3-Nitropropionic acid (Synonyms: β-Nitropropionic Acid, 3-NP, NSC 64266) |
Catalog No.GC17394
One-Click Copy Product Info
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3-Nitropropionic acid (β-Nitropropionic acid) is an irreversible inhibitor of succinate dehydrogenase.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 504-88-1
Sample solution is provided at 25 µL, 10mM.
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3-Nitropropionic acid, produced by certain plants and fungi, is a substance that specifically inhibits mitochondrial respiratory chain complex II. 3-Nitropropionic acid exhibits potent antimycobacterial activity with the minimum inhibition concentration of 3.3µM, but is inactive against NCI-H187, BC, KB, and Vero cell lines. 3-Nitropropionic acid, which produces neurodegenerative lesions, is commonly used to establish animal models of Huntington's disease. 3-Nitropropionic acid can also be used to induce epilepsy models[1][2].
In vitro, 3-Nitropropionic acid (5mM; 3h) induced autophagy and disrupted mitochondrial morphology in SH-SY5Y cells[3]. 3-Nitropropionic acid (5mM; 30min) induced swelling in mitochondria isolated from rat liver[3]. 3-Nitropropionic acid (0.1–5mM; 24h) did not affect granulosa cell viability, while 5-10mM significantly inhibited viability in a dose-dependent manner[4]. Treatment with 3-Nitropropionic acid (5mM; 24h) induced ROS production and apoptosis and inhibits the viability of granulosa cells in geese[4]. 3-Nitropropionic acid (0-15mM; 48h) induced a dose-dependent decrease in the number of primary hippocampal neurons[5].
In vivo, a single injection of 3-Nitropropionic acid (100-120mg/kg; i.p.) induced epileptic seizures in mice within 120min, manifesting as tremors or head twitching[6]. 3-Nitropropionic acid (20mg/kg/d; i.p.; 4d) increased lipid peroxidation in the striatum and synaptosomes, while decreasing enzyme activity and increasing SOD activity in both the striatum and cortex in Wistar rats[7].
References:
[1] Huang LS, Sun G, Cobessi D, et al. 3-nitropropionic acid is a suicide inhibitor of mitochondrial respiration that, upon oxidation by complex II, forms a covalent adduct with a catalytic base arginine in the active site of the enzyme. J Biol Chem. 2006;281(9):5965-5972.
[2] Chomcheon P, Wiyakrutta S, Sriubolmas N, Ngamrojanavanich N, Isarangkul D, Kittakoop P. 3-Nitropropionic acid (3-NPA), a potent antimycobacterial agent from endophytic fungi: is 3-NPA in some plants produced by endophytes?. J Nat Prod. 2005;68(7):1103-1105.
[3] Solesio ME, Saez-Atienzar S, Jordan J, Galindo MF. 3-Nitropropionic acid induces autophagy by forming mitochondrial permeability transition pores rather than activating the mitochondrial fission pathway. Br J Pharmacol. 2013;168(1):63-75.
[4] Kang B, Wang X, Xu Q, Wu Y, Si X, Jiang D. Effect of 3-nitropropionic acid inducing oxidative stress and apoptosis of granulosa cells in geese. Biosci Rep. 2018;38(5):BSR20180274.
[5] Pang Z, Geddes JW. Mechanisms of cell death induced by the mitochondrial toxin 3-nitropropionic acid: acute excitotoxic necrosis and delayed apoptosis. J Neurosci. 1997;17(9):3064-3073.
[6] Urbanska EM, Blaszczak P, Saran T, Kleinrok Z, Turski WA. Mitochondrial toxin 3-nitropropionic acid evokes seizures in mice. Eur J Pharmacol. 1998;359(1):55-58.
[7] Túnez I, Montilla P, Del Carmen Muñoz M, Feijóo M, Salcedo M. Protective effect of melatonin on 3-nitropropionic acid-induced oxidative stress in synaptosomes in an animal model of Huntington's disease. J Pineal Res. 2004;37(4):252-256.
| Cell experiment [1]: | |
Cell lines | SH-SY5Y |
Preparation Method | SH-SY5Y cells were transfected with GFP-LC3 (for autophagy) or pDsRed2-mito plasmid (for mitochondrial morphology) and kept for 24h. 3-Nitropropionic acid was added to culture medium at a final concentration of 5mM for 3h. |
Reaction Conditions | 5mM; 3h |
Applications | 3-Nitropropionic acid induced autophagy and disrupted mitochondrial morphology. |
| Animal experiment [2]: | |
Animal models | Male Albino–Swiss mice |
Preparation Method | 3-Nitropropionic acid was dissolved in water or suspended in 1% Tween 80. 3-Nitropropionic acid was given intraperitoneally. Behavioral observations were performed within 120min following application of 3-Nitropropionic acid. Mortality rate was evaluated at 120min after 3-Nitropropionic acid injection. |
Dosage form | 100-120mg/kg; i.p.; once |
Applications | Within 5-10min of systemic application of 3-Nitropropionic acid, the mice became akinetic and displayed diminished responsiveness to external stimuli. When 3-Nitropropionic acid was given at the doses of 100-120mg/kg, occasional tremor or head twitches were observed. |
References: | |
| Cas No. | 504-88-1 | SDF | |
| Synonyms | β-Nitropropionic Acid, 3-NP, NSC 64266 | ||
| Chemical Name | 3-nitropropanoic acid | ||
| Canonical SMILES | OC(CC[N+]([O-])=O)=O | ||
| Formula | C3H5NO4 | M.Wt | 119.08 |
| Solubility | ≥ 6mg/mL in DMSO | Storage | 4°C, away from moisture and light |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 8.3977 mL | 41.9886 mL | 83.9772 mL |
| 5 mM | 1.6795 mL | 8.3977 mL | 16.7954 mL |
| 10 mM | 839.8 μL | 4.1989 mL | 8.3977 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
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Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )
Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
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- Purity: >99.50% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 22 reference(s) in Google Scholar.)