Synonym
Pifithrin-β; Pifithrin-beta; PFTβ; PFT-β; QB102; QB102; QB102; Cyclic-Pifithrin-α
IUPAC/Chemical Name
5,6,7,8-Tetrahydro-2-(4-methylphenyl)imidazo[2,1-b]benzothiazole hydrobromide
InChi Key
SGNCOAOESGSEOP-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H16N2S.BrH/c1-11-6-8-12(9-7-11)13-10-18-14-4-2-3-5-15(14)19-16(18)17-13;/h6-10H,2-5H2,1H3;1H
SMILES Code
CC1=CC=C(C2=CN3C(SC4=C3CCCC4)=N2)C=C1.[H]Br
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
Biological target:
Pifithrin-β hydrobromide (PFT β hydrobromide) is a potent p53 inhibitor with an IC50 of 23 μM.
In vitro activity:
The present study aimed to examine the functional and molecular effects of miR‑128 in epilepsy, in order to investigate its potential protective mechanisms. Firstly, miR‑128 expression in rats with lithium chloride‑induced epilepsy was demonstrated to be increased compared with the control rats. Subsequently, results from an in vitro epilepsy model demonstrated that overexpression of miR‑128 promoted nerve cell apoptosis, increased the protein expression of tumor protein p53, BCL2 associated X (Bax) and Cytochrome c, and enhanced caspase‑3/9 activity, whereas it suppressed the protein expression of sirtuin 1 (SIRT1). In addition, these alterations may be reversed by the downregulation of miR‑128. Furthermore, treatment with CAY10602, a SIRT1 agonist, reduced the effects of miR‑128 on nerve cells in vitro. Treatment with pifithrin‑β hydrobromide, a p53 inhibitor, was additionally able to mitigate the effects of miR‑128 in vitro.
Reference: Int J Mol Med. 2019 Aug;44(2):694-704. https://pubmed.ncbi.nlm.nih.gov/31173166/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
10.0 |
28.63 |
| DMF:PBS (pH 7.2) (1:6) |
0.1 |
0.40 |
| DMSO |
18.1 |
51.84 |
| Ethanol |
1.8 |
5.01 |
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
349.29
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.
| 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. Chen DZ, Wang WW, Chen YL, Yang XF, Zhao M, Yang YY. miR‑128 is upregulated in epilepsy and promotes apoptosis through the SIRT1 cascade. Int J Mol Med. 2019 Aug;44(2):694-704. doi: 10.3892/ijmm.2019.4223. Epub 2019 May 30. PMID: 31173166.
2. Da Pozzo E, La Pietra V, Cosimelli B, Da Settimo F, Giacomelli C, Marinelli L, Martini C, Novellino E, Taliani S, Greco G. p53 functional inhibitors behaving like pifithrin-β counteract the Alzheimer peptide non-β-amyloid component effects in human SH-SY5Y cells. ACS Chem Neurosci. 2014 May 21;5(5):390-9. doi: 10.1021/cn4002208. Epub 2014 Mar 28. PMID: 24646317; PMCID: PMC4030802.
In vitro protocol:
1. Chen DZ, Wang WW, Chen YL, Yang XF, Zhao M, Yang YY. miR‑128 is upregulated in epilepsy and promotes apoptosis through the SIRT1 cascade. Int J Mol Med. 2019 Aug;44(2):694-704. doi: 10.3892/ijmm.2019.4223. Epub 2019 May 30. PMID: 31173166.
2. Da Pozzo E, La Pietra V, Cosimelli B, Da Settimo F, Giacomelli C, Marinelli L, Martini C, Novellino E, Taliani S, Greco G. p53 functional inhibitors behaving like pifithrin-β counteract the Alzheimer peptide non-β-amyloid component effects in human SH-SY5Y cells. ACS Chem Neurosci. 2014 May 21;5(5):390-9. doi: 10.1021/cn4002208. Epub 2014 Mar 28. PMID: 24646317; PMCID: PMC4030802.
1: Chen DZ, Wang WW, Chen YL, Yang XF, Zhao M, Yang YY. miR‑128 is upregulated in epilepsy and promotes apoptosis through the SIRT1 cascade. Int J Mol Med. 2019 Aug;44(2):694-704. doi: 10.3892/ijmm.2019.4223. Epub 2019 May 30. PMID: 31173166.
2: Gui WF, Xu S, Dang ZS, Zhao YM. In Vitro and in Vivo Effect of MAPK Signal Transduction Pathway Inhibitors on Echinococcus multilocularis. J Parasitol. 2019 Feb;105(1):146-154. PMID: 30807708.
3: Lisachev PD, Pustylnyak VO, Shtark MB. Sirt1 Regulates p53 Stability and Expression of Its Target S100B during Long-Term Potentiation in Rat Hippocampus. Bull Exp Biol Med. 2016 Feb;160(4):432-4. doi: 10.1007/s10517-016-3189-5. Epub 2016 Feb 23. PMID: 26902357.
4: Da Pozzo E, La Pietra V, Cosimelli B, Da Settimo F, Giacomelli C, Marinelli L, Martini C, Novellino E, Taliani S, Greco G. p53 functional inhibitors behaving like pifithrin-β counteract the Alzheimer peptide non-β-amyloid component effects in human SH-SY5Y cells. ACS Chem Neurosci. 2014 May 21;5(5):390-9. doi: 10.1021/cn4002208. Epub 2014 Mar 28. PMID: 24646317; PMCID: PMC4030802.
5: Fernández-Cruz ML, Valdehita A, Alonso M, Mann E, Herradón B, Navas JM. Biological and chemical studies on aryl hydrocarbon receptor induction by the p53 inhibitor pifithrin-α and its condensation product pifithrin-β. Life Sci. 2011 Apr 25;88(17-18):774-83. doi: 10.1016/j.lfs.2011.02.019. Epub 2011 Feb 26. PMID: 21362431.
6: Christodoulou MS, Colombo F, Passarella D, Ieronimo G, Zuco V, De Cesare M, Zunino F. Synthesis and biological evaluation of imidazolo[2,1-b]benzothiazole derivatives, as potential p53 inhibitors. Bioorg Med Chem. 2011 Mar 1;19(5):1649-57. doi: 10.1016/j.bmc.2011.01.039. Epub 2011 Jan 25. PMID: 21324703.
7: Waters FJ, Shavlakadze T, McIldowie MJ, Piggott MJ, Grounds MD. Use of pifithrin to inhibit p53-mediated signalling of TNF in dystrophic muscles of mdx mice. Mol Cell Biochem. 2010 Apr;337(1-2):119-31. doi: 10.1007/s11010-009-0291-2. Epub 2009 Oct 27. PMID: 19859789.
