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SML2205

Sigma-Aldrich

Octyl-α-KG

≥95% (HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):
C13H22O5
Número de CAS:
876150-14-0
Peso molecular:
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

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

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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
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
Jing-Yi Chen et al.
Scientific reports, 6, 32428-32428 (2016-09-01)
Mutations of isocitrate dehydrogenase 1 (IDH1) and IDH2 in acute myeloid leukemia (AML) cells produce the oncometabolite R-2-hydroxyglutarate (R-2HG) to induce epigenetic alteration and block hematopoietic differentiation. However, the effect of R-2HG released by IDH-mutated AML cells on the bone
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