BIX 01294 trihydrochloride hydrate | CAS# 935693-62-2

BIX 01294 trihydrochloride hydrate
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 573453

CAS#: 935693-62-2 (trihydrochloride hydrate)

Description: BIX 01294 trihydrochloride hydrate, a diazepin-quinazolinamine derivative, is a histone-lysine methyltransferase (HMTase) inhibitor that modulates the epigenetic status of chromatin. BIX-01294 inhibits the G9aHMTase dependent levels of histone-3 lysine (9) methylation (H3K9me). Bix-01294 and valproic acid, a histone deacetylase (HDAC) inhibitor, may replace the requirement for ectopic OCT4 (POU5F1) and cMyc respectively in pluripotent stem cell induction (iPS) recipes.

Chemical Structure

BIX 01294 trihydrochloride hydrate

CAS# 935693-62-2 (trihydrochloride hydrate)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 573453
Name: BIX 01294 trihydrochloride hydrate
CAS#: 935693-62-2 (trihydrochloride hydrate)
Chemical Formula: C28H38N6O2·3HCl · xH2O
Exact Mass: 600.25
Molecular Weight: 600.040
Elemental Analysis: C, 54.42; H, 7.01; Cl, 17.21; N, 13.60; O, 7.77

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450	2 weeks
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 #: 935693-62-2 (free base) 1392399-03-9 ( HCl) 935693-62-2 (trihydrochloride hydrate)

Synonym: BIX 01294 trihydrochloride hydrate; BIX01294 trihydrochloride hydrate, BIX-01294 trihydrochloride hydrate; BIX01294 3HCl hydrate

IUPAC/Chemical Name: 2-(Hexahydro-4-methyl-1H-1,4-diazepin-1-yl)-6,7-dimethoxy-N-[1-(phenylmethyl)-4-piperidinyl]-4-quinazolinamine trihydrochloride hydrate

InChi Key: BZOWJAYUMMHCDW-UHFFFAOYSA-N

InChi Code: InChI=1S/C28H38N6O2.3ClH.H2O/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;1H2

SMILES Code: COC1=C(OC)C=C2C(N=C(N3CCCN(C)CC3)N=C2NC4CCN(CC5=CC=CC=C5)CC4)=C1.O.Cl.Cl.Cl

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: >3 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:	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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	110.0	183.32

Preparing Stock Solutions

The following data is based on the product molecular weight 600.04 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. 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. 3. 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. 4. 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.
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.

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1: Wang Q, Wang X, Lai D, Deng J, Hou Z, Liang H, Liu D. BIX-01294 promotes the differentiation of adipose mesenchymal stem cells into adipocytes and neural cells in Arbas Cashmere goats. Res Vet Sci. 2018 Aug;119:9-18. doi: 10.1016/j.rvsc.2018.05.009. Epub 2018 May 14. PubMed PMID: 29783122.

2: Huang Y, Zou Y, Lin L, Ma X, Huang X. Effect of BIX-01294 on proliferation, apoptosis and histone methylation of acute T lymphoblastic leukemia cells. Leuk Res. 2017 Nov;62:34-39. doi: 10.1016/j.leukres.2017.09.015. Epub 2017 Sep 25. PubMed PMID: 28982057.

3: Huang Y, Jiang X, Yu M, Huang R, Yao J, Li M, Zheng F, Yang X. Beneficial effects of diazepin-quinazolin-amine derivative (BIX-01294) on preimplantation development and molecular characteristics of cloned mouse embryos. Reprod Fertil Dev. 2017 Jun;29(6):1260-1269. doi: 10.1071/RD15463. PubMed PMID: 27477633.

4: Huang J, Zhang H, Yao J, Qin G, Wang F, Wang X, Luo A, Zheng Q, Cao C, Zhao J. BIX-01294 increases pig cloning efficiency by improving epigenetic reprogramming of somatic cell nuclei. Reproduction. 2016 Jan;151(1):39-49. doi: 10.1530/REP-15-0460. PubMed PMID: 26604326.

5: Shin JH, Kim PS, Kim ES, Park SJ, Jo YK, Hwang JJ, Park TJ, Chang JW, Seo JH, Cho DH. BIX-01294-induced autophagy regulates elongation of primary cilia. Biochem Biophys Res Commun. 2015 May 1;460(2):428-33. doi: 10.1016/j.bbrc.2015.03.050. Epub 2015 Mar 18. PubMed PMID: 25796328.

6: Kim Y, Kim YS, Kim DE, Lee JS, Song JH, Kim HG, Cho DH, Jeong SY, Jin DH, Jang SJ, Seol HS, Suh YA, Lee SJ, Kim CS, Koh JY, Hwang JJ. BIX-01294 induces autophagy-associated cell death via EHMT2/G9a dysfunction and intracellular reactive oxygen species production. Autophagy. 2013 Dec;9(12):2126-39. doi: 10.4161/auto.26308. PubMed PMID: 24322755.

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BIX 01294 trihydrochloride hydrate featured