3-Nitropropanoic acid

3-Nitropropanoic acid (β-Nitropropionic acid) is an irreversible and orally active inhibitor of succinate dehydrogenase. 3-Nitropropanoic acid exhibits potent antimycobacterial activity with a MIC value of 3.3 μM. 3-Nitropropanoic acid can induce cell apoptosis[1][2].

Product Specifications

CAS Number

[504-88-1]

Product Name Alternative

β-Nitropropionic acid; Bovinocidin

UNSPSC

12352211

Hazard Statement

H301

Target

Apoptosis; Autophagy; Bacterial

Type

Natural Products

Related Pathways

Anti-infection; Apoptosis; Autophagy

Applications

Metabolism-sugar/lipid metabolism

Field of Research

Infection; Inflammation/Immunology; Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/3-Nitropropanoic_acid.html

Concentration

10mM

Purity

99.94

Solubility

DMSO : 125 mg/mL (ultrasonic) |H2O : 100 mg/mL (ultrasonic)

Smiles

O=C(O)CC[N+]([O-])=O

Molecular Formula

C3H5NO4

Molecular Weight

119.08

Precautions

H301

References & Citations

[1]Huang LS, 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 Mar 3;281 (9) :5965-72.|[2]Chomcheon P, et al. 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 Jul;68 (7) :1103-5.|[3]Solesio ME, et al. 3-Nitropropionic acid induces autophagy by forming mitochondrial permeability transition pores rather than activating the mitochondrial fission pathway. Br J Pharmacol. 2013 Jan;168 (1) :63-75.|[4]Kang B, et al. Effect of 3-nitropropionic acid inducing oxidative stress and apoptosis of granulosa cells in geese. Biosci Rep. 2018 Sep 12;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 May 1;17 (9) :3064-73.|[6]Túnez I, et al. 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 Nov;37 (4) :252-6.|[7]Urbanska EM, et al. A. Mitochondrial toxin 3-nitropropionic acid evokes seizures in mice. Eur J Pharmacol. 1998 Oct 16;359 (1) :55-8. |[8]Borlongan CV, et al. Hyperactivity and hypoactivity in a rat model of Huntington's disease: the systemic 3-nitropropionic acid model. Brain Res Brain Res Protoc. 1997 Aug;1 (3) :253-7.|[9]Tsang TM, et al. Metabonomic characterization of the 3-nitropropionic acid rat model of Huntington's disease. Neurochem Res. 2009 Jul;34 (7) :1261-71.|[10]Shear DA, et al. Comparison of intrastriatal injections of quinolinic acid and 3-nitropropionic acid for use in animal models of Huntington's disease. Prog Neuropsychopharmacol Biol Psychiatry. 1998 Oct;22 (7) :1217-40.|[11]Túnez I, et al. 3-Nitropropionic acid as a tool to study the mechanisms involved in Huntington's disease: past, present and future. Molecules. 2010 Feb 10;15 (2) :878-916.