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SML0343

Sigma-Aldrich

Methylstat

≥98% (HPLC)

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Synonym(s):
(2E)-4-[Hydroxy[4-[[[4-[[[(1-naphthalenylamino)carbonyl]oxy]methyl]phenyl]methyl]amino]butyl]amino]-4-oxo-2-butenoic acid methyl ester
Empirical Formula (Hill Notation):
C28H31N3O6
CAS Number:
1310877-95-2
Molecular Weight:
505.56
MDL number:
MFCD22572723
UNSPSC Code:
12352200
PubChem Substance ID:
329825348
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: >5 mg/mL

storage temp.

2-8°C

SMILES string

O=C(NC1=CC=CC2=C1C=CC=C2)OCC3=CC=C(CNCCCCN(O)C(/C=C/C(OC)=O)=O)C=C3

InChI

1S/C28H31N3O6/c1-36-27(33)16-15-26(32)31(35)18-5-4-17-29-19-21-11-13-22(14-12-21)20-37-28(34)30-25-10-6-8-23-7-2-3-9-24(23)25/h2-3,6-16,29,35H,4-5,17-20H2,1H3,(H,30,34)/b16-15+

InChI key

MUJOCHRZXRZONW-FOCLMDBBSA-N

Biochem/physiol Actions

Methylstat is an inhibitor of the Jumonji C domain-containing histone trimethyl demethylases (JHDMs). Methylstat inhibits the activity of JMJD2C (IC50 = 4.3 μM), with similar potency against JMJD2E and JMJD3. The compound has poor activity against dimethyl demethylases, and does not inhibit class I or II HDACs. Methylsat blocks proliferation of the esophageal carcinoma cell line KYSE150 with an IC50 value of 5.1 μM.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Alexandre Fellous et al.
Genes, 10(9) (2019-09-13)
Histone methylation patterns are important epigenetic regulators of mammalian development, notably through stem cell identity maintenance by chromatin remodeling and transcriptional control of pluripotency genes. But, the implications of histone marks are poorly understood in distant groups outside vertebrates and
Qingsong Hu et al.
Nature immunology, 20(7), 835-851 (2019-06-05)
How tumor cells genetically lose antigenicity and evade immune checkpoints remains largely elusive. We report that tissue-specific expression of the human long noncoding RNA LINK-A in mouse mammary glands initiates metastatic mammary gland tumors, which phenotypically resemble human triple-negative breast
Qingsong Hu et al.
Cell research, 29(4), 286-304 (2019-01-12)
Despite the structural conservation of PTEN with dual-specificity phosphatases, there have been no reports regarding the regulatory mechanisms that underlie this potential dual-phosphatase activity. Here, we report that K27-linked polyubiquitination of PTEN at lysines 66 and 80 switches its phosphoinositide/protein
Emily O Wisniewski et al.
Science advances, 6(31), eaba6505-eaba6505 (2020-08-14)
How migrating cells differentially adapt and respond to extracellular track geometries remains unknown. Using intravital imaging, we demonstrate that invading cells exhibit dorsoventral (top-to-bottom) polarity in vivo. To investigate the impact of dorsoventral polarity on cell locomotion through different confining
Wenyu Wang et al.
The Journal of experimental medicine, 215(11), 2833-2849 (2018-09-30)
PTEN deficiency in breast cancer leads to resistance to PI3K-AKT inhibitor treatment despite aberrant activation of this signaling pathway. Here, we report that genetic depletion or small molecule inhibition of KDM4B histone demethylase activates the unfolded protein response (UPR) pathway
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