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P4359

Sigma-Aldrich

Pifithrin-α

≥95% (HPLC), powder

Synonyme(s) :

2-(2-Imino-4,5,6,7-tetrahydrobenzothiazol-3-yl)-1-p-tolylethanone hydrobromide, PFT-α

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About This Item

Formule linéaire :
C16H18N2OS·HBr
Numéro CAS:
63208-82-2
Poids moléculaire :
367.30
Numéro MDL:
MFCD00417851
Code UNSPSC :
12352200
ID de substance PubChem :
24898529
Nomenclature NACRES :
NA.77

Pureté

≥95% (HPLC)

Forme

powder

Conditions de stockage

protect from light

Couleur

off-white

Pf

192.1-192.5 °C (lit.)

Solubilité

DMSO: 20 mg/mL

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

Br[H].Cc1ccc(cc1)C(=O)CN2C(=N)SC3=C2CCCC3

InChI

1S/C16H18N2OS.BrH/c1-11-6-8-12(9-7-11)14(19)10-18-13-4-2-3-5-15(13)20-16(18)17;/h6-9,17H,2-5,10H2,1H3;1H

Clé InChI

HAGVCKULCLQGRF-UHFFFAOYSA-N

Application

Pifithrin-α has been used:
  • to study the effect of specific p53 inhibitor on p53-upregulated modulator of apoptosis (PUMA) expression after transient global cerebral ischemia (tGCI)
  • as p53 inhibitor to treat PA1 cells
  • as a tumor protein p53 (TRP53) inhibitor, to treat mouse lung epithelial-12 (MLE-12) cells

Actions biochimiques/physiologiques

Pifithrin-α is a reversible inhibitor of p53-mediated apoptosis and p53-dependent gene transcription such as cyclin G, p21/waf1, and mdm2 expression. Pifithrin-α enhances cell survival after genotoxic stress such as UV irradiation and treatment with cytotoxic compounds including doxorubicin, etopoxide, paclitaxel, and cytosine-β-D-arabinofuranoside. Pifithrin-α protects mice from lethal whole body γ-irradiation without an increase in cancer incidence. The protective effect is not seen in p53-null mice or cells expressing a dominant negative mutant of the p53 gene. Protection is conferred by the transient expression of p53 in p53-deficient cell lines.

Caractéristiques et avantages

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Inhibition of regulatory-associated protein of mechanistic target of rapamycin prevents hyperoxia-induced lung injury by enhancing autophagy and reducing apoptosis in neonatal mice
Sureshbabu A, et al.
American Journal of Respiratory Cell and Molecular Biology, 55(5), 722-735 (2016)
E A Komarova et al.
Biochemistry. Biokhimiia, 65(1), 41-48 (2000-03-07)
The p53 protein is traditionally believed to be a tumor suppressor. Activation of p53-dependent apoptosis in response to damage to cell DNA provides for the elimination of possible tumor cell precursors. However, in some cases the activity of p53 can
Ahmed Malki et al.
Bioorganic chemistry, 72, 57-63 (2017-04-04)
Small molecules that can target human cancers have been highly sought to increase the anticancer efficacy, the present work describes the design and synthesis of novel series of five quinuclidinone derivatives (2a-2e). Their anticancer activities were investigated against breast cancer
Potential role of PUMA in delayed death of hippocampal CA1 neurons after transient global cerebral ischemia
Niizuma K, et al.
Stroke, 40(2), 618-625 (2009)
Hui Zhang et al.
The Journal of biological chemistry, 290(2), 1129-1140 (2014-11-22)
Growth arrest is one of the essential features of cellular senescence. At present, the precise mechanisms responsible for the establishment of the senescence-associated arrested phenotype are still incompletely understood. Given that ERK1/2 is one of the major kinases controlling cell
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