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MedKoo Cat#: 561690 | Name: Pifithrin-alpha
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pifithrin-alpha is a p53 inactivator. It also has neuroprotective activity against strokes. The inhibition of p53 with pifithrin-alpha rescued 2ME-induced endoreduplication.

Chemical Structure

Pifithrin-alpha
Pifithrin-alpha
CAS#63208-82-2

Theoretical Analysis

MedKoo Cat#: 561690

Name: Pifithrin-alpha

CAS#: 63208-82-2

Chemical Formula: C16H19BrN2OS

Exact Mass: 366.0401

Molecular Weight: 367.31

Elemental Analysis: C, 52.32; H, 5.21; Br, 21.75; N, 7.63; O, 4.36; S, 8.73

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
200mg USD 750.00 2 Weeks
500mg USD 1,650.00 2 Weeks
1g USD 2,950.00 2 Weeks
2g USD 5,250.00 2 Weeks
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Synonym
Pifithrin-alpha; Pifithrin alpha; PFT-alpha; PFTalpha; PFT alpha;
IUPAC/Chemical Name
2-(2-Imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3-yl)-1-(4-methylphenyl)ethanone;hydrobromide
InChi Key
HAGVCKULCLQGRF-UHFFFAOYSA-N
InChi Code
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
SMILES Code
CC1=CC=C(C(CN2C(SC3=C2CCCC3)=N)=O)C=C1.[H]Br
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pifithrin-α hydrobromide is a p53 inhibitor which blocks its transcriptional activity and prevents cells from apoptosis. Pifithrin-α hydrobromide is also an aryl hydrocarbon receptor (AhR) agonist.
In vitro activity:
This study investigated the effect of pifithrin (PFT)-α, an inhibitor of p53-dependent transcriptional activation, on self-renewal of ES cells. These results revealed that treatment of ES cells with PFT-α resulted in the inhibition of ES cell propagation in a dose-dependent manner, as indicated by a marked reduction in the cell number and colony size. Also, PFT-α caused a cell cycle arrest and significant reduction in DNA synthesis. Reference: Biochem Biophys Res Commun. 2012 Apr 13;420(3):605-10. https://pubmed.ncbi.nlm.nih.gov/22445757/
In vivo activity:
Chemotherapy and radiation therapy for cancer often have severe side effects that limit their efficacy. Because these effects are in part determined by p53-mediated apoptosis, temporary suppression of p53 has been suggested as a therapeutic strategy to prevent damage of normal tissues during treatment of p53-deficient tumors. To test this possibility, a small molecule was isolated for its ability to reversibly block p53-dependent transcriptional activation and apoptosis. This compound, pifithrin-alpha, protected mice from the lethal genotoxic stress associated with anticancer treatment without promoting the formation of tumors. Reference: Science. 1999 Sep 10;285(5434):1733-7. https://pubmed.ncbi.nlm.nih.gov/10481009/
Solvent mg/mL mM comments
Solubility
DMF 1.0 2.72
DMSO 40.2 109.40
DMSO:PBS (pH 7.2) (1:10) 0.1 0.27
Water 1.3 3.40
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 367.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Yu H, Han Y, Cui C, Li G, Zhang B. Loss of SV2A promotes human neural stem cell apoptosis via p53 signaling. Neurosci Lett. 2023 Mar 13;800:137125. doi: 10.1016/j.neulet.2023.137125. Epub 2023 Feb 11. PMID: 36780942. 2. Abdelalim EM, Tooyama I. The p53 inhibitor, pifithrin-α, suppresses self-renewal of embryonic stem cells. Biochem Biophys Res Commun. 2012 Apr 13;420(3):605-10. doi: 10.1016/j.bbrc.2012.03.041. Epub 2012 Mar 16. PMID: 22445757. 3. Culmsee C, Zhu X, Yu QS, Chan SL, Camandola S, Guo Z, Greig NH, Mattson MP. A synthetic inhibitor of p53 protects neurons against death induced by ischemic and excitotoxic insults, and amyloid beta-peptide. J Neurochem. 2001 Apr;77(1):220-8. doi: 10.1046/j.1471-4159.2001.t01-1-00220.x. PMID: 11279278. 4. Komarov PG, Komarova EA, Kondratov RV, Christov-Tselkov K, Coon JS, Chernov MV, Gudkov AV. A chemical inhibitor of p53 that protects mice from the side effects of cancer therapy. Science. 1999 Sep 10;285(5434):1733-7. doi: 10.1126/science.285.5434.1733. PMID: 10481009.
In vitro protocol:
1. Yu H, Han Y, Cui C, Li G, Zhang B. Loss of SV2A promotes human neural stem cell apoptosis via p53 signaling. Neurosci Lett. 2023 Mar 13;800:137125. doi: 10.1016/j.neulet.2023.137125. Epub 2023 Feb 11. PMID: 36780942. 2. Abdelalim EM, Tooyama I. The p53 inhibitor, pifithrin-α, suppresses self-renewal of embryonic stem cells. Biochem Biophys Res Commun. 2012 Apr 13;420(3):605-10. doi: 10.1016/j.bbrc.2012.03.041. Epub 2012 Mar 16. PMID: 22445757.
In vivo protocol:
1. Culmsee C, Zhu X, Yu QS, Chan SL, Camandola S, Guo Z, Greig NH, Mattson MP. A synthetic inhibitor of p53 protects neurons against death induced by ischemic and excitotoxic insults, and amyloid beta-peptide. J Neurochem. 2001 Apr;77(1):220-8. doi: 10.1046/j.1471-4159.2001.t01-1-00220.x. PMID: 11279278. 2. Komarov PG, Komarova EA, Kondratov RV, Christov-Tselkov K, Coon JS, Chernov MV, Gudkov AV. A chemical inhibitor of p53 that protects mice from the side effects of cancer therapy. Science. 1999 Sep 10;285(5434):1733-7. doi: 10.1126/science.285.5434.1733. PMID: 10481009.
1: Wu A, Zhao C. Astilbin Induces Apoptosis in Oral Squamous Cell Carcinoma through p53 Reactivation and Mdm-2 Inhibition. Dokl Biochem Biophys. 2024 Aug 28. doi: 10.1134/S1607672924600374. Epub ahead of print. PMID: 39196525. 2: Shang J, Wen Y, Zhang X, Huang G, Chen W, Wang B, Wu K, Xiang Q, Liu X. Naoxintong capsule accelerates mitophagy in cerebral ischemia-reperfusion injury via TP53/PINK1/PRKN pathway based on network pharmacology analysis and experimental validation. J Ethnopharmacol. 2024 Aug 20:118721. doi: 10.1016/j.jep.2024.118721. Epub ahead of print. PMID: 39173723. 3: Strasser AS, Gonzalez-Reiche AS, Zhou X, Valdebenito-Maturana B, Ye X, Zhang B, Wu M, van Bakel H, Jabs EW. Limb reduction in an Esco2 cohesinopathy mouse model is mediated by p53-dependent apoptosis and vascular disruption. Nat Commun. 2024 Aug 21;15(1):7154. doi: 10.1038/s41467-024-51328-3. PMID: 39168984; PMCID: PMC11339411. 4: Xia Y, Wang D, Zhao H, Meng T, Jiang Q, Pan Z, Wang G, An T, Li B, Bi S, Wang H, Lu J, Liu H, Lin H, Lin C, Zheng Q, Li D. Silencing of tropomodulin 1 inhibits acute myeloid leukemia cell proliferation and tumor growth by elevating karyopherin alpha 2-mediated autophagy. Pharmacol Res. 2024 Sep;207:107327. doi: 10.1016/j.phrs.2024.107327. Epub 2024 Jul 28. PMID: 39079577. 5: Li Y, Xu H, Shi J, Li C, Li M, Zhang X, Xue Q, Qiu J, Cui L, Sun Y, Song X, Chen L. Regulation of the p53/SLC7A11/GPX4 Pathway by Gentamicin Induces Ferroptosis in HEI-OC1 Cells. Otol Neurotol. 2024 Sep 1;45(8):947-953. doi: 10.1097/MAO.0000000000004271. Epub 2024 Aug 6. PMID: 39072683. 6: Lu G, Tang Y, Chen O, Guo Y, Xiao M, Wang J, Liu Q, Li J, Gao T, Zhang X, Zhang J, Cheng Q, Kuang R, Gu J. Aberrant activation of p53-TRIB3 axis contributes to diabetic myocardial insulin resistance and sulforaphane protection. J Adv Res. 2024 Jul 26:S2090-1232(24)00307-2. doi: 10.1016/j.jare.2024.07.025. Epub ahead of print. PMID: 39069209. 7: Li J, Tang Y, Lu G, Liu Q, Guo Y, Wang J, Xiao M, Gao T, Zhang X, Gu J. Elevation of p53 sensitizes obese kidney to adriamycin-induced aberrant lipid homeostasis via repressing HNF4α-mediated FGF21 sensitivity. J Adv Res. 2024 Jul 15:S2090-1232(24)00299-6. doi: 10.1016/j.jare.2024.07.014. Epub ahead of print. PMID: 39019110. 8: Schaufelberger SA, Schaettin M, Azzarito G, Rosselli M, Leeners B, Dubey RK. 2-Methoxyestradiol, an Endogenous 17β-Estradiol Metabolite, Induces Antimitogenic and Apoptotic Actions in Oligodendroglial Precursor Cells and Triggers Endoreduplication via the p53 Pathway. Cells. 2024 Jun 22;13(13):1086. doi: 10.3390/cells13131086. PMID: 38994940; PMCID: PMC11240791. 9: Wu E, Wu C, Jia K, Zhou S, Sun L. HSPA8 inhibitors augment cancer chemotherapeutic effectiveness via potentiating necroptosis. Mol Biol Cell. 2024 Aug 1;35(8):ar108. doi: 10.1091/mbc.E24-04-0194. Epub 2024 Jul 3. PMID: 38959101; PMCID: PMC11321035. 10: Mahboubi H, Yu H, Malca M, McCusty D, Stochaj U. Pifithrin-µ Induces Stress Granule Formation, Regulates Cell Survival, and Rewires Cellular Signaling. Cells. 2024 May 21;13(11):885. doi: 10.3390/cells13110885. PMID: 38891018; PMCID: PMC11172192. 11: Kang F, Wu J, Hong L, Zhang P, Song J. Iodine-125 seed inhibits proliferation and promotes apoptosis of cholangiocarcinoma cells by inducing the ROS/p53 axis. Funct Integr Genomics. 2024 Jun 12;24(3):114. doi: 10.1007/s10142-024-01392-1. PMID: 38862667; PMCID: PMC11166828. 12: Giraldo-Berrio D, Mendivil-Perez M, Velez-Pardo C, Jimenez-Del-Rio M. Rotenone Induces a Neuropathological Phenotype in Cholinergic-like Neurons Resembling Parkinson's Disease Dementia (PDD). Neurotox Res. 2024 Jun 6;42(3):28. doi: 10.1007/s12640-024-00705-3. PMID: 38842585; PMCID: PMC11156752. 13: Park JI, Jung SY, Song KH, Lee DH, Ahn J, Hwang SG, Jung IS, Lim DS, Song JY. Predictive DNA damage signaling for low‑dose ionizing radiation. Int J Mol Med. 2024 Jun;53(6):56. doi: 10.3892/ijmm.2024.5380. Epub 2024 May 2. PMID: 38695243; PMCID: PMC11093554. 14: Ding R, Wang Y, Xu L, Sang S, Wu G, Yang W, Zhang Y, Wang C, Qi A, Xie H, Liu Y, Dai A, Jiao L. QiDongNing induces lung cancer cell apoptosis via triggering P53/DRP1-mediated mitochondrial fission. J Cell Mol Med. 2024 May;28(9):e18353. doi: 10.1111/jcmm.18353. PMID: 38682742; PMCID: PMC11057058. 15: Yang L, Gao YL, Jiang S, Qian B, Che L, Wu JS, Du ZB, Wang MZ, Yang Y, Lin YC, Liu G, Lin ZN. Aflatoxin B1-exposed hepatocyte-derived extracellular vesicles: Initiating hepatic stellate cell-mediated liver fibrosis through a p53-Parkin-dependent mitophagy pathway. Ecotoxicol Environ Saf. 2024 Jun 1;277:116363. doi: 10.1016/j.ecoenv.2024.116363. Epub 2024 Apr 25. PMID: 38663190. 16: Wang X, Pan S, Chen L, Liang C, Zhu Y, Zhou K, Shi X. Sijunzi decoction enhances sensitivity of colon cancer cells to NK cell destruction by modulating P53 expression. J Ethnopharmacol. 2024 Jul 15;329:118115. doi: 10.1016/j.jep.2024.118115. Epub 2024 Apr 3. PMID: 38580190. 17: Ulhaq ZS, You MS, Jiang YJ, Tse WKF. p53 inhibitor or antioxidants reduce the severity of ethmoid plate deformities in zebrafish Type 3 Treacher Collins syndrome model. Int J Biol Macromol. 2024 May;266(Pt 2):131216. doi: 10.1016/j.ijbiomac.2024.131216. Epub 2024 Mar 29. PMID: 38556235. 18: Wang S, Zou Z, Tang Z, Deng J. AMPK/MTOR/TP53 Signaling Pathway Regulation by Calcitonin Gene-Related Peptide Reduces Oxygen-Induced Lung Damage in Neonatal Rats through Autophagy Promotion. Inflammation. 2024 Aug;47(4):1083-1108. doi: 10.1007/s10753-023-01963-7. Epub 2024 Mar 19. PMID: 38502251. 19: Ma JW, Xiong ZY, Cai XC, Li X, Ren SY, An SQ, Zhang ZY, Zhang YZ. Ningxin- Tongyu-Zishen formula alleviates the senescence of granulosa cells on D-galactose-induced premature ovarian insufficiency mice. Aging (Albany NY). 2024 Feb 28;16(5):4541-4562. doi: 10.18632/aging.205607. Epub 2024 Feb 28. PMID: 38428403; PMCID: PMC10968698. 20: Naik L, Patel S, Kumar A, Ghosh A, Mishra A, Das M, Nayak DK, Saha S, Mishra A, Singh R, Behura A, Dhiman R. 4-(Benzyloxy)phenol-induced p53 exhibits antimycobacterial response triggering phagosome-lysosome fusion through ROS- dependent intracellular Ca2+ pathway in THP-1 cells. Microbiol Res. 2024 May;282:127664. doi: 10.1016/j.micres.2024.127664. Epub 2024 Feb 24. PMID: 38422860.