Pifithrin-alpha hydrobromide An inhibitor of p53 that reversibly blocks p53 dependent transcriptional activation and apoptosis

Pifithrin-α hydrobromide (CAS 63208-82-2)

Pifithrin-α hydrobromide | CAS 63208-82-2 is rated 5.0 out of 5 by 1.
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Synonym: PFT-α; 1-(4-Methylphenyl)-2-(4,5,6,7-tetrahydro-2-imino-3(2H)-benzothiazolyl)ethanone hydrobromide
Application: An inhibitor of p53 that reversibly blocks p53 dependent transcriptional activation and apoptosis
CAS Number: 63208-82-2
Purity: ≥98%
Molecular Weight: 367.30
Molecular Formula: C16H18N2OS•HBr
* Refer to Certificate of Analysis for lot specific data (including water content).
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Pifithrin-α is a reversible inhibitor of p53-mediated apoptosis and p53-dependent gene transcription such as cyclin G, p21/waf1, and mdm2 expression. It enhances cell survival after genotoxic stress such as UV irradiation and treatment with cytotoxic compounds including doxorubicin (sc-280681), etopoxide, paclitaxel, and cytosine-β-D-arabinofuranoside. Pifithrin-α protects mice from lethal whole body γ-irradiation, and does not induce visible tumors. Protects against neuronal death in models of stroke and neurodegenerative disorders. Pifithrin-α is also an aryl hydrocarbon receptor (AHR) agonist, which leads to the upregulation of AHR target gene CYP1A1 (EC50 = 1.1 μM).


References

1. Komarov, P G., et al., 1999. A chemical inhibitor of p53 that protects mice from the side effects of cancer therapy. Science (New York, N.Y.). 285(5434): 1733-7. PMID: 10481009
2. Komarova, E A., et al., 2000. Suppression of p53: a new approach to overcome side effects of antitumor therapy. Biochemistry. Biokhimia. 65(1): 41-8. PMID: 10702639
3. Culmsee, C., et al., 2001. A synthetic inhibitor of p53 protects neurons against death induced by ischemic and excitotoxic insults, and amyloid beta-peptide. Journal of neurochemistry. 77(1): 220-8. PMID: 11279278
4. Lorenzo, Elisa., et al., 2002. Doxorubicin induces apoptosis and CD95 gene expression in human primary endothelial cells through a p53-dependent mechanism. The Journal of biological chemistry. 277(13): 10883-92. PMID: 11779855
5. Hoagland, Martin S., et al., 2005. The p53 inhibitor pifithrin-alpha is a potent agonist of the aryl hydrocarbon receptor. The Journal of pharmacology and experimental therapeutics. 314(2): 603-10. PMID: 15843497
6. Sohn, D., et al., 2009. Pifithrin-alpha protects against DNA damage-induced apoptosis downstream of mitochondria independent of p53. Cell death and differentiation. 16(6): 869-78. PMID: 19229248

Physical State :
Solid
Solubility :
Soluble in DMSO (20 mg/ml), water, DMF (~1 mg/ml), 1:10 DMSO:PBS (pH 7.2) (~ 0.1 mg/ml), 100% ethanol, and methanol. Sparingly soluble in aqueous buffers.
Storage :
Store at -20° C
Melting Point :
192.1-192.5° C
IC50 :
CYP1A1 upregulation: EC5050 = 1.1 µM
pK Values :
pKb: 3.19 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
9929138
Merck Index :
14: 7421
MDL Number :
MFCD00417851
SMILES :
CC1=CC=C(C=C1)C(=O)CN2C3=C(CCCC3)SC2=N.Br

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Certificate of Analysis

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Pifithrin-alpha hydrobromide  Product Citations

See how others have used Pifithrin-alpha hydrobromide. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 23 total

PMID: # 28608259  Qiu, M. et al. 2017. Cancer Chemother. Pharmacol. 80: 275-286.

PMID: # 27464000  Zhang, Y. et al. 2016. Autophagy. 12: 1538-59.

PMID: # 26884717  Yu, W. et al. 2016. Int. J. Biol. Sci. 12: 198-209.

PMID: # 26431790  Yin, R. et al. 2016. Respir Physiol Neurobiol. 220: 81-7.

PMID: # 25466893  Liu, W. et al. 2015. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 29: 1113-23.

PMID: # 25727698  Wang, Y. et al. 2015. J. Neurochem. 133: 828-43.

PMID: # 24722580  Moretti, RM. et al. 2014. PloS one. 9: e93713.

PMID: # 25193078  Das, A. et al. 2014. Exp. Cell Res. 328: 361-78.

PMID: # 24946002  Sun, H. et al. 2014. Br. J. Cancer. 111: 281-91.

PMID: # 21521785  Verma, S. et al. 2011. Blood. 117: 6600-7.

Citations 1 to 10 of 23 total

Is this product cell permeable?

Asked by: SCchem16
Thank you for your question. This chemical, Pifithrin-α hydrobromide: sc-45050, is a cell-permeable chemical inhibitor of p53.
Answered by: Chemical Support 2
Date published: 2017-04-05

What are the recommended conditions for long term storage?

Asked by: SCchem16
Thank you for your question. For this chemical, Pifithrin-α hydrobromide (CAS 63208-82-2), we recommend this be stored long-term at -20ºC and away from light and moisture.
Answered by: Chemical Support 2
Date published: 2017-04-05
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Rated 5 out of 5 by from Luo Luo, et. al. (PubMed ID 19475672) used Pifithrin- hydrobromide, a p53 inhibitor, to treat rats post middle cerebral artery occlusion. They found that p53 was indeed reduced. -SCBT Publication Review
Date published: 2015-01-25
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