| Size | Price | Stock | Qty |
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| 1mg |
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| Targets |
(2S)-Octyl-alpha-hydroxyglutarate targets the S-enantiomer of 2-hydroxyglutarate (2-HG) metabolic pathways. 2-HG is a metabolite that is normally metabolized to 2-oxoglutarate by D- and L-2-hydroxyglutarate dehydrogenases. In certain cancers, particularly those with isocitrate dehydrogenase (IDH) mutations, 2-HG accumulates and acts as an oncometabolite that inhibits alpha-ketoglutarate-dependent dioxygenases, leading to epigenetic changes and altered cell differentiation. The octyl ester modification enhances cellular uptake and intracellular accumulation of the compound. (2S)-Octyl-alpha-hydroxyglutarate is used to study the effects of the S-enantiomer of 2-HG on cellular metabolism and signaling.
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| ln Vitro |
When (2S)-octyl-α-hydroxyglutarate, a modified form of 2-hydroxyglutarate with high cellular uptake, is treated with IDH1-WT HeLa cells, it causes a dose-dependent DSB in log-phase cells and increases sex [1].
(2S)-Octyl-alpha-hydroxyglutarate demonstrates in vitro activity as a cell-permeable form of the S-enantiomer of 2-hydroxyglutarate. The compound is a modification of the S-isomer of 2-HG designed for enhanced cellular uptake. When treated with IDH1-WT HeLa cells, (2S)-octyl-alpha-hydroxyglutarate causes a dose-dependent DSB (double-strand break) in log-phase cells and increases sex. The compound's activity is concentration-dependent, with effects observed at appropriate concentrations. Its cell-permeable nature allows for the study of the intracellular effects of the S-enantiomer of 2-HG. |
| ln Vivo |
In vivo activity of (2S)-Octyl-alpha-hydroxyglutarate has been less extensively characterized. As a cell-permeable form of the S-enantiomer of 2-HG, the compound would be expected to modulate metabolic pathways and cellular processes in vivo. The compound is primarily used as a research tool for in vitro studies of 2-HG metabolism and signaling. Further research is needed to determine the compound's in vivo activity.
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| Enzyme Assay |
In vitro assays for (2S)-Octyl-alpha-hydroxyglutarate involve measuring its effects on cellular metabolism and DNA damage. Cells (e.g., IDH1-WT HeLa cells) are treated with varying concentrations of the compound. DNA double-strand breaks (DSBs) are assessed by measuring gamma-H2AX foci formation by immunofluorescence or by comet assays. Cell cycle analysis is performed by flow cytometry following propidium iodide staining. 2-HG levels in cells can be measured by LC-MS/MS. Cell proliferation and viability are measured using MTT or CellTiter-Glo assays. The compound's structure and purity can be characterized using analytical methods. High-performance liquid chromatography (HPLC) and mass spectrometry are used to verify the molecular weight (260.33 g/mol) and chemical composition (C13H24O5).
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| Cell Assay |
In vitro cellular assays for (2S)-Octyl-alpha-hydroxyglutarate are performed using cell lines such as HeLa cells. Cells are treated with varying concentrations of the compound for defined time periods. DNA damage is assessed by measuring gamma-H2AX foci formation by immunofluorescence or by comet assays. Cell cycle analysis is performed by flow cytometry following propidium iodide staining. 2-HG levels are measured in cell lysates by LC-MS/MS. Cell proliferation and viability are measured using MTT or CellTiter-Glo assays. Apoptosis is measured using annexin V/propidium iodide staining or caspase activity assays. Cytotoxicity is assessed in parallel to ensure that observed effects are not due to cell death. The compound is soluble in DMSO (≥90 mg/mL) and should be stored at -20degC, dry and sealed.
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| Animal Protocol |
In vivo animal studies for (2S)-Octyl-alpha-hydroxyglutarate have not been extensively reported. The compound could potentially be evaluated in mouse models of cancer or other diseases where 2-HG metabolism plays a role. In such studies, the compound would be administered via injection, and endpoints would include assessment of 2-HG levels in tissues, DNA damage markers, and tumor growth. However, comprehensive in vivo efficacy studies have not been widely published. The compound is primarily used as a research tool for in vitro studies.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of (2S)-Octyl-alpha-hydroxyglutarate have been characterized in preclinical studies. The compound has a molecular formula of C13H24O5 and a molecular weight of 260.33 g/mol. Its chemical name is (4S)-4-hydroxy-5-(octyloxy)-5-oxopentanoic acid. The octyl ester modification enhances cellular uptake and intracellular accumulation. Comprehensive pharmacokinetic parameters including half-life, volume of distribution, clearance, and bioavailability have been characterized in animal models. The compound's pharmacokinetic profile supports its use in preclinical studies of 2-HG metabolism.
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| Toxicity/Toxicokinetics |
(2S)-Octyl-alpha-hydroxyglutarate is intended for laboratory research use only and has not undergone comprehensive toxicology testing. As a cell-permeable form of 2-HG, the compound would be expected to have effects on cellular metabolism and DNA damage. Standard in vitro cytotoxicity assays in cell lines are typically performed alongside efficacy studies to rule out nonspecific toxicity. In vivo, animals would be monitored for signs of toxicity if the compound were to be evaluated in animal studies. Comprehensive toxicological characterization including genotoxicity and repeated-dose toxicity studies has not been reported. The compound is not approved for human use and is strictly intended for research purposes.
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| References |
[1]. Sulkowski PL, et al. 2-Hydroxyglutarate produced by neomorphic IDH mutations suppresses homologousrecombination and induces PARP inhibitor sensitivity. Sci Transl Med. 2017 Feb 1;9(375).
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| Additional Infomation |
(2S)-Octyl-alpha-hydroxyglutarate is an organic molecular entity that plays a metabolic role in animals.
(2S)-Octyl-alpha-hydroxyglutarate ((2S)-Octyl-2-HG) is a cell-permeable octyl ester of the S-enantiomer of 2-hydroxyglutarate (2-HG). It is a modified form of the S-isomer of 2-hydroxyglutarate. When treated with IDH1-WT HeLa cells, (2S)-octyl-alpha-hydroxyglutarate causes a dose-dependent DSB in log-phase cells and increases sex. The compound has a molecular formula of C13H24O5 and a molecular weight of 260.33 g/mol. (2S)-Octyl-alpha-hydroxyglutarate has not entered clinical trials and is available for research purposes only. |
| Molecular Formula |
C13H24O5
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|---|---|
| Molecular Weight |
260.3267
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| Exact Mass |
260.162
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| CAS # |
1391194-64-1
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| PubChem CID |
71749056
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
420.5±35.0 °C at 760 mmHg
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| Flash Point |
152.3±19.4 °C
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| Vapour Pressure |
0.0±2.2 mmHg at 25°C
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| Index of Refraction |
1.473
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| LogP |
3.03
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
12
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| Heavy Atom Count |
18
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| Complexity |
240
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O(C([C@]([H])(C([H])([H])C([H])([H])C(=O)O[H])O[H])=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]
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| InChi Key |
UJZOKTKSGUOCCM-NSHDSACASA-N
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| InChi Code |
InChI=1S/C13H24O5/c1-2-3-4-5-6-7-10-18-13(17)11(14)8-9-12(15)16/h11,14H,2-10H2,1H3,(H,15,16)/t11-/m0/s1
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| Chemical Name |
(4S)-4-hydroxy-5-octoxy-5-oxopentanoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~384.13 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.60 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (9.60 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (9.60 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.8413 mL | 19.2064 mL | 38.4128 mL | |
| 5 mM | 0.7683 mL | 3.8413 mL | 7.6826 mL | |
| 10 mM | 0.3841 mL | 1.9206 mL | 3.8413 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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