Octyl-alpha-ketoglutarate

Hypoxia-inducible factor 1alpha (HIF-1alpha) turnover is initiated by prolyl hydroxylases (PHD), which hydroxylate proline residues on HIF-1alpha, facilitating ubiquitination. PHD activity is linked to the tricarboxylic acid (TCA) cycle, since the intermediate alpha-ketoglutarate is a PHD substrate and succinate and fumarate inhibit PHD. Mutations in enzymes associated with the TCA cycle occur in certain cancers. Octyl-alpha-ketoglutarate is a stable, cell-permeable form of alpha-ketoglutarate which accumulates rapidly and preferentially in cells with a dysfunctional TCA cycle. When used at 1 mM, it stimulates PHD activity, increasing HIF-1alpha turnover. In addition, octyl-alpha-ketoglutarate competitively blocks succinate- or fumarate-mediated inhibition of PHD.Formal Name: 2-oxo-pentanedioic acid, 1-octyl ester. CAS Number: 876150-14-0. Synonyms: alpha-KG octyl ester. Molecular Formula: C13H22O5. Formula Weight: 258.3. Purity: >95%. Formulation: (Request formulation change), A solution in methyl acetate. Solubility: DMF: 10 mg/ml, DMSO: 10 mg/ml, Ethanol: 20 mg/ml, PBS (pH 7.2): 2 mg/ml. SMILES: OC(CCC(C(OCCCCCCCC)=O)=O)=O. InChi Code: InChI=1S/C13H22O5/c1-2-3-4-5-6-7-10-18-13(17)11(14)8-9-12(15)16/h2-10H2,1H3,(H,15,16). InChi Key: QNFIHKFBQFJVKV-UHFFFAOYSA-N.