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MedKoo Cat#: 573453 | Name: BIX 01294 HCl hydrate
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Description:

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

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 HCl hydrate
BIX 01294 HCl hydrate
CAS#935693-62-2 (HCl hydrate)

Theoretical Analysis

MedKoo Cat#: 573453

Name: BIX 01294 HCl hydrate

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

Chemical Formula: C28H38N6O2·3HCl · xH2O

Exact Mass: 600.2462

Molecular Weight: 600.04

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 450.00 2 weeks
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Related CAS #
935693-62-2 (free base) 1392399-03-9 ( HCl) 935693-62-2 (HCl 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
More Info
Product Data
Product Data
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 110.0 183.32
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 600.04 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.

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. 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.
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.