| Size | Price | |
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| 5mg | ||
| 10mg | ||
| 50mg | ||
| Other Sizes |
| Targets |
α-glucosidase α-amylase
The primary targets of 2,4,6-Triphenylaniline are the carbohydrate-hydrolyzing enzymes alpha-glucosidase and alpha-amylase. It inhibits alpha-glucosidase and alpha-amylase. By inhibiting these enzymes, it delays the breakdown of carbohydrates into glucose, thereby reducing postprandial hyperglycemia (blood sugar spikes after meals). This mechanism is similar to that of acarbose, a standard anti-diabetic drug. The compound is also a potential inhibitor of protein tyrosine phosphatase 1B (PTP1B). It is a marine-derived natural product found in Alternaria longipes. It has anti-diabetic activity. |
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| ln Vitro |
In vitro enzyme inhibition assays show that 2,4,6-Triphenylaniline is a potent inhibitor of alpha-glucosidase with an IC50 of approximately 5-15 uM (vs. acarbose IC50 ~ 200 uM). It also inhibits alpha-amylase with an IC50 of ~10-20 uM. The inhibition is competitive. It has been shown to be non-cytotoxic to normal cells (HEK293, IC50 > 100 uM). The compound is encapsulated in nano-emulsions (NE) to enhance stability and permeability. The NE loaded with 2,4,6-Triphenylaniline inhibits alpha-glucosidase and alpha-amylase. It is a potent inhibitor. These in vitro data support its potential as an anti-diabetic agent.
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| ln Vivo |
In vivo efficacy has been demonstrated in a streptozotocin (STZ)-induced diabetic rat model. Rats are treated orally with 2,4,6-Triphenylaniline (10-40 mg/kg) for 14 days. The compound significantly reduces fasting blood glucose levels (by 30-50% at 20 mg/kg) and improves oral glucose tolerance (OGTT). It also lowers HbA1c levels. It does not cause hypoglycemia. The nano-emulsion formulation (NE) enhances oral bioavailability and reduces the required dose by 50%. These results indicate strong anti-diabetic activity in vivo. The compound is a marine-derived natural product. It has anti-diabetic activity. It can be encapsulated in nano-emulsions.
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| Enzyme Assay |
Non-cellular assay: alpha-glucosidase inhibition. In a 96-well plate, 50 uL of alpha-glucosidase (0.1 U/mL in 0.1 M phosphate buffer, pH 6.8) is mixed with 50 uL of 2,4,6-Triphenylaniline (0-100 uM in DMSO). Pre-incubate at 25degC for 10 min. Add 50 uL of substrate (4-nitrophenyl-alpha-D-glucopyranoside, pNPG, 1 mM). Incubate at 37degC for 30 min. Add 100 uL of 0.2 M Na2CO3 to stop the reaction. Absorbance is measured at 405 nm (yellow p-nitrophenol). % inhibition = (control - test)/control × 100. IC50 is calculated. A similar protocol is used for alpha-amylase using starch as substrate and dinitrosalicylic acid (DNS) reagent. This is the standard assay for anti-diabetic screening.
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| Cell Assay |
Cell-based assays for glucose uptake: C2C12 mouse myoblasts are differentiated into myotubes. Cells are serum-starved for 2-3 hours. Then, 2,4,6-Triphenylaniline (1-25 uM) is added for 24 h. Glucose uptake is measured by adding 2-NBDG (fluorescent glucose analog, 100 uM) for 1 h. Fluorescence is quantified (Ex/Em 485/535 nm). Insulin (100 nM) is a positive control. The compound increases 2-NBDG uptake by 30-60% (p<0.05). This indicates improved insulin sensitivity. The cells are also stained for Oil Red O to check lipid accumulation. No cytotoxicity is observed. This assay demonstrates the cellular mechanism. It is an alpha-glucosidase and alpha-amylase inhibitor.
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| Animal Protocol |
In vivo diabetes study: Male Sprague-Dawley rats (180-200 g) are rendered diabetic by a single intraperitoneal injection of streptozotocin (STZ, 55 mg/kg). After 7 days (fasting blood glucose >250 mg/dL), rats are randomized into groups (n=8). Group 1: vehicle (0.5% CMC), Group 2: 2,4,6-Triphenylaniline (20 mg/kg, oral), Group 3: acarbose (50 mg/kg), Group 4: metformin (100 mg/kg). Treatment is given daily for 14 days. Blood glucose is measured on days 0, 7, 14. An OGTT (oral glucose tolerance test, 2 g/kg glucose) is performed on day 13. Blood is collected at 0, 30, 60, 90, 120 min. Serum insulin is measured by ELISA. The treatment group shows a significant reduction in AUC (area under the curve) for glucose and increased insulin levels. This confirms the in vivo anti-diabetic efficacy of the compound.
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| ADME/Pharmacokinetics |
Pharmacokinetic data in rats: After oral administration (20 mg/kg), 2,4,6-Triphenylaniline is rapidly absorbed with a Tmax of 1-2 hours. The Cmax is ~0.5 ug/mL. The bioavailability is ~20% (due to poor solubility). The half-life (t1/2) is approximately 6-8 hours. Encapsulation in nano-emulsions (NE) increases bioavailability to ~45% and prolongs t1/2 to 12 h. The compound is metabolized by CYP450 enzymes (hydroxylation, glucuronidation). It is eliminated in feces and urine. It is a solid powder. LogP: 6.1. It is marine-derived. It has anti-diabetic activity. It can be encapsulated in nano-emulsions.
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| Toxicity/Toxicokinetics |
2,4,6-Triphenylaniline has low acute toxicity. The oral LD50 in rats is estimated >2000 mg/kg. It is not a skin irritant (H315, H319, H335). It may cause mild eye irritation. Standard safety: Use gloves, lab coat, goggles. It is not a drug. It is a research chemical. It is a marine-derived natural product. It is not classified as a carcinogen. It is potentially hepatoprotective. The compound is stable at -20degC for 3 years as a powder. In solution, store at -80degC. It is a biochemical assay reagent. The product is for research use only. It has anti-diabetic activity.
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| References | |
| Additional Infomation |
2,4,6-Triphenylaniline is a type of biphenyl compound. It has been reported that 2,4,6-triphenylaniline has been detected in *Alternaria longipes*, and relevant data are available. This metabolite was isolated from the endophytic fungus *Alternaria longipes* strain VITN14G, belonging to the mangrove plant *Avicennia officinalis*.
2,4,6-Triphenylaniline is a promising lead compound for the treatment of type 2 diabetes. Its potent alpha-glucosidase/alpha-amylase inhibition makes it a candidate for development as a functional food or nutraceutical. Because it is a marine natural product, its structure is unique and can be patented. The nano-emulsion formulation technology solves its poor solubility. It is currently in preclinical development. It is not approved by the FDA. The product is for research use only. It is a marine-derived natural product found in Alternaria longipes. It has anti-diabetic activity. It is an alpha-glucosidase and alpha-amylase inhibitor. |
| Molecular Formula |
C24H19N
|
|---|---|
| Molecular Weight |
321.42
|
| Exact Mass |
321.152
|
| CAS # |
6864-20-6
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| PubChem CID |
629425
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| Appearance |
White to yellow solid powder
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| Density |
1.117g/cm3
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| Boiling Point |
465.4ºC at 760 mmHg
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| Melting Point |
122-125ºC
|
| Flash Point |
245.5ºC
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| Index of Refraction |
1.645
|
| LogP |
6.851
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| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
1
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
25
|
| Complexity |
359
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C1=CC=C(C=C1)C2=CC(=C(C(=C2)C3=CC=CC=C3)N)C4=CC=CC=C4
|
| InChi Key |
AGWKGKUGJDMKMT-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C24H19N/c25-24-22(19-12-6-2-7-13-19)16-21(18-10-4-1-5-11-18)17-23(24)20-14-8-3-9-15-20/h1-17H,25H2
|
| Chemical Name |
2,4,6-triphenylaniline
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | 3.1112 mL | 15.5560 mL | 31.1119 mL | |
| 5 mM | 0.6222 mL | 3.1112 mL | 6.2224 mL | |
| 10 mM | 0.3111 mL | 1.5556 mL | 3.1112 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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