A refined model for the somatostatin pharmacophore: Conformational analysis of lanthionine-sandostatin analogs

Journal of Medicinal Chemistry

Volumn 40, Issue 14, 1997, Pages 2252-2258

  Melacini, Giuseppe ^a   Zhu, Qin ^a,b   Ösapay, George ^a,c   Goodman, Murray ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b PURDUE UNIVERSITY   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG CARRIER; LANTHIONINE; OCTREOTIDE; SOMATOSTATIN; SULFIDE;

ARTICLE; BINDING AFFINITY; DRUG FORMULATION; METHYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ALANINE; AMINO ACID SEQUENCE; ANIMALS; CALORIMETRY; HUMANS; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OCTREOTIDE; PEPTIDES, CYCLIC; PROTEIN STRUCTURE, SECONDARY; RECEPTORS, SOMATOSTATIN; STRUCTURE-ACTIVITY RELATIONSHIP; SULFIDES; THREONINE;

EID: 0030837553     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960851a     Document Type: Article

References (38)

1. Brazeau, P.; Vale, W.; Burgus, R.; Ling, N.; Bucher, M.; Rivier, J.; Guillemin, R. Hypothalamic Polypeptide That Inhibits the Secretion of the Immunoreactive Growth Hormone. Science 1973, 179, 77-79.
2. Koerker, D. J.; Harker, L. A.; Goddner, C. J. N. Effects of Somatostatin on Hemostasis in Baboons. N. Engl. J. Med. 1975, 293, 476-479.
3. Gerich, J. E.; Lovinger, R.; Grodsky, G. M. Inhibition by Somatostatin of Glucagon and Insulin Release from the Perfused Rat Pancreas in Response to Arginine, Isoproterenol and Theophylline: Evidence for a Preferential Effect on Glucagon Secretion. Endocrinology 1975, 96, 749-754.
4. Johansson, C.; Wisen, O.; Efendic, S.; Uvnas-Wallensten, K. Effects of Somatostatin on Gastrointestinal Propagation and Absorpton of Oral Glucose in Man. Digestion 1981, 22, 126-137.
5. Iverson, L. L. Nonopioid Neuropeptides in Mammalian CNS. Annu. Rev. Pharmacol. Toxicol. 1983, 23, 1-27.
6. Delfs, J. R.; Dichter, M. A. Effects of Somatostatin on Mammalian Cortical Neurons in Culture: Physiological Actions and Unusual Dose Response Characteristics. J. Neurosci. 1983, 3 (6), 1176-1188.
7. Epelbaum, J. Somatostatin in the Central Nervous System: Physiology and Pathological Modifications. Prog. Neurobiol. 1986, 27, 63-100.
8. Seybold, V. S.; Hylden, J. L. K.; Wilcox, G. L. Intrathecal Substance P and Somatostatin in Rats: Behaviors Indicative of Sensation. Peptides 1982, 3 (1), 49-54.
9. Veber, D. F.; Freidinger, R. M.; Perlow, D. S.; Paleveda, W. J., Jr.; Holly, F. W.; Strachan, R. G.; Nutt, R. F.; Arison, B. J.; Homnick, C.; Randall, W. C.; Glitzer, M. S.; Saperstein, R.; Hirschmann, R. A Potent Cyclic Hexapeptide Analogue of Somatostatin. Nature 1981, 292, 55-58.
10. Mierke, D. F.; Pattaroni, C.; Delaet, N.; Toy, A.; Goodman, M.; Tancredi, T.; Motta, A.; Temussi, P. A.; Moroder, L.; Bovermann, G.; Wunsch, E. Cyclic Hexapeptides Related to Somatostatin. Int. J. Pept. Protein Res. 1990, 36, 418-432.
11. (a) Huang, Z.; He, Y.-B.; Raynor, K.; Tallent, M.; Reisine, T.; Goodman, M. Main Chain and Side Chain Chiral Methylated Somatostatin Analogs: Synthesis and Conformational Analysis. J. Am. Chem. Soc. 1992, 114 (24), 9390-9401.
12. (b) He, Y.-B.; Huang, Z.; Raynor, K.; Reisine, T.; Goodman, M. Synthesis and Conformations of Somatostatin Related Cyclic Hexapeptides Incorporating Specific α-Methylated and β-Methylated Residues. J. Am. Chem. Soc. 1993, 115, 8066-8072.
13. Bauer, W.; Briner, U.; Doepfner, W.; Haller, R.; Huguenin, R.; Merbach, P.; Petcher, T. J.; Pless, J. SMS 201-995: A Very Potent and Selective Octapeptide Analogue of Somatostatin with Prolonged Action. Life Sci. 1982, 31, 1133-1140.
14. Van Binst, G.; Tourwe', D. Backbone Modifications in Somatostatin Analogues: Relation Between Conformation and Activity. Peptide Res. 1992, 5 (1), 8-13.
15. Osapay, G.; Prokai, L.; Kim, H. S.; Medzihradszky, K. F.; Coy, D. H.; Liapakis, G.; Reisine, T.; Melacini, G.; Zhu, Q.; Wang, S. H-H.; Goodman, M. Lanthionine-Somatostatin Analogs: Synthesis, Characterization, Biological Activity and Enzymatic Stability Studies. J. Med. Chem. 1997, 40, 2241-2251.
16. Jung, G. Peptides with Sulfide Bridges and Dehydroamino Acids: Their Prepropeptides and Possibilities for Bioengineering. In Peptides. Proceedings of the Eleventh American Peptide Symposium; Rivier, J., Marshall, G. R., Eds.; ESCOM: Leiden 1990; pp 865-869.
17. Melacini, G.; Zhu, Q.; Goodman, M. Multiconformational NMR Analysis of Sandostatin (Octreotide): Equilibrium between β-Sheet and Helical Structures. Biochemistry 1997, 36, 1233-1241.
18. (a) Aue, W. P.; Bartholdi, E.; Ernst, R. R. Two-Dimensional Spectroscopy. Application to Nuclear Magnetic Resonance. J. Chem. Phys. 1976, 64, 2229-2246.
19. (b) Bodenhausen, G.; Vold, R. L.; Vold, R. R. Multiple Quantum Spin-Echo Spectroscopy. J. Magn. Reson. 1980, B37, 93-106.
20. Bax, A.; Freeman, R. Investigations of Complex Networks of Spin-Spin Coupling by Two-Dimensional NMR. J. Magn. Reson. 1981, 44, 542-561.
21. 1H-NMR Spectra of Proteins via Double Quantum Filters. Biochem Biophys. Res. Commun. 1984, 117, 479-485.
22. 1H-NMR Spectra via Two-Dimensional Homonuclear Hartmann-Hahn Spectroscopy. J. Am. Chem. Soc. 1985, 107, 2820-2821.
23. Bothner-By, A. A.; Stephens, R. L.; Lee, J.; Warren, C. D.; Jeanloz, R. W. Structure Determination of a Tetrasaccharide: Transient Nuclear Overhauser Effects in the Rotating Frame. J. Am. Chem. Soc. 1984, 106, 811-813.
24. Wüthrich, K. NMR of Proteins and Nucleic Acids; Wiley: New York, 1986.
25. 4]-Morphiceptin Analogs Incorporating Cis-2-Aminocyclopentane Carboxylic Acid as Peptidomimetic for Proline. Int. J. Pept. Protein Res. 1991, 37, 364-381.
26. (b) Pachler, K. G. P. Nuclear Magnetic Resonance Study of Some α-Amino Acids-II. Rotational Isomerism. Spectrochim. Acta 1964, 20, 581-587.
27. β Bond in Peptides. Biopolymers 1982, 21, 953-967.
28. αH Coupling Constant. Tetrahedron 1973, 29, 873-877.
29. Kessler, H. Conformation and Biological Activity of Cyclic Peptides. Angew. Chem., Int. Ed. Engl. 1982, 21, 512-523.
30. Biosym/MSI, Inc.
31. McCammon, J. A.; Wolynes, P. G.; Karplus, M. Picosecond Dynamics of Tyrosine Side Chains in Proteins. Biochemistry 1979, 18 (6), 927-942.
32. Kazmierski, W. M.; Ferguson, R. D.; Lipkowski, A. W.; Hruby, V. J. A Topographical Model of μ-Opioid and Brain Somatostatin Receptor Selective Ligands. Int. J. Pept. Protein Res. 1995, 46, 265-278.
33. Polinsky, A.; Cooney, M. G.; Toy-Palmer, A.; Ösapay, G.; Goodman, M. Synthesis and Conformational Properties of the Lanthionine-Bridged Opioid Peptide [D-AlaL2,AlaL5] Enkephalin as Determined by NMR and Computer Simulations. J. Med. Chem. 1992, 35, 4185-4194.
34. 7 resonances of the disulfide heptamer W (Table 4).
35. Wynants, C.; Van Binst, G.; Loosli, H. R. Hexapeptide Analogue of Somatostatin, Sandoz 201-456; Conformational Study in Dimethylsulfoxide by 1D and 2D NMR Methods. Int. J. Pept. Protein Res. 1985, 25, 622-627.
36. 29
37. 1H 500 MHz NMR Spectra and Conformational Analysis of SMS 201-995 in Dimethylsulfoxide. Int. J. Pept. Protein Res. 1985, 25, 615-621.
38. Brady, S. F.; Paleveda, W. J.; Arison, B. H.; Saperstein, R.; Brady, E. J.; Raynor, K.; Reisine, T.; Veber, D. F.; Freidinger, R. M. Approaches to Peptidomimetics which Serve as Surrogates for the cis Amide Bond: Novel Disulfide-Constrained Bicyclic Hexapeptide Analogs of Somatostatin. Tetrahedron 1993, 49 (17), 3449-3466.