| Size | Price | Stock | Qty |
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| 5mg |
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| Other Sizes |
| Targets |
(R)-BEL selectively inhibits calcium-independent phospholipase gamma (iPLA2gamma) with an IC50 of approximately 0.6 uM for human recombinant iPLA2gamma. Unlike the (S)-BEL enantiomer, (R)-BEL does not inhibit iPLA2beta except at high doses of 20-30 uM, making it a useful tool for discriminating between iPLA2 isoforms. iPLA2gamma is involved in the release of arachidonic acid and the activation of inflammasomes.
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| ln Vitro |
In vitro, (R)-BEL irreversibly binds to the active site of iPLA2gamma and blocks its enzymatic activity. It inhibits human recombinant iPLA2gamma with an IC50 of approximately 0.6 uM. The (R)-enantiomer shows significantly reduced activity against iPLA2beta compared to the (S)-enantiomer, providing isoform selectivity. (R)-BEL is used to study the role of iPLA2gamma in arachidonic acid mobilization, eicosanoid production, and inflammatory signaling pathways.
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| ln Vivo |
In vivo, (R)-BEL has been used to investigate the role of iPLA2gamma in the activation of caspase-1 induced by lipopolysaccharides (LPS) and in the secretion of IL-1beta via the Nlrc4 inflammasome. By inhibiting iPLA2gamma, BEL blocks the release of arachidonic acid and downstream inflammatory mediators. Dosing protocols typically involve intraperitoneal administration of (R)-BEL in rodent models of inflammation.
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| Enzyme Assay |
Systematic protocols for (R)-BEL as an iPLA2gamma inhibitor involve incubating recombinant human iPLA2gamma protein with varying concentrations of (R)-BEL in assay buffer containing a phospholipid substrate, typically 1-palmitoyl-2-[14C]arachidonoyl-sn-glycero-3-phosphocholine. Reactions are allowed to proceed for a set time (e.g., 30-60 minutes) before termination, and the released radioactive arachidonic acid is extracted and quantified by scintillation counting to determine IC50 values.
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| Cell Assay |
For in vitro cell assays, cells (e.g., macrophages or HEK293 cells expressing iPLA2gamma) are treated with escalating concentrations of (R)-BEL (typically 0.1-10 uM) for 1-4 hours. After treatment, cells are stimulated with agents such as LPS or ATP to activate iPLA2gamma-dependent pathways. Supernatants are collected to measure arachidonic acid release, IL-1beta secretion, or other inflammatory markers via ELISA. Cell viability is assessed using MTT or ATP-based luminescence assays.
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| Animal Protocol |
For in vivo studies, (R)-BEL is typically dissolved in DMSO or a DMSO:PBS mixture and administered via intraperitoneal injection at doses of 1-10 mg/kg in rodent models. Animals are challenged with an inflammatory stimulus (e.g., LPS) prior to or following drug administration. Plasma, peritoneal lavage fluid, or tissue samples are collected at defined time points to measure cytokine levels (IL-1beta, IL-18), arachidonic acid metabolites, and signs of inflammasome activation.
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| ADME/Pharmacokinetics |
Detailed pharmacokinetic data specific to (R)-BEL are limited in the literature. Based on its lipophilic nature, the compound is expected to distribute widely into tissues. For in vivo studies, (R)-BEL is typically formulated in a vehicle such as DMSO:PBS or a mixture with cyclodextrin to enhance solubility. Researchers should perform pilot PK studies or refer to primary literature for strain- and species-specific parameters.
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| Toxicity/Toxicokinetics |
Published toxicology data for (R)-BEL are limited. In vitro cytotoxicity assays suggest that (R)-BEL is relatively well tolerated at concentrations up to 10 uM in most cell lines. In animal studies at doses used for iPLA2gamma inhibition (e.g., 5-10 mg/kg i.p.), no severe acute toxicity has been typically reported. However, as with any irreversible enzyme inhibitor, potential off-target effects should be assessed. Full toxicological profiling has not been publicly released.
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| References | |
| Additional Infomation |
(R)-BEL is a research tool and is not approved for clinical use. Its mechanism involves irreversible alkylation or covalent modification of the active site serine residue of iPLA2gamma. This irreversible inhibition differentiates it from reversible inhibitors and allows for prolonged blockade of enzyme activity even after compound washout. (R)-BEL is often compared to (S)-BEL in studies to dissect the specific contributions of iPLA2beta versus iPLA2gamma. It is stored at -20degC, protected from light and moisture.
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| Molecular Formula |
C16H13BRO2
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|---|---|
| Molecular Weight |
317.18
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| Exact Mass |
316.009
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| CAS # |
478288-90-3
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| Related CAS # |
Bromoenol lactone;88070-98-8
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| PubChem CID |
40486928
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
467.0±45.0 °C at 760 mmHg
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| Flash Point |
236.2±28.7 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.716
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| LogP |
4.36
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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 |
1
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| Heavy Atom Count |
19
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| Complexity |
377
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1=CC=C2C(=C1)C=CC=C2[C@H]3CC/C(=C\Br)/OC3=O
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| InChi Key |
BYUCSFWXCMTYOI-HBIYDYFMSA-N
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| InChi Code |
InChI=1S/C16H13BrO2/c17-10-12-8-9-15(16(18)19-12)14-7-3-5-11-4-1-2-6-13(11)14/h1-7,10,15H,8-9H2/b12-10+/t15-/m1/s1
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| Chemical Name |
(3R,6E)-6-(bromomethylidene)-3-naphthalen-1-yloxan-2-one
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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 | 3.1528 mL | 15.7639 mL | 31.5278 mL | |
| 5 mM | 0.6306 mL | 3.1528 mL | 6.3056 mL | |
| 10 mM | 0.3153 mL | 1.5764 mL | 3.1528 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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