Furanodienone

CAS# 24268-41-5

Furanodienone

Catalog No. BCN3010----Order now to get a substantial discount!

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Quality Control of Furanodienone

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Chemical structure

Furanodienone

3D structure

Chemical Properties of Furanodienone

Cas No. 24268-41-5 SDF Download SDF
PubChem ID 6442374 Appearance Powder
Formula C15H18O2 M.Wt 230.3
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (5Z,9Z)-3,6,10-trimethyl-8,11-dihydro-7H-cyclodeca[b]furan-4-one
SMILES CC1=CC(=O)C2=C(CC(=CCC1)C)OC=C2C
Standard InChIKey XVOHELPNOXGRBQ-LXQMTTSMSA-N
Standard InChI InChI=1S/C15H18O2/c1-10-5-4-6-11(2)8-14-15(13(16)7-10)12(3)9-17-14/h6-7,9H,4-5,8H2,1-3H3/b10-7-,11-6-
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 Furanodienone

The rhizoma of Curcuma zedoaria

Biological Activity of Furanodienone

DescriptionFuranodienone inhibits EGFR/HER2 signaling pathway in BT474 and SKBR3 cells, the effect is specifically dependent on the expression of HER2 but not EGFR; it also has effects on MCF-7 cells are mediated, at least in part, by inhibiting ERα signaling.
TargetsEGFR | HER2 | GSK-3 | Akt | p27 | Estrogen receptor | c-Myc | Progestogen receptor
In vitro

Furanodienone induces cell cycle arrest and apoptosis by suppressing EGFR/HER2 signaling in HER2-overexpressing human breast cancer cells.[Pubmed: 21461888]

Cancer Chemother Pharmacol. 2011 Nov;68(5):1315-23.

Overexpression of EGFR and HER2 is seen in breast cancers and results in poor prognosis and decreased patient survival. Clinically, EGFR and HER2 are effective therapeutic targets. The objective of this study is to investigate the in vitro effects of Furanodienone, an active chemical component isolated from Rhizoma Curcumae, on the activation of EGFR/HER2 signaling, cell cycle, and apoptosis in HER2-overexpressing BT474 and SKBR3 cells.
METHODS AND RESULTS:
Cell growth was assessed by SRB protein assay. Cell cycle analysis was carried out by flow cytometry, and apoptosis was observed by Annexin V and DAPI staining. Effects of Furanodienone on the activation of EGFR/HER2 signaling-related proteins were analyzed by western blotting. RESULTS: Furanodienone inhibited cell growth in BT474 and SKBR3 cells. Furanodienone caused G1 arrest in BT474 cells and induced apoptosis in SKBR3 cells. Furanodienone interfered with EGFR/HER2 signaling in treated cells as shown by decreases in phosphorylated EGFR, HER2, Akt, Gsk3β and an increase in p27(kip1) protein. Accordingly, Furanodienone inhibited EGF-induced phosphorylation of EGFR, HER2, Akt, and Gsk3β. EGFR-specific siRNA knockdown did not affect the cell growth inhibitory effect of Furanodienone. On the contrary, specific siRNA knockdown of HER2 increased cellular resistance to Furanodienone toxicity. In HER-2-deficient MDA-MB-231 cells, the transfection and expression of HER2 increased the sensitivity of cells to Furanodienone toxicity.
CONCLUSIONS:
Furanodienone inhibited EGFR/HER2 signaling pathway in BT474 and SKBR3 cells. More importantly, the effect of Furanodienone was specifically dependent on HER2, but not EGFR, expression.

Protocol of Furanodienone

Cell Research

Furanodienone inhibits cell proliferation and survival by suppressing ERα signaling in human breast cancer MCF-7 cells.[Pubmed: 21069738]

J Cell Biochem. 2011 Jan;112(1):217-24.

Estrogen receptor alpha (ERα) plays an important role in the development and progression of breast cancer and thus the attenuation of ERα activities is a promising treatment strategy. Furanodienone is one of the main bioactive chemical components of Rhizoma Curcumae which is commonly used in Chinese medicine for the treatment of cancer.
METHODS AND RESULTS:
In this study, we investigated the effects of Furanodienone on human breast cancer MCF-7, T47D, and MDA-MB-231 cells. Our results showed that Furanodienone could inhibit MCF-7, T47D, and MDA-MB-231 cells proliferation in a dose (10-160 μM) dependent manner. ERα-negative MDA-MB-231 cells were less sensitive to Furanodienone than ERα-positive MCF-7 and T47D cells. Furanodienone could effectively block 17β-estradiol (E2)-stimulated MCF-7 cell proliferation and cell cycle progression and induce apoptosis evidenced by the flow cytometric detection of sub-G1 DNA content and the appearance of apoptotic nuclei after DAPI staining. Furanodienone specifically down-regulated ERα protein and mRNA expression levels without altering ERβ expression. Furanodienone treatment inhibited E2-stimulation of estrogen response element (ERE)-driven reporter plasmid activity and ablated E2-targeted gene (e.g., c-Myc, Bcl-2, and cyclin D1) expression which resulted in the inhibition of cell cycle progression and cell proliferation, and in the induction of apoptosis. Knockdown of ERα in MCF-7 cells by ERα-specific siRNA decreased the cell growth inhibitory effect of Furanodienone.
CONCLUSIONS:
These findings suggest that effects of Furanodienone on MCF-7 cells are mediated, at least in part, by inhibiting ERα signaling.

Furanodienone Dilution Calculator

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Preparing Stock Solutions of Furanodienone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.3422 mL 21.7108 mL 43.4216 mL 86.8432 mL 108.5541 mL
5 mM 0.8684 mL 4.3422 mL 8.6843 mL 17.3686 mL 21.7108 mL
10 mM 0.4342 mL 2.1711 mL 4.3422 mL 8.6843 mL 10.8554 mL
50 mM 0.0868 mL 0.4342 mL 0.8684 mL 1.7369 mL 2.1711 mL
100 mM 0.0434 mL 0.2171 mL 0.4342 mL 0.8684 mL 1.0855 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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References on Furanodienone

Furanodienone inhibits cell proliferation and survival by suppressing ERalpha signaling in human breast cancer MCF-7 cells.[Pubmed:21069738]

J Cell Biochem. 2011 Jan;112(1):217-24.

Estrogen receptor alpha (ERalpha) plays an important role in the development and progression of breast cancer and thus the attenuation of ERalpha activities is a promising treatment strategy. Furanodienone is one of the main bioactive chemical components of Rhizoma Curcumae which is commonly used in Chinese medicine for the treatment of cancer. In this study, we investigated the effects of Furanodienone on human breast cancer MCF-7, T47D, and MDA-MB-231 cells. Our results showed that Furanodienone could inhibit MCF-7, T47D, and MDA-MB-231 cells proliferation in a dose (10-160 microM) dependent manner. ERalpha-negative MDA-MB-231 cells were less sensitive to Furanodienone than ERalpha-positive MCF-7 and T47D cells. Furanodienone could effectively block 17beta-estradiol (E2)-stimulated MCF-7 cell proliferation and cell cycle progression and induce apoptosis evidenced by the flow cytometric detection of sub-G1 DNA content and the appearance of apoptotic nuclei after DAPI staining. Furanodienone specifically down-regulated ERalpha protein and mRNA expression levels without altering ERbeta expression. Furanodienone treatment inhibited E2-stimulation of estrogen response element (ERE)-driven reporter plasmid activity and ablated E2-targeted gene (e.g., c-Myc, Bcl-2, and cyclin D1) expression which resulted in the inhibition of cell cycle progression and cell proliferation, and in the induction of apoptosis. Knockdown of ERalpha in MCF-7 cells by ERalpha-specific siRNA decreased the cell growth inhibitory effect of Furanodienone. These findings suggest that effects of Furanodienone on MCF-7 cells are mediated, at least in part, by inhibiting ERalpha signaling.

Furanodienone induces cell cycle arrest and apoptosis by suppressing EGFR/HER2 signaling in HER2-overexpressing human breast cancer cells.[Pubmed:21461888]

Cancer Chemother Pharmacol. 2011 Nov;68(5):1315-23.

PURPOSE: Overexpression of EGFR and HER2 is seen in breast cancers and results in poor prognosis and decreased patient survival. Clinically, EGFR and HER2 are effective therapeutic targets. The objective of this study is to investigate the in vitro effects of Furanodienone, an active chemical component isolated from Rhizoma Curcumae, on the activation of EGFR/HER2 signaling, cell cycle, and apoptosis in HER2-overexpressing BT474 and SKBR3 cells. METHODS: Cell growth was assessed by SRB protein assay. Cell cycle analysis was carried out by flow cytometry, and apoptosis was observed by Annexin V and DAPI staining. Effects of Furanodienone on the activation of EGFR/HER2 signaling-related proteins were analyzed by western blotting. RESULTS: Furanodienone inhibited cell growth in BT474 and SKBR3 cells. Furanodienone caused G1 arrest in BT474 cells and induced apoptosis in SKBR3 cells. Furanodienone interfered with EGFR/HER2 signaling in treated cells as shown by decreases in phosphorylated EGFR, HER2, Akt, Gsk3beta and an increase in p27(kip1) protein. Accordingly, Furanodienone inhibited EGF-induced phosphorylation of EGFR, HER2, Akt, and Gsk3beta. EGFR-specific siRNA knockdown did not affect the cell growth inhibitory effect of Furanodienone. On the contrary, specific siRNA knockdown of HER2 increased cellular resistance to Furanodienone toxicity. In HER-2-deficient MDA-MB-231 cells, the transfection and expression of HER2 increased the sensitivity of cells to Furanodienone toxicity. CONCLUSION: Furanodienone inhibited EGFR/HER2 signaling pathway in BT474 and SKBR3 cells. More importantly, the effect of Furanodienone was specifically dependent on HER2, but not EGFR, expression.

Description

Furanodienone is one of the major bioactive constituents derived from Rhizoma Curcumae. Furanodienone induced apoptosis.

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