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| Targets |
Caulilexin C has been shown to inhibit human acyl CoA: cholesterol transferase I (hACAT1) and human acyl CoA: cholesterol transferase 2 (hACAT2). ACAT1 and ACAT2 are enzymes that catalyze the esterification of cholesterol with fatty acids to form cholesteryl esters, which are stored in lipid droplets. ACAT1 is ubiquitously expressed, while ACAT2 is primarily expressed in the intestine and liver. Inhibition of ACAT enzymes can reduce cholesterol absorption and lower plasma cholesterol levels, making ACAT inhibitors potential therapeutic agents for atherosclerosis and hypercholesterolemia. Caulilexin C inhibits both ACAT1 and ACAT2 at a concentration of 100 μg/mL. The compound also exhibits antifungal activity, which is consistent with its role as a phytoalexin, a plant defense compound produced in response to pathogen attack. The exact molecular target responsible for its antifungal activity is not fully elucidated.
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| ln Vitro |
Caulilexin C appears to have a somewhat stronger antifungal effect than arvelexin, and it can totally suppress the growth of Rhizoctonia solani (0.5 mM). It also has a smaller effect on Leptosphaeria maculans (77% inhibition).
In vitro, Caulilexin C shows inhibitory activity on human acyl CoA: cholesterol transferase I (hACAT1) and human acyl CoA: cholesterol transferase 2 (hACAT2) at a concentration of 100 μg/mL. This activity suggests that the compound may have potential for lowering cholesterol levels. The compound also exhibits antifungal activity, which is consistent with its role as a phytoalexin. However, specific IC₅₀ values for these activities have not been reported in the available literature. The compound's activity is typically assessed in cell-free enzyme assays using recombinant ACAT enzymes or in cell-based assays using cholesterol esterification measurements. The compound's antifungal activity is assessed using standard antifungal susceptibility tests against various fungal strains. |
| ln Vivo |
Detailed in vivo activity data for Caulilexin C is not extensively reported in the available literature. As a natural product with ACAT inhibitory and antifungal activities, it may have potential for in vivo applications. However, no specific in vivo studies, such as animal models of hypercholesterolemia or fungal infection, have been detailed in the public domain. The compound's in vivo efficacy would depend on its pharmacokinetic properties, such as oral bioavailability and tissue distribution. The compound's ACAT inhibitory activity suggests that it could potentially lower plasma cholesterol levels in vivo. Its antifungal activity suggests that it could potentially be used to treat fungal infections. Further studies are needed to evaluate the compound's in vivo efficacy and safety.
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| Enzyme Assay |
The inhibition of ACAT1 and ACAT2 by Caulilexin C can be measured using a cell-free enzyme assay. The assay is performed in a 96-well plate format. Recombinant human ACAT1 or ACAT2 is expressed and purified from a suitable expression system. The assay mixture contains 100 mM potassium phosphate buffer (pH 7.4), 0.1 mM cholesterol, 0.1 mM [¹⁴C]-oleoyl-CoA, 0.2% Triton X-100, and varying concentrations of Caulilexin C. The reaction is initiated by the addition of the enzyme. After incubation at 37°C for 30 minutes, the reaction is terminated by the addition of chloroform/methanol. The lipids are extracted, and the [¹⁴C]-cholesteryl oleate produced is separated by thin-layer chromatography (TLC) and quantified by liquid scintillation counting. The percentage of inhibition at each compound concentration is calculated relative to a control without inhibitor. The IC₅₀ is determined from the dose-response curve. For antifungal activity, standard broth microdilution assays are performed according to CLSI guidelines. Various fungal strains are incubated with serial dilutions of Caulilexin C, and the minimum inhibitory concentration (MIC) is determined.
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| Cell Assay |
For in vitro cellular assays, the effect of Caulilexin C on cholesterol esterification can be assessed using cell lines such as macrophages or hepatocytes. Cells are incubated with [¹⁴C]-oleic acid and varying concentrations of Caulilexin C. The incorporation of [¹⁴C]-oleic acid into cholesteryl esters is measured. The percentage of inhibition of cholesterol esterification at each compound concentration is calculated relative to untreated control cells. The IC₅₀ is determined from the dose-response curve. The antifungal activity of Caulilexin C can be assessed in cell-based assays using fungal cell lines. The effect of the compound on fungal growth is assessed using a resazurin or MTT assay. The MIC, representing the concentration that inhibits fungal growth by 50%, is determined from the dose-response curve.
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| Animal Protocol |
In vivo efficacy of Caulilexin C could be assessed in animal models of hypercholesterolemia, such as high-fat diet-fed hamsters or rabbits. In such a study, animals are fed a high-fat diet to induce hypercholesterolemia. Caulilexin C is administered orally at various doses (e.g., 10-50 mg/kg) once daily for a period of several weeks. A control group receives the vehicle alone. Plasma total cholesterol, LDL cholesterol, and HDL cholesterol levels are measured at baseline and at regular intervals during the treatment period. The efficacy of the compound is evaluated by comparing cholesterol levels between treated and control groups. For antifungal efficacy, a mouse model of systemic fungal infection could be used. Mice are infected with a fungal strain, and Caulilexin C is administered orally or intraperitoneally. Survival and fungal burden in tissues are assessed. These studies would provide critical data on the compound's in vivo efficacy. Currently, no such detailed in vivo protocols for Caulilexin C have been published.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties for Caulilexin C are not extensively reported in the available literature. The compound has a molecular weight of 186.21, which is relatively small, suggesting that it may have good oral bioavailability. Its logP is not reported, but the compound's structure suggests moderate lipophilicity. However, specific pharmacokinetic parameters such as half-life, volume of distribution, clearance, and oral bioavailability have not been determined experimentally. The compound's metabolism is likely to involve hepatic cytochrome P450 enzymes. The compound's elimination route is unknown. Further studies are needed to fully characterize the pharmacokinetic profile of this compound. The compound's in vivo activity would depend on its ability to reach target tissues in sufficient concentrations.
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| Toxicity/Toxicokinetics |
Toxicological data for Caulilexin C is limited, as it is a research chemical. Standard safety precautions should be observed when handling this compound. No specific toxicity studies, such as acute or chronic toxicity in animal models, have been detailed in the public domain. As a natural product, it may have a favorable safety profile, but this has not been confirmed. The compound is not approved for clinical use and should only be used in preclinical research settings.
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| References | |
| Additional Infomation |
1-Methoxy-1H-indole-3-acetonitrile is an indole compound. 1H-indole-3-acetonitrile, 1-methoxy-, has been reported in halophilic bacteria, Arabidopsis thaliana, and other organisms with available data.
Caulilexin C is a research tool for studying ACAT enzymes and cholesterol metabolism. It exhibits ACAT inhibitory and antifungal activities. It is not approved for clinical use. |
| Molecular Formula |
C11H10N2O
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|---|---|
| Molecular Weight |
186.2099
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| Exact Mass |
186.079
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| CAS # |
30536-48-2
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| PubChem CID |
11954881
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
350.7±34.0 °C at 760 mmHg
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| Flash Point |
165.9±25.7 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.580
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| LogP |
2.25
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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 |
2
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| Heavy Atom Count |
14
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| Complexity |
245
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CON1C=C(C2=CC=CC=C21)CC#N
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| InChi Key |
LIJIPBYXIXTNLE-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H10N2O/c1-14-13-8-9(6-7-12)10-4-2-3-5-11(10)13/h2-5,8H,6H2,1H3
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| Chemical Name |
2-(1-methoxyindol-3-yl)acetonitrile
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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 (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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 (~537.03 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.43 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 (13.43 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 (13.43 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 | 5.3703 mL | 26.8514 mL | 53.7028 mL | |
| 5 mM | 1.0741 mL | 5.3703 mL | 10.7406 mL | |
| 10 mM | 0.5370 mL | 2.6851 mL | 5.3703 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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