Bovinocidin
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| Category | Antibiotics |
| Catalog number | BBF-00167 |
| CAS | 504-88-1 |
| Molecular Weight | 119.08 |
| Molecular Formula | C3H5NO4 |
| Purity | >98% |
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Description
Bovinocidin is a fatty acid derivative produced by Streptomyces sp., Aspergillus avenaceus, Asp. flavust, Asp. oryzae and Penicillum atrovenetum. The minimum inhibitory concentration for BCG tuberculosis (BCG) is 50-100 ㎍/mL.
Specification
| Synonyms | Hiptagenic acid |
| IUPAC Name | 3-nitropropanoic acid |
| Canonical SMILES | C(C[N+](=O)[O-])C(=O)O |
| InChI | InChI=1S/C3H5NO4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6) |
| InChI Key | WBLZUCOIBUDNBV-UHFFFAOYSA-N |
| Source | 3-Nitropropionic acid is a neurotoxin produced by certain plants and fungi, such as those of the genus Astragalus, Coronilla, Lotus, Hippocrepis, Scorpiurus, and Securigera. |
Properties
| Appearance | Powder |
| Application | Antihypertensive Agents |
| Boiling Point | 303°C at 760 mmHg |
| Melting Point | 68-70°C(lit.) |
| Density | 1.393 g/cm3 |
| Solubility | Soluble in Water, methanol, ethyl acetate, acetone, chloroform |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | 3-Nitropropionic acid (Bovinocidin) is a suicide inhibitor of succinate dehydrogenase, an enzyme required for the activity of the tricarboxylic acid (TCA) cycle as well as mitochondrial respiratory complex II of the electron transport chain. It forms a covalent adduct with the side chain of Arg297, inactivating the succinate dehydrogenase. This affects neurons by leading to NMDA-receptor activation, excessive calcium influx, and formation of reactive oxygen species, eventually causing neuronal cell death. |
Reference Reading
1.[Determination of 3-nitropropionic acid in poisoning samples by ultra-performance liquid chromatography-tandem mass spectrometry].
Liu H, Liu G, Kang L, Chen Y, Jiang J. Wei Sheng Yan Jiu. 2016 Jan;45(1):56-60.
OBJECTIVE: An ultra-performance liquid chromatography-tandem mass spectrometric method was established for determination of 3-nitropropionic acid of sugarcane, sugarcane bagasse, vomit, serum and urine.
2.Anle138b Partly Ameliorates Motor Deficits Despite Failure of Neuroprotection in a Model of Advanced Multiple System Atrophy.
Fellner L1, Kuzdas-Wood D1, Levin J2, Ryazanov S3, Leonov A3, Griesinger C3, Giese A4, Wenning GK1, Stefanova N1. Front Neurosci. 2016 Mar 10;10:99. doi: 10.3389/fnins.2016.00099. eCollection 2016.
The neurodegenerative disorder multiple system atrophy (MSA) is characterized by autonomic failure, cerebellar ataxia and parkinsonism in any combination associated with predominantly oligodendroglial α-synuclein (α-syn) aggregates (glial cytoplasmic inclusions = GCIs). To date, there is no effective disease modifying therapy. Previous experiments have shown that the aggregation inhibitor anle138b reduces neurodegeneration, as well as behavioral deficits in both transgenic and toxin mouse models of Parkinson's disease (PD). Here we analyzed whether anle138b improves motor skills and reduces neuronal loss, as well as oligodendroglial α-syn aggregation in the PLP-α-syn transgenic mouse challenged with the mitochondrial toxin 3-nitropropionic acid (3-NP) to model full-blown MSA. Following 1 month of treatment with anle138b, MSA mice showed signs of motor improvement affecting stride length, but not pole, grip strength, and beam test performance.
3.Two Defensive Lines in Juvenile Leaf Beetles; Esters of 3-nitropropionic Acid in the Hemolymph and Aposematic Warning.
Pauls G1, Becker T1, Rahfeld P1, Gretscher RR1, Paetz C2, Pasteels J3, von Reuss SH1, Burse A1, Boland W4. J Chem Ecol. 2016 Mar 31. [Epub ahead of print]
Juveniles of the leaf beetles in subtribe Chrysomelina have efficient defense strategies against predators. When disturbed, they transiently expose volatile deterrents in large droplets from nine pairs of defensive glands on their back. Here, we report on an additional line of defense consisting of the non-volatile isoxazolin-5-one glucoside and its 3-nitropropanoyl ester in the larval hemolymph. Because isoxazolin-5-one derivatives were not detectable in related leaf beetle taxa, they serve as a diagnostic marker for the Chrysomelina subtribe. Conjugation of isotopically labelled 3-nitropropionic acid to isoxazolin-5-one glucoside in vivo demonstrates its function as a carrier for the 3-nitropropanoyl esters. The previous identification of characteristic glucosides as precursors of the volatile deterrents underlines the general importance of glucosides for sequestration from food plants, and the subsequent transport in the hemolymph to the defense system.
4.L-theanine, a Component of Green Tea Prevents 3-Nitropropionic Acid (3-NP)-Induced Striatal Toxicity by Modulating Nitric Oxide Pathway.
Jamwal S1,2, Kumar P3. Mol Neurobiol. 2016 Mar 9. [Epub ahead of print]
L-theanine is unique amino acid which readily crosses blood brain barrier and possesses neuroprotective potential against neurodegenerative disorders including Huntington disease (HD). HD is characterized by selective loss of GABAergic medium spiny neurons. 3-nitropropionic acid (3-NP) induces a spectrum of HD-like neuropathology in rat striatum and widely used as experimental tool to study HD. Therefore, the present study was intended to investigate the effect of L-theanine against 3-NP-induced striatal toxicity and to explore its possible mechanism. Rats were administered with 3-NP for 21 days. L-theanine was given once a day, 1 h prior to 3-NP treatment for 21 days and L-NAME (10 mg/kg, i.p.), NO inhibitor and L-arginine (50 mg/kg; i.p.), NO precursor were administered 1 h prior to L-theanine treatment. Body weight and behavioral observation were made on weekly basis. On the 22nd day, animals were sacrificed, and the striatum was isolated for biochemical (LPO, GSH, and nitrite), pro-inflammatory cytokines and neurochemical analysis.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C3H5NO4
Molecular Weight (Monoisotopic Mass): 119.0219 Da
Molecular Weight (Avergae Mass): 119.0761 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C3H5NO4
Molecular Weight (Monoisotopic Mass): 119.0219 Da
Molecular Weight (Avergae Mass): 119.0761 Da
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C3H5NO4
Molecular Weight (Monoisotopic Mass): 119.0219 Da
Molecular Weight (Avergae Mass): 119.0761 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C3H5NO4
Molecular Weight (Monoisotopic Mass): 119.0219 Da
Molecular Weight (Avergae Mass): 119.0761 Da
1H NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 1H
Frequency: 100
Nucleus: 1H
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
