Art. -Nr.: HY-N2194

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Bergamottin

(Synonyms: 5-Geranoxypsoralen; Bergamotine; Bergaptin)

8 Cited Publications

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Based on 8 publication(s) in Google Scholar

Bergamottin is a potent and competitive CYP1A1 inhibitor with a K_i of 10.703 nM.

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Reinheit: 99.94%
CAS. Nr.: 7380-40-7
Formel: C₂₁H₂₂O₄
Molecular Weight:338.40

Speicherung:

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Bergamottin Chemical Structure

CAS. Nr.: 7380-40-7

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Use of MCE Products

Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Publications (8)
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Protokoll
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

Bergamottin is a potent and competitive CYP1A1 inhibitor with a K_i of 10.703 nM.

IC₅₀ & Target^[1]

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)

Alle Cytochrome P450 Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
Calu-3	CC₅₀	>100 μM Compound: 98	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	[PMID: 37597436]

In Vitro

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.

In Vivo

The anticancer efficacy of Bergamottin under in vivo conditions using female BALB/c nude mice (a total of 20 mice are used) is determined. Tumors are induced in the mice by injecting non-small cell lung cancer A549 cells (1×10⁶ cells/mouse). After tumor formation, the mice are sacrificed and tumors are removed and their weights and volumes are calculated. The results show that 25, 50 and 100 mg/kg Bergamottin injection reduce the tumor weight from 1.61 g in the PBS-treated group (control) to 1.21, 0.42 and 0.15 g, respectively. Tumor weight in the nude mice is reduced much more significantly in the highest-concentration Bergamottin group (100 mg/kg body weight) compared with the vehicle group (P<0.05). Likewise, 25, 50 and 100 mg/kg Bergamottin injection reduces the tumor volume from 2.2 cm³ in the PBS-treated group (control) to 1.71, 1.1 and 0.51 cm3, respectively. The periodic measurement of the tumor xenograft volume indicates that the tumor volume in the nude mice is reduced considerably in the highest-concentration Bergamottin group (100 mg/kg body weight) compared with the vehicle group (P<0.05)^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Chemical Information

CAS. Nr. 7380-40-7
Appearance Solid
Molecular Weight 338.40
Formel C₂₁H₂₂O₄
Color White to off-white
SMILES

O=C1C=CC2=C(OC/C=C(C)/CC/C=C(C)/C)C3=C(OC=C3)C=C2O1
Synonyms

5-Geranoxypsoralen; Bergamotine; Bergaptin
Structure Classification
- Phenylpropanoids
- Coumarins
Initial Source
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Publications (8)

All Cell Imaging/StainingCell Proliferation/Viability AssayHistological Imaging/StainingWBRT-PCR

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Journal Impact Factor

Int J Mol Sci

Bergamottin and PAP-1 Induced ACE2 Degradation to Alleviate Infection of SARS-CoV-2. [Abstract]

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.
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
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.
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.).
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
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
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

Lösungsmittel & Löslichkeit

In Vitro:

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)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

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

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.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

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.

Protocol 1

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.

Protocol 2

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2.5 mg/mL (7.39 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
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

Protokoll

Kinase Assay^[1]

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.

Cell Assay^[2]

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.

Animal Administration^[2]

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.

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (281 KB)
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)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[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]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

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

Keywords

Bergamottin

8 Cited Publications

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Publications Citing Use of MedChemExpress (MCE) Bergamottin

Alle Cytochrome P450 Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Publications (8)

Lösungsmittel & Löslichkeit

Protokoll

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Bergamottin Related Classifications

HY-N2194 Related Classifications