Targeted antioxidative and neuroprotective properties of the dopamine agonist pramipexole and its nondopaminergic enantiomer SND919CL2x [(+)2-amino-4,5,6,7-tetrahydro-6-L-propylamino-benzathiazole dihydrochloride]

Journal of Pharmacology and Experimental Therapeutics

Volumn 316, Issue 1, 2006, Pages 189-199

  Danzeisen, R ^a   Schwalenstoecker, B ^a   Gillardon, F ^b   Buerger, E ^b   Krzykalla, V ^b   Klinder, K ^b   Schild, L ^c   Hengerer, B ^b   Ludolph, A C ^a   Dorner Ciossek, C ^b   Kussmaul, L ^b  

^a UNIVERSITY OF ULM   (Germany)

^b BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG   (Germany)

^c OTTO VON GUERICKE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 4,5,6,7 TETRAHYDRO 6 LEVO PROPYLAMINOBENZATHIAZOLE; ACONITATE HYDRATASE; DOPAMINE RECEPTOR STIMULATING AGENT; ETHYLENEDIAMINE DERIVATIVE; GLUTATHIONE; HYDROGEN PEROXIDE; MANGANESE 3 METHOXY N.N' BIS(SALICYLIDENE)ETHYLENEDIAMINE CHLORIDE; MANGANESE N,N' ETHYLENEBIS(3 METHOXYSALICYLIDENEAMINE); NITROGEN OXIDE; PRAMIPEXOLE; REACTIVE OXYGEN METABOLITE; SND 919CL2X; SUPEROXIDE DISMUTASE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

AMYOTROPHIC LATERAL SCLEROSIS; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; BINDING AFFINITY; CELL COMPARTMENTALIZATION; CONTROLLED STUDY; DETOXIFICATION; DOPAMINERGIC ACTIVITY; DRUG ACCUMULATION; DRUG POTENCY; DRUG SAFETY; DRUG TRANSPORT; ENZYME ACTIVITY; EXPERIMENTAL MODEL; FEMALE; IC 50; MALE; MITOCHONDRION; MOTOR PERFORMANCE; MOUSE; NEUROBLASTOMA CELL; NEUROPROTECTION; NEWBORN; NONHUMAN; PRIORITY JOURNAL; PROTEIN DEPLETION; RAT; RUNNING; SURVIVAL TIME; TREATMENT OUTCOME;

ACONITATE HYDRATASE; ANIMALS; ANTIOXIDANTS; ASTROCYTES; BENZOTHIAZOLES; BRAIN CHEMISTRY; CELL LINE, TUMOR; CEREBELLUM; CULTURE MEDIA; DOPAMINE AGONISTS; HYDROGEN PEROXIDE; HYPERKINESIS; MALE; MICE; MICE, INBRED C57BL; MICE, KNOCKOUT; MITOCHONDRIA; MOTOR ACTIVITY; NEUROPROTECTIVE AGENTS; OXIDANTS; STEREOISOMERISM; SUPEROXIDE DISMUTASE; THIAZOLES;

EID: 29244439896     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.105.092312     Document Type: Article

References (41)

1. Abramova NA, Cassarino DS, Khan SM, Painter TW, and Bennett JP Jr (2002) Inhibition by R(+)- or S(-)-pramipexole of caspase activation and cell death induced by methylpyridinium ion or beta amyloid peptide in SH-SY5Y neuroblastoma. J Neurosci Res 67:494-500.
2. Andersen JK (2004) Oxidative stress in neurodegeneration: cause or consequence? Nat Med 10 (Suppl):18-25.
3. Anderson DW, Neavin T, Smith JA, and Schneider JS (2001) Neuroprotective effects of pramipexole in young and aged MPTP-treated mice. Brain Res 905:44-53.
4. Bendotti C, Calvaresi N, Chiveri L, Prelle A, Moggio M, Braga M, Silani V, and De Biasi S (2001) Early vacuolization and mitochondrial damage in motor neurons of FALS mice are not associated with apoptosis or with changes in cytochrome oxidase histochemical reactivity. J Neurol Sci 191(1-2):25-33.
5. Bendotti C and Carri MT (2004) Lessons from models of SOD1-linked familial ALS. Trends Mol Med 10:393-400.
6. Cassarino DS, Fall CP, Smith TS, and Bennett JP Jr (1998) Pramipexole reduces reactive oxygen species production in vivo and in vitro and inhibits the mitochondrial permeability transition produced by the parkinsonian neurotoxin methylpyridinium ion. J Neurochem 71:295-301.
7. Dringen R and Hamprecht B (1998) Glutathione restoration as indicator for cellular metabolism of astroglial cells. Dev Neurosci 20:401-407.
8. Ferger B, Teismann P, and Mierau J (2000) The dopamine agonist pramipexole scavenges hydroxyl free radicals induced by striatal application of 6-hydroxydopamine in rats: an in vivo microdialysis study. Brain Res 883:216-223.
9. Floyd RA, Watson JJ, and Wong PK (1984) Sensitive assay of hydroxyl free radical formation utilizing high pressure liquid chromatography with electrochemical detection of phenol and salicylate hydroxylation products. J Biochem Biophys Methods 10:221-235.
10. Fridovich I (1970) Quantitative aspects of the production of superoxide anion radical by milk xanthine oxidase. J Biol Chem 245:4053-4057.
11. Gardner PR, Nguyen DD, and White CW (1994) Aconitase is a sensitive and critical target of oxygen poisoning in cultured mammalian cells and in rat lungs. Proc Natl Acad Sci USA 91:12248-12252.
12. Gu M, Irvani M, Cooper JM, King D, Jenner P, and Schapira AH (2004) Pramipexole protects against apoptotic cell death by non-dopaminergic mechanisms. J Neurochem 91:1075-1081.
13. Halestrap AP and Quinlan PT (1983) The intramitochondrial volume measured using sucrose as an extramitochondrial marker overestimates the true matrix volume determined with mannitol. Biochem J 214:387-393.
14. Halliwell B (1999) Antioxidant defense mechanisms: from the beginning to the end (of the beginning). Free Radic Res 31:261-272.
15. Jung C, Rong Y, Doctrow S, Baudry M, Malfroy B, and Xu Z (2001) Synthetic superoxide dismutase/catalase mimetics reduce oxidative stress and prolong survival in a mouse amyotrophic lateral sclerosis model. Neurosci Lett 304:157-160.
16. Kakimura J, Kitamura Y, Takata K, Kohno Y, Nomura Y, and Taniguchi T (2001) Release and aggregation of cytochrome c and alpha-synuclein are inhibited by the antiparkinsonian drugs, talipexole and pramipexole. Eur J Pharmacol 417:59-67.
17. Kitamura Y, Kosaka T, Kakimura JI, Matsuoka Y, Kohno Y, Nomura Y, and Taniguchi T (1998) Protective effects of the antiparkinsonian drugs talipexole and pramipexole against 1-methyl-4-phenylpyridinium-induced apoptotic death in human neuroblastoma SH-SY5Y cells. Mol Pharmacol 54:1046-1054.
18. Kostic V, Gurney ME, Deng HX, Siddique T, Epstein CJ, and Przedborski S (1997) Midbrain dopaminergic neuronal degeneration in a transgenic mouse model of familial amyotrophic lateral sclerosis. Ann Neurol 41:497-504.
19. Le WD, Jankovic J, Xie W, and Appel SH (2000) Antioxidant property of pramipexole independent of dopamine receptor activation in neuroprotection. J Neural Transm 107:1165-1173.
20. Ling ZD, Robie HC, Tong CW, and Carvey PM (1999) Both the antioxidant and D3 agonist actions of pramipexole mediate its neuroprotective actions in mesencephalic cultures. J Pharmacol Exp Ther 289:202-210.
21. Ling ZD, Tong CW, and Carvey PM (1998) Partial purification of a pramipexoleinduced trophic activity directed at dopamine neurons in ventral mesencephalic cultures. Brain Res 791:137-145.
22. Maher P and Davis JB (1996) The role of monoamine metabolism in oxidative glutamate toxicity. J Neurosci 16:6394-6401.
23. Mahoney DJ, Rodriguez C, Devries M, Yasuda N, and Tarnopolsky MA (2004) Effects of high-intensity endurance exercise training in the G93A mouse model of amyotrophic lateral sclerosis. Muscle Nerve 29:656-662.
24. Melov S, Doctrow SR, Schneider JA, Haberson J, Patel M, Coskun PE, Huffman K, Wallace DC, and Malfroy B (2001) Lifespan extension and rescue of spongiform encephalopathy in superoxide dismutase 2 nullizygous mice treated with superoxide dismutase-catalase mimetics. J Neurosci 21:8348-8353.
25. Menzies FM, Cookson MR, Taylor RW, Turnbull DM, Chrzanowska-Lightowlers ZM, Dong L, Figlewicz DA, and Shaw PJ (2002) Mitochondrial dysfunction in a cell culture model of familial amyotrophic lateral sclerosis. Brain 125:1522-1533.
26. Mierau J (1995) Pramipexole: a dopamine receptor agonist for treatment of Parkinson's disease. Clin Neuropharmacol 18:195-206.
27. Mierau J, Schneider FJ, Ensinger HA, Chio CL, Lajiness ME, and Huff RM (1995) Pramipexole binding and activation of cloned and expressed dopamine D2, D3 and D4 receptors. Eur J Pharmacol 290:29-36.
28. Murphy TH, Miyamoto M, Sastre A, Schnaar RL, and Coyle JT (1989) Glutamate toxicity in a neuronal cell line involves inhibition of cystine transport leading to oxidative stress. Neuron 2:1547-1558.
29. Nagata N, Momose K, and Ishida Y (1999) Inhibitory effects of catecholamines and anti-oxidants on the fluorescence reaction of 4,5-diaminofluorescein, DAF-2, a novel indicator of nitric oxide. J Biochem 125:658-661.
30. Pan T, Xie W, Jankovic J, and Le W (2005) Biological effects of pramipexole on dopaminergic neuron-associated genes: relevance to neuroprotection. Neurosci Lett 377:106-109.
31. Pattee GL, Post GR, Gerber RE, and Bennett JP Jr (2003) Reduction of oxidative stress in amyotrophic lateral sclerosis following pramipexole treatment. Amyotroph Lateral Scler Other Motor Neuron Disord 4:90-95.
32. Presgraves SP, Borwege S, Millan MJ, and Joyce JN (2004) Involvement of dopamine D(2)/D(3) receptors and BDNF in the neuroprotective effects of S32504 and pramipexole against 1-methyl-4-phenylpyridinium in terminally differentiated SH-SY5Y cells. Exp Neurol 190:157-170.
33. Przedborski S, Dhawan V, Donaldson DM, Murphy PL, McKenna-Yasek D, Mandel FS, Brown RH Jr, and Eidelberg D (1996) Nigrostriatal dopaminergic function in familial amyotrophic lateral sclerosis patients with and without copper/zinc superoxide dismutase mutations. Neurology 47:1546-1551.
34. Ramirez AD, Wong SK, and Menniti FS (2003) Pramipexole inhibits MPTP toxicity in mice by dopamine D3 receptor dependent and independent mechanisms. Eur J Pharmacol 475:29-35.
35. Ross MF, Kelso GF, Blaikie FH, James AM, Cocheme HM, Filipovska A, Da Ros T, Hurd TR, Smith RA, and Murphy MP (2005) Lipophilic triphenylphosphonium cations as tools in mitochondrial bioenergetics and free radical biology. Biochemistry 70:222-230.
36. Sims NR (1990) Rapid isolation of metabolically active mitochondria from rat brain and subregions using Percoll density gradient centrifugation. J Neurochem 55:698-707.
37. Tan S, Wood M, and Maher P (1998) Oxidative stress induces a form of programmed cell death with characteristics of both apoptosis and necrosis in neuronal cells. J Neurochem 71:95-105.
38. Tarpey MM, Wink DA, and Grisham MB (2004) Methods for detection of reactive metabolites of oxygen and nitrogen: in vitro and in vivo considerations. Am J Physiol 286:R431-R444.
39. Trapp S and Horobin RW (2005) A predictive model for the selective accumulation of chemicals in tumor cells. Eur Biophys J 34:959-966.
40. Zhou M, Diwu Z, Panchuk-Voloshina N, and Haugland RP (1997) A stable nonfluorescent derivative of resorufin for the fluorometric determination of trace hydrogen peroxide: applications in detecting the activity of phagocyte NADPH oxidase and other oxidases. Anal Biochem 253:162-168.
41. Zou L, Xu J, Jankovic J, He Y, Appel SH, 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.