| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
The primary target of cereulide is the mitochondrial membrane, where it acts as a potassium ionophore. Its high selectivity for K⁺ leads to disruption of mitochondrial membrane potential, causing swelling and respiratory stimulation in mitochondria. This mitochondrial dysfunction results in ATP depletion and apoptosis induction in various cell types. It does not target a specific protein receptor but rather acts by forming ion channels in lipid membranes.
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|---|---|
| ln Vitro |
In vitro, cereulide induces apoptosis in various cell types. It acts on mitochondria, causing dysfunction characterized by swelling and respiratory stimulation. It has been shown to stimulate swelling and respiration in rat liver mitochondria. Its ionophore activity with high selectivity for K⁺ disrupts mitochondrial membrane potential, leading to ATP depletion and cell death. The toxin affects different organs including liver, pancreas, brain, and intestines.
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| ln Vivo |
In vivo, cereulide is rapidly absorbed in the gut and transported into the bloodstream. It causes emesis (vomiting) in humans and animals, which is the hallmark of Bacillus cereus emetic food poisoning. It acts on mitochondria in various organs, leading to dysfunction of the liver, pancreatic islet, brain, intestines, and other organs. It also affects the immune and nervous systems. Its stability to heat, acids, alkalis, and digestive enzymes contributes to its toxicity in food poisoning.
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| Enzyme Assay |
In vitro non-cellular binding assays for cereulide typically involve ionophore activity studies. A common protocol is: (1) prepare isolated rat liver mitochondria or artificial lipid membranes; (2) add cereulide at various concentrations (1-100 nM); (3) measure mitochondrial swelling by monitoring absorbance at 540 nm; (4) assess respiratory activity using an oxygen electrode; (5) measure mitochondrial membrane potential using fluorescent dyes (e.g., JC-1 or TMRM); (6) evaluate K⁺ flux using K⁺-selective electrodes; and (7) determine ion selectivity by comparing effects with different cations.
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| Cell Assay |
In vitro cell-based assays for cereulide typically involve: (1) culture relevant cell lines (e.g., human intestinal epithelial cells, hepatocytes, or neuronal cells); (2) treat cells with cereulide at various concentrations (0.1-100 ng/mL) for 2-24 hours; (3) assess cell viability using MTT or LDH release assays; (4) evaluate apoptosis by flow cytometry (Annexin V/PI staining) and caspase activity assays; (5) measure mitochondrial membrane potential using fluorescent dyes; (6) assess ATP levels; and (7) evaluate cytokine production by ELISA.
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| Animal Protocol |
In vivo animal experiments with cereulide typically involve emetic toxicity studies. A common protocol is: (1) administer cereulide to mice, rats, or ferrets via oral gavage or intraperitoneal injection at doses of 10-200 μg/kg; (2) monitor animals for emesis (in species that can vomit, e.g., ferrets) or other signs of toxicity; (3) collect blood and tissue samples at various time points; (4) measure cereulide levels in plasma and tissues by LC-MS/MS; (5) evaluate organ pathology by histology; (6) assess mitochondrial function in isolated tissues; and (7) determine the LD50 and dose-response relationships.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of cereulide: It is rapidly absorbed in the gut and transported into the bloodstream. As a lipophilic cyclopeptide, it distributes widely in tissues. It is stable to heat, acids, alkalis, and digestive enzymes, which contributes to its persistence in the gastrointestinal tract and its toxicity. It is not extensively metabolized and is excreted primarily in feces. Its half-life in the body is not well-characterized but its stability suggests prolonged persistence.
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| Toxicity/Toxicokinetics |
The toxicity of cereulide is significant, causing emetic food poisoning. It acts on mitochondria, leading to dysfunction in different organs (liver, pancreatic islet, brain, intestines, etc.) and body systems (immune and nervous systems). It induces apoptosis in various cell types. Its stability to heat, acids, alkalis, and digestive enzymes makes it a potent foodborne toxin. Symptoms include nausea, vomiting, and in severe cases, liver failure. It is classified as a toxin and should be handled with extreme care.
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| References | |
| Additional Infomation |
Reports indicate that Bacillus cereus contains Bacillus cereus toxin, and relevant data is available for reference.
This compound is a toxin peptide produced by Bacillus cereus. It is a cyclic depsipeptide composed of three repeats of [D-O-Leu-D-Ala-L-O-Val-L-Val]. It is extensively studied and analyzed as a toxin responsible for food poisoning. It has a molecular weight of approximately 1150 g/mol. This product is not a drug and has no clinical trial or regulatory approval status; it is sold exclusively for research purposes as a reference standard for food safety testing. |
| Molecular Formula |
C57H96N6O18
|
|---|---|
| Molecular Weight |
1153.40
|
| Exact Mass |
1152.678
|
| CAS # |
157232-64-9
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| PubChem CID |
10057089
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
10.2
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| Hydrogen Bond Donor Count |
6
|
| Hydrogen Bond Acceptor Count |
18
|
| Rotatable Bond Count |
12
|
| Heavy Atom Count |
81
|
| Complexity |
1960
|
| Defined Atom Stereocenter Count |
12
|
| SMILES |
O1C([C@H](C(C)C)NC([C@H](C(C)C)OC([C@@H](C)NC([C@@H](CC(C)C)OC([C@H](C(C)C)NC([C@H](C(C)C)OC([C@@H](C)NC([C@@H](CC(C)C)OC([C@H](C(C)C)NC([C@H](C(C)C)OC([C@@H](C)NC([C@H]1CC(C)C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O
|
| InChi Key |
JWWAHGUHYLWQCQ-UHZBFKKDSA-N
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| InChi Code |
InChI=1S/C57H96N6O18/c1-25(2)22-37-46(64)58-34(19)52(70)79-44(32(15)16)50(68)62-41(29(9)10)56(74)77-39(24-27(5)6)48(66)60-36(21)54(72)81-45(33(17)18)51(69)63-42(30(11)12)57(75)78-38(23-26(3)4)47(65)59-35(20)53(71)80-43(31(13)14)49(67)61-40(28(7)8)55(73)76-37/h25-45H,22-24H2,1-21H3,(H,58,64)(H,59,65)(H,60,66)(H,61,67)(H,62,68)(H,63,69)/t34-,35-,36-,37-,38-,39-,40+,41+,42+,43+,44+,45+/m1/s1
|
| Chemical Name |
(3R,6R,9S,12S,15R,18R,21S,24S,27R,30R,33S,36S)-3,15,27-trimethyl-6,18,30-tris(2-methylpropyl)-9,12,21,24,33,36-hexa(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.8670 mL | 4.3350 mL | 8.6700 mL | |
| 5 mM | 0.1734 mL | 0.8670 mL | 1.7340 mL | |
| 10 mM | 0.0867 mL | 0.4335 mL | 0.8670 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.
Products are for research use only; We do not sell to patients
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