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SML2200

Sigma-Aldrich

Octyl-(R)-2HG

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

Synonyme(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

Formule empirique (notation de Hill) :
C13H24O5
Numéro CAS:
1391194-67-4
Poids moléculaire :
260.33
Numéro MDL:
MFCD30735809
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Nom du produit

Octyl-(R)-2HG, ≥98% (HPLC)

Essai

≥98% (HPLC)

Forme

film

Conditions de stockage

desiccated

Couleur

colorless

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

O[C@H](CCC(=O)O)C(=O)OCCCCCCCC

Clé InChI

UJZOKTKSGUOCCM-LLVKDONJSA-N

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.

Actions biochimiques/physiologiques

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.

Notes préparatoires

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Consulter la Bibliothèque de documents

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
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
Javier A Menendez et al.
Stem cell reports, 6(3), 273-283 (2016-02-16)
By impairing histone demethylation and locking cells into a reprogramming-prone state, oncometabolites can partially mimic the process of induced pluripotent stem cell generation. Using a systems biology approach, combining mathematical modeling, computation, and proof-of-concept studies with live cells, we found
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)
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