Pifithrin-beta | CAS#60477-34-1

Pifithrin-beta HBr
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 555210

CAS#: 511296-88-1 (HBr)

Description: Pifithrin-beta, also known as QB102 and Cyclic-Pifithrin-α, is is p53 functional inhibitor. Pifithrin-β counteracts the Alzheimer peptide non-β-amyloid component effects in human SH-SY5Y cells.

Chemical Structure

Pifithrin-beta HBr

CAS# 511296-88-1 (HBr)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 555210
Name: Pifithrin-beta HBr
CAS#: 511296-88-1 (HBr)
Chemical Formula: C16H17BrN2S
Exact Mass: 0.00
Molecular Weight: 349.290
Elemental Analysis: C, 55.02; H, 4.91; Br, 22.88; N, 8.02; S, 9.18

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 250
100mg	USD 450
200mg	USD 750
500mg	USD 1450
1g	USD 2250
2g	USD 4250
5g	USD 6850
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 60477-34-1 (free base) 511296-88-1 (HBr) 2109248-93-1 (HCl)

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

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

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Product Data:

Product Data

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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/
In vivo activity:	TBD

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. 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

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.
In vivo protocol:	TBD

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1: 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. PubMed PMID: 26902357.

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. PubMed PMID: 24646317; PubMed Central PMCID: PMC4030802.

3: 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. PubMed PMID: 21362431.

4: 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. PubMed PMID: 21324703.

5: 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. PubMed PMID: 19859789.

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