Optimization of a small tropomyosin-related kinase B (TrkB) agonist 7,8-dihydroxyflavone active in mouse models of depression

Journal of Medicinal Chemistry

Volumn 55, Issue 19, 2012, Pages 8524-8537

  Liu, Xia ^a   Chan, Chi Bun ^a   Qi, Qi ^a   Xiao, Ge ^b   Luo, Hongbo R ^c   He, Xiaolin ^d   Ye, Keqiang ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b CENTERS FOR DISEASE CONTROL AND PREVENTION   (United States)

^c BOSTON CHILDREN S HOSPITAL   (United States)

^d NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYL 8[4' (PYRROLIDIN 1 YL) PHENYL] CHROMENO [7,8 D] IMIDAZOL 6(1H) ONE DERIVATIVE; 4' DIMETHYLAMINO 7,8 DIHYDROXYFLAVONE; 7,8 DIHYDROXYFLAVONE; 8[4 (DIMETHYLAMINO) PHENYL] CHROMENO [7,8 D] IMIDAZOL 6(1H) ONE; ANTIDEPRESSANT AGENT; BRAIN DERIVED NEUROTROPHIC FACTOR RECEPTOR; FLAVONOID; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIDEPRESSANT ACTIVITY; AREA UNDER THE CURVE; ARTICLE; BRAIN TISSUE; CONTROLLED STUDY; CYTOTOXICITY; DEPRESSION; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG HALF LIFE; DRUG POTENCY; DRUG SYNTHESIS; FORCED SWIMMING TEST; HIPPOCAMPUS; HUMAN; HUMAN CELL; LOCOMOTION; MALE; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; REACTION OPTIMIZATION; STRUCTURE ACTIVITY RELATION; TIME TO MAXIMUM PLASMA CONCENTRATION;

ANIMALS; ANTIDEPRESSIVE AGENTS; BRAIN; DEPRESSION; FLAVANONES; HEP G2 CELLS; HUMANS; IMIDAZOLES; INDOLES; MALE; MICE; MICE, INBRED C57BL; MOTOR ACTIVITY; NEUROGENESIS; RECEPTOR, TRKB; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84867352628     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301099x     Document Type: Article

References (31)

1. Nibuya, M.; Morinobu, S.; Duman, R. S. Regulation of BDNF and trkB mRNA in rat brain by chronic electroconvulsive seizure and antidepressant drug treatments J. Neurosci. 1995, 15, 7539-7547
2. Saarelainen, T.; Hendolin, P.; Lucas, G.; Koponen, E.; Sairanen, M.; MacDonald, E.; Agerman, K.; Haapasalo, A.; Nawa, H.; Aloyz, R.; Ernfors, P.; Castren, E. Activation of the TrkB neurotrophin receptor is induced by antidepressant drugs and is required for antidepressant-induced behavioral effects J. Neurosci. 2003, 23, 349-357
3. Monteggia, L. M.; Barrot, M.; Powell, C. M.; Berton, O.; Galanis, V.; Gemelli, T.; Meuth, S.; Nagy, A.; Greene, R. W.; Nestler, E. J. Essential role of brain-derived neurotrophic factor in adult hippocampal function Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 10827-10832
4. Li, Y.; Luikart, B. W.; Birnbaum, S.; Chen, J.; Kwon, C. H.; Kernie, S. G.; Bassel-Duby, R.; Parada, L. F. TrkB regulates hippocampal neurogenesis and governs sensitivity to antidepressive treatment Neuron 2008, 59, 399-412
5. Sahay, A.; Hen, R. Adult hippocampal neurogenesis in depression Nat. Neurosci. 2007, 10, 1110-1115
6. Schmidt, H. D.; Duman, R. S. The role of neurotrophic factors in adult hippocampal neurogenesis, antidepressant treatments and animal models of depressive-like behavior Behav. Pharmacol. 2007, 18, 391-418
7. Banasr, M.; Duman, R. S. Regulation of neurogenesis and gliogenesis by stress and antidepressant treatment CNS Neurol. Disord.: Drug Targets 2007, 6, 311-320
8. Lindsay, R. M. Role of neurotrophins and trk receptors in the development and maintenance of sensory neurons: an overview Philos. Trans. R. Soc. London, Ser. B 1996, 351, 365-373
9. Siegel, G. J.; Chauhan, N. B. Neurotrophic factors in Alzheimer's and Parkinson's disease brain Brain Res. Rev. 2000, 33, 199-227
10. Jang, S. W.; Liu, X.; Yepes, M.; Shepherd, K. R.; Miller, G. W.; Liu, Y.; Wilson, W. D.; Xiao, G.; Blanchi, B.; Sun, Y. E.; Ye, K. A selective TrkB agonist with potent neurotrophic activities by 7,8-DHF Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 2687-2692
11. Jang, S. W.; Liu, X.; Chan, C. B.; France, S. A.; Sayeed, I.; Tang, W.; Lin, X.; Xiao, G.; Andero, R.; Chang, Q.; Ressler, K. J.; Ye, K. Deoxygedunin, a natural product with potent neurotrophic activity in mice PLoS One 2010, 5, e11528
12. Liu, X.; Chan, C. B.; Jang, S. W.; Pradoldej, S.; Huang, J.; He, K.; Phun, L. H.; France, S.; Xiao, G.; Jia, Y.; Luo, H. R.; Ye, K. A synthetic 7,8-DHF derivative promotes neurogenesis and exhibits potent antidepressant effect J. Med. Chem. 2010, 53, 8274-8286
13. Devi, L.; Ohno, M. 7,8-DHF, a small-molecule TrkB agonist, reverses memory deficits and BACE1 elevation in a mouse model of Alzheimer's disease Neuropsychopharmacology 2012, 37, 434-444
14. Blugeot, A.; Rivat, C.; Bouvier, E.; Molet, J.; Mouchard, A.; Zeau, B.; Bernard, C.; Benoliel, J. J.; Becker, C. Vulnerability to depression: from brain neuroplasticity to identification of biomarkers J. Neurosci. 2011, 31, 12889-12899
15. Zeng, Y.; Tan, M.; Kohyama, J.; Sneddon, M.; Watson, J. B.; Sun, Y. E.; Xie, C. W. Epigenetic enhancement of BDNF signaling rescues synaptic plasticity in aging J. Neurosci. 2011, 31, 17800-17810
16. Johnson, R. A.; Lam, M.; Punzo, A. M.; Li, H.; Lin, B. R.; Ye, K.; Mitchell, G. S.; Chang, Q. 7,8-DHF exhibits therapeutic efficacy in a mouse model of Rett syndrome J. Appl. Physiol. 2012, 112, 704-710
17. LeWitt, P. A. Subcutaneously administered apomorphine: pharmacokinetics and metabolism Neurology 2004, 62, S8-S11
18. Di Stefano, A.; Sozio, P.; Cerasa, L. S.; Iannitelli, A. L-Dopa prodrugs: an overview of trends for improving Parkinson's disease treatment Curr. Pharm. Des. 2011, 17, 3482-3493
19. Cryan, J. F.; Markou, A.; Lucki, I. Assessing antidepressant activity in rodents: recent developments and future needs Trends Pharmacol. Sci. 2002, 23, 238-245
20. Petit-Demouliere, B.; Chenu, F.; Bourin, M. Forced swimming test in mice: a review of antidepressant activity Psychopharmacology (Berlin, Ger.) 2005, 177, 245-255
21. Cryan, J. F.; Mombereau, C.; Vassout, A. The tail suspension test as a model for assessing antidepressant activity: review of pharmacological and genetic studies in mice Neurosci. Biobehav. Rev. 2005, 29, 571-625
22. Kozics, K.; Valovicova, Z.; Slamenova, D. Structure of flavonoids influences the degree inhibition of benzo(a)pyrene-induced DNA damage and micronuclei in HepG2 cells Neoplasma 2011, 58, 516-524
23. Wang, J.; Urban, L.; Bojanic, D. Maximising use of in vitro ADMET tools to predict in vivo bioavailability and safety Expert Opin. Drug Metab. Toxicol. 2007, 3, 641-665
24. Sanguinetti, M. C.; Tristani-Firouzi, M. hERG potassium channels and cardiac arrhythmia Nature 2006, 440, 463-469
25. Redfern, W. S.; Carlsson, L.; Davis, A. S.; Lynch, W. G.; MacKenzie, I.; Palethorpe, S.; Siegl, P. K.; Strang, I.; Sullivan, A. T.; Wallis, R.; Camm, A. J.; Hammond, T. G. Relationships between preclinical cardiac electrophysiology, clinical QT interval prolongation and torsade de pointes for a broad range of drugs: evidence for a provisional safety margin in drug development Cardiovasc. Res. 2003, 58, 32-45
26. Goldkind, L.; Laine, L. A systematic review of NSAIDs withdrawn from the market due to hepatotoxicity: lessons learned from the bromfenac experience Pharmacoepidemiol. Drug Saf. 2006, 15, 213-220
27. Miller, B. M.; Pujadas, E.; Gocke, E. Evaluation of the micronucleus test in vitro using Chinese hamster cells: results of four chemicals weakly positive in the in vivo micronucleus test Environ. Mol. Mutagen. 1995, 26, 240-247
28. Kivovich, V.; Gilbert, L.; Vuento, M.; Naides, S. J. The putative metal coordination motif in the endonuclease domain of human parvovirus B19 NS1 is critical for NS1 induced S phase arrest and DNA damage Int. J. Biol. Sci. 2012, 8, 79-92
29. Wehrman, T.; He, X.; Raab, B.; Dukipatti, A.; Blau, H.; Garcia, K. C. Structural and mechanistic insights into nerve growth factor interactions with the TrkA and p75 receptors Neuron 2007, 53, 25-38
30. Eswar, N.; Webb, B.; Marti-Renom, M. A.; Madhusudhan, M. S.; Eramian, D.; Shen, M. Y.; Pieper, U.; Sali, A. Comparative Protein Structure Modeling Using Modeller. In Current Protocols in Bioinformatics; Wiley: New York, 2006; Chapter 5, Unit 5 6.
31. Chang, D. T.; Oyang, Y. J.; Lin, J. H. MEDock: a Web server for efficient prediction of ligand binding sites based on a novel optimization algorithm Nucleic Acids Res. 2005, 33, W233-W238