| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| 100mg | |||
| 250mg | |||
| Other Sizes |
| Targets |
Bergamottin targets cytochrome P450 enzymes, including CYP1A1, CYP1A2, CYP2B1, and CYP2B2. It is a competitive inhibitor of CYP1A1. It inhibits CYP1A1, CYP1A2, CYP2B1, and CYP2B2 with IC50 values of 0.192 ± 0.029 μM for CYP1A1. It also inhibits CYP3A4, which is responsible for the metabolism of many drugs, leading to potential drug-drug interactions.
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| ln Vitro |
Bergamot is a competitive inhibitor of CYP1A1. Bergamotin inhibits CYP1A1, CYP1A2, CYP2B1 and CYP2B2, with IC50 of 0.192±0.029 μM, 5.077±0.31 μM, 9.495±0.979 μM, and 4.535±0.092 μM correspondingly [1]. Bergamot has powerful antiproliferative effects on A549 cells. Bergamot displayed concentration- and time-dependent growth inhibitory effects on these cells. Bergamot also suppresses the clonogenic activity of A549 cancer cells by lowering the amount of cancer colony-forming cells. Bergamot concentration-dependence also leads to a reduction in clonogenicity [2].
In vitro, Bergamottin has potent antiproliferative effects on A549 lung cancer cells. It shows both concentration-dependent and time-dependent growth inhibitory effects against these cells. It is a competitive inhibitor of CYP1A1 and inhibits CYP1A2, CYP2B1, and CYP2B2 with IC50 values in the sub-micromolar range. Its inhibition of CYP3A4 is responsible for the "grapefruit juice effect". |
| ln Vivo |
A total of 20 female BALB/c nude mice were employed to assess the anticancer efficaciousness of bergamot in vivo. Mice were given injections of 1×106 cells/mouse of non-small cell lung carcinoma A549, which caused tumors. Mice were slaughtered when the tumors formed, the tumors were excised, and the volume and weight of the tumors were determined. According to the findings, the tumor weight decreased from 1.61 g in the PBS-treated group (control group) to 1.21, 0.42, and 0.15 g, respectively, after injections of 25, 50, and 100 mg/kg of bergamot. The tumor weight of nude mice in the bergamot group with the highest dose (100 mg/kg body weight) dropped more considerably (P<0.05) than the vehicle group. Similarly, the tumor volume in the PBS-treated group (control group) was decreased from 2.2 cm3 to 1.71, 1.1, and 0.51 cm3 by injections of 25, 50, and 100 mg/kg bergamot. Frequent measurements of the transplanted tumor volume revealed that the tumor volume of nude mice in the highest dose bergamot group (100 mg/kg body weight) was significantly (P<0.05) lower than that of the vehicle group [2].
In vivo, Bergamottin is known for its ability to inhibit CYP3A4, leading to increased plasma concentrations of co-administered drugs that are metabolized by this enzyme (the "grapefruit juice effect"). Its antiproliferative effects in vitro suggest potential anticancer activity, but in vivo efficacy data are limited. |
| Enzyme Assay |
In vitro enzyme inhibition assays for Bergamottin are conducted using recombinant or human liver microsomal CYP450 enzymes. Enzyme activity is measured using fluorogenic or luminescent substrates specific for each CYP isoform. The compound is incubated with the enzyme, substrate, and NADPH at varying concentrations, and IC50 values are calculated from dose-response curves.
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| Cell Assay |
Cellular assays for Bergamottin are performed using A549 lung cancer cells. Cells are seeded in 96-well plates and treated with compound concentrations ranging from 0.1 to 100 µM for 24-72 hours. Cell viability is assessed using MTT or CCK-8 assays. Cell cycle analysis and apoptosis assays (Annexin V/PI staining) can also be performed.
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| Animal Protocol |
In vivo animal studies for Bergamottin are typically conducted to study its effects on drug metabolism and pharmacokinetics. Rodents are administered Bergamottin (often as grapefruit juice or purified compound) prior to or concurrently with a probe drug metabolized by CYP3A4. Plasma concentrations of the probe drug are measured to assess the extent of CYP3A4 inhibition.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Bergamottin have been studied due to its role in drug-drug interactions. It is absorbed following oral consumption and can reach the systemic circulation. It inhibits CYP3A4 in the liver and intestine, leading to increased bioavailability of drugs metabolized by this enzyme. Its half-life and metabolic pathways have been characterized in pharmacokinetic studies.
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| Toxicity/Toxicokinetics |
Toxicological data for Bergamottin are limited. As a natural compound found in citrus fruits, it is generally recognized as safe at dietary levels. High doses may cause hepatotoxicity due to CYP450 inhibition. The compound is designated for research use only.
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| References |
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| Additional Infomation |
Bergamot lactone is a furanocoumarin, a metabolite. It has been reported in Angelica dahurica, Citrus aurantium, and other organisms with relevant data. See also: Lime (Citrus) (partial).
Bergamottin is a natural furanocoumarin from citrus fruits that competitively inhibits CYP1A1 and CYP3A4. It inhibits CYP1A1, CYP1A2, CYP2B1, and CYP2B2 with IC50 values in the sub-micromolar range. It exhibits potent antiproliferative effects on A549 cancer cells. It is responsible for the "grapefruit juice effect" on drug metabolism. It is not a drug and has no clinical approval. |
| Molecular Formula |
C21H22O4
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|---|---|
| Molecular Weight |
338.3970
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| Exact Mass |
338.151
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| CAS # |
7380-40-7
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| PubChem CID |
5471349
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
503.7±50.0 °C at 760 mmHg
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| Melting Point |
75-80ºC
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| Flash Point |
258.4±30.1 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.583
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| LogP |
5.92
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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 |
6
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| Heavy Atom Count |
25
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| Complexity |
570
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(=CCC/C(=C/COC1=C2C=CC(=O)OC2=CC3=C1C=CO3)/C)C
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| InChi Key |
DBMJZOMNXBSRED-OQLLNIDSSA-N
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| InChi Code |
InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+
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| Chemical Name |
4-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-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 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) |
DMSO : ~50 mg/mL (~147.75 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (7.39 mM) in 10% DMSO + 90% (20% SBE-β-CD in 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 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. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.39 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9551 mL | 14.7754 mL | 29.5508 mL | |
| 5 mM | 0.5910 mL | 2.9551 mL | 5.9102 mL | |
| 10 mM | 0.2955 mL | 1.4775 mL | 2.9551 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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