| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
The compound targets free thiol groups (-SH) on cysteine residues within proteins. It can non-specifically alkylate thiols via a Michael addition reaction. A specific reported target is rat liver glucose-6-phosphatase, whose activity is inhibited by this compound.
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|---|---|
| ln Vitro |
N-Octylmaleimide acts as a potent inhibitor of rat liver microsomal glucose-6-phosphatase. It covalently modifies free thiol groups essential for catalytic activity. At concentrations around 50-100 uM, it can cause nearly complete inhibition of this enzyme, as demonstrated in isolated microsomal preparations.
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| ln Vivo |
No significant direct in vivo activity studies are publicly available for this compound. Its primary use is as an ex vivo or in vitro biochemical tool to probe enzyme mechanisms and thiol-dependent processes. Any in vivo effects would likely stem from non-specific alkylation of critical protein thiols, leading to cellular toxicity.
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| Enzyme Assay |
In a non-cellular assay, the maleimide is incubated with small thiol-containing molecules (e.g., glutathione or cysteine) in a buffered solution (pH 6.5-7.5). The reaction progress is monitored by measuring the decrease in free thiols using Ellman‘s reagent (DTNB) or by HPLC analysis to quantify the formation of the thiosuccinimide adduct product.
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| Cell Assay |
N-Octylmaleimide is typically tested in cell lysates or purified enzyme systems. For glucose-6-phosphatase, liver microsomes are isolated and pre-incubated with varying concentrations (0-500 uM) of the compound for 5-10 minutes. The residual enzymatic activity is then measured by adding [U-14C]-glucose-6-phosphate and quantifying the release of radioactive inorganic phosphate after a 10-minute incubation at 37degC.
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| Animal Protocol |
In vivo animal protocols are not well-documented, as the compound is primarily a research tool for ex vivo studies. Typically, it is administered via injection (e.g., intraperitoneal) to rodents to study its effect on glucose metabolism or liver function. However, due to its high reactivity with thiols, it is more commonly used as a probe in tissue homogenates rather than in live animals.
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| ADME/Pharmacokinetics |
Pharmacokinetic data is not available. As a reactive alkylating agent, it is expected to be rapidly metabolized and conjugated upon absorption to glutathione and other nucleophiles in the blood and liver. Its high lipophilicity (due to the octyl chain) suggests it can readily cross cell membranes, leading to widespread non-specific protein binding.
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| Toxicity/Toxicokinetics |
Due to its non-specific reactivity with cysteine thiols, N-Octylmaleimide is considered toxic, causing general protein alkylation that disrupts cellular function. It is an irritant to skin and eyes and should be handled as a hazardous chemical. No human toxicity data exists as it is not a therapeutic agent.
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| References |
[1]. B Vakili, M Banner, et al. Inhibition of rat liver glucose 6-phosphatase by N-alkylmaleimides. Biochem Soc Trans. 1979 Feb;7(1):168-70.
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| Additional Infomation |
The maleimide functional group is the active part of the molecule, reacting with thiols to form stable thiosuccinimide linkages. The octyl chain increases lipophilicity, allowing it to target membrane-associated proteins. It is a research chemical, not a pharmaceutical, and has no approved therapeutic indications or clinical trial history.
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| Molecular Formula |
C12H19NO2
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|---|---|
| Molecular Weight |
209.28
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| Exact Mass |
209.142
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| CAS # |
4080-76-6
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| Related CAS # |
26714-91-0
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| PubChem CID |
512829
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| Appearance |
White to off-white solid powder
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| Melting Point |
35-37ºC
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| LogP |
2.209
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
15
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| Complexity |
240
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCCCCCN1C(=O)C=CC1=O
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| InChi Key |
KIKBJYQCJJXCBZ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H19NO2/c1-2-3-4-5-6-7-10-13-11(14)8-9-12(13)15/h8-9H,2-7,10H2,1H3
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| Chemical Name |
1-octylpyrrole-2,5-dione
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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 |
| 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 (477.83 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.95 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 (11.95 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 (11.95 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 | 4.7783 mL | 23.8914 mL | 47.7829 mL | |
| 5 mM | 0.9557 mL | 4.7783 mL | 9.5566 mL | |
| 10 mM | 0.4778 mL | 2.3891 mL | 4.7783 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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