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SML2886

Sigma-Aldrich

O4I3

≥98% (HPLC)

Synonym(s):

2-(4-Methylphenyl)-6-methylimidazo[1,2-a]pyridine, 6-Methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine, OCT4-inducing compound 3

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About This Item

Empirical Formula (Hill Notation):
C15H14N2
CAS Number:
88965-00-8
Molecular Weight:
222.29
MDL number:
MFCD00444739
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

CC1=CC=C(C2=CN3C=C(C=CC3=N2)C)C=C1

InChI

1S/C15H14N2/c1-11-3-6-13(7-4-11)14-10-17-9-12(2)5-8-15(17)16-14/h3-10H,1-2H3

InChI key

AWEWSJJCANQFRB-UHFFFAOYSA-N

Biochem/physiol Actions

O4I3 is a highly potent and KDM5A (JARID1A) subtype-selective H3K4 demethylase KDM5 inhibitor (KDM5A IC50 = 0.15 nM vs KDM5B/C/D IC50 = 125.2/9.76/4.7 nM, KDM4 IC50 = 249 nM, LSD1 IC50 >100 μM) that effectively induces OCT4 expresson and improves OSKM-induced pluripotent stem cell (iPSC) reprogramming efficiency of human primary fibroblasts (50 nM) by preventing KDM5A from interfering with H3K4Me3 enrichment at the OCT4 promoter. O4I3 promotes hPSC homeostasis and represses cellular differentiation, increasing hPSCs viability up to 4-fold at a low 10 nM concentration when compared with Rock inhibitor Y-27632 treatment at 10 μM.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

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Yasamin Dabiri et al.
iScience, 12, 168-181 (2019-01-28)
Pioneering human induced pluripotent stem cell (iPSC)-based pre-clinical studies have raised safety concerns and pinpointed the need for safer and more efficient approaches to generate and maintain patient-specific iPSCs. One approach is searching for compounds that influence pluripotent stem cell

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