Synthesis and biological activities of position one and three transposed analogs of the opioid peptide YKFA

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 24, 1999, Pages 3441-3446

  Burden, John E ^a   Davis, Peg ^b   Porreca, Frank ^b   Spatola, Arno F ^a  

^a UNIVERSITY OF LOUISVILLE   (United States)

^b UNIVERSITY OF ARIZONA COLLEGE OF MEDICINE   (United States)

Author keywords

Agonists; Analgesics; Peptides and polypeptides; Receptors

Indexed keywords

ANALGESIC AGENT; DELTA OPIATE RECEPTOR; DELTORPHIN; DERMORPHIN; DRUG ANALOG; MU OPIATE RECEPTOR; OPIATE PEPTIDE; PHENYLALANINE; SOMATOSTATIN DERIVATIVE; TRYPTOPHAN;

AGONIST; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CHEMICAL MODIFICATION; DRUG ACTIVITY; DRUG ANTAGONISM; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; GUINEA PIG; MOUSE; NONHUMAN; SMOOTH MUSCLE CONTRACTILITY;

EID: 0033590274     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00625-3     Document Type: Article

References (20)

1. Hughes, J.; Smith, T. W.; Kosterlitz, H. W.; Fothergill, L. A.; Morgan, B. A.; Moriss, H. R. Nature, 1975, 258, 577.
2. Höllt, V. Ann. Rev. Pharmacol. Tox. 1986, 26, 59.
3. Zadina, J. E.; Hackler, L.; Ge, L.-J.; Kastin, A. J. Nature 1997, 386, 499.
4. Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249.
5. Hruby, V. J.; Gehrig, C. A. Med. Res. Rev. 1989, 9, 343.
6. DiMaio, J.; Schiller, P. W. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 7162.
7. DiMaio, J.; Nguyen, T. M. D.; Lemieus, C.; Schiller, P. W. J. Med. Chem. 1982, 25, 1432.
8. Mosberg, H. I.; Hurst, R.; Hruby, V. J.; Gee, K.; Yamamura, H. I.; Galligan, J. J.; Burks, T. F. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 5871.
9. st European Peptide Symposium; Giralt, E., Andreau, D., Eds.; ESCOM: Leiden; 1991, pp 401-403.
10. Ro, S.; Zhu, Q.; Lee, C. -W.; Goodman, M.; Darlak, K.; Spatola, A. F.; Chung, N. N.; Schiller, P. W.; Malmberg, A. B.; Yaksh, T. L.; Burks, T. F. J. Peptide Sci. 1995, 1, 157.
11. Pelton, J. T.; Gulya, K.; Hruby, V. J.; Duckles, S. P.; Yamamura, H. I. Proc. Natl. Acad. Sci., U.S.A. 1985, 82, 236.
12. Kazmierski, W.; Wire, W. S.; Lui, G. K.; Knapp, R. J.; Shook, J. E.; Burks, T. F.; Yamamura, H. I.; Hruby, V. J. J. Med. Chem. 1988, 31, 2170.
13. Fujii, N.; Otaka, A.; Ikemura, O.; Akaji, K.; Funakoshi S.; Hayashi, Y.; Kuroda, Y.; Yajima, H. J. Chem. Soc., Chem. Comm. 1987, 274.
14. Shiori, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203.
15. Kosterlitz, H. W.; Lord, F. A. H.; Paterson, S. J.; Waterfield, A. A. Br. J. Pharmacol. 1980, 68, 333.
16. Kazmierski, W.; Ferguson, R. D.; Lipkowski, A. W.; Hruby, V. J. Int. J. Peptide Protein Res. 1995, 46, 265.
17. Morgan, B. A.; Smith, C. F. C.; Waterfield, A. A.; Hughes, J.; Kosterlitz, H. W. J. Pharm. Pharm. 1976, 28, 660.
18. Schiller, P. W.; DiMaio, J. In Peptides: Structure and Function; Hruby, V. J., Rich, D., Eds.; Pierce Chemical Co.: Rockford, 1983; pp 269-278.
19. Mosberg, H. I.; Ho, J. C.; Sobczyk-Kojiro, K. Bioorg. Med. Chem. Lett. 1998, 8, 2681.
20. Pogozheva, I.; Lomize, A. L.; Mosberg, H. I. Biophys. J. 1998, 75, 612.