am. Chem. Soc. 1981, 103, 3654-3658.
21. Macura, S.; Ernst, R. R. Elucidation of cross-relaxation in liquids by two-dimensional NMR spectroscopy. Mol. Phys. 1980, 41, 95-117.
22. Macura, S.; Huang, Y.; Suter, D.; Ernst, R. R. Two-dimensional chemical exchange and cross-relaxation spectroscopy of coupled nuclear spins. J. Magn. Reson. 1981, 43, 259-281.
23. Güntert, P.; Dotsch, V.; Wider, G.; Wüthrich, K. Processing of multidimensional NMR data with the new software PROSA. J. Biolmol. NMR 1992, 2, 619-629.
24. Eccles, C.; Güntert, P.; Billeter, M.; Wüthrich, K. Efficient analysis of protein 2D NMR spectra using the software package EASY. J. Biomol. NMR 1991, 1, 111-130.
25. Wüthrich, K. NMR of Proteins and Nucleic Acids; J. Wiley & Sons: New York, 1986.
26. Hagler, A. T. Theoretical simulation of conformation, energetics and dynamics of peptides. The Peptides: Analysis, Synthesis, Biology; Academic Press: Orlando, FL, 1985; pp 213-299.
27. Koradi, R.; Billeter, M. MOLMOL: A program for display and analysis of macromolecular structures. PDB Newsletter 1998, 84, 5-7.
28. Hocart, S. J.; Jain, R.; Murphy, W. A.; Taylor, J. E.; Coy, D. H. Highly potent cyclic disulfide antagonists of somatostatin. J. Med. Chem. 1999, 42, 1863-1871.