Synthesis and opioid activity of [D-Pro10]Dynorphin A-(1-11) analogues with N-terminal alkyl substitution

Journal of Medicinal Chemistry

Volumn 40, Issue 17, 1997, Pages 2733-2739

  Choi, Heekyung ^b   Murray, Thomas F ^a   DeLander, Gary E ^a   Schmidt, William K ^c,d   Aldrich, Jane V ^b  

^a OREGON STATE UNIVERSITY   (United States)

^b UNIVERSITY OF MARYLAND SCHOOL OF PHARMACY   (United States)

^c DUPONT COMPANY   (United States)

^d NorthStar R and D Ltd   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DICHLORO N METHYL N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZENEACETAMIDE; DYNORPHIN DERIVATIVE; KAPPA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR AGONIST; KAPPA OPIATE RECEPTOR ANTAGONIST; N METHYL N [7 (1 PYRROLIDINYL) 1 OXASPIRO[4.5]DEC 8 YL]BENZENEACETAMIDE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINOCICEPTION; ARTICLE; DRUG ACTIVITY; DRUG EFFECT; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; GUINEA PIG; ILEUM; MALE; MOUSE; NONHUMAN; RECEPTOR AFFINITY;

ALKYLATION; AMINO ACIDS; ANIMALS; CHO CELLS; CRICETINAE; DYNORPHINS; KINETICS; MALE; MICE; MODELS, CHEMICAL; RECEPTORS, OPIOID; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030808338     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960747t     Document Type: Article

References (28)

1. Chavkin, C.; James, I. F.; Goldstein, A. Dynorphin is a Specific Endogenous Ligand of the κ Opioid Receptor. Science 1982, 215, 413-415.
2. Aldrich, J. V. Analgesics. In Burger's Medicinal Chemistry and Drug Discovery; Wolff, M. E., Ed.; John Wiley & Sons, Inc.: New York, 1996; Vol. 3: Therapeutic Agents, pp 321-441.
3. Chavkin, C.; Goldstein, A. Specific Receptor for the Opioid Peptide Dynorphin: Structure-Activity Relationships. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 6543-6547.
4. Turcotte, A.; Lalonde, J.-M.; St.-Pierre, S.; Lemaire, S. Dynorphin-(1-13). I. Structure - Function Relationships of AlaContaining Analogs. Int. J. Pept. Protein Res. 1984, 23, 361-367.
5. Shaw, J. S.; Miller, L.; Turnbull, M. J.; Gormley, J. J.; Morley, J. S. Selective Antagonists at the Opiate Delta-Receptor. Life Sci, 1982, 31, 1259-1262.
6. 2-Met-enkephalin. Nature (London) 1977, 269, 73-75.
7. 10]-Dynorphin A(1-11). Br. J. Pharmacol. 1988, 95, 1023-1030.
8. Lemaire, S.; Parent, P.; Lapierre, C.; Michelot, R. N,N-Diallylated Analogs of Dynorphin A-(1-13) as Potent Antagonists for the Endogenous Peptide and Selective κ Opioid Analgesics. In International Narcotics Research Conference (INRC) '89; Quirion, R., Jhamandas, K., Gianoulakis, C., Eds.; Alan R. Liss, Inc.: New York, 1990; Vol. 328, pp 77-80.
9. 10]Dynorphin-(1-11) is a Highly Potent and Selective Ligand for κ Opioid Receptors. Eur. J. Pharmacol. 1985, 106, 457-458.
10. 10]dynorphin A-(1-11) are Highly Selective for κ-Opioid Receptors. J. Med. Chem. 1992, 35, 4638-4639.
11. Cheung, S. T.; Benoiton, L. N. N-Methylamino Acids in Peptide Synthesis, V. The Synthesis of N-tert-Butyloxycarbonyl,N-methylamino Acids by N-Methylation. Can. J. Chem. 1977, 55, 906-910.
12. Castro, B.; Dormoy, J.-R.; Evin, G.; Selve, C. Reactifs de Couplage Peptidique IV (1)-L'hexafluorophosphate de Benzotriazolyl N-Oxytrisdimethylamino Phosphonium (B.O.P.). Tetrahedron Lett. 1975, 1219-1222.
13. Hudson, D. Methodological Implications of Simultaneous Solid-Phase Peptide Synthesis. 1. Comparison of Different Coupling Procedures. J. Org. Chem. 1988, 53, 617-624.
14. Robson, L. E.; Foote, R. W.; Maurer, R.; Kosterlitz, H. W. Opioid Binding Sites of the κ-Type in Guinea Pig Cerebellum. Neuroscience 1984, 12, 621-627.
15. Gillan, M. G. C.; Kosterlitz, H. W. Spectrum of the μ-, δ-and κ-Binding Sites in Homogenates of Rat Brain. Br. J. Pharmacol. 1982, 77, 461-469.
16. 10]Dynorphin A-(1-11) are High Affinity Partial Agonists at the Cloned Rat κ-Opioid Receptor, submitted.
17. 2. J. Med. Chem. 1995, 38, 585-586.
18. Choi, H.; Aldrich, J. V. Comparison of Methods for the Fmoc Solid-Phase Synthesis and Cleavage of a Peptide Containing Both Tryptophan and Arginine. Int. J. Pept. Protein Res. 1993, 42, 58-63.
19. NMR data for N-monoalkylated tyrosine derivatives could not be obtained due to their insolubility in any solvent except DMA.
20. Stewart, J. M.; Young, J. D. Solid Phase Peptide Synthesis, 2nd ed.; Pierce Chemical Co.: Rockford, IL, 1984; p 176.
21. Story, S. C.; Murray, T. F.; DeLander, G. E.; Aldrich, J. V. Synthesis and Opioid Activity of 2-Substituted Dynorphin A-(1-13) Amide Analogues. Int. J. Pept. Protein Res. 1992, 40, 89-96.
22. 50) of an Enzymatic Reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
23. + Ions and Gpp(NH)p. Eur. J. Pharmacol. - Mol. Pharmacol. Sect. 1989, 172, 381-384.
24. Schild, H. O. Br. J. Pharmacol. 1947, 2, 189-206.
25. Tallarida, R. J.; Murray, R. B. Pharmacolgical Calculations, 2nd ed.; Springer-Verlag: New York, 1987.
26. Hughes, J.; Kosterlitz, H. W.; Leslie, F. M. Assessment of the Agonist and Antagonist Activities of Narcotic Analgesic Drugs by Means of the Mouse vas deferens. Br. J. Pharmacol. 1974, 51, 139P-140P.
27. Rónai, A. Z.; Gráf, L.; Székely, J. I.; Dunai-Kovács, Z.; Bajusz, S. Differential Behaviour of LPH-(61-91)-Peptide in Different Model Systems: Comparison of the Opioid Activities of LPH-(61-91)-Peptides and its Fragments. FEBS Lett. 1977, 74, 182-184.
28. Thompson, W. R. Use of Moving Averages and Interpolation to Estimate Median Effective Dose. I. Fundamental Formulas, Estimation of Error, and Relation to Other Methods. Bacteriological Rev. 1947, 11, 115-145.