Design and Synthesis of Conformationally Constrained Somatostatin Analogues with High Potency and Specificity for μ Opioid Receptors

Journal of Medicinal Chemistry

Volumn 29, Issue 11, 1986, Pages 2370-2375

  Pelton, John T ^a   Kazmierski, Wieslaw ^a   Hruby, Victor J ^a   Gulya, Karoly ^a   Yamamura, Henry I ^a  

^a UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CGP 23996 I 125; CYSTEINYLTYROSYL DEXTRO TRYPTOPHYLORNITHYLTHREONYLPENICILLAMINYLTHREONINAMIDE 1,6 DISULFIDE; ENKEPHALIN[2,5 DEXTRO PENICILLAMINE] H 3; MU OPIATE RECEPTOR; NALOXONE H 3; NEW DRUG; OPIATE RECEPTOR; RADIOISOTOPE; SOMATOSTATIN; SOMATOSTATIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BRAIN; CENTRAL NERVOUS SYSTEM; DRUG ANALYSIS; DRUG BINDING; DRUG COMPARISON; DRUG DESIGN; DRUG IDENTIFICATION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROPHORESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PHARMACOKINETICS; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY;

ANIMALS; PROTEIN CONFORMATION; RATS; RATS, INBRED STRAINS; RECEPTORS, NEUROTRANSMITTER; RECEPTORS, OPIOID; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, MU; RECEPTORS, SOMATOSTATIN; SOMATOSTATIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0023028494     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00161a037     Document Type: Article

References (24)

1. Vale, W.; Rivier, C.; Brown; M. Ann. Rev. Physiol. 1977, 39, 437.
2. Kastin, A. J.; Coy, D. H.; Jacquet, Y.; Schally, A. V.; Plotnikoff, N. Metabolism 1978, 27, 1347.
3. Patel, Y. C.; Reichlin, S. Endocrinology 1978, 102, 523.
4. Veber, D.; Saperstein, R. Ann. Rep. Med. Chem. 1979, 14, 209.
5. Hruby, V. J.; Krstenansky, J. L.; Cody, W. L. Ann. Rep. Med. Chem. 1984, 190, 303.
6. Veber, D. F.; Saperstein, R.; Nutt, R. F.; Freidinger, R. M.; Brady, S. F.; Curley, P.; Perlow, D. S.; Paleveda, W. J.; Colton, C. D.; Zacchei, A. G.; Tocco, D. J.; Hoff, D. R.; Vandlen, R. L.; Gehrich, J. E.; Hall, L.; Mandarino, L.; Cordes, E. H.; Anderson, P. S.; Hirschmann, R. Life Sci. 1984, 34, 1371.
7. Maurer, R.; Gaehwiler, B. H.; Buescher, H. H.; Hill, R. C.; Roemer, D. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 4815.
8. Tran, W. T.; Beals, M. F.; Martin, J. B. Science (Washington, D. C.) 1985, 228, 492.
9. Freidinger, R. M.; Veber, D. F. Conformationally Directed Drug Design; ACS Monograph Series No. 251; Vida, J. A.; Gordon, M., Eds.; American Chemical Society: Washington, DC, 1984; pp 169–187.
10. Terenius, L. Eur. J. Pharmacol. 1976, 38, 211.
11. Rezek, M.; Havlicek, V.; Leybin, L.; LaBella, F. S.; Friesen, H. Can. J. Pharmacol. 1981, 56, 227.
12. Hruby, V. J. Conformationally Directed Drug Design; ACS Monograph Series No. 251; Vida, J. A., Gordon, M., Eds.; American Chemical Society: Washington, DC, 1984; pp 9–27.
13. Hruby, V. J. Trends Pharm. Sci. 1985, 6, 259.
14. Pelton, J. T.; Gulya, K.; Hruby, V. J.; Duckles, S.; Yamamura, H. I. Peptides Suppl. 1 1985, 6, 159.
15. Pelton, J. T.; Gulya, K.; Hruby, V. J.; Duckles, S. P.; Yamamura, H. I. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 236.
16. Gulya, K.; Pelton, J. T.; Hruby, V. J.; Yamamura, H. I. Life. Sci. 1986, 38, 2221.
17. Nutt, R. F.; Veber, D. F.; Curley, P. E.; Saperstein, R.; Hirschmann, R. Int. J. Peptide Protein Res. 1983, 21, 66.
18. Upson, D. A.; Hruby, V. J. J. Org. Chem. 1976, 41, 1353.
19. Sawyer, T. K.; Hruby, V. J.; Wilkes, B. C.; Draelos, M. T.; Hadley, M. E.; Bergsneider, M. J. Med. Chem. 1982, 25, 1022.
20. Gisin, B. F. Helv. Chim. Acta 1973, 56, 1476.
21. Hagenmeier, H.; Frank, H. Hoppe-Seyler’s Z. Physiol. Chem. 1972, 353, 1973.
22. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595.
23. Christensen, T. Peptides, Structure and Biological Function; Gross, E., Meienhofer, J., Eds.; Pierce Chemical Co.: Rockford, IL, 1979; pp 385–388.
24. Yamashiro, D. Nature (London) 1964, 201, 76.