Bergaptol

Alias: Psoralin, 5-hydroxy- 5-Hydroxypsoralen
Cat No.:V7346 Purity: ≥98%
Bergaptol is an inhibitor (blocker/antagonist) of debenzylation of the CYP3A4 enzyme with IC50 of 24.92 μM.
Bergaptol Chemical Structure CAS No.: 486-60-2
Product category: Cytochrome P450
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Bergaptol is an inhibitor (blocker/antagonist) of debenzylation of the CYP3A4 enzyme with IC50 of 24.92 μM. Recent studies suggest it has antiproliferation and anticancer properties.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
According to ABTS and DPPH tests, bergaptol (0-800 ppm) exhibits definite activity [1]. In RAW264.7 cells, LPS-induced NO, IL-6, and TNF are inhibited by 50 μg/mL of Bergaptol for 24 hours. Additionally, LPS-induced MAPK phosphorylation and NF-κB activation are inhibited in RAW264.7 cells [3].
ln Vivo
LPS-treated mice's cognitive function is improved when bergamot alcohol (10–40 mg/kg) is administered intraperitoneally once a day, during sleep [Disorder 4].
Cell Assay
Western Blot Analysis[3]
Cell Types: Production of LPS--α[3]. Induction of RAW264.7 cells
Tested Concentrations: 50 μg/mL
Incubation Duration: 24 hrs (hours)
Experimental Results: Inhibition of JNK phosphorylation and NF-κB activation. Inhibits the translocation of NF-κB P65 from the cytoplasm to the nucleus.
Animal Protocol
Animal/Disease Models: LPS (40 μg/kg, icv) treated mice [4] ]
Doses: 10-40 mg/kg
Route of Administration: intraperitoneal (ip) injection, one time/day for two weeks
Experimental Results: diminished LPS-induced hippocampal CA1 area nerves Fixation and lysis of metanuclei (H&E staining). Increased dendritic spine density in mice. Inhibits LPS-induced neuroinflammation.
References
[1]. Basavaraj Girennavar et al. Radical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit. Bioorganic & Medicinal Chemistry.June 2007, Pages 3684-3691
[2]. Yucheng Zhao et al. Cloning, Functional Characterization, and Catalytic Mechanism of a Bergaptol O-Methyltransferase from Peucedanum praeruptorum Dunn. Front Plant Sci, 2016, 7: 722.
[3]. Shen CY, et al. Bergaptol from blossoms of Citrus aurantium L. var. amara Engl inhibits LPS-induced inflammatory responses and ox-LDL-induced lipid deposition. Food Funct. 2020 Jun 24;11(6):4915-4926.
[4]. Wu J, et al. Bergaptol Alleviates LPS-Induced Neuroinflammation, Neurological Damage and Cognitive Impairment via Regulating the JAK2/STAT3/p65 Pathway. J Inflamm Res. 2022 Nov 9;15:6199-6211.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H6O4
Molecular Weight
202.165
Exact Mass
202.0266
CAS #
486-60-2
SMILES
O1C([H])=C([H])C2C(=C3C([H])=C([H])C(=O)OC3=C([H])C1=2)O[H]
Synonyms
Psoralin, 5-hydroxy- 5-Hydroxypsoralen
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)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 50 mg/mL (~247.33 mM)
H2O : ~0.67 mg/mL (~3.31 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.5 mg/mL (12.37 mM) in 10% DMSO + 40% PEG300 +5% Tween-80 + 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 DMSO 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.9463 mL 24.7317 mL 49.4633 mL
5 mM 0.9893 mL 4.9463 mL 9.8927 mL
10 mM 0.4946 mL 2.4732 mL 4.9463 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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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