Pifithrin-α hydrobromide

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Cat.No. 1267 - Pifithrin-a hydrobromide | C16H18N2OS.HBr | CAS No. 63208-82-2
Description: p53 inhibitor. Also aryl hydrocarbon receptor agonist
Chemical Name: 1-(4-Methylphenyl)-2-(4,5,6,7-tetrahydro-2-imino-3(2H)-benzothiazolyl)ethanone hydrobromide
Datasheet
Citations (2)
Literature
Pathways

Biological Activity

Inhibitor of p53; reversibly blocks p53-dependent transcriptional activation and apoptosis. Protects against neuronal death in models of stroke and neurodegenerative disorders. Active in vivo; protects mice from the side-effects of cancer therapy associated with p53 induction. Supresses self-renewal of embryonic stem cells. Also aryl hydrocarbon receptor (AHR) agonist, causes upregulation of AHR target gene CYP1A1 (EC50 = 1.1 μM). Cyclic analog available (Cat. No. 3843).

Compound Libraries

Pifithrin-α hydrobromide is also offered as part of the Tocriscreen Stem Cell Toolbox. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 367.3
Formula C16H18N2OS.HBr
Storage Desiccate at -20°C
CAS Number 63208-82-2
PubChem ID 9929138
InChI Key HAGVCKULCLQGRF-UHFFFAOYSA-N
Smiles Br.CC1=CC=C(C=C1)C(=O)CN1C(=N)SC2=C1CCCC2

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 36.73 100

Preparing Stock Solutions

The following data is based on the product molecular weight 367.3. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.72 mL 13.61 mL 27.23 mL
5 mM 0.54 mL 2.72 mL 5.45 mL
10 mM 0.27 mL 1.36 mL 2.72 mL
50 mM 0.05 mL 0.27 mL 0.54 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Culmsee et al (2001) A synthetic inhibitor of p53 protects neurons against death induced by ischemic and excitotoxic insults, and amyloid β-peptide. J.Neurochem. 77 220 PMID: 11279278

Hoagland et al (2005) The p53 inhibitor pifithrin-α is a potent agonist of the aryl hydrocarbon receptor. J.Pharmacol.Exp.Ther. 314 603 PMID: 15843497

Komarov et al (1999) A chemical inhibitor of p53 that protects mice from the side effects of cancer therapy. Science 285 1733 PMID: 10481009

Komarova and Gudkov (2000) Suppression of p53: a new approach to overcome side effects of antitumor therapy. Biochemistry 65 41 PMID: 10702639

Abdelalim and Tooyama (2012) The p53 inhibitor, pifithrin-α, suppresses self-renewal of embryonic stem cells. Biochem.Biophys.Res.Comm. 420 605 PMID: 22445757


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View Related Products by Product Action

View all p53 Inhibitors

Keywords: p53 inhibitors inhibits aryl hydrocarbon receptors agonists AHR Transcription Factors Pifithrin-alpha hydrobromide p53

2 Citations for Pifithrin-α hydrobromide

Citations are publications that use Tocris products. Selected citations for Pifithrin-α hydrobromide include:

Fraser et al (2006) Regulation of p53 and suppression of apoptosis by the soluble guanylyl cyclase/cGMP pathway in human ovarian cancer cells. Cell Commun Signal 25 2203 PMID: 16288207

Guha et al (2015) Novel Pactamycin Analogs Induce p53 Dependent Cell-Cycle Arrest at S-Phase in Human Head and Neck Squamous Cell Carcinoma (HNSCC) Cells. PLoS One 10 e0125322 PMID: 25938491


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Reviews

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Literature in this Area

Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Cell Cycle & DNA Damage Repair

Cell Cycle & DNA Damage Repair Poster

In normal cells, each stage of the cell cycle is tightly regulated, however in cancer cells many genes and proteins that are involved in the regulation of the cell cycle are mutated or over expressed. Adapted from the 2015 Cancer Product Guide, Edition 3, this poster summarizes the stages of the cell cycle and DNA repair. It also highlights strategies for enhancing replicative stress in cancer cells to force mitotic catastrophe and cell death.

Pathways for Pifithrin-α hydrobromide

p53

p53 Signaling Pathway

p53 signaling plays an important role in the co-ordination of the cellular response different types of stress such as DNA damage and hypoxia. The downstream signals lead to apoptosis, senescence and cell cycle arrest.

Protocols

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