Disodium (R)-2-Hydroxyglutarate
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Disodium (R)-2-Hydroxyglutarate

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Disodium (R)-2-Hydroxyglutarate is a competitive inhibitor of α-ketoglutarate-dependent dioxygenases with Ki of 0.628 mM. In U-87MG cells, (R)-2-Hydroxyglutarate acts as a weak antagonist of α-KG to inhibit α-KG-dependent histone demethylases and increase dimethylation on both H3K9 and H3K79.

Category
Others
Catalog number
BAT-008968
CAS number
103404-90-6
Molecular Formula
C5H6Na2O5
Molecular Weight
192.08
Disodium (R)-2-Hydroxyglutarate
Size Price Stock Quantity
100 mg $199 In stock
IUPAC Name
disodium;(2R)-2-hydroxypentanedioate
Synonyms
MDK4906; MDK 4906; MDK-4906; d-α-hydroxyglutaric acid disodium salt; (2R)-2-Hydroxyglutaric Acid Disodium Salt; D-alpha-Hydroxyglutaric acid (disodium salt)
Appearance
Pale Orange Solid
Purity
98%
Storage
3 years -20℃ powder; 6 months -80℃ in solvent
Solubility
Soluble to 38mg/mL in warmed water; Soluble to < 1mg/mL in DMSO; Soluble to < 1mg/mL in ethanol
InChI
InChI=1S/C5H8O5.2Na/c6-3(5(9)10)1-2-4(7)8;;/h3,6H,1-2H2,(H,7,8)(H,9,10);;/q;2*+1/p-2/t3-;;/m1../s1
InChI Key
DZHFTEDSQFPDPP-HWYNEVGZSA-L
Canonical SMILES
C(CC(=O)[O-])C(C(=O)[O-])O.[Na+].[Na+]
1. Quantitation of isocitrate dehydrogenase (IDH)-induced D and L enantiomers of 2-hydroxyglutaric acid in biological fluids by a fully validated liquid tandem mass spectrometry method, suitable for clinical applications
Vianney Poinsignon, Koïchi Nakabayashi, Cyril Quivoron, Alexandre Lalli, Véronique Saada, Sophie Broutin, Lionel Mercier, Stéphane De Botton, Muriel D David, Angelo Paci, Virginie Penard-Lacronique J Chromatogr B Analyt Technol Biomed Life Sci . 2016 Jun 1;1022:290-297. doi: 10.1016/j.jchromb.2016.04.030.
A recent update of the hallmarks of cancer includes metabolism with deregulating cellular energetics. Activating mutations in isocitrate dehydrogenase (IDH) metabolic enzymes leading to the abnormal accumulation of 2-hydroxyglutaric acid (2-HGA) have been described in hematologic malignancies and solid tumours. The diagnostic value of 2-HGA levels in blood to identify IDH mutations and its prognostic significance have been reported. We developed a liquid chromatography tandem mass spectrometry method allowing a rapid, accurate and precise simultaneous quantification of both L and D enantiomers of 2-HGA in blood samples from acute myeloid leukaemia (AML) patients, suitable for clinical applications. The method was also develop for preclinical applications from cellular and tissues samples. Deuterated (R,S)-2-hydroxyglutaric acid, disodium salt was used as internal standard and added to samples before a solid phase extraction on Phenomenex STRATA™-XL-A (200mg-3mL) 33μm cartridges. A derivatization step with (+)- o,o'-diacetyl-l-tartaric anhydride permitted to separate the two resulting diastereoisomers without chiral stationary phase, on a C18 column combined to a Xevo TQ-MS Waters mass spectrometer with an electrospray ionization (ESI) source. This method allows standard curves to be linear over the range 0.34-135.04μM with r(2) values>0.999 and low matrix effects (<11.7%). This method, which was validated according to current EMA guidelines, is accurate between-run (<3.1%) and within-run (<7.9%) and precise between-run (<5.3CV%) and within-run (<6.2CV%), and is suitable for clinical and preclinical applications.
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