BIX01294 hydrochloride | CAS#1392399-03-9 | 935693-62-2 | HMTase inhibitor

MedKoo Cat#: 406565 | Name: BIX01294 HCl

Description:

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

BIX01294 is a potent chemical inhibitor of G9a methyltransferase that catalyzes the mono-and di-methylation of the lysine 9 residue of histone H3. BIX01294 suppresses osteoclast differentiation on mouse macrophage-like Raw264.7 cells. BIX01294 enhances the cardiac potential of bone marrow cells.

Chemical Structure

BIX01294 HCl

CAS#1392399-03-9 ( HCl)

Theoretical Analysis

MedKoo Cat#: 406565

Name: BIX01294 HCl

CAS#: 1392399-03-9 ( HCl)

Chemical Formula: C28H41Cl3N6O2

Exact Mass: 0.0000

Molecular Weight: 600.03

Elemental Analysis: C, 56.05; H, 6.89; Cl, 17.72; N, 14.01; O, 5.33

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,250.00	Ready to ship
500mg	USD 2,650.00	Ready to ship
1g	USD 3,750.00	Ready to ship
2g	USD 6,150.00	Ready to ship

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Related CAS #

935693-62-2 (free base) 1392399-03-9 ( HCl) 935693-62-2 (HCl hydrate)

Synonym

BIX01294; BIX-01294; BIX 01294; BIX01294 HCl

IUPAC/Chemical Name

N-(1-benzylpiperidin-4-yl)-6,7-dimethoxy-2-(4-methyl-1,4-diazepan-1-yl)quinazolin-4-amine trihydrochloride.

InChi Key

FMURUEPQXKJIPS-UHFFFAOYSA-N

InChi Code

InChI=1S/C28H38N6O2.3ClH/c1-32-12-7-13-34(17-16-32)28-30-24-19-26(36-3)25(35-2)18-23(24)27(31-28)29-22-10-14-33(15-11-22)20-21-8-5-4-6-9-21;;;/h4-6,8-9,18-19,22H,7,10-17,20H2,1-3H3,(H,29,30,31);3*1H

SMILES Code

CN1CCN(C2=NC(NC3CCN(CC4=CC=CC=C4)CC3)=C5C=C(OC)C(OC)=CC5=N2)CCC1.[H]Cl.[H]Cl.[H]Cl

Appearance

White to off-white 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, not in water

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

BIX01294 free base CAS#935693-62-2 Chemical Formula: C28H38N6O2 Exact Mass: 490.3056 Molecular Weight: 490.6520 Elemental Analysis: C, 68.54; H, 7.81; N, 17.13; O, 6.52

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A20T07K16

QC Data

View QC data: current batch, Lot# A20T07K16

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

BIX-01294 is an inhibitor of G9a Histone Methyltransferase with an IC50 of 1.9 μM.

In vitro activity:

Here it’s demonstrated that BIX01294, an inhibitor of a G9a histone methyltransferase (introducing H3K9me2 and H3K27me3 repressive marks) triggers autophagy in human glioma cells. Pharmacological or genetic inhibition of autophagy decreased LC3-II accumulation and GFP-LC3 punctation in BIX01294-treated cells. GSCs-enriched spheres originating from glioma cells and GBM patient-derived cultures express lower levels of autophagy related (ATG) genes than the parental glioma cell cultures. Typical differentiation inducers that upregulate neuronal and astrocytic markers in sphere cultures, increase the level of ATG mRNAs. G9a binds to the promoters of autophagy (LC3B, WIPI1) and differentiation-related (GFAP, TUBB3) genes in GSCs. Higher H3K4me3 (an activation mark) and lower H3K9me2 (the repressive mark) levels at the promoters of studied genes were detected in serum-differentiated cells than in sphere cultures. BIX01294 treatment upregulates the expression of autophagy and differentiation-related genes in GSCs. Pharmacological inhibition of autophagy decreases GFAP and TUBB3 expression in BIX01294-treated GSCs suggesting that BIX01294-induced differentiation of GSCs is autophagy-dependent. Reference: Sci Rep. 2016 Dec 9;6:38723. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/27934912/

In vivo activity:

To determine if BIX01294 can suppress VEGF-induced angiogenesis in vivo, mice were injected with 200 μl of VEGF containing Matrigel with or without BIX01294. VEGF induced endothelial cells from the neighboring blood vessels to develop functional neo-vessels into the Matrigel plug. BIX01294 treatment reduced the extent of VEGF-induced microvessel formation within the Matrigel plug (Fig. 3C). These results demonstrated that BIX01294 potently blocked in vivo neovascularization. Reference: Mol Cells. 2015 Jun;38(6):528-34. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/26013382/

	Solvent	mg/mL	mM
Solubility
	DMSO	98.0	166.33
	Ethanol	8.0	13.33

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 600.03 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:

In vitro protocol:

1. Ciechomska IA, Przanowski P, Jackl J, Wojtas B, Kaminska B. BIX01294, an inhibitor of histone methyltransferase, induces autophagy-dependent differentiation of glioma stem-like cells. Sci Rep. 2016 Dec 9;6:38723. doi: 10.1038/srep38723. PMID: 27934912; PMCID: PMC5146656. 2. Tsuda H, Zhao N, Imai K, Ochiai K, Yang P, Suzuki N. BIX01294 suppresses osteoclast differentiation on mouse macrophage-like Raw264.7 cells. Bosn J Basic Med Sci. 2013 Nov;13(4):271-5. doi: 10.17305/bjbms.2013.2339. PMID: 24289765; PMCID: PMC4334004.

In vivo protocol:

1. Oh SY, Seok JY, Choi YS, Lee SH, Bae JS, Lee YM. The Histone Methyltransferase Inhibitor BIX01294 Inhibits HIF-1α Stability and Angiogenesis. Mol Cells. 2015 Jun;38(6):528-34. doi: 10.14348/molcells.2015.0026. Epub 2015 May 27. PMID: 26013382; PMCID: PMC4469910. 2. Deng BB, Jiao BP, Liu YJ, Li YR, Wang GJ. BIX-01294 enhanced chemotherapy effect in gastric cancer by inducing GSDME-mediated pyroptosis. Cell Biol Int. 2020 Sep;44(9):1890-1899. doi: 10.1002/cbin.11395. Epub 2020 Jun 8. PMID: 32437063; PMCID: PMC7496303.

1: Pang AL, Title AC, Rennert OM. Modulation of microRNA expression in human lung cancer cells by the G9a histone methyltransferase inhibitor BIX01294. Oncol Lett. 2014 Jun;7(6):1819-1825. Epub 2014 Apr 4. PubMed PMID: 24932239; PubMed Central PMCID: PMC4049738. 2: Tsuda H, Zhao N, Imai K, Ochiai K, Yang P, Suzuki N. BIX01294 suppresses osteoclast differentiation on mouse macrophage-like Raw264.7 cells. Bosn J Basic Med Sci. 2013 Nov;13(4):271-5. PubMed PMID: 24289765. 3: Mezentseva NV, Yang J, Kaur K, Iaffaldano G, RÃ©mond MC, Eisenberg CA, Eisenberg LM. The histone methyltransferase inhibitor BIX01294 enhances the cardiac potential of bone marrow cells. Stem Cells Dev. 2013 Feb 15;22(4):654-67. doi: 10.1089/scd.2012.0181. Epub 2012 Nov 7. PubMed PMID: 22994322; PubMed Central PMCID: PMC3564468. 4: Imai K, Togami H, Okamoto T. Involvement of histone H3 lysine 9 (H3K9) methyltransferase G9a in the maintenance of HIV-1 latency and its reactivation by BIX01294. J Biol Chem. 2010 May 28;285(22):16538-45. doi: 10.1074/jbc.M110.103531. Epub 2010 Mar 24. PubMed PMID: 20335163; PubMed Central PMCID: PMC2878073.