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3-Nitropropionic acid

Catalog No.
B5734
Mitochondrial respiratory complex II (succinate dehydrogenase) inhibitor
Grouped product items
SizePriceStock Qty
100mg
$50.00
In stock
500mg
$72.00
In stock
For scientific research use only and should not be used for diagnostic or medical purposes.

Tel: +1-832-696-8203

Email: [email protected]

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Background

3-Nitropropionic acid (CAS No.: 504-88-1) is a naturally occurring nitroaliphatic toxin produced by certain plants and fungi and is widely utilized as a biochemical tool compound in studies of mitochondrial dysfunction and neurodegeneration. It acts as an irreversible inhibitor of mitochondrial respiratory complex II (succinate dehydrogenase), forming a covalent adduct within the enzyme active site and thereby disrupting electron transport chain function, leading to impaired ATP production, cellular energy depletion, and enhanced generation of reactive oxygen species. This mitochondrial impairment is associated with oxidative stress, mitochondrial DNA damage, and induction of apoptotic cell death pathways. In vitro, 3-nitropropionic acid exhibits biological activity in the low micromolar range, including reported antimycobacterial effects, and is frequently employed to model oxidative stress and mitochondrial toxicity in cultured cells. In vivo, it is extensively used to induce striatal neurodegeneration and reproduce key pathological and behavioral features of Huntington’s disease, as well as to study seizure susceptibility and neuroprotective interventions in rodent and primate models. Its applications in biomedical research include probing mitochondrial bioenergetics, evaluating antioxidant or anti-apoptotic strategies, and screening compounds targeting neurodegenerative disease mechanisms, with experimental concentrations or dosing regimens varying depending on specific study designs.

Chemical Properties

Physical AppearanceA solid
Storage-20°C
M.Wt119.08
Cas No.504-88-1
FormulaC3H5NO4
Synonymsβ-Nitropropionic Acid; 3-NP; NSC 64266
Solubility≥103 mg/mL in H2O; ≥114.2 mg/mL in EtOH; ≥6 mg/mL in DMSO
Chemical Name3-nitropropanoic acid
Canonical SMILESClC1=CC=C(C=C1)C[C@H](C(O)=O)N
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

Protocol

Cell experiment:[3]

Cell lines

PC12 cells

Reaction Conditions

4 or 8 mM 3-nitropropionic acid for 48 h incubation

Applications

3-Nitropropionic acid induced cytotoxicity by triggering ROS production and mitochondrial DNA damage, which could be avoided by overexpressing Bcl-2 in PC12 cells.

Animal experiment:[2]

Animal models

Female ICR mice

Dosage form

6.25, 12.5 and 25 mg/kg

Continuous intraperitoneal injection for 7 days

Applications

3-Nitropropionic acid induced granulosa cell apoptosis, large follicle atresia, and an increase of ROS levels in the ovary. Thus, 3-nitropropionic acid could be used to establish an in vivo model of ovarian oxidative stress for studying the mechanism of resulting damage induced by free radicals and for the screening of novel antioxidants.

Note

The technical data provided above is for reference only.

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. Journal of Biological Chemistry, 2006, 281(9): 5965-5972.

2. Zhang JQ, Shen M, Zhu CC, et al. 3-Nitropropionic acid induces ovarian oxidative stress and impairs follicle in mouse. PLoS One, 2014, 9(2): e86589.

3. Mandavilli BS, Boldogh I, Van Houten B. 3-Nitropropionic acid-induced hydrogen peroxide, mitochondrial DNA damage, and cell death are attenuated by Bcl-2 overexpression in PC12 cells. Brain research. Molecular brain research, 2005, 133(2): 215-223.

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