All Photos(1)
Synonym(s):
N-Benzylidene-tert-butylamine N-oxide, PBN, Phenyl N-t-butylnitrone
Linear Formula:
C6H5CH=N(O)C(CH3)3
CAS Number:
Molecular Weight:
177.24
Beilstein:
2044028
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
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Quality Level
Assay
≥98% (GC)
form
powder
color
white
mp
73-74 °C (lit.)
solubility
DMSO: soluble
storage temp.
−20°C
SMILES string
CC(C)(C)[N+](\[O-])=C\c1ccccc1
InChI
1S/C11H15NO/c1-11(2,3)12(13)9-10-7-5-4-6-8-10/h4-9H,1-3H3/b12-9-
InChI key
IYSYLWYGCWTJSG-XFXZXTDPSA-N
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Application
N-tert-Butyl-α-phenylnitrone has been used:
- as a component of Dneasy Blood&Tissue buffer to preserve the oxidized state of DNA extracted from human non-tumorigenic epithelial breast (MCF10A) cells
- as a free radical scavenger of reactive oxygen species (ROS) in microglial (MG) cell lines
- to attenuate fibroblast senescence in unstable oral squamous cell carcinomas (GU-OSCC)
Biochem/physiol Actions
N-tert-butyl-α-phenylnitrone (PBN) is a commonly used free-radical spin trap. It has been shown to reduce the number of emboli-induced cerebral microinfarctions in the rabbit cortex and prevent neoplasia by its radical scavenging activity and its ability to inhibit cyclooxygenase-2 activity. Reported to inhibit the induction of nitric oxide synthase (iNOS), thereby preventing the overproduction of nitric oxide (NO). PBN in a dose of 100 mg/kg i.p. reduced necrosis of the substantia nigra, pars reticulate in flurothyl-induced status epilepticus in rats. It protects against some types of post-trauma epileptogenic events in an animal model of epilepsy. The lethal dose of PBN in rats was found to be approximately 100 mg/100 g body weight (0.564 mmol/100Å g).
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Bhattacharjee S, et al.
Testing, 11(3), e0150211-e0150211 (2016)
Progression of genotype-specific oral cancer leads to senescence of cancer-associated fibroblasts and is mediated by oxidative stress and TGF-beta
Hassona Y, et al.
Carcinogenesis, 34(6), 1286-1295 (2013)
Jiwon Yang et al.
Journal of neurochemistry, 124(4), 523-535 (2012-12-04)
Oxidative stress after stroke is associated with the inflammatory system activation in the brain. The complement cascade, especially the degradation products of complement component 3, is a key inflammatory mediator of cerebral ischemia. We have shown that pro-inflammatory complement component
Jian-Jun Wen et al.
Journal of the American College of Cardiology, 55(22), 2499-2508 (2010-06-01)
The purpose of this study was to determine the pathological importance of oxidative stress-induced injurious processes in chagasic heart dysfunction. Trypanosoma cruzi-induced inflammatory pathology and a feedback cycle of mitochondrial dysfunction and oxidative stress may contribute to Chagas disease. Sprague-Dawley
Robert A Floyd et al.
Anti-cancer agents in medicinal chemistry, 11(4), 373-379 (2011-06-10)
The nitrone compound PBN, α-phenyl-tert-butylnitrone, and closely related nitrones have anti-cancer activity in several experimental cancer models. The three experimental models most extensively studied include A) the rat choline deficiency liver cancer model, B) the rat C6 glioma model and
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