1. Immunology/Inflammation
    NF-κB
    Metabolic Enzyme/Protease
    Membrane Transporter/Ion Channel
    PI3K/Akt/mTOR
  2. Reactive Oxygen Species
    ATP Synthase
    mTOR
    Endogenous Metabolite
  3. D-α-Hydroxyglutaric acid disodium

D-α-Hydroxyglutaric acid disodium (Synonyms: Disodium (R)-2-hydroxyglutarate)

Cat. No.: HY-100542 Purity: ≥98.0%
Handling Instructions

D-α-Hydroxyglutaric acid disodium (Disodium (R)-2-hydroxyglutarate) is the principal metabolite accumulating in neurometabolic disease D-2-hydroxyglutaric aciduria. D-α-Hydroxyglutaric acid disodium is a weak competitive antagonist of α-ketoglutarate (α-KG) and inhibits multiple α-KG-dependent dioxygenases with a Ki of 10.87 mM. D-α-Hydroxyglutaric acid disodium increases reactive oxygen species (ROS) production. D-α-Hydroxyglutaric acid disodium binds and inhibits ATP synthase and inhibits mTOR signaling.

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D-α-Hydroxyglutaric acid disodium Chemical Structure

D-α-Hydroxyglutaric acid disodium Chemical Structure

CAS No. : 103404-90-6

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Based on 1 publication(s) in Google Scholar

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Description

D-α-Hydroxyglutaric acid disodium (Disodium (R)-2-hydroxyglutarate) is the principal metabolite accumulating in neurometabolic disease D-2-hydroxyglutaric aciduria. D-α-Hydroxyglutaric acid disodium is a weak competitive antagonist of α-ketoglutarate (α-KG) and inhibits multiple α-KG-dependent dioxygenases with a Ki of 10.87 mM. D-α-Hydroxyglutaric acid disodium increases reactive oxygen species (ROS) production. D-α-Hydroxyglutaric acid disodium binds and inhibits ATP synthase and inhibits mTOR signaling[1][2][3][4][5].

IC50 & Target

Ki: 10.87 mM (α-KG-dependent dioxygenases)[1]
ATP synthase[2]
mTOR[2]
Reactive oxygen species (ROS) [5]

In Vitro

D-α-Hydroxyglutaric acid ((R)-2-hydroxyglutarate) accumulates in human cancers carrying neomorphic mutations in the isocitrate dehydrogenase (IDH) 1 and 2 genes[1][2].
A partial inhibition of KDM7A toward both H3K9me2 and H3K27me2 peptides is observed in the presence of 50 mM D-2-HG and 100 μM α-ketoglutarate (α-KG). Addition of 300 μM α-KG is capable of reversing the inhibition of Caenorhabditis elegans KDM7A (CeKDM7A) by 50 mM D-2-HG, indicating that D-2-HG is a weak competitive inhibitor against α-KG toward the CeKDM7A demethylase[1].
D-α-Hydroxyglutaric acid is a weak inhibitor of TET hydroxylases. In the presence of 0.1 mM of α-KG, addition of 10 mM D-α-Hydroxyglutaric acid results in a partial (33%) inhibition of TET2 and addition of 50 mM D-α-Hydroxyglutaric acid results in more inhibition (83%) of TET2. D-α-Hydroxyglutaric acid exhibits a less pronounced inhibitory effect toward TET1[1].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

D-α-Hydroxyglutaric acid strongly inhibits glucose utilization, CO2 production and the respiratory chain in rat cerebral cortex and human skeletal muscle, as well as in submitochondrial particles from bovine heart, suggesting an impairment of the aerobic metabolism[5].
D-α-Hydroxyglutaric acid has also been proposed as an endogenous excitotoxic organic acid because it significantly decreased cell viability in neuronal cultures from chick embryo telencephalons and from neonatal rat hippocampus through stimulation of specific NMDA glutamate receptors[5].
D-α-Hydroxyglutaric acid (0.01-1 mM) significantly increases chemiluminescence and thiobarbituric acid-reactive substances (TBA-RS) and decreased total antioxidant reactivity (TAR) values in the cortical supernatants in 30-day-old-rats[5].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

192.08

Formula

C₅H₆Na₂O₅

CAS No.

103404-90-6

SMILES

O=C(O[Na])[[email protected]](O)CCC(O[Na])=O

Shipping

Room temperature in continental US; may vary elsewhere.

Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

H2O : 75 mg/mL (390.46 mM; Need ultrasonic)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 5.2062 mL 26.0308 mL 52.0616 mL
5 mM 1.0412 mL 5.2062 mL 10.4123 mL
10 mM 0.5206 mL 2.6031 mL 5.2062 mL
*Please refer to the solubility information to select the appropriate solvent.
References
Cell Assay
[2]

U87 cells, HCT 116 IDH1(R132H/+) cells, and HEK 293 cells are seeded in 12-well plates and after overnight incubation are treated with indicated concentrations of each compound (e.g., 400 and 800 μM D-α-Hydroxyglutaric acid). After harvesting, cells are stained with Acridine Orange (AO) and DAPI. Cell number and viability are measured based on AO and DAPI fluorescence measured by NC3000[2].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

References

Purity: ≥98.0%

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Keywords:

D-α-Hydroxyglutaric acid disodiumDisodium (R)-2-hydroxyglutarateReactive Oxygen SpeciesATP SynthasemTOREndogenous MetaboliteMammalian target of RapamycinCeKDM7Aα-ketoglutarateH3K9me2H3K27me2competitorIDH1IDH25-methlycytosineexcitotoxicneurotoxicInhibitorinhibitorinhibit

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D-α-Hydroxyglutaric acid disodium
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