Acta Med. 2000, 43: 9-13
https://doi.org/10.14712/18059694.2019.110
3-Nitropropionic Acid and Similar Nitrotoxins
References
1. Exp Neurol 1998; 153:74-93.
< T, Hughes PE, Knusel B, Tobin AJ. Metabolic compromise with systemic 3-nitropropionic acid produces striatal apoptosis ins Sprague-Dawley rats but not in BALB/c ByJ mice. https://doi.org/10.1006/exnr.1998.6842>
2. Proc Natl Acad Sci USA 1977; 74:3767-71.
< TA, Mela L, Bright HJ. 3-Nitropropionate, the toxic substance of Indiofera, is a suicide inactivator of succinate dehydrogenase. https://doi.org/10.1073/pnas.74.9.3767>
<PubMed>
3. Appl Environ Microbiol 1996; 62:3885-6.
RC, Rasmussen MA, Allison MJ. Enrichment and isolation of a nitropropanol-metabiolizing bacterium from the rumen.
4. Can J Microbiol 1997; 43:617-24.
< RC, Rasmussen MA, Di Spirito AA, Allison MJ. Characteristics of a nitropropanol-metabolizing bacterium isolated from the rumen. https://doi.org/10.1139/m97-088>
5. Neuron 1995; 14:961-73.
< M, Dypbukt JM, Bonfoco E, Zhivotovski B, Orrenius S, Lipton SA, Nicotera P. Glutamate-induced neuronal death: a succession of necrosis or apoptosis depending on mitochondrial function. https://doi.org/10.1016/0896-6273(95)90186-8>
6. J Chem Soc Perkin Trans I 1994; 16:2297-300.
< RL, Smith SL, Martin JR, Hanley AB. The Fungal Biosynthesis of 3-Nitropropionic Acid: Is the Decarboxylation of L-Nitrosuccinate an Enzymatic Reaction? https://doi.org/10.1039/p19940002297>
7. Curr Opin Neurol 1994; 7:542-7.
< MF. Neurochemistry and toxin models of Huntingtons’s disease. https://doi.org/10.1097/00019052-199412000-00012>
8. Ann Neurol 1995; 38:357-66.
< MF. Aging, energy, and oxidative stress in neurodegenerative diseases. https://doi.org/10.1002/ana.410380304>
9. J Neurosci 1993; 13:4181-92.
< MF, Brouillet E, Jenkins BG et al. Neurochemical and histologic characterization of striatal excitotoxic lesions produced by the mitochondrial toxin 3-nitropropionic acid. https://doi.org/10.1523/JNEUROSCI.13-10-04181.1993>
<PubMed>
10. J Neurochem 1995; 65:919-22.
< MF, Ferrante RJ, Henshaw R et al. 3-Nitropropionic acid neurotoxicity is attenuated in copper/zinc dismutase transgenic mice. https://doi.org/10.1046/j.1471-4159.1995.65020919.x>
11. Neuroreport 1995; 6:545-8.
< MI, Koh J, Canzoniero LM, Sensi SL, Csernansky CA, Cchoi DW. 3-Nitropropionic acid induces apoptosis in cultured striatal and cortical neurons. https://doi.org/10.1097/00001756-199502000-00034>
12. Toxicol Lett 1989; 47:165-72.
< MH, McDiarmid RE, Majak W. In vitro biotransformation of 3-nitropropanol (miserotoxin aglycone) by horse liver alcohol dehydrogenase. https://doi.org/10.1016/0378-4274(89)90071-4>
13. Neurosci Lett 1997; 230:199-201.
< Z, Kim CS. Increase in levels of total free fatty acids in rat brain regions following 3-nitropropionic acid administration. https://doi.org/10.1016/S0304-3940(97)00514-4>
14. Neurosci Lett 1998; 251:173-6.
< Z, Simmons C, Hussain S, Slikker W, Jr., Ali SF. Effect of acute exposure to 3-nitropropionic acid on activities of endogenous antioxidants in the rat brain. https://doi.org/10.1016/S0304-3940(98)00539-4>
15. J Pharm Pharmacol 1996; 48:85-9.
< A, Meunier M, Doble A. 3-Nitropropionic acid exacerbates (3H)GABA release evoked by glucose deprivation in rat striatal slices. https://doi.org/10.1111/j.2042-7158.1996.tb05883.x>
16. Proc Natl Acad Sci USA 1995; 92:7162-6.
< E, Krainc D, Ankarcrona M, Nicotera P, Lipton SA. Apoptosis and necrosis: two distinct events induced, respectively, by mild and intense insult with N-methyl-D-aspartate or nitric oxide/superoxide in cortical cell cultures. https://doi.org/10.1073/pnas.92.16.7162>
<PubMed>
17. Prog Neurobiol 1999; 59:427-68.
< E, Conde F, Beal MF, Hantraye P. Replicating Huntington’s disease phenotype in experimental animals. https://doi.org/10.1016/S0301-0082(99)00005-2>
18. Cheeke PR, Shull LR. Natural Toxicants in Feeds and Poisonous Plants. AVI Publ Comp Inc, Westport, USA, 1985, pp. 492.
19. Neuroscience 1999; 92:1035-41.
< T, Chang C. Temporal evolution of 3-nitropropionic acid-induced neurodegeneration in the rat brain by T2-wighted, diffusion-weighted, and perfusion magnetic resonance imaging. https://doi.org/10.1016/S0306-4522(99)00076-7>
20. J Biol Chem 1979; 254:5161-7.
CJ, Edmondson DE, Singer TP. Inactivation of succinate dehydrogenase by 3-nitropropionic acid.
21. Neurobiol Dis 1999; 6:259-68.
< C, Conde F, Brouillet E et al. Serial 1H-NMR spectroscopy study of metabolic impairment in primates chronically treated with the succinate dehydrogenase inhibitor 3-nitropropionic acid. https://doi.org/10.1006/nbdi.1999.0244>
22. Arch Neurol 1993; 50:1197-208.
< S, Moraes CT. Mitochondrial encephalomyopathies. https://doi.org/10.1001/archneur.1993.00540110075008>
23. Exo Neurol 1996; 138:298-304.
< SL, Ho DY, Sapolsyk RM. Energy and glutamate dependency of 3-nitropropionic acid neurotoxicity in culture. https://doi.org/10.1006/exnr.1996.0068>
24. J Neurosci Res 1993; 35:452-8.
< DM, Simpson J, Uhler TA et al. Striatal degeneration induced by mitochondrial blockade is prevented by biologically delivered NGF. https://doi.org/10.1002/jnr.490350413>
25. Toxicon 1995; 33:327-31.
< Y, He F, Zhang S, Zhang J. Lipid peroxidation in rats intoxicated with 3-nitropropionic acid. https://doi.org/10.1016/0041-0101(94)00173-6>
26. Neuroscience 1998; 87:494-507.
< A, Deshpande SB, Shimano Y, Nishino H. Astrocytes are more vulnerable than neurons to cellular Ca2+ overload induced by a mitochondrial toxin, 3-nitropropionic acid. https://doi.org/10.1016/S0306-4522(98)00139-0>
27. Toxicol Lett 1985; 27:83-9.
< DH, Wilson MP, Hamar DW. Brain enzyme and clinical alternations induced in rats and mice by nitroaliphatic toxicants. https://doi.org/10.1016/0378-4274(85)90123-7>
28. J Neurol Sci 1998; 153:251-63.
< MB, Muller U. Recent developments in the molecular genetics of mitochondrial disorders. https://doi.org/10.1016/S0022-510X(97)00295-5>
29. Neuroscience 1998; 84:503-10.
< JG, Sheu SS, Gross RA, Greenamyre JT. 3-Nitropropionic acid excacerbates N-methyl-D-aspartate toxicity in striatal culture by multiple mechanisms. https://doi.org/10.1016/S0306-4522(97)00389-8>
30. Neuroscience 1997; 70:45-56.
< MC, Hantrye P, Dolan R, Palfi S, Maziére M, Brouillet E. Quantifiable bradykinesia, gait abnormalities nad Huntington‘s disease-like striatal lesions in rats chronically treated with 3-nitropropionic acid. https://doi.org/10.1016/S0306-4522(96)00602-1>
31. Neuroscience 1997; 81:141-9.
< MC, Palfi S, Stutzmann JM, Maziére M, Hantrye P, Brouillet E. Riluzole protects from motor deficits and striatal degeneration produced by systemic 3-nitropropionic acid intoxication in rats. https://doi.org/10.1016/S0306-4522(97)00192-9>
32. Biochem J 1999; 340:491-5.
< CR, Salem MA, Simpson D, Wainwright SJ. 3-Nitropropionic acid oxidase from horseshoe vetch (Hippocrepis comosa): a novel plant enzyme. https://doi.org/10.1042/bj3400491>
33. Vet Hum Toxicol 1990; 32:168-9.
JG, Burrows GI. Locoism in horses.
34. J Neurochem 1999; 72:716-23.
< JY, Kim DK, Hwang JY, Kim YH, Seo, JH. Antioxidative nad proapoptotic effects of riluzole on cultured cortical neurons. https://doi.org/10.1046/j.1471-4159.1999.0720716.x>
35. Naunyn Shiedbergers Arch Pharmacol 1998; 358:181-90.
< BD, Kratzer U, Schmidt WJ. Riluzole, a glutamate release inhibitor, and motor behavior. https://doi.org/10.1007/PL00005241>
36. Biomed Environ Sci 1992; 5:161-77.
X, Luo X, Hu W. Studies on the epidemiology and etiology of moldy sugarcane poisoning in China.
37. Toxicol Lett 1983; 19:171-8.
< W, Pass MA, Madryga FJ. Toxicity of miserotoxin and its aglycone (3-nitropropanol) to rats. https://doi.org/10.1016/0378-4274(83)90279-5>
38. Toxicol Lett 1984; 23:9-15.
< W, Pass MA, Muir AD, Rode LM. Absorption of 3-nitropropanol (miserotoxin aglycone) from the compound stomach of cattle. https://doi.org/10.1016/0378-4274(84)90003-1>
39. J Toxicol Clin Toxicol 1995; 33:363-7.
< L. Moldy sugarcane poisoning - a case report with a brief review. https://doi.org/10.3109/15563659509028924>
40. Science (Wash) 1982; 216:190-1.
< RJ, James LF. Loco intoxication: indolizidine alkaloids of spotted locoweed (Astragalus lentiginosus). https://doi.org/10.1126/science.6801763>
41. Toxicol Lett 1984; 20:137-41.
< AD, Majak W, Pass MA, Yost GS. Conversion of 3-nitropropanol (miserotoxin aglycone) to 3-nitropropionic acid in cattle and sheep. https://doi.org/10.1016/0378-4274(84)90138-3>
42. Metab Brain Dis 1999; 14:83-94.
< PA, Scallet AC, Rountree RL, Ye X, Binienda Z. 3-Nitropropionic acid (3-NPA) produces hypothermia and inhibits histochemical labeling of succinate dehydrogenase (SDH) in rat brain. https://doi.org/10.1023/A:1020753629477>
43. Synthesis 1986; 7:535-8.
< R, Schwab W, Ehrler R, Jaeger V. 3-Nitropropanal and 3-nitropropanol: preparation of the parent compounds and derivatives. https://doi.org/10.1055/s-1986-31694>
44. J Neurosci 1997; 17:3064-73.
< Z, Geddes JW. Mechanisms of cell death induced by the mitochondrial toxin 3-nitropropionic acid: Acute excitotoxic necrosis and delayed apoptosis. https://doi.org/10.1523/JNEUROSCI.17-09-03064.1997>
<PubMed>
45. Nat Toxins 1994; 2:386-94.
MA, Carlise CH, Reuhl KR. 3-Nitropropionic acid toxicity in cultured murine embryonal carcinoma cells.
46. Toxicol Appl Pharmacol 1985; 78:310-15.
< MA, Muir AD, Majak W, Yost GS. Effect of alcohol and aldehyde dehydrogenase inhibitors on the toxicity of 3-nitropropanol in rats. https://doi.org/10.1016/0041-008X(85)90294-7>
47. Bull World Health Organ 1999; 77:754-66.
M, Radic B, Lucic A, Pavlovic M. Toxic effects of mycotoxins in humans.
48. J Neurosci 1995; 15:3775-87.
< C, Hedreen JC, Price DL, Koliatsos VE. Evidence for apoptotic cell death in Huntington disease and excitotoxic animal models. https://doi.org/10.1523/JNEUROSCI.15-05-03775.1995>
<PubMed>
49. J Anim Sci 1988; 66:3124-30.
< MH, James LF, Nielsen DB, Baker DC, Molyneus RJ. Cattle grazing Wahweap Milkvetch in southeastern Utah. https://doi.org/10.2527/jas1988.66123124x>
50. J Anim Sci 1990; 68:1354-62.
< MH, Panter KE, James LF. Feed preferences and habituation of sheep poisoned by Locoweed. https://doi.org/10.2527/1990.6851354x>
51. Nervenartz 1993; 64:215-20.
H, Janetzky B, Klinge M, Riederer P. Parkinson disease - a mitochondrial myopathy? (Article in Germany).
52. Brain Res 1997; 778:140-9.
< NC, Jr, Lin W, Cameron CM, Roerig DL. Differential responses of extracellular GABA to intrastriatal perfusions of 3-nitropropionic acid and quinolinic acid in the rat. https://doi.org/10.1016/S0006-8993(97)01048-2>
53. Brain Res Brain Res Protoc 1999; 4:124-31.
< NC, Jr, Lin W, Cameron CM, Roerig DL. Extracellular perfusion of rat brain nuclei using microdialysis: a method for studying differential neurotransmitter release in response to neurotoxins. https://doi.org/10.1016/S1385-299X(99)00008-2>
54. Brain Res 1992; 586:61-6.
< M, Hori N, Ludolph AC, Carpenter DO, Spencer PS, Allen CN. Inhibition of energy metabolism by 3-nitropropionic acid activates ATP-sensitive potassium channels. https://doi.org/10.1016/0006-8993(92)91371-K>
55. Science 1999; 283:1488-93.
< M. Oxidative phosphorylation at the fin de siecle. https://doi.org/10.1126/science.283.5407.1488>
56. Biochim Biophys Acta 1998; 1366:225-33.
< AH. Mitochondrial dysfunction in neurodegenerative disorders. https://doi.org/10.1016/S0005-2728(98)00115-7>
57. Progr Neuro-Psychopharmacol Biol Psych 1998; 22:1217-40.
< DA, Dong J., Gundy CD, Haik-Creguer KL, Dunbar GL. Comparison of intrastriatal injections of quinolinic acid and 3-nitropropionic acid for use in animal models of Huntington’s disease. https://doi.org/10.1016/S0278-5846(98)00070-0>
58. Vet Rec 1999; 145:169-71.
< DJ, Wainwright SJ, Hipkin CR. Presence of 3-nitropropionic acid in widely distributed pasture legumes in Britain. https://doi.org/10.1136/vr.145.6.169>
59. Neurosci Lett 1999; 259:9-12.
< I, Nozaki K, Takagi Y, Hashimoto N. 3-Nitropropionic acid induces ischemic tolerance in gerbil hippocampus in vivo. https://doi.org/10.1016/S0304-3940(98)00875-1>
60. Neurosci Lett 1999w; 275:145-8.
< I, Nozaki K, Takagi Y, Hashimoto N, Yodoi J. Expression and distribution of redox regulatory protein, thioredoxin after metabolic impairment by 3-nitropropionic acid in rat brain. https://doi.org/10.1016/S0304-3940(99)00763-6>
61. Neurosci Lett 1997; 237:121-4.
< T, Nozaki K., Tokime T, Hashimoto N, Kikuchi H. 3-Nitropropionic acid induces poly(ADP-ribosyl)ation and apoptosis related gene expression in the striatum in vivo. https://doi.org/10.1016/S0304-3940(97)00827-6>
62. Eur J Pharmacol 1999; 370:251-6.
< EM, Blaszczak P, Saran T, Kleinrok Z, Turski WA. AMPA/Kainate-related mechanisms contribute to convulsant and preconvulsant effects of 3-nitropropionic acid. https://doi.org/10.1016/S0014-2999(99)00147-8>
63. Votoček E. Chemie organická. Second edition. Vol. I. Praha:Politika, 1927, p. 346.
64. Ann Pharmacother 1997; 31:738-44.
< ML, Landis BE. Riluzole: a new agent for amyotrophic lateral sclerosis. https://doi.org/10.1177/106002809703100614>
65. J Bioenerg Biomembr 1994; 26:241-50.
< DC. Mitochondrial DNA mutations in diseases of energy metabolism. https://doi.org/10.1007/BF00763096>
66. Neurosci Lett 1999; 272:207-10.
< M, Bergk A, Isaev NK et al. Induction of ischemic tolerance in rat cortical neurons by 3-nitropropionic acid: chemical preconditioning. https://doi.org/10.1016/S0304-3940(99)00594-7>
67. Eur J Pharmacol 1993; 248:223-8.
M, Paul SM. 3-Nitropropioic acid is an indirect excitotoxin to cultured cerebellar granule neurons.
68. Soc Neurosci Abstr 1998; 23:2183.
F, Lindauer U, Busch C, Liao W, Megow D, Dirnagl U. Tolerance to focal ischemie induced by 3-NPA is mediated by formation of reactive oxygen species.
69. Am J Vet Res 1970; 31:259-62.
MC, Norris FA, Van Kampen KR. Metabolism of miserotoxin to 3-nitro-1-propanol in bovine and ovine ruminal fluids.