BIX01294 (hydrochloride hydrate)

Cayman Chemical Item Number 13124

BIX01294 (hydrochloride hydrate)

Description

The methylation of lysine residues on histones plays a central role in determining euchromatin structure and gene expression. The histone methyltransferase (HMTase) G9a can mono- or dimethylate lysine 9 on histone 3 (H3), contributing to early embryogenesis, genomic imprinting, and lymphocyte development.^1,2,3 BIX01294 (hydrochloride hydrate) is a selective inhibitor of G9a HMTase (IC₅₀ = 1.7 μM).⁴ It less effectively inhibits the HMTase G9a-like protein (GLP; IC₅₀ = 38 μM) and has no effect on other known HMTases.⁴ BIX01294 has been used in combination with the calcium channel activator BayK8644 to facilitate the generation of induced pluripotent stem cells from somatic cells in vitro.⁵

1 Tachibana, M., Sugimoto, K., Nozaki, M., et al. G9a histone methyltransferase plays a dominant role in euchromatic histone H3 lysine 9 methylation and is essential for early embryogenesis. Genes Dev 16 1779-1791 (2002).

2 Wagschal, A., Sutherland, H.G., Woodfine, K., et al. G9a histone methyltransferase contributes to imprinting in the mouse placenta. Mol Cell Biol 28(3) 1104-1113 (2008).

3 Thomas, L.R., Miyashita, H., Cobb, R.M., et al. Functional analysis of histone methyltransferase G9a in B and T lymphocytes. J Immunol 181 485-493 (2008).

4 Kubicek, S., O'Sullivan, R.J., August, E.M., et al. Reversal of H3K9me2 by a small-molecule inhibitor for the G9a histone methyltransferase. Mol Cell 25 473-481 (2007).

5 Shi, Y., Desponts, C., Do, J.T., et al. Induction of pluripotent stem cells from mouse embryonic fibroblasts by Oct4 and Klf4 with small-molecule compounds. Cell Stem Cell 3(5) 568-574 (2008).

Formal Name

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

Molecular Formula

C₂₈H₃₈N₆O₂ · 3HCl [XH₂O]

Formula Weight

600.0

Formulation

A crystalline solid

Purity

≥98%

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

Copy SMILES to clipboard

COC(C(OC)=C1)=CC2=C1C(NC3CCN(CC4=CC=CC=C4)CC3)=NC(N5CCCN(C)CC5)=N2.[·3HCl].O

Background Reading

Tachibana, M., Sugimoto, K., Nozaki, M., et al. G9a histone methyltransferase plays a dominant role in euchromatic histone H3 lysine 9 methylation and is essential for early embryogenesis. Genes Dev 16 1779-1791 (2002).

Wagschal, A., Sutherland, H.G., Woodfine, K., et al. G9a histone methyltransferase contributes to imprinting in the mouse placenta. Mol Cell Biol 28(3) 1104-1113 (2008).

Thomas, L.R., Miyashita, H., Cobb, R.M., et al. Functional analysis of histone methyltransferase G9a in B and T lymphocytes. J Immunol 181 485-493 (2008).

Shi, Y., Desponts, C., Do, J.T., et al. Induction of pluripotent stem cells from mouse embryonic fibroblasts by Oct4 and Klf4 with small-molecule compounds. Cell Stem Cell 3(5) 568-574 (2008).

Kubicek, S., O'Sullivan, R.J., August, E.M., et al. Reversal of H3K9me2 by a small-molecule inhibitor for the G9a histone methyltransferase. Mol Cell 25 473-481 (2007).

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BIX01294 (hydrochloride hydrate)