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B9311

BIX 01294 trihydrochloride hydrate

Name: BIX 01294 trihydrochloride hydrate
Brand: SIGMA

≥98% (HPLC), powder

Synonym(s):

2-(Hexahydro-4-methyl-1H-1,4-diazepin-1-yl)-6,7-dimethoxy-N-[1-(phenylmethyl)-4-piperidinyl]-4-quinazolinamine trihydrochloride hydrate, BIX 01294

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About This Item

Empirical Formula (Hill Notation):

C₂₈H₃₈N₆O₂·3HCl · xH₂O

CAS Number:

935693-62-2

Molecular Weight:

600.02 (anhydrous basis)

MDL number:

MFCD14560563

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

desiccated

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Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white

solubility

H₂O: >20 mg/mL

storage temp.

2-8°C

SMILES string

N2(CCC(CC2)Nc3nc(nc5c3cc(c(c5)OC)OC)N4CCN(CCC4)C)Cc1ccccc1

InChI

1S/C28H38N6O2/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)

InChI key

OSXFATOLZGZLSK-UHFFFAOYSA-N

Related Categories

Bioactive Small Molecule Inhibitors

General description

BIX-01294, 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.

Application

BIX 01294 trihydrochloride hydrate has been used:

as a histone methylation inhibitor to treat E4 cells for analysing green fluorescent protein (d2EGFP) expression
to investigate the role of G9a in neuroblastoma tumor growth
as specific inhibitor of G9a to treat the SK-N-AS, BE(2)-C, SK-N-DZ, SK-N-F1, and SHEP1 neuroblastoma cell lines

Biochem/physiol Actions

BIX 01294 is a selective histone methyl transferase inhibitor.

BIX 01294 is a selective histone methyl transferase inhibitor. In its inhibition of the histone lysine methyltransferases, BIX 01294 does not compete with cofactor S-adenosyl-methionine. The target enzyme is G9a, and it selectively impairs G9a HMTase and the generation of H3K9me2 in vitro.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Other Notes

BIX-01294 has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the BIX-01294 probe summary on the Chemical Probes Portal website.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000141717

0000138556

0000144771

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Inhibition of H3K9 methyltransferase G9a repressed cell proliferation and induced autophagy in neuroblastoma cells

Ke XX, et al.

PLoS ONE, 9(9), e106962-e106962 (2014)

Increased expression of G9A contributes to carcinogenesis and indicates poor prognosis in hepatocellular carcinoma.

Jian Qin et al.

Oncology letters, 15(6), 9757-9765 (2018-06-22)

Euchromatic histone-lysine N-methyltransferase (G9A), the primary histone methyltransferase for histone H3 Lys9, has been identified to be upregulated in numerous types of cancer. The aim of the present study was to analyze the clinical significance of G9A, and preliminarily explore

New regulators of the tetracycline-inducible gene expression system identified by chemical and genetic screens.

Valeria Colicchia et al.

FEBS open bio, 12(10), 1896-1908 (2022-09-06)

The tetracycline repressor (tetR)-regulated system is a widely used tool to specifically control gene expression in mammalian cells. Based on this system, we generated a human osteosarcoma cell line, which allows for the inducible expression of an EGFP fusion of

Inhibition of Histone Methyltransferases EHMT1/2 Reverses Amyloid-β-Induced Loss of AMPAR Currents in Human Stem Cell-Derived Cortical Neurons.

Lin Lin et al.

Journal of Alzheimer's disease : JAD, 70(4), 1175-1185 (2019-07-20)

Emerging evidence suggests that epigenetic dysregulation of gene expression is one of the key molecular mechanisms of neurodegeneration and Alzheimer's disease (AD). However, little is known about the role of epigenetic dysregulation on synaptic dysfunction in humans, because of the

HIV-1 infection of microglial cells in a reconstituted humanized mouse model and identification of compounds that selectively reverse HIV latency.

George N Llewellyn et al.

Journal of neurovirology, 24(2), 192-203 (2017-12-20)

Most studies of HIV latency focus on the peripheral population of resting memory T cells, but the brain also contains a distinct reservoir of HIV-infected cells in microglia, perivascular macrophages, and astrocytes. Studying HIV in the brain has been challenging

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Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Global Trade Item Number

SKU	GTIN
B9311-5MG	04061833443712
B9311-25MG	04061832631073

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