Bivalent diketopiperazine-based tropomysin receptor kinase C (TrkC) antagonists

Journal of Medicinal Chemistry

Volumn 53, Issue 13, 2010, Pages 5044-5048

  Liu, Jing ^a   Brahimi, Fouad ^b   Saragovi, H Uri ^b   Burgess, Kevin ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

NEUROTROPHIN; PEPTIDOMIMETIC AGENT; PIPERAZINEDIONE; TROPOMYSIN RECEPTOR KINASE C ANTAGONIST; TROPOMYSIN RECEPTOR KINASE C RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; BETA TURN; BINDING ASSAY; BIOASSAY; CONTROLLED STUDY; HUMAN; HUMAN CELL; MOLECULE;

AMINO ACID MOTIFS; ANIMALS; CELL SURVIVAL; DIKETOPIPERAZINES; MICE; NEUROTROPHIN 3; NIH 3T3 CELLS; PROTEIN KINASE INHIBITORS; RECEPTOR, TRKC; SIGNAL TRANSDUCTION;

EID: 77954346851     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100148d     Document Type: Article

References (28)

1. Skaper, S. D. The biology of neurotrophins, signalling pathways, and functional peptide mimetics of neurotrophins and their receptors CNS Neurol. Disord.: Drug Targets 2008, 7, 46-62
2. Ivanisevic, L.; Saragovi, H. U. The Neurotrophins. In Handbook of Biologically Active Peptides; Kastin, A. J., Ed. Elsevier: New York, 2006; pp 1407 - 1413.
3. Pollack, S. J.; Harper, S. J. Small molecule Trk receptor agonists and other neurotrophic factor mimetics Curr. Drug Targets: CNS Neurol. Disord. 2002, 1, 59-80
4. Friedman, W. J.; Greene, L. A. Neurotrophin signaling via Trks and p75 Exp. Cell Res. 1999, 253, 131-142
5. N2 macrocyclization reactions to form β-turn mimics Org. Lett. 1999, 1, 121-124
6. NAr macrocyclizations to give turn-extended-turn peptidomimetics Chem.-Eur. J. 1999, 5, 3261-3272
7. NAr cyclizations to form cyclic peptidomimetics of β-turns J. Am. Chem. Soc. 1998, 120, 10768-10769
8. Maliartchouk, S.; Feng, Y.; Ivanisevic, L.; Debeir, T.; Cuello, A. C.; Burgess, K.; Saragovi, H. U. A designed peptidomimetic agonistic ligand of TrkA nerve growth factor receptors Mol. Pharmacol. 2000, 57, 385-391
9. Brahimi, F.; Malakhov, A.; Lee, H. B.; Pattarawarapan, M.; Ivanisevic, L.; Burgess, K.; Saragovi, H. U. A peptidomimetic of NT-3 acts as a TrkC antagonist Peptides 2009, 30, 1833-1839
10. Pattarawarapan, M.; Reyes, S.; Xia, Z.; Zaccaro, M. C.; Saragovi, H. U.; Burgess, K. Selective formation of homo- and heterobivalent peptidomimetics J. Med. Chem. 2003, 46, 3565-3567
11. Brahimi, F.; Liu, J.; Malakhov, A.; Chowdhury, S.; Purisima, E.; Ivanisevic, L.; Caron, A.; Burgess, K.; Saragovi, H. Dimerization of a monovalent small molecule ligand changes a TrkA receptor agonist into an antagonist: implications for conformational changes. 2010, submitted for publication.
12. Chen, D.; Brahimi, F.; Angell, Y.; Li, Y.-C.; Moscowicz, J.; Saragovi, H. U.; Burgess, K. Bivalent peptidomimetic ligands of TrkC are biased agonists, selectively induce neuritogenesis, or potentiate neurotrophin-3 trophic signals ACS Chem. Biol. 2009, 4, 769-781
13. Angell, Y.; Chen, D.; Brahimi, F.; Saragovi, H. U.; Burgess, K. A combinatorial method for solution-phase synthesis of labeled bivalent β-turn mimics J. Am. Chem. Soc. 2008, 130, 556-565
14. Martins, M. B.; Carvalho, I. Diketopiperazines: Biological activity and synthesis Tetrahedron 2007, 63, 9923-9932
15. α-cyclization strategy J. Org. Chem. 2001, 66, 3538-3547
16. Bohn Rhoden, C. R.; Westermann, B.; Wessjohann, L. A. One-pot multicomponent synthesis of n -substituted tryptophan-derived diketopiperazines Synthesis 2008, 2077-2082
17. Mehta, A.; Jaouhari, R.; Benson, T. J.; Douglas, K. T. Improved efficiency and selectivity in peptide synthesis: use of triethylsilane as a carbocation scavenger in deprotection of tert -butyl esters and tert -butoxycarbonyl-protected sites Tetrahedron Lett. 1992, 33, 5441-5444
18. Zaccaro, M. C.; Lee, B. H.; Pattarawarapan, M.; Xia, Z.; Caron, A.; LHeureux, P.-J.; Bengio, Y.; Burgess, K.; Saragovi, H. U. Selective small molecule peptidomimetic ligands of TrkC and of TrkA receptors afford discrete or complete neurotrophic activities Chem. Biol. 2005, 12, 1015-1028
19. Kaplan, D. R.; Miller, F. D. Neurotrophin signal transduction in the nervous system Curr. Opin. Neurobiol. 2000, 10, 381-391
20. LeSauteur, L.; Wei, L.; Gibbs, B.; Saragovi, H. U. Small peptide mimics of nerve growth factor bind TrkA receptors and affect biological responses J. Biol. Chem. 1995, 270, 6564-6569
21. LeSauteur, L.; Cheung, N. K. V.; Lisbona, R.; Saragovi, H. U. Small molecule nerve growth factor analogs image receptors in vivo Nature Biotechnol. 1996, 14, 1120-1122
22. Maliartchouk, S.; Debeir, T.; Beglova, N.; Cuello, A.; Gehring, K.; Saragovi, H. Genuine monovalent ligands of TrkA nerve growth factor receptors reveal a novel pharmacological mechanism of action J. Biol. Chem. 2000, 275, 9946-9956
23. Longo, F. M.; Manthorpe, M.; Xie, Y. M.; Varon, S. Synthetic NGF peptide derivatives prevent neuronal death via a p75 receptor-dependent mechanism J. Neurosci. Res. 1997, 48, 1-17
24. Xie, Y.; Tisi, M. A.; Yeo, T. T.; Longo, F. M. Nerve growth factors(NGF) loop 4 dimeric mimetics activate ERK and AKT and promote NGF-like neurotropic effects J. Biol. Chem. 2000, 275, 29868-29874
25. Xie, Y.; Longo, F. M. Neurotrophin small-molecule mimetics Prog. Brain Res. 2000, 128, 333-347
26. OLeary, P. D.; Hughes, R. A. Design of potent peptide mimetics of brain-derived neurotrophic factor J. Biol. Chem. 2003, 278, 25738-25744
27. NAr macrocyclizations: 13- to 16-membered ring systems Chem.-Eur. J. 1999, 5, 3273-3278
28. 10 β-turn peptidomimetics leading to the first reported small-molecule mimic of neurotrophin-3 J. Med. Chem. 2002, 45, 4387-4390