SML2200

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

Propriétés

• Product Name: 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

Description

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.

Informations sur la sécurité

• 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