Novel [D-Arg2]dermorphin(1-4) analogs with μ-opioid receptor antagonist activity

Chemical and Pharmaceutical Bulletin

Volumn 50, Issue 10, 2002, Pages 1401-1403

  Ambo, Akihiro ^a   Terashima, Takanori ^a   Sasaki, Yusuke ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Antagonist; Dermorphin; Opioid peptide; Opioid receptor binding; Peptoid

Indexed keywords

(N 4 HYDROXYBENZYLGLYCYL 1)TYROSYL DEXTRO ARGINYLPHENYLALANYL BETA ALANINAMIDE; (N 4 HYDROXYBENZYLTYROSYL 1)TYROSYL DEXTRO ARGINYLPHENYLALANYL BETA ALANINAMIDE; (N BENZYLGLYCYL 3)TYROSYL DEXTRO ARGINYLPHENYLALANYL BETA ALANINAMIDE; (N GUANIDINOPROPYLGLYCYL 2}TYROSYL DEXTRO ARGINYLPHENYLALANYL BETA ALANINAMIDE; [N,N BIS(4 HYDROXYBENZYL)GLYCYL 1 ARGINYL 2]TYROSYL DEXTRO ARGINYLPHENYLALANYL BETA ALANINAMIDE; [N,N BIS(4 HYDROXYBENZYL)GLYCYL 1 NOR BETA ALANYL 4]TYROSYL DEXTRO ARGINYLPHENYLALANYL BETA ALANINAMIDE; [N,N BIS(4 HYDROXYBENZYL)GLYCYL 1 NORPHENYLALANYL 3 NOR BETA ALANYL 4]TYROSYL DEXTRO ARGINYLPHENYLALANYL BETA ALANINAMIDE; [N,N BIS(4 HYDROXYBENZYL)GLYCYL 1]TYROSYL DEXTRO ARGINYLPHENYLALANYL BETA ALANINAMIDE; [N,N BIS(BENZYL)GLYCYL 1]TYROSYL DEXTRO ARGINYLPHENYLALANYL BETA ALANINAMIDE; [NORTYROSYL 1 N ALPHA,N ALPHA BIS(4 HYDROXYBENZYL) DEXTRO ARGINYL 2]TYROSYL DEXTRO ARGINYLPHENYLALANYL BETA ALANINAMIDE; AMINO ACID DERIVATIVE; DERMORPHIN DERIVATIVE; GLYCINE DERIVATIVE; MU OPIATE RECEPTOR; MU OPIATE RECEPTOR ANTAGONIST; PEPTIDE DERIVATIVE; TYROSINE; UNCLASSIFIED DRUG; NARCOTIC ANTAGONIST; OLIGOPEPTIDE; TYROSYL ALANYL PHENYLALANYL GLYCINE; TYROSYL-ALANYL-PHENYLALANYL-GLYCINE;

AMINO ACID SUBSTITUTION; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; IN VITRO STUDY; NONHUMAN; RECEPTOR BINDING; ANIMAL; BRAIN; CHEMISTRY; DOSE RESPONSE; DRUG ANTAGONISM; GUINEA PIG; MALE; METABOLISM; RAT;

ANIMALS; BRAIN; DOSE-RESPONSE RELATIONSHIP, DRUG; GUINEA PIGS; MALE; NARCOTIC ANTAGONISTS; OLIGOPEPTIDES; RATS; RECEPTORS, OPIOID, MU;

EID: 0036782841     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.50.1401     Document Type: Article

References (22)

1. 5]enkephalin, Tos-tosyl, Fmoc=N-9-fluorenylmethyloxycarbonyl, PyBOP=benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate, MBHA resin=methoxybenzohydrylamine resin, GPI=guinea pig ileum.
2. Dhawan B. N., Cesselin F., Raghubir R., Reisine T., Bradley P. B., Portoghese P. S., Hamon M., Pharmacol. Rev., 48, 567-592 (1996).
3. Sasaki Y., Ambo A., Suzuki K., Chem. Pharm. Bull., 39, 2316-2318 (1991).
4. Simon R. J., Kania R. S., Zuckermann R. N., Huebner V. D., Jewell D. A., Banbille S., Ng S., Wang L., Rosenberg S., Marlowe C. K., Spellmeyer D. C., Tan R., Frankel A. D., Santi D. V., Cohen F. E., Bartlett P. A., Proc. Natl. Acad. Sci. U.S.A., 89, 9367-9371 (1992).
5. Suh J. T., Skiles J. W., Williams B. E., Youssefyeh R. D., Jones H., Loev B., Neiss E. S., Schwab A., Mann W. S., Khandwala A., Wolf P. S., Weinryb I., J. Med. Chem., 28, 57-66 (1985).
6. Skiles J. W., Fuchs V., Miao C., Sorcek R., Grozinger K. G., Mauldin S. C., Virous J., Mui P. W., Jacober S., Chow G., Matteo M., Skoog M., Weldon S. M., Possanza G., Keirns J., Letts G., Rosenthal A. S., J. Med. Chem., 35, 641-662 (1992).
7. Heizmann G., Felder E. R., Peptide Res., 7, 328-332 (1994).
8. Sasaki Y., Chiba T., J. Med. Chem., 38, 3995-3999 (1995).
9. Sasaki Y., Ambo A., Midorikawa K., Suzuki K., Chem. Pharm. Bull., 41, 1391-1394 (1993).
10. Sasaki Y., Coy D. H., Peptides, 8, 119-121 (1987).
11. Castiglione-Morelli M. A., Lelj F., Pastore A., Salvadori S., Tancredi T., Tomatis R., Trivellone E., Temussi P. A., J. Med. Chem., 30, 2067-2073 (1987).
12. Champion H. C., Zadina J. E., Kastin A. J., Hackler L., Ge L. J., Kadowitz P. J., Biochem. Biophys. Res. Commun., 235, 567-570 (1997).
13. Champion H. C., Zadina J. E., Kastin A. J., Kadowitz P. J., Life Sci., 61, PL409-415 (1997).
14. Pelton J. T., Kazmierski W., Gulya K., Yamamura H. I., Hruby V. J., J. Med. Chem., 29, 2370-2375 (1986).
15. Kazmierski W., Wire W. S., Lui G. K., Knap R. J., Shook J. E., Burks T. F., Yamamura H. I., Hruby V. J., J. Med. Chem., 31, 2170-2177 (1988).
16. Hansen P. E., Morgan B. A., "The Peptides," Vol. 6 Chap. 8, eds. by Udenfriend S., Meienhofer J., Academic Press, London, 1984, pp. 269-321.
17. Frerot E., Coste J., Pantaloni A., Dufour M.-N., Jouin P., Tetrahedron, 47, 259-270 (1991).
18. Habbeb A., Methods Enzymol., 25B, 558-566 (1972).
19. Sasaki Y., Ambo A, Suzuki K., Biochem. Biophys. Res. Commun., 180, 822-827 (1991).
20. Cheng Y., Prusoff W. H., Biochem. Pharmacol., 22, 3099-3108 (1973).
21. Rang H. P., Br. J. Pharmacol., 22, 356-365 (1964).
22. Arunlakshana O., Schild H. O., Br. J. Pharmacol., 14, 48-58 (1959).