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SML2200

Sigma-Aldrich

Octyl-(R)-2HG

≥98% (HPLC), film, α-KG-dependent dioxygenases prolyl hydroxylases inhibitor

Synonym(s):

(2R)-2-Hydroxyglutarate octyl ester, (2R)-Octyl-α-hydroxyglutarate, 1-Octyl-D-2-hydroxyglutarate, 1-octyl ester, 2R-Hydroxy-pentanedioic acid, Octyl-2HG, Octyl-D-2HG, R-2HG octyl ester

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About This Item

Empirical Formula (Hill Notation):
C13H24O5
CAS Number:
1391194-67-4
Molecular Weight:
260.33
MDL number:
MFCD30735809
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Octyl-(R)-2HG, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

film

storage condition

desiccated

color

colorless

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

Application

Octyl-(R)-2 hydroxyglutarate (HG) has been used as a membrane permeamble oncometabolite in gliblostoma cells to test its effects on NANOG transcription factor expression. It has also been used as a competitive inhibitor of the enzyme α-ketoglutarate (α-KG)-dependent deoxygenase.

Biochem/physiol Actions

Octyl-(R)-2HG (Octyl-D-2HG) is a membrane-permeant precursor form of the oncometabolite D-2-hydroxyglutarate (D-2HG) produced by tumor cells due to mutations in the NADP+-dependent isocitrate dehydrogenase genes IDH1 and IDH2. D-2HG inhibits multiple α-ketoglutarate/α-KG-dependent dioxygenases by competing against α-KG binding. Cellular D-2HG delivery by Octyl-(R)-2HG treatment (1-50 mM) is shown to suppress demethylase activity (~148% H3K9me2 and ~310% H3K79me2 upregulation; 50 mM in U-87MG) as well as increase HIF-1α and decrease endostatin levels as a result of inhibiting α-KG-dependent dioxygenases prolyl hydroxylases (PHDs) and collagen prolyl-4-hydroxylase (C-P4H), respectively.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Zachary J Reitman et al.
The Journal of biological chemistry, 289(34), 23318-23328 (2014-07-06)
Mutations in the cytosolic NADP(+)-dependent isocitrate dehydrogenase (IDH1) occur in several types of cancer, and altered cellular metabolism associated with IDH1 mutations presents unique therapeutic opportunities. By altering IDH1, these mutations target a critical step in reductive glutamine metabolism, the
alpha-Ketoglutarate-Activated NF-$\kappa$B Signaling Promotes Compensatory Glucose Uptake and Brain Tumor Development
Wang X, et al.
Molecular Cell, 76(1), 148-162 (2019)
IDH1R132H Causes Resistance to HDAC Inhibitors by Increasing NANOG in Glioblastoma Cells
Kim G H, et al.
International Journal of Molecular Sciences, 20(11), 2679-2679 (2019)
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
Parker L Sulkowski et al.
Science translational medicine, 9(375) (2017-02-06)
2-Hydroxyglutarate (2HG) exists as two enantiomers, (R)-2HG and (S)-2HG, and both are implicated in tumor progression via their inhibitory effects on α-ketoglutarate (αKG)-dependent dioxygenases. The former is an oncometabolite that is induced by the neomorphic activity conferred by isocitrate dehydrogenase
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