Bergapten

CAS# 484-20-8

Bergapten

Catalog No. BCN5582----Order now to get a substantial discount!

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Quality Control of Bergapten

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Chemical structure

Bergapten

3D structure

Chemical Properties of Bergapten

Cas No. 484-20-8 SDF Download SDF
PubChem ID 2355 Appearance White powder
Formula C12H8O4 M.Wt 216.2
Type of Compound Coumarins Storage Desiccate at -20°C
Synonyms 5-Methoxypsoralen
Solubility DMSO : 10 mg/mL (46.26 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name 4-methoxyfuro[3,2-g]chromen-7-one
SMILES COC1=C2C=CC(=O)OC2=CC3=C1C=CO3
Standard InChIKey BGEBZHIAGXMEMV-UHFFFAOYSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Bergapten

The root of Angelica dahurica

Biological Activity of Bergapten

DescriptionBergapten is a psoralen that can be photoactivated and is capable of crossing-linking DNA, covalently modifying proteins and lipids, and consequently inhibiting cell replication. Bergapten has anti-inflammatory and anti-tumor agent, it exhibits significant inhibition of the production of pro-inflammatory cytokines, namely tumour necrotic factor-α(TNF-α) and interleukin-6 (IL-6) by peripheral blood mononuclear cells (PBMCs) stimulated with lipopolysaccharide in a concentration-dependent manner. Bergapten effectively prevents LPS-induced osteoclastogenesis, bone resorption and survival via apoptotic response of osteoclasts and their precursors.
TargetsTGF-β/Smad | Caspase | TNF-α | IL Receptor | PI3K | p53 | Akt | p21
In vitro

Bergapten prevents lipopolysaccharide mediated osteoclast formation, bone resorption and osteoclast survival.[Pubmed: 24305787]

Int Orthop. 2014 Mar;38(3):627-34.


METHODS AND RESULTS:
To investigate the effect of Bergapten on osteoclastic bone resorption, RAW264.7 cells were treated with Bergapten for six days in the presence of LPS, and the area of bone resorption was analyzed with Image Pro-Plus. Next, we examined apoptosis of RAW264.7 cells after Bergapten incubation for 48 hours by flow cytometer using annexin V/propidium iodide (PI) double labeling. Finally, osteoclast survival was observed by Hoechst 33342 labeling and Western blotting after Bergapten treatment for 24 hours. RESULTS: Data showed that Bergapten (5-40 μmol/L) dose-dependently inhibited LPS-induced osteoclast formation and bone resorption. Treatment with Bergapten triggered apoptotic death of osteoclast precursor RAW264.7 cells in a dose-dependent manner. Furthermore, Bergapten significantly reduced the survival of mature osteoclast, as demonstrated by emergence of apoptotic nuclei and activation of apoptotic protein caspase 3/9.
CONCLUSIONS:
These findings suggest that Bergapten effectively prevents LPS-induced osteoclastogenesis, bone resorption and survival via apoptotic response of osteoclasts and their precursors. The study identifies Bergapten as an inhibitor of osteoclast formation and bone resorption and provides evidence that Bergapten might be beneficial as an alternative for prevention and treatment of inflammatory bone loss.

Effect of bergapten from Heracleum nepalense root on production of proinflammatory cytokines.[Pubmed: 19662568]

Nat Prod Res. 2011 Sep;25(15):1444-9.

In the present investigation, the anti-inflammatory activity of isolated Bergapten from hydroalcoholic extract of Heracleum nepalense root was evaluated in vitro using human peripheral blood mononuclear cells (PBMCs).
METHODS AND RESULTS:
Bergapten exhibited significant inhibition of the production of pro-inflammatory cytokines, namely tumour necrotic factor-α (TNF-α) and interleukin-6 (IL-6) by PBMCs stimulated with lipopolysaccharide in a concentration-dependent manner.

In vivo

5-Methoxypsoralen (Bergapten) for photochemotherapy. Bioavailability, phototoxicity, and clinical efficacy in psoriasis of a new drug preparation.[Pubmed: 3279089]

J Am Acad Dermatol. 1988 Feb;18(2 Pt 1):333-8.

In a previous study we evaluated a microcrystalline preparation of 5-methoxypsoralen (5-MOP; Bergapten) for its photochemotherapeutic properties. Preliminary data indicated that the clinical efficacy of 5-MOP is comparable to that of 8-methoxypsoralen. 5-MOP appeared as a promising alternative photosensitizer for the management of psoriasis because of the almost complete lack of phototoxic and drug intolerance reactions that are frequently encountered in patients undergoing 8-MOP photochemotherapy.
METHODS AND RESULTS:
With a new liquid preparation of 5-MOP we have now extended our earlier investigation on a larger clinical scale and have correlated the clinical response with the bioavailability of the drug. Serum level determinations showed an absorption rate of only approximately 25% that of 8-MOP. When administered in the same dosage as 8-MOP, 5-MOP turned out to be significantly less effective; however, by doubling the oral dosage, comparable results in terms of clearing of psoriasis were obtained. Also with this high-dose 5-MOP regimen, no drug intolerance was noted and other side effects, such as severe erythema, pruritus, and nausea, occurred only rarely.
CONCLUSIONS:
We propose 5-MOP as a valuable alternative for photochemotherapy (PUVA) of PUVA-responsive diseases.

Protocol of Bergapten

Kinase Assay

Breast cancer cell survival signal is affected by bergapten combined with an ultraviolet irradiation.[Pubmed: 20371365]

Bergapten induces ER depletion in breast cancer cells through SMAD4-mediated ubiquitination.[Pubmed: 23053665]

Breast Cancer Res Treat. 2012 Nov;136(2):443-55.

ERα function is crucial for the development of normal mammary gland as well as in the process of progression of breast cancer cells. Signals that target receptor levels contribute to regulate estrogens effects in the cells. An intricate cross-regulation has been documented between ERα and TGF-β down-stream molecules: SMAD2, SMAD3, and SMAD4, that can bind ERα and regulate their signaling. Thus, identification of natural anticancer drugs able to influence the latter molecule might provide alternative choices for breast cancer treatment. Taking into account our previous published data we wanted to study the effect of 5-Methoxypsoralen (Bergapten) on ERα and on TGF-β pathway.
METHODS AND RESULTS:
We reported that Bergapten, a coumarin containing compound, effectively depletes ERα in MCF-7 breast cancer sensitive cells and in tamoxifen-resistant clone. The decrease of ERα protein after Bergapten treatment results from the ubiquitine-proteasome pathway as demonstrated by the use of MG-132. IP experiments with ER antibody, demonstrated that the protein has physical interaction with SMAD4 and poly-ubiquitine and the amount of ubiquitinated receptor, linked to SMAD4, is greater under Bergapten. The crucial role played by SMAD4, in this process, emerges from the observation that in breast cancer cells, silencing of SMAD4, resulted in increased expression of endogenous ERα in both control and Bergapten-treated cells, compared to wild- type cells. The same results were confirmed in siRNA TGF-β RII cells.
The results suggest a novel negative regulation of ERα by TGF-β/SMAD4 in breast cancer cells and indicate that the SMAD4 protein is involved in the degradation of ERα induced by Bergapten. CONCLUSIONS:
We propose that Bergapten may efficiently act as a natural antitumoral agent, able to deplete ERα from breast cancer tamoxifen-sensitive and resistant cells, thereby retraining the effect of membrane signals targeting ERα and in such way its mitogenic potentiality.

FEBS Lett. 2010 Jun 3;584(11):2321-6.


METHODS AND RESULTS:
In this study we have reported that Bergapten (B) and Bergapten plus UV (PUVA) are able to significantly affect MCF-7, ZR-75 and SKBR-3 breast cancer cell proliferations. B induced a lowering of PI3K/AKT survival signal in MCF-7 cells even in presence of IGF-I stimulation. Furthermore, B and in a higher extent, PUVA up-regulated the p53 mRNA and the protein content. An increased co-association between p21 WAF and proliferating cell nuclear antigen (PCNA) has been observed in PUVA-treated MCF-7 cells, thus inhibiting DNA replication.
CONCLUSIONS:
These results highlight how B, and its photoactivated compound, exert antiproliferative effects and induce apoptotic responses in breast cancer cells.

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Preparing Stock Solutions of Bergapten

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.6253 mL 23.1267 mL 46.2535 mL 92.5069 mL 115.6337 mL
5 mM 0.9251 mL 4.6253 mL 9.2507 mL 18.5014 mL 23.1267 mL
10 mM 0.4625 mL 2.3127 mL 4.6253 mL 9.2507 mL 11.5634 mL
50 mM 0.0925 mL 0.4625 mL 0.9251 mL 1.8501 mL 2.3127 mL
100 mM 0.0463 mL 0.2313 mL 0.4625 mL 0.9251 mL 1.1563 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Bergapten

Bergapten is a natural anti-inflammatory and anti-tumor agent isolated from bergamot essential oil, other citrus essential oils and grapefruit juice. Bergapten is inhibitory towards mouse and human CYP isoforms.

In Vitro:There is decreased N-acetyltransferase (NAT) activity in SC-M1 cells at concentrations of Bergapten (5-Methoxypsoralen, 5-MOP) from 0.05 mM to 25 mM, but no obvious dose-dependent effect is found between these doses (r=0.5687). In COLO 205 cells, there is decreased NAT activity at low doses of Bergapten (0.05 mM and 0.5 mM) and increased NAT activity at a high dose (50 mM). Bergapten induces a dosedependent effect in our experimental concentrations on COLO 205 cells (r=0.8912); a promotion effect at a higher dose (50 mM) and an inhibition effect at lower doses (0.05-0.5 mM), while the concentrations 5-25 mM has no significant difference compared with the control regimen[1]. Bergapten (5-Methoxypsoralen) exerts inhibitory effects on diabetes-related osteoporosis via the regulation of the PI3K/AKT, JNK/MAPK and NF-κB signaling pathways in osteoprotegerin knockout mice. Bergapten has also been shown to significantly inhibit the production of pro-inflammatory cytokines. Bergapten exhibits the ability to significantly inhibit RANKL-RANK signaling transduction, and to suppress the activation of the PI3K/AKT, JNK/MAPK and NF-κB signaling pathways, thus protecting trabecular structure and decreasing osteoclastogenic differentiation[2].

In Vivo:The metabolic activity of NAT of the rat colon is higher than that of the stomach, and Bergapten (5-Methoxypsoralen, 5-MOP) causes a decrease of AF concentration in the stomach at the 24-h time-period. The concentrations of AAF in the stomach and colon are low. Although DMSO (solvent) influenced the metabolism of AAF, compared with the control regimen, Bergapten still causes an increase in the further metabolism of AAF, and a decrease in the concentration of AAF in the stomach at 24 h, and in the colon during the 24- to 72-h time-period[1].

References:
[1]. Lee YM, et al. Effects of 5-methoxypsoralen (5-MOP) on arylamine N-acetyltransferase activity in the stomach and colon of rats and human stomach and colon tumor cell lines. In Vivo. 2005 Nov-Dec;19(6):1061-9. [2]. Li XJ, et al. Bergapten exerts inhibitory effects on diabetes-related osteoporosis via the regulation of the PI3K/AKT, JNK/MAPK and NF-κB signaling pathways in osteoprotegerin knockout mice. Int J Mol Med. 2016 Dec;38(6):1661-1672.

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References on Bergapten

Bergapten induces ER depletion in breast cancer cells through SMAD4-mediated ubiquitination.[Pubmed:23053665]

Breast Cancer Res Treat. 2012 Nov;136(2):443-55.

ERalpha function is crucial for the development of normal mammary gland as well as in the process of progression of breast cancer cells. Signals that target receptor levels contribute to regulate estrogens effects in the cells. An intricate cross-regulation has been documented between ERalpha and TGF-beta down-stream molecules: SMAD2, SMAD3, and SMAD4, that can bind ERalpha and regulate their signaling. Thus, identification of natural anticancer drugs able to influence the latter molecule might provide alternative choices for breast cancer treatment. Taking into account our previous published data we wanted to study the effect of 5-Methoxypsoralen (Bergapten) on ERalpha and on TGF-beta pathway. We reported that Bergapten, a coumarin containing compound, effectively depletes ERalpha in MCF-7 breast cancer sensitive cells and in tamoxifen-resistant clone. The decrease of ERalpha protein after Bergapten treatment results from the ubiquitine-proteasome pathway as demonstrated by the use of MG-132. IP experiments with ER antibody, demonstrated that the protein has physical interaction with SMAD4 and poly-ubiquitine and the amount of ubiquitinated receptor, linked to SMAD4, is greater under Bergapten. The crucial role played by SMAD4, in this process, emerges from the observation that in breast cancer cells, silencing of SMAD4, resulted in increased expression of endogenous ERalpha in both control and Bergapten-treated cells, compared to wild- type cells. The same results were confirmed in siRNA TGF-beta RII cells. The results suggest a novel negative regulation of ERalpha by TGF-beta/SMAD4 in breast cancer cells and indicate that the SMAD4 protein is involved in the degradation of ERalpha induced by Bergapten. We propose that Bergapten may efficiently act as a natural antitumoral agent, able to deplete ERalpha from breast cancer tamoxifen-sensitive and resistant cells, thereby retraining the effect of membrane signals targeting ERalpha and in such way its mitogenic potentiality.

5-Methoxypsoralen (Bergapten) for photochemotherapy. Bioavailability, phototoxicity, and clinical efficacy in psoriasis of a new drug preparation.[Pubmed:3279089]

J Am Acad Dermatol. 1988 Feb;18(2 Pt 1):333-8.

In a previous study we evaluated a microcrystalline preparation of 5-methoxypsoralen (5-MOP; Bergapten) for its photochemotherapeutic properties. Preliminary data indicated that the clinical efficacy of 5-MOP is comparable to that of 8-methoxypsoralen. 5-MOP appeared as a promising alternative photosensitizer for the management of psoriasis because of the almost complete lack of phototoxic and drug intolerance reactions that are frequently encountered in patients undergoing 8-MOP photochemotherapy. With a new liquid preparation of 5-MOP we have now extended our earlier investigation on a larger clinical scale and have correlated the clinical response with the bioavailability of the drug. Serum level determinations showed an absorption rate of only approximately 25% that of 8-MOP. When administered in the same dosage as 8-MOP, 5-MOP turned out to be significantly less effective; however, by doubling the oral dosage, comparable results in terms of clearing of psoriasis were obtained. Also with this high-dose 5-MOP regimen, no drug intolerance was noted and other side effects, such as severe erythema, pruritus, and nausea, occurred only rarely. We propose 5-MOP as a valuable alternative for photochemotherapy (PUVA) of PUVA-responsive diseases.

Effect of bergapten from Heracleum nepalense root on production of proinflammatory cytokines.[Pubmed:19662568]

Nat Prod Res. 2011 Sep;25(15):1444-9.

In the present investigation, the anti-inflammatory activity of isolated Bergapten from hydroalcoholic extract of Heracleum nepalense root was evaluated in vitro using human peripheral blood mononuclear cells (PBMCs). Bergapten exhibited significant inhibition of the production of pro-inflammatory cytokines, namely tumour necrotic factor-alpha (TNF-alpha) and interleukin-6 (IL-6) by PBMCs stimulated with lipopolysaccharide in a concentration-dependent manner.

Bergapten prevents lipopolysaccharide mediated osteoclast formation, bone resorption and osteoclast survival.[Pubmed:24305787]

Int Orthop. 2014 Mar;38(3):627-34.

PURPOSE: This study was designed to investigate the potential effect of Bergapten on lipopolysaccharide (LPS)-mediated osteoclast formation, bone resorption and osteoclast survival in vitro. METHODS: After osteoclast precursor RAW264.7 cells were treated with Bergapten (5, 20, 40 mumol/L) for 72 hours in the presence of LPS (100 ng/ml), osteoclastogenesis was identified by tartrate-resistant acid phosphatase (TRAP) staining, and the number of TRAP-positive multinucleated cells [TRAP(+)MNCs] per well were counted. To investigate the effect of Bergapten on osteoclastic bone resorption, RAW264.7 cells were treated with Bergapten for six days in the presence of LPS, and the area of bone resorption was analyzed with Image Pro-Plus. Next, we examined apoptosis of RAW264.7 cells after Bergapten incubation for 48 hours by flow cytometer using annexin V/propidium iodide (PI) double labeling. Finally, osteoclast survival was observed by Hoechst 33342 labeling and Western blotting after Bergapten treatment for 24 hours. RESULTS: Data showed that Bergapten (5-40 mumol/L) dose-dependently inhibited LPS-induced osteoclast formation and bone resorption. Treatment with Bergapten triggered apoptotic death of osteoclast precursor RAW264.7 cells in a dose-dependent manner. Furthermore, Bergapten significantly reduced the survival of mature osteoclast, as demonstrated by emergence of apoptotic nuclei and activation of apoptotic protein caspase 3/9. CONCLUSIONS: These findings suggest that Bergapten effectively prevents LPS-induced osteoclastogenesis, bone resorption and survival via apoptotic response of osteoclasts and their precursors. The study identifies Bergapten as an inhibitor of osteoclast formation and bone resorption and provides evidence that Bergapten might be beneficial as an alternative for prevention and treatment of inflammatory bone loss.

Description

Bergapten is a natural anti-inflammatory and anti-tumor agent isolated from bergamot essential oil, other citrus essential oils and grapefruit juice. Bergapten is inhibitory towards mouse and human CYP isoforms.

Keywords:

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