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B7263

Sigma-Aldrich

N-tert-Butyl-α-phenylnitrone

≥98% (GC)

Synonyme(s) :

N-Benzylidene-tert-butylamine N-oxide, PBN, Phenyl N-t-butylnitrone

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About This Item

Formule linéaire :
C6H5CH=N(O)C(CH3)3
Numéro CAS:
3376-24-7
Poids moléculaire :
177.24
Numéro Beilstein :
2044028
Numéro CE :
222-168-6
Numéro MDL:
MFCD00008799
Code UNSPSC :
12352202
ID de substance PubChem :
24891981
Nomenclature NACRES :
NA.77

Pureté

≥98% (GC)

Forme

powder

Couleur

white

Pf

73-74 °C (lit.)

Solubilité

DMSO: soluble

Température de stockage

−20°C

Chaîne SMILES 

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-

Clé InChI

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)

Actions biochimiques/physiologiques

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).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

microRNA-34a-mediated down-regulation of the microglial-enriched triggering receptor and phagocytosis-sensor TREM2 in age-related macular degeneration
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)
Genome-wide mapping of 8-oxo-7, 8-dihydro-2?-deoxyguanosine reveals accumulation of oxidatively-generated damage at DNA replication origins within transcribed long genes of mammalian cells
Amente S, et al.
Nucleic Acids Research, 47(1), 221-236 (2018)
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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