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SML2205

Sigma-Aldrich

Octyl-α-KG

≥95% (HPLC)

Synonym(s):

α-KG octyl ester, α-Ketoglutarate octyl ester, 1-Octyl-2-Oxo-pentanedioate, 1-Octyl-2-ketoglutarate, 2-Oxo-pentanedioic acid, 1-octyl ester, Octyl-α-ketoglutarate, Octyl-2KG

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About This Item

Empirical Formula (Hill Notation):
C13H22O5
CAS Number:
876150-14-0
Molecular Weight:
258.31
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥95% (HPLC)

form

oil

storage condition

desiccated
under inert gas

color

colorless to yellow

storage temp.

−20°C

SMILES string

CCCCCCCCOC(C(CCC(O)=O)=O)=O

InChI

1S/C13H22O5/c1-2-3-4-5-6-7-10-18-13(17)11(14)8-9-12(15)16/h2-10H2,1H3,(H,15,16)

InChI key

QNFIHKFBQFJVKV-UHFFFAOYSA-N

Application

Octyl-α-KG has been used to study its effects on the cell viability and to replenish α-KG levels in human glioblastoma cells.

Biochem/physiol Actions

Membrane-permeant precursor of α-ketoglutarate that restores activity of α-KG-dependent dioxygenases in cancer cells.
Octyl-α-KG (Octyl-2KG) is a membrane-permeant precursor form of α-ketoglutarate (α-KG or 2KG) whose downregulation is often seen with concomitant upregulated D-2-hydroxyglutarate (D-2HG) in tumor cells due to mutations in the NADP+-dependent isocitrate dehydrogenase genes IDH1 and IDH2, leading to reduced activity of multiple α-KG-dependent dioxygenases. Cellular α-KG delivery by Octyl-α-KG treatment (1-5 mM) is shown to restore cellular demethylase activity following octyl-2-HG (1-50 mM) treatment or IDH1(R132H) mutant expression. Octyl-α-KG also effectively reactivates α-KG-dependent dioxygenases prolyl hydroxylase (PHD) activity in cells with a dysfunctional tricarboxylic acid (TCA) cycle due to succinate dehydrogenase (SDH) and/or fumarate hydratase (FH) deficiency.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Shizhong Ke et al.
Hepatology (Baltimore, Md.), 65(1), 134-151 (2016-10-25)
Erythrocytosis is a common paraneoplastic syndrome associated with hepatocellular carcinoma. Although increased erythropoietin (EPO) is found in these patients, the clinical significance and molecular mechanisms underlying this observation are unclear. We demonstrate an inverse relationship between EPO production and overall
Randa Abdel Malik et al.
Circulation research, 120(1), 99-109 (2016-10-26)
The AMP-activated protein kinase (AMPK) is stimulated by hypoxia, and although the AMPKα1 catalytic subunit has been implicated in angiogenesis, little is known about the role played by the AMPKα2 subunit in vascular repair. To determine the role of the
Shimin Zhao et al.
Science (New York, N.Y.), 324(5924), 261-265 (2009-04-11)
Heterozygous mutations in the gene encoding isocitrate dehydrogenase-1 (IDH1) occur in certain human brain tumors, but their mechanistic role in tumor development is unknown. We have shown that tumor-derived IDH1 mutations impair the enzyme's affinity for its substrate and dominantly
Elaine D MacKenzie et al.
Molecular and cellular biology, 27(9), 3282-3289 (2007-02-28)
Succinate dehydrogenase (SDH) and fumarate hydratase (FH) are components of the tricarboxylic acid (TCA) cycle and tumor suppressors. Loss of SDH or FH induces pseudohypoxia, a major tumor-supporting event, which is the activation of hypoxia-inducible factor (HIF) under normoxia. In
L Zeng et al.
Oncogene, 34(36), 4758-4766 (2014-12-23)
Cancer cells gain a growth advantage through the so-called Warburg effect by shifting glucose metabolism from oxidative phosphorylation to aerobic glycolysis. Hypoxia-inducible factor 1 (HIF-1) has been suggested to function in metabolic reprogramming; however, the underlying mechanism has not been
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