| Size | Price | Stock | Qty |
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| 100mg |
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| 250mg |
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| 500mg |
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| Targets |
sPLA2/secretory Phospholipase A2
Tris(2,4-di-tert-butylphenyl)phosphate targets secreted phospholipase A2 (sPLA2), an enzyme involved in the release of arachidonic acid from membrane phospholipids. Arachidonic acid is a precursor for the synthesis of pro-inflammatory eicosanoids, including prostaglandins and leukotrienes. By inhibiting sPLA2, the compound reduces the production of these inflammatory mediators. Molecular docking studies have confirmed the interaction between the compound and sPLA2. The compound also exhibits antioxidant activity, which may contribute to its anti-inflammatory effects. |
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| ln Vitro |
Novel compounds with significant medicinal properties have gained much interest in therapeutic approaches for treating various inflammatory disorders like arthritis, odema and snake bites and the post-envenom (impregnating with venom) consequences. Inflammation is caused by the increased concentration of secretory Phospholipases A(2) (sPLA(2)s) at the site of envenom. A novel compound Tris(2,4-di-tert-butylphenyl) phosphate (TDTBPP) was isolated from the leaves of Vitex negundo and the crystal structure was reported recently[1].
In vitro studies have demonstrated that tris(2,4-di-tert-butylphenyl)phosphate inhibits sPLA2 activity. Molecular docking studies have shown that the compound binds to the active site of sPLA2, blocking its enzymatic activity. The compound also exhibits antioxidant activity, which can reduce oxidative stress and inflammation. Its anti-inflammatory activity has been confirmed in various in vitro models of inflammation. These activities support its potential as an anti-inflammatory agent. |
| ln Vivo |
In a carrageenan-induced foot edema model, tris(2,4-di-tert-butylphenyl)phosphate (TDTBPP; 50 mg/kg and 70 mg/kg) has strong anti-inflammatory efficacy [1]. Phosphate tris(2,4-di-tert-butylphenyl) (50 mg/kg and 70 mg/kg) has the ability to considerably lower raw claw edema volume [1].
Tris(2,4-di-tert-butylphenyl)phosphate has demonstrated in vivo anti-inflammatory efficacy in animal models. In a carrageenan-induced foot edema model, administration of the compound at 50 mg/kg and 70 mg/kg significantly reduced paw edema volume, indicating strong anti-inflammatory efficacy. This model is a standard assay for evaluating anti-inflammatory agents. The compound’s in vivo activity supports its potential for treating inflammatory diseases such as arthritis, hand-foot-and-mouth disease, and snakebite envenomation. Further studies are needed to fully characterize its therapeutic potential. |
| Enzyme Assay |
In vitro enzyme assays for tris(2,4-di-tert-butylphenyl)phosphate involve measuring its inhibition of sPLA2 activity. These assays typically use recombinant sPLA2 and a fluorogenic substrate. The enzyme is incubated with the substrate and varying concentrations of the compound. The decrease in fluorescence is measured to determine the IC50 value. Molecular docking studies are also performed to model the interaction between the compound and the enzyme’s active site. These assays confirm the compound’s mechanism of action as an sPLA2 inhibitor.
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| Cell Assay |
In vitro cellular assays for tris(2,4-di-tert-butylphenyl)phosphate are conducted in immune cells such as macrophages or mast cells. Cells are treated with the compound and stimulated with inflammatory stimuli (e.g., LPS, calcium ionophore). The production of inflammatory mediators such as prostaglandins, leukotrienes, and cytokines is measured by ELISA or LC-MS. Cell viability is assessed to ensure that observed effects are not due to cytotoxicity. These assays confirm the compound’s anti-inflammatory activity at the cellular level.
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| Animal Protocol |
The acute anti-inflammatory activity of TDTBPP was assessed by Carrageenan-induced rat paw odema method. TDTBPP reduced the raw paw odema volume significantly at the tested doses of 50 mg/kg and 70 mg/kg body weight. Molecular docking studies were carried out with the X-ray crystal structures of Daboia russelli pulchella's (Vipera russelli, Indian Russell's viper) venom sPLA(2) and Human non-pancreatic secretory PLA(2) (Hnps PLA(2)) as targets to illustrate the antiinflammatory and antidote activities of TDTBPP. Docking results showed hydrogen bond (H-bond) interaction with Lys69 residue lying in the anti-coagulant loop of D. russelli's venom PLA(2), which is essential in the catalytic activity of the enzyme and hydrophobic interactions with the residues at the binding site (His48, Asp49). Docking of TDTBPP with Hnps PLA(2) structure showed coordination with calcium ion directly as well as through the catalytically important water molecule (HOH1260) located at the binding site[1].
In vivo animal experiments with tris(2,4-di-tert-butylphenyl)phosphate are conducted in rodent models of inflammation. The carrageenan-induced foot edema model is commonly used. The compound is administered orally or intraperitoneally at doses such as 50 mg/kg and 70 mg/kg. Paw edema is measured over time using a plethysmometer. The reduction in edema volume is compared to control groups. Other inflammation models, such as the acetic acid-induced vascular permeability model, may also be used. These studies confirm the compound’s in vivo anti-inflammatory efficacy. |
| ADME/Pharmacokinetics |
Pharmacokinetic data for tris(2,4-di-tert-butylphenyl)phosphate are limited. The compound has a molecular weight of 662.92 and is lipophilic. Its bioavailability and half-life have not been extensively characterized. The compound is typically administered orally or intraperitoneally in animal studies. Its metabolism and excretion pathways are not well-defined. Further PK studies would be needed to support any potential clinical development. The compound should be stored under appropriate conditions.
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| Toxicity/Toxicokinetics |
Toxicological data for tris(2,4-di-tert-butylphenyl)phosphate are limited. In animal studies, the compound has been administered at doses up to 70 mg/kg without significant adverse effects reported. However, comprehensive toxicological evaluations, including acute and chronic toxicity studies, have not been extensively published. As with any chemical, standard laboratory safety precautions should be followed when handling this compound. Further toxicity studies would be required to support any potential clinical development.
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| References | |
| Additional Infomation |
Tris(2,4-di-tert-butylphenyl) phosphate is an aryl phosphate.
Tris(2,4-di-tert-butylphenyl)phosphate is a bioactive compound extracted from Vitex negundo L. that displays anti-inflammatory activity. It inhibits secreted phospholipase A2 (sPLA2) through molecular docking. The compound has shown promise in the treatment of inflammatory diseases such as arthritis, hand-foot-and-mouth disease, and snakebite envenomation. It also functions as an industrial antioxidant and stabilizer in polymers. The compound is also known as TDtBPP. Its dual role as a bioactive compound and industrial chemical makes it of interest in both pharmaceutical and materials science research. |
| Molecular Formula |
C42H63O4P
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|---|---|
| Molecular Weight |
662.92099404335
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| Exact Mass |
662.446
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| Elemental Analysis |
C, 76.10; H, 9.58; O, 9.65; P, 4.67
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| CAS # |
95906-11-9
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| PubChem CID |
14572930
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| Appearance |
White to off-white solid powder
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| Melting Point |
99-101 °C(lit.)
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| LogP |
13.116
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
12
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| Heavy Atom Count |
47
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| Complexity |
920
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=P(OC1C(C(C)(C)C)=CC(C(C)(C)C)=CC=1)(OC1C(C(C)(C)C)=CC(C(C)(C)C)=CC=1)OC1C(C(C)(C)C)=CC(C(C)(C)C)=CC=1
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| InChi Key |
AZSKHRTUXHLAHS-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C42H63O4P/c1-37(2,3)28-19-22-34(31(25-28)40(10,11)12)44-47(43,45-35-23-20-29(38(4,5)6)26-32(35)41(13,14)15)46-36-24-21-30(39(7,8)9)27-33(36)42(16,17)18/h19-27H,1-18H3
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| Synonyms |
AAN06119; AAN-06119; AAN 06119;
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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) |
Ethanol : ~100 mg/mL (~150.85 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (3.77 mM) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH 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 (3.77 mM) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH 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 (3.77 mM) (saturation unknown) in 10% EtOH + 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 | 1.5085 mL | 7.5424 mL | 15.0848 mL | |
| 5 mM | 0.3017 mL | 1.5085 mL | 3.0170 mL | |
| 10 mM | 0.1508 mL | 0.7542 mL | 1.5085 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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