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SML1603

BAY-598

≥98% (HPLC)

Synonym(s):

(S)-N-[1-{N′-Cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl}-3-(3,4-dichlorophenyl)-4,5-dihydro-1H-pyrazol-4-yl]-N-ethyl-2-hydroxyacetamide

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About This Item

Empirical Formula (Hill Notation):
C22H20Cl2F2N6O3
Molecular Weight:
525.34
UNSPSC Code:
51111800
PubChem Substance ID:
329825489
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
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Quality Level

100

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -85 to -95°, c = 1 in methanol

color

white to beige

solubility

DMSO: 25 mg/mL, clear

storage temp.

2-8°C

SMILES string

ClC1=C(Cl)C=C(C2=NN(/C(NC3=CC=CC(OC(F)F)=C3)=N\C#N)C[C@@H]2N(CC)C(CO)=O)C=C1

InChI

1S/C23H21Cl2F2N5O3/c1-2-16(20(34)11-33)17-10-32(31-21(17)13-6-7-18(24)19(25)8-13)23(29-12-28)30-14-4-3-5-15(9-14)35-22(26)27/h3-9,16-17,22,33H,2,10-11H2,1H3,(H,29,30)/t16?,17-/m1/s1

InChI key

LOHNYXGTWKNYDF-ZYMOGRSISA-N

Biochem/physiol Actions

BAY-598 is a potent, peptide-competitive chemical probe for SET and MYND domain-containing protein 2 (SMYD2), a lysine methyl transferase inhibitor that dimethylates histone H3K36 and methylates histone H3K4. SMYD2 also methylates Lys-370 of p53, leading to decreased DNA-binding activity. SMYD2 is over-expressed in several cancers with poor prognosis. BAY-598 inhibits in vitro methylation of p53K370 with an IC50 value of 27 nM and in cells with an IC50 value < 1 μM. BAY-598 is more than 100-fold selective over other histone methyltransferases and non-epigenetic targets. BAY-598 can be used with in vivo experiments. For full characterization details, please visit the BAY-598 probe summary on the Structural Genomics Consortium (SGC) website.

BAY-369 is the negative control for the active probe, BAY-598. To request a sample of the negative control from the SGC, click here.

To learn about other SGC chemical probes for epigenetic targets, visit sigma.com/sgc
BAY-598 is a potent, peptide-competitive chemical probe for SET and MYND domain-containing protein 2 (SMYD2).

Features and Benefits

BAY-598 is an epigenetic chemical probe available through a partnership with the Structural Genomics Consortium (SGC). To learn more and view other SGC epigenetic probes, visit sigma.com/SGC.
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

BAY-598 has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the BAY-598 probe summary on the Chemical Probes Portal website.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000406350
0000406350
0000195714
0000195714
0000114315

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Zhenchuan Liu et al.
Clinical and translational medicine, 11(9), e545-e545 (2021-09-30)
Esophageal squamous cell carcinoma (ESCC) is a highly aggressive and treatment-resistant tumor. The biological implications and molecular mechanism of cancer stem-like cells (CSCs) in ESCC, which contribute to therapeutic resistance such as radioresistance, remain elusive. Quantitative real-time polymerase chain reaction