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SML3395

Sigma-Aldrich

KDM5-C70

≥95% (HPLC)

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Synonym(s):
C 70, C-70, C70, Ethyl 2-(((2-((2-(dimethylamino)ethyl)ethylamino)-2-oxoethyl)amino)methyl)-4-pyridinecarboxylate, Ethyl 2-(((2-((2-(dimethylamino)ethyl)ethylamino)-2-oxoethyl)amino)methyl)isonicotinate, KDM5-C49 ethyl ester, KDOAM-20 ethyl ester, KDOAM-21, KDOAM20 ethyl ester, KDOAM21
Empirical Formula (Hill Notation):
C17H28N4O3
CAS Number:
Molecular Weight:
336.43
MDL number:

Quality Level

assay

≥95% (HPLC)

form

oil

color

, Light yellow to very dark red-bown

storage temp.

-10 to -25°C

SMILES string

CN(CCN(C(CNCC1=CC(C(OCC)=O)=CC=N1)=O)CC)C

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This Item
PHR1207W242810SML2774
vibrant-m

SML3395

KDM5-C70

vibrant-m

PHR1207

Methyl Ethyl Ketone

vibrant-m

W242810

Ethyl isobutyrate

vibrant-m

SML2774

KDOAM25 hydrochloride hydrate

Quality Level

100

Quality Level

300

Quality Level

400

Quality Level

100

assay

≥95% (HPLC)

assay

-

assay

≥98%

assay

≥98% (HPLC)

storage temp.

-10 to -25°C

storage temp.

2-30°C

storage temp.

-

storage temp.

−20°C

color

, Light yellow to very dark red-bown

color

-

color

-

color

white to beige

Biochem/physiol Actions

KDM5-C70 (KDOAM-21) corresponds to the ethyl ester precursor of a selective αKG-competitive KDM5 histone demethylase inhibitor KDM5-C49 (KDOAM-21; KDM5A/B/C/D Ki = 2/1/6.1/3.4 nM vs. KDM4C/6B/3A/2A Ki = 0.51/4.55/2.59/4.4 μM; KDM5A/B/C/D IC50 = 1.1/0.8/3.2/2.7 μM by FDH assay with [αKG] = 1 mM & [E]/[S] = 0.5/15 μM; KDM5A/B/C IC50 = 25/30/59 nM by alphaLISA with [αKG] = 25 μM & [E]/[S] = 10/100 nM). KDM5-C70 treatment selectively upregulates cellular histone H3 trimethylation on Lys4 (H3K4me3), but not on Lys9/7/36 (5 μM, 3d), and inhibits KDM5-dependent cancer growth (by 85%/MCF7/11d, 97%/BT474/24d, and 70%/ZR-75-1/24d; 5 μM).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Structural Basis for KDM5A Histone Lysine Demethylase Inhibition by Diverse Compounds
Cell Chemical Biology, 23(7), 769-781 (2016)
Lauren P Blair et al.
Science advances, 2(11), e1501662-e1501662 (2017-02-01)
The complexity by which cells regulate gene and protein expression is multifaceted and intricate. Regulation of 3' untranslated region (UTR) processing of mRNA has been shown to play a critical role in development and disease. However, the process by which
Catrine Johansson et al.
Nature chemical biology, 12(7), 539-545 (2016-05-24)
Members of the KDM5 (also known as JARID1) family are 2-oxoglutarate- and Fe(2+)-dependent oxygenases that act as histone H3K4 demethylases, thereby regulating cell proliferation and stem cell self-renewal and differentiation. Here we report crystal structures of the catalytic core of
John R Horton et al.
Journal of medicinal chemistry, 61(7), 3193-3208 (2018-03-15)
Isomers of chiral drugs can exhibit marked differences in biological activities. We studied the binding and inhibitory activities of 12 compounds against KDM5A. Among them are two pairs of enantiomers representing two distinct inhibitor chemotypes, namely, ( R)- and (
Stephanie B Hatch et al.
Epigenetics & chromatin, 10, 9-9 (2017-03-08)
Histone lysine demethylases (KDMs) are of interest as drug targets due to their regulatory roles in chromatin organization and their tight associations with diseases including cancer and mental disorders. The first KDM inhibitors for KDM1 have entered clinical trials, and

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