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SML1430

Sigma-Aldrich

Bis-Imidazole phenol IDH1 inhibitor

≥98% (HPLC), solubility: 30 mg/mL in DMSOclear

Synonym(s):

2,6-Bis((1H-Imidazol-1-yl)methyl)-4-(2,4,4-trimethylpentan-2-yl)phenol

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About This Item

Empirical Formula (Hill Notation):
C22H30N4O
CAS Number:
1648909-73-2
Molecular Weight:
366.50
UNSPSC Code:
12352200
PubChem Substance ID:
329825871
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 30 mg/mL, clear

storage temp.

2-8°C

SMILES string

OC1=C(CN2C=CN=C2)C=C(C(C)(CC(C)(C)C)C)C=C1CN3C=NC=C3

InChI

1S/C22H30N4O/c1-21(2,3)14-22(4,5)19-10-17(12-25-8-6-23-15-25)20(27)18(11-19)13-26-9-7-24-16-26/h6-11,15-16,27H,12-14H2,1-5H3

InChI key

PCIJWPBOCDNTJF-UHFFFAOYSA-N

Biochem/physiol Actions

Bis-imidazole phenol blocks D-2-hydroxyglutaric acid synthesis in cells.[1]
bis-Imidazole phenol is a potent and cell permeable inhibitor of isocitrate dehydrogenase 1 (IDH1) mutant R132H that inhibits D-2-hydroxyglutaric acid (2HG) production in cells. bis-Imidazole phenol binds to an IDH1 R132H allosteric site at the dimer interface containing residue involved in binding of the catalytically essential divalent cation.
bis-Imidazole phenol is a potent and cell permeable inhibitor of isocitrate dehydrogenase 1 (IDH1) mutant R132H.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
095M4614V

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Gejing Deng et al.
The Journal of biological chemistry, 290(2), 762-774 (2014-11-14)
Cancer-associated point mutations in isocitrate dehydrogenase 1 and 2 (IDH1 and IDH2) confer a neomorphic enzymatic activity: the reduction of α-ketoglutarate to d-2-hydroxyglutaric acid, which is proposed to act as an oncogenic metabolite by inducing hypermethylation of histones and DNA.

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