SML2200
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:
Molecular Weight:
260.33
MDL number:
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
SMILES string
O[C@H](CCC(=O)O)C(=O)OCCCCCCCC
InChI key
UJZOKTKSGUOCCM-LLVKDONJSA-N
Related Categories
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
Membrane-permeant precursor form of the oncometabolite D-2-hydroxyglutarate that inhibits α-ketoglutarate/α-KG-dependent dioxygenases.
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.
Preparation Note
The density is not reported for this compound. The molecular weight is 260.33. The solubility is tested at 2mg/mL in DMSO, however other sources suggest that it is soluble in DMSO up to 10mg/mL.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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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)
Steven M Chan et al.
Nature medicine, 21(2), 178-184 (2015-01-20)
Mutant isocitrate dehydrogenase (IDH) 1 and 2 proteins alter the epigenetic landscape in acute myeloid leukemia (AML) cells through production of the oncometabolite (R)-2-hydroxyglutarate (2-HG). Here we performed a large-scale RNA interference (RNAi) screen to identify genes that are synthetic
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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