D-512 and D-440 as novel multifunctional dopamine agonists: Characterization of neuroprotection properties and evaluation of in vivo efficacy in a parkinson's disease animal model

ACS Chemical Neuroscience

Volumn 4, Issue 10, 2013, Pages 1382-1392

  Santra, Soumava ^a   Xu, Liping ^a   Shah, Mrudang ^a   Johnson, Mark ^a   Dutta, Aloke ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

6 OHDA; Dopamine; dopamine agonist; MN9D cells; MPTP; multifunctional drugs; Parkinson's disease

Indexed keywords

CASPASE 3; CASPASE 7; D 440; D 512; DOPAMINE RECEPTOR STIMULATING AGENT; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; OXIDOPAMINE; PROTEIN KINASE B; TYROSINE 3 MONOOXYGENASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIOXIDANT ACTIVITY; APOPTOSIS; ARTICLE; CELL SURVIVAL; CONTROLLED STUDY; ENZYME INHIBITION; FEMALE; IN VIVO STUDY; LIPID PEROXIDATION; NEUROPROTECTION; NEUROTOXICITY; NONHUMAN; PARKINSON DISEASE; PRIORITY JOURNAL; RAT;

ANIMALS; CAROTENOIDS; DISEASE MODELS, ANIMAL; DOPAMINE AGONISTS; INDOLES; MITOGEN-ACTIVATED PROTEIN KINASE 1; MITOGEN-ACTIVATED PROTEIN KINASE 3; NEUROPROTECTIVE AGENTS; OXIDOPAMINE; PARKINSON DISEASE; PROTO-ONCOGENE PROTEINS C-AKT; RATS; THIAZOLES; TUMOR CELLS, CULTURED;

EID: 84885962765     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn400106n     Document Type: Article

References (52)

1. Hornykiewicz, O. (1989) Ageing and neurotoxins as causative factors in idiopathic Parkinson's disease - a critical analysis of the neurochemical evidence Prog. Neuro-Psychopharmacol. Biol. Psychiatry 13, 319-328
2. Hornykiewicz, O. and Kish, S. J. (1987) Biochemical pathophysiology of Parkinson's disease Adv. Neurol. 45, 19-34
3. Hornykiewicz, O. (1998) Biochemical aspects of Parkinson's disease Neurology 51, 2-9
4. Braak, H., Del Tredici, K., Rub, U., de Vos, R. A., Jansen Steur, E. N., and Braak, E. (2003) Staging of brain pathology related to sporadic Parkinson's disease Neurobiol. Aging 24, 197-211
5. Di Monte, D. A. (2003) The environment and Parkinson's disease: Is the nigrostriatal system preferentially targeted by neurotoxins? Lancet Neurol. 2, 531-538
6. Jenner, P. (2003) Oxidative stress in Parkinson's disease Ann. Neurol. 53, 26-36
7. Beal, M. F. (2009) Therapeutic approaches to mitochondrial dysfunction in Parkinson's disease Parkinsonism Relat. Disord. 15, 189-194
8. Linert, W. and Jameson, G. N. (2000) Redox reactions of neurotransmitters possibly involved in the progression of Parkinson's disease J. Inorg. Biochem. 79, 319-326
9. Linert, W., Herlinger, E., Jameson, R. F., Kienzl, E., Jellinger, K., and Youdim, M. B. (1996) Dopamine, 6-hydroxydopamine, iron, and dioxygen - their mutual interactions and possible implication in the development of Parkinson's disease Biochim. Biophys. Acta 1316, 160-168
10. Exner, N., Lutz, A. K., Haass, C., and Winklhofer, K. F. (2012) Mitochondrial dysfunction in Parkinson's disease: Molecular mechanisms and pathophysiological consequences EMBO J. 31, 3038-3062
11. Lin, M. T. and Beal, M. F. (2006) Mitochondrial dysfunction and oxidative stress in neurodegenerative diseases Nature 443, 787-795
12. Birkmayer, W. and Hornykiewicz, O. (2001) The effect of l-3,4-dihydroxyphenylalanine (= DOPA) on akinesia in Parkinsonism. 1961 Wien. Klin. Wochenschr. 113, 851-4
13. Cotzias, G. C., Papavasiliou, P. S., and Gellene, R. (1969) Modification of Parkinsonism - chronic treatment with L-dopa N. Engl. J. Med. 280, 337-345
14. Marsden, C. D. and Parkes, J. D. (1976) "On-off" effects in patients with Parkinson's disease on chronic levodopa therapy Lancet 1, 292-296
15. Fahn, S. (1996) Is levodopa toxic? Neurology 47, 184-195
16. Olanow, C. W. (1990) Oxidation reactions in Parkinson's disease Neurology 40, 37-39
17. Dutta, A. K. L., W. (2006) Existing dopaminergic therapies for Parkinson's disease Expert Opin. Ther. Pat. 16, 1613-1625
18. Zou, L., Xu, J., Jankovic, J., He, Y., Appel, S. H., and Le, W. (2000) Pramipexole inhibits lipid peroxidation and reduces injury in the substantia nigra induced by the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine in C57BL/6 mice Neurosci. Lett. 281, 167-170
19. Ramirez, A. D., Wong, S. K., and Menniti, F. S. (2003) Pramipexole inhibits MPTP toxicity in mice by dopamine D3 receptor dependent and independent mechanisms Eur. J. Pharmacol. 475, 29-35
20. Iida, M., Miyazaki, I., Tanaka, K., Kabuto, H., Iwata-Ichikawa, E., and Ogawa, N. (1999) Dopamine D2 receptor-mediated antioxidant and neuroprotective effects of ropinirole, a dopamine agonist Brain Res. 838, 51-59
21. Li, C., Biswas, S., Li, X., Dutta, A. K., and Le, W. (2010) Novel D3 dopamine receptor-preferring agonist D-264: Evidence of neuroprotective property in Parkinson's disease animal models induced by 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine and lactacystin J. Neurosci. Res. 88, 2513-2523
22. Youdim, M. B. and Buccafusco, J. J. (2005) CNS targets for multi-functional drugs in the treatment of Alzheimer's and Parkinson's diseases J. Neural Transm. 112, 519-537
23. Youdim, M. B. and Buccafusco, J. J. (2005) Multi-functional drugs for various CNS targets in the treatment of neurodegenerative disorders Trends Pharmacol. Sci. 26, 27-35
24. Cavalli, A., Bolognesi, M. L., Minarini, A., Rosini, M., Tumiatti, V., Recanatini, M., and Melchiorre, C. (2008) Multi-target-directed ligands to combat neurodegenerative diseases J. Med. Chem. 51, 347-372
25. Koller, W. C. and Cersosimo, M. G. (2004) Neuroprotection in Parkinson's disease: An elusive goal Curr. Neurol. Neurosci. Rep. 4, 277-283
26. Dutta, A. K., Venkataraman, S. K., Fei, X. S., Kolhatkar, R., Zhang, S., and Reith, M. E. (2004) Synthesis and biological characterization of novel hybrid 7-[[2-(4-phenyl-piperazin-1-yl)-ethyl]-propyl-amino]-5,6,7,8-tetrahydro- naphthalen-2-ol and their heterocyclic bioisosteric analogues for dopamine D2 and D3 receptors Bioorg. Med. Chem. 12, 4361-4373
27. Biswas, S., Hazeldine, S., Ghosh, B., Parrington, I., Kuzhikandathil, E., Reith, M. E., and Dutta, A. K. (2008) Bioisosteric heterocyclic versions of 7-{[2-(4-phenyl-piperazin-1-yl)ethyl]propylamino}-5,6,7,8-tetrahydronaphthalen- 2-ol: Identification of highly potent and selective agonists for dopamine D3 receptor with potent in vivo activity J. Med. Chem. 51, 3005-3019
28. Biswas, S., Zhang, S., Fernandez, F., Ghosh, B., Zhen, J., Kuzhikandathil, E., Reith, M. E., and Dutta, A. K. (2008) Further structure-activity relationships study of hybrid 7-{[2-(4-phenylpiperazin-1-yl) ethyl]propylamino}-5,6,7,8-tetrahydronaphthalen-2-ol analogues: Identification of a high-affinity D3-preferring agonist with potent in vivo activity with long duration of action J. Med. Chem. 51, 101-117
29. Gogoi, S., Antonio, T., Rajagopalan, S., Reith, M., Andersen, J., and Dutta, A. K. (2011) Dopamine D(2)/D(3) agonists with potent iron chelation, antioxidant and neuroprotective properties: Potential implication in symptomatic and neuroprotective treatment of Parkinson's disease ChemMedChem 6, 991-995
30. Johnson, M., Antonio, T., Reith, M. E., and Dutta, A. K. (2012) Structure-activity relationship study of N(6)-(2-(4-(1H-indol-5-yl)piperazin-1- yl)ethyl)-N(6)-propyl-4,5,6,7-tetrahydroben zo[d]thiazole-2,6-diamine analogues: Development of highly selective D3 dopamine receptor agonists along with a highly potent D2/D3 agonist and their pharmacological characterization J. Med. Chem. 55, 5826-5840
31. Ungerstedt, U. (1968) 6-Hydroxy-dopamine induced degeneration of central monoamine neurons Eur. J. Pharmacol. 5, 107-10
32. Xia, Z., Dickens, M., Raingeaud, J., Davis, R. J., and Greenberg, M. E. (1995) Opposing effects of ERK and JNK-p38 MAP kinases on apoptosis Science 270, 1326-1331
33. Yan, C. Y. and Greene, L. A. (1998) Prevention of PC12 cell death by N-acetylcysteine requires activation of the Ras pathway J. Neurosci. 18, 4042-4049
34. Dudek, H., Datta, S. R., Franke, T. F., Birnbaum, M. J., Yao, R., Cooper, G. M., Segal, R. A., Kaplan, D. R., and Greenberg, M. E. (1997) Regulation of neuronal survival by the serine-threonine protein kinase Akt Science 275, 661-665
35. Kauffmann-Zeh, A., Rodriguez-Viciana, P., Ulrich, E., Gilbert, C., Coffer, P., Downward, J., and Evan, G. (1997) Suppression of c-Myc-induced apoptosis by Ras signalling through PI(3)K and PKB Nature 385, 544-548
36. Choi, H. K., Won, L., Roback, J. D., Wainer, B. H., and Heller, A. (1992) Specific modulation of dopamine expression in neuronal hybrid cells by primary cells from different brain regions Proc. Natl. Acad. Sci. U.S.A. 89, 8943-8947
37. Breese, G. R. and Traylor, T. D. (1970) Effect of 6-hydroxydopamine on brain norepinephrine and dopamine evidence for selective degeneration of catecholamine neurons J. Pharmacol. Exp. Ther. 174, 413-420
38. Bove, J., Prou, D., Perier, C., and Przedborski, S. (2005) Toxin-induced models of Parkinson's disease NeuroRx 2, 484-494
39. Langston, J. W. and Ballard, P. A., Jr. (1983) Parkinson's disease in a chemist working with 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine N. Engl. J. Med. 309, 310
40. Przedborski, S., Jackson-Lewis, V., Djaldetti, R., Liberatore, G., Vila, M., Vukosavic, S., and Almer, G. (2000) The parkinsonian toxin MPTP: Action and mechanism Restor. Neurol. Neurosci. 16, 135-142
41. Jackson-Lewis, V. and Przedborski, S. (2007) Protocol for the MPTP mouse model of Parkinson's disease Nat. Protoc. 2, 141-151
42. Signore, A. P., Weng, Z., Hastings, T., Van Laar, A. D., Liang, Q., Lee, Y. J., and Chen, J. (2006) Erythropoietin protects against 6-hydroxydopamine- induced dopaminergic cell death J. Neurochem. 96, 428-443
43. Prigol, M., Wilhelm, E. A., Schneider, C. C., and Nogueira, C. W. (2008) Protective effect of unsymmetrical dichalcogenide, a novel antioxidant agent, in vitro and an in vivo model of brain oxidative damage Chem.-Biol. Interact. 176, 129-136
44. Degterev, A., Boyce, M., and Yuan, J. (2003) A decade of caspases Oncogene 22, 8543-8567
45. Cryns, V. and Yuan, J. (1998) Proteases to die for Genes Dev. 12, 1551-1570
46. Choi, W. S., Yoon, S. Y., Oh, T. H., Choi, E. J., O'Malley, K. L., and Oh, Y. J. (1999) Two distinct mechanisms are involved in 6-hydroxydopamine- and MPP+-induced dopaminergic neuronal cell death: Role of caspases, ROS, and JNK J. Neurosci. Res. 57, 86-94
47. Han, B. S., Hong, H. S., Choi, W. S., Markelonis, G. J., Oh, T. H., and Oh, Y. J. (2003) Caspase-dependent and -independent cell death pathways in primary cultures of mesencephalic dopaminergic neurons after neurotoxin treatment J. Neurosci. 23, 5069-5078
48. Huot, P., Levesque, M., and Parent, A. (2007) The fate of striatal dopaminergic neurons in Parkinson's disease and Huntington's chorea Brain 130, 222-232
49. Margolis, E. B., Coker, A. R., Driscoll, J. R., Lemaitre, A. I., and Fields, H. L. (2010) Reliability in the identification of midbrain dopamine neurons PLoS One 5, e15222-1-e15222-6
50. Taravini, I. R., Chertoff, M., Cafferata, E. G., Courty, J., Murer, M. G., Pitossi, F. J., and Gershanik, O. S. (2011) Pleiotrophin over-expression provides trophic support to dopaminergic neurons in parkinsonian rats Mol. Neurodegener. 6, 40
51. Lin, E., Cavanaugh, J. E., Leak, R. K., Perez, R. G., and Zigmond, M. J. (2008) Rapid activation of ERK by 6-hydroxydopamine promotes survival of dopaminergic cells J. Neurosci. Res. 86, 108-117
52. Burgering, B. M. and Coffer, P. J. (1995) Protein kinase B (c-Akt) in phosphatidylinositol-3-OH kinase signal transduction Nature 376, 599-602