Bergamottin
Based on 8 publication(s) in Google Scholar
Bergamottin is a potent and competitive CYP1A1 inhibitor with a Ki of 10.703 nM.
For research use only. We do not sell to patients.
- Purity: 99.94%
- CAS No.: 7380-40-7
- Formula: C21H22O4
- Molecular Weight:338.40
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Storage:
4°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Protocol
- Purity & Documentation
- References
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Publications Citing Use of MedChemExpress (MCE) Bergamottin
More- Chem Biol Interact. 2024 Apr 1:392:110923. [Abstract]
- Int J Mol Sci. 2022 Oct 19;23(20):12565. [Abstract]
- J Med Virol. 2025 Jul;97(7):e70495. [Abstract]
- Antiviral Res. 2022 Aug:204:105365. [Abstract]
- Viruses. 2024 Aug 13;16(8):1287. [Abstract]
- Viruses. 2023 Jun 13;15(6):1367. [Abstract]
- Immunol Res. 2022 Feb;70(1):33-43. [Abstract]
- Chin J Traumatol. 2024 Jul 3:S1008-1275(24)00075-0. [Abstract]
Customer Validation & Images
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Histological Imaging/Staining
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Cell Proliferation/Viability Assay
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WB
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RT-PCR
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Cell Imaging/Staining
Biological Activity
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CYP1A1 10.703 nM (Ki) |
CYP1A1 0.192 μM (IC50) |
CYP1A2 5.077 μM (IC50) |
CYP2B2 4.535 μM (IC50) |
CYP2B1 9.495 μM (IC50) |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| Calu-3 | CC50 |
>100 μM
Compound: 98
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Cytotoxicity against human Calu-3 cells assessed as reduction in cell viability measured after 48 hrs by Hoechst 33342 staining based analysis
Cytotoxicity against human Calu-3 cells assessed as reduction in cell viability measured after 48 hrs by Hoechst 33342 staining based analysis
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[PMID: 37597436] |
Bergamottin is a competitive inhibitor of CYP1A1. Bergamottin inhibits CYP1A1, CYP1A2, CYP2B1, and CYP2B2 with IC50s of 0.192±0.029 μM, 5.077±0.31 μM, 9.495±0.979 μM, 4.535±0.092 μM, respectively[1]. Bergamottin has potent antiproliferative effects on the A549 cells. Bergamottin shows both concentration-dependent as well as time dependent growth inhibitory effects against these cells. Bergamottin also inhibits the clonogenic activity of the A549 cancer cells by reducing the number of cancer colony forming cells. A reduction in clonogenicity also follows the concentration dependence on Bergamottin[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 7380-40-7
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Appearance Solid
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Molecular Weight 338.40
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Formula C21H22O4
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Color White to off-white
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SMILES
O=C1C=CC2=C(OC/C=C(C)/CC/C=C(C)/C)C3=C(OC=C3)C=C2O1
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Synonyms
5-Geranoxypsoralen; Bergamotine; Bergaptin
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
4°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
Publications (8)
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Journal Impact Factor
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Most Recent
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Chem Biol Interact
Human CYP1A1-activated aneugenicity of aflatoxin B1 in mammalian cells and its combined effect with benzo(a)pyrene. [Abstract]2024 Apr 1:392:110923. PMID: 38382706 -
Int J Mol Sci
2022 Oct 19;23(20):12565. PMID: 36293419
Bergamottin purchased from MedChemExpress. Usage Cited in: Int J Mol Sci. 2022 Oct 19;23(20):12565. [Abstract]
Effects of Bergamottin on viability of AT-II cells for 24, 48, and 72 h by CCK-8 kit, comparison of cell viability at 24 h of bergamottin with different concentrations.
Bergamottin purchased from MedChemExpress. Usage Cited in: Int J Mol Sci. 2022 Oct 19;23(20):12565. [Abstract]
Western blot detection of expression of ACE2 proteins in AT-II cells treated with Bergamottin.
Bergamottin purchased from MedChemExpress. Usage Cited in: Int J Mol Sci. 2022 Oct 19;23(20):12565. [Abstract]
mRNA expression levels of ACE2 relative to AT-II cells with Bergamottin.
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J Med Virol
Bergamottin, A Natural Bioactive Compound, Inhibits Dabie Bandavirus Infection In Vitro and In Vivo. [Abstract]2025 Jul;97(7):e70495. PMID: 40673712 -
Antiviral Res
Bergamottin, a bioactive component of bergamot, inhibits SARS-CoV-2 infection in golden Syrian hamsters. [Abstract]2022 Aug:204:105365. PMID: 35732228
Bergamottin purchased from MedChemExpress. Usage Cited in: Antiviral Res. 2022 Aug:204:105365. [Abstract]
Bergamottin inhibited SARS-CoV-2 S protein-mediated membrane fusion. Vero E6 cells co-transfected with SARS-CoV-2 spike and EGFP plasmids. After 4 h post-transfection, the medium was replaced by bergamottin and the images were acquired 24 h later using fluorescent microcopy.
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Viruses
Bergamottin Inhibits Bovine Viral Diarrhea Virus Replication by Suppressing ROS-Mediated Endoplasmic Reticulum Stress and Apoptosis. [Abstract]2024 Aug 13;16(8):1287. PMID: 39205261
Bergamottin purchased from MedChemExpress. Usage Cited in: Viruses. 2024 Aug 13;16(8):1287. [Abstract]
Representative histopathological changes in intestine, lungs, liver, and spleen tissues in mice treated with Bergamottin (Berg) (50, 75 mg/kg, i.g.).
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Viruses
Bergamottin Inhibits PRRSV Replication by Blocking Viral Non-Structural Proteins Expression and Viral RNA Synthesis. [Abstract]2023 Jun 13;15(6):1367. PMID: 37376666 -
Immunol Res
Bergamottin protects against LPS-induced endotoxic shock by regulating the NF-κB signaling pathway. [Abstract]2022 Feb;70(1):33-43. PMID: 34632552 -
Chin J Traumatol
The cytochrome P4501A1 (CYP1A1) inhibitor bergamottin enhances host tolerance to multidrug-resistant Vibrio vulnificus infection. [Abstract]2024 Jul 3:S1008-1275(24)00075-0. PMID: 38981821
Solvent & Solubility
DMSO : 50 mg/mL (147.75 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: 2.5 mg/mL (7.39 mM); Suspended solution; Need ultrasonic
This protocol yields a suspended solution of 2.5 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL. * In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Protocol
CYP1A1 Supersomes and different concentrations of 7-ethoxyresorufin (ER) are used to determine CYP1A1 enzymatic kinetics. A typical Michaelis-Menten curve is found. The final reaction mixture contains: 1 pmol CYP1A1, 0.5 mM NADPH, different ER concentrations and 0, 4, 8 and 16 nM of Bergamottin (BG). The reaction is started with the addition of NADPH. Kinetic constants are obtained by a nonlinear regression analysis of experimental data fitted to Michaelis-Menten equation with competitive-type inhibition. Kinetic analysis is also shown by using the Lineweaver-Burk, Dixon and replot of the slopes of the Dixon plot[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Inhibition of cell proliferation by Bergamottin is measured by the MTT assay. Briefly, the human lung adenocarcinoma cancer A549 cells are plated in 96-well culture plates (1×105 cells/well). After 24 h of incubation, the cells are treated with Bergamottin (0, 5, 10, 25, 50, 75 and 100 μM) for 24 and 48 h, MTT solution (10 mg/mL) is then added to each well. After a 4-h incubation, the formazan precipitate is dissolved in 100 μL DMSO, and then the absorbance is measured in an automated microplated reader at 570 nm. The cell viability ratio is calculated. Cytotoxicity is expressed as the concentration of Bergamottin needed to inhibit cell growth by 50% (IC50 value)[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Mice[2]
Female BALB/c nude mice (six weeks old) (a total of 20 are obtained) are maintained with water and food ad libitum in a pathogen-free environment with a 12 h light and 12 h dark cycle in an animal care facility. Human non‑small cell lung carcinoma A549 cells (2×106 cells/mouse) are injected into the right axilla of the nude mice (5 mice/group) to create tumors in the mice. Subsequent to tumor development, the mice are divided into 4 groups and treated with Bergamottin injected intraperitoneally. The control group in the study is treated with an equal amount of PBS while the other three groups are treated with 25, 50 and 100 mg/kg of Bergamottin. Afterwards, the mice are sacrificed after 18 days, and the tumor weight and volume of each mouse are evaluated. Tumor length and width are measured using a Vernier caliper and the tumor volume (TV) is calculated[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Purity & Documentation
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Data Sheet (281 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Handling Instructions (2659 KB)
References
[1]. Olguín-Reyes S, et al. Bergamottin is a competitive inhibitor of CYP1A1 and is antimutagenic in the Ames test. Food Chem Toxicol. 2012 Sep;50(9):3094-9. [Content Brief]
[2]. Wu HJ, et al. Bergamottin isolated from Citrus bergamia exerts in vitro and in vivo antitumor activity in lung adenocarcinoma through the induction of apoptosis, cell cycle arrest, mitochondrial membrane potential loss and inhibition of cell migration and invasion. Oncol Rep. 2016 Jul;36(1):324-32. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 2.9551 mL | 14.7754 mL | 29.5508 mL | 73.8771 mL |
| 5 mM | 0.5910 mL | 2.9551 mL | 5.9102 mL | 14.7754 mL | |
| 10 mM | 0.2955 mL | 1.4775 mL | 2.9551 mL | 7.3877 mL | |
| 15 mM | 0.1970 mL | 0.9850 mL | 1.9701 mL | 4.9251 mL | |
| 20 mM | 0.1478 mL | 0.7388 mL | 1.4775 mL | 3.6939 mL | |
| 25 mM | 0.1182 mL | 0.5910 mL | 1.1820 mL | 2.9551 mL | |
| 30 mM | 0.0985 mL | 0.4925 mL | 0.9850 mL | 2.4626 mL | |
| 40 mM | 0.0739 mL | 0.3694 mL | 0.7388 mL | 1.8469 mL | |
| 50 mM | 0.0591 mL | 0.2955 mL | 0.5910 mL | 1.4775 mL | |
| 60 mM | 0.0493 mL | 0.2463 mL | 0.4925 mL | 1.2313 mL | |
| 80 mM | 0.0369 mL | 0.1847 mL | 0.3694 mL | 0.9235 mL | |
| 100 mM | 0.0296 mL | 0.1478 mL | 0.2955 mL | 0.7388 mL |
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