Synthesis and dopamine receptor modulating activity of novel peptidomimetics of L-prolyl-L-leucyl-glycinamide featuring α,α- disubstituted amino acids

Journal of Medicinal Chemistry

Volumn 42, Issue 8, 1999, Pages 1441-1447

  Evans, Margaret C ^a   Pradhan, Ashish ^c   Venkatraman, Shankar ^a   Ojala, William H ^b   Gleason, William B ^b   Mishra, Ram K ^c   Johnson, Rodney L ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

^c MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DOPAMINE 2 RECEPTOR STIMULATING AGENT; PEPTIDE DERIVATIVE; PROLYLLEUCYLDIETHYLGLYCINAMIDE HYDROCHLORIDE; PROLYLLEUCYLGLYCINAMIDE; UNCLASSIFIED DRUG;

ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PARKINSON DISEASE; PROTEIN CONFORMATION; RAT; X RAY CRYSTALLOGRAPHY;

ANIMALS; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; MOLECULAR MIMICRY; MOTOR ACTIVITY; MSH RELEASE-INHIBITING HORMONE; OXIDOPAMINE; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; RATS; RECEPTORS, DOPAMINE; SUBSTANTIA NIGRA;

EID: 0033594361     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980656r     Document Type: Article

References (35)

1. Mishra, R. K.; Chiu, P.; Mishra, C. P. Pharmacology of L-Prolyl-L-Leucyl-Glycinamide (PLG): A Review. Methods Find. Exp. Clin. Pharmacol. 1983, 5, 203-233.
2. Kostrzewa, R. M.; Kastin, A. J.; Spirtes, M. A. α-MSH and MIF-1 Effects on Catecholamine Levels and Synthesis in Various Rat Brain Areas. Pharmacol. Biochem. Behav. 1975, 3, 1017-1023.
3. Kostrzewa, R. M.; Spirtes, M. A.; Klava, M. W.; Christensen, C. W.; Kastin, A. J.; Job, T. H. Effects of L-Pro-L-leucyl-glycine Amide (MIF-1) on Dopaminergic Neurons. Pharmacol. Biochem. Behav. 1976, 5 (Suppl. 1), 125-127.
4. Kostrzewa, R. M.; Fukushima, H.; Harston, C. T.; Perry, K. W.; Fuller, R. W.; Kastin, A. J. Striatal Dopamine Turnover and MIF-1. Brain Res. Bull. 1979, 4, 799-802.
5. 2 (PLG; MIF-1): Influence on Dopamine (DA) Uptake in Crude Synaptosomal Preparations From Rat Mediobasal Hypothalamus (MBH) and Caudate Putamen (CP). Peptides 1984, 5, 669-674.
6. Chiu, S.; Paulose, C. S.; Mishra, R. K. Effect of L-Prolyl-L-Leucyl-Glycinamide (PLG) on Neuroleptic-Induced Catalepsy and Dopamine/Neuroleptic Receptor Binding. Peptides 1981, 2, 105-111.
7. 2 Receptor: Evidence for Modulation of Agonist Affinity States in Bovine Striatal Membranes. J. Neurochem. 1988, 50, 960-968.
8. Mishra, R. K.; Chiu, S.; Singh, A. N.; Kazmi, S. M.; Rajakumar, A.; Johnson, R. L. L-Prolyl-L-Leucyl-Glycinamide (PLG) and its Analogues: Clinical Implications in Extrapyramidal Motor Disorders and Depression. Drugs Future 1986, 1, 203-207.
9. Higashijima, T.; Tasumi, M.; Miyazawa, T.; Miyoshi, M. Nuclear-Magnetic-Resonance Study of Aggregations and Conformations of Melanostatin and Related Peptides. Eur. J. Biochem. 1978, 89, 543-556.
10. 2O. J. Am. Chem. Soc. 1993, 36, 256-263.
11. 2. J. Med. Chem. 1988, 31, 1430-1436.
12. 2 Receptor by L-Pro-L-Leu-Glycinamide (PLG) Analogue 3(R)-(N-L-Prolylamino)-2-Oxo-1-Pyrrolidineacetamide. Prog. Neuro-Psychopharmacol. Biol. Psychiat. 1990, 14, 821-827.
13. 2 (PLG). Peptides 1997, 18, 1209-1215.
14. 2 (PLG, MIF-1). Peptides 1998, 19, 403-406.
15. Genin, M. J.; Sreenivasan, U.; Johnson, R. L. Conformationally Constrained Analogues of L-Prolyl-L-Leucyl-Glycinamide. In Peptides Chemistry and Biology. Proceedings of the 12th American Peptide Symposium; Smith, J. A., Rivier, J. E., Eds.; ESCOM Science Publishers: Leiden, The Netherlands, 1992; pp 757-758.
16. 2 Hemihydrate and Two Lactam-restricted Analogues. J. Chem. Soc., Perkin Trans. 2 1989, 83-87.
17. Toniolo, C. Structure of Conformationally Constrained Peptides: From Model Compounds to Bioactive Peptides. Biopolymers 1989, 28, 247-257.
18. Spencer, R. J.; Antonenko, V. V.; Delaet, N. G. J.; Goodman, M. Comparative Study of Methods to Couple Hindered Peptides. Int. J. Pept. Protein Res. 1992, 40, 282-293.
19. 2. J. Med. Chem. 1993, 36, 2356-2361.
20. Freidinger, R. M.; Perlow, D. S.; Veber, D. F. Protected Lactam-Bridged Dipeptides for Use as Conformational Constraints in Peptides. J. Org. Chem. 1982, 47, 104-109.
21. The authors have deposited atomic coordinates for these structures with the Cambridge Crystallographic Data Centre. The deposition number for 8a is CCDC 115703, and that for 14b is CCDC 115702. The coordinates can be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K., or via the internet at www.ccdc.cam.ac.uk.
22. Kitagawa, O.; Velde, D. V.; Dutta, D.; Morton, M.; Takusagawa, F.; Aube, J. Structural Analysis of β-Turn Mimics Containing a Substituted 6-Aminocaproic Acid Linker. J. Am. Chem. Soc. 1995, 117, 5169-5178.
23. 3-amaninamide Analogues in DMSO Solution as Determined by NMR Spectroscopy. Strong CD Effects Induced by βI, βII Conformational Change. J. Am. Chem Soc. 1996, 188, 4380-4387.
24. Burgess, K.; Lim, D. Spirocyclic Peptidomimetics Featuring 2,3-Methanoamino Acids. J. Am. Chem. Soc. 1997, 119, 9632-9640.
25. Hollosi, M.; Majer, Z. S.; Ronai, A. Z.; Magyar, A.; Medzihradszky, K.; Holly, S.; Perczel, A.; Fasman, G. D. CD and Fourier Transform IR Spectroscopic Studies of Peptides. II. Detection of β-Turns in Linear Peptides. Biopolymers 1994, 34, 177-185.
26. Rao, M. H.; Yang, W.; Joshua, H.; Becker, J. M.; Naider, F. Studies on Conformational Consequences of i to i+3 Side-chain Cyclization in Model Cyclic Tetrapeptides. Int. J. Pept. Protein Res. 1995, 45, 418-429.
27. Prasad, S.; Roa, R. B.; Balaram, P. Contrasting Solution Conformations of Peptides Containing α,α-Dialkylated Residues with Linear and Cyclic Side Chains. Bioplymers 1995, 35, 11-20.
28. Ott, M C.; Mishra, R. K.; Johnson, R. L. Modulation of Dopaminergic Neurotransmission in the 6-Hydroxydopamine Lesioned Rotational Model by Peptidomimetic Analogues of L-Prolyl-L-leucyl-glycinamide. Brain Res. 1996, 737, 287-291.
29. Costain, W. J.; Buckley, A. T.; Evans, M. C.; Mishra, R. K.; Johnson, R. L. Modulatory Effects of PLG and Its Peptidomimetics on Haloperidol Induced Catalepsy in Rats. Peptides, in press.
30. 2. J. Med. Chem. 1993, 36, 3481-3483.
31. 2 Analogues Possessing Cyclic Amino Acid Residues at the C-Terminal Position. J. Med. Chem. 1986, 29, 2100-2104.
32. Sheldrick, G. M. SHELXS86. In Crystallographic Computing 3; Sheldrick, G. M., Kruger, C., Goddard, R., Eds.; Oxford University Press: Oxford, England, 1985; pp 175-189.
33. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M. The DIRDIF-94 Program System. Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1994.
34. teXsan Crystal Structure Analysis Package; Molecular Structure Corp., 3200 Research Forest Dr., The Woodlands, TX 77381; 1992.
35. SHELXTL-Plus V5.0; Siemens Industrial Automation, Inc., Madison, WI.