Fumitremorgin CInhibitor of BCRP-mediated multidrug resistance CAS# 118974-02-0 |
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 118974-02-0 | SDF | Download SDF |
| PubChem ID | 403923 | Appearance | Powder |
| Formula | C22H25N3O3 | M.Wt | 379.45 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Synonyms | 12α-Fumitremorgin C | ||
| Solubility | DMSO : 50 mg/mL (131.77 mM; Need ultrasonic) H2O : < 0.1 mg/mL (insoluble) | ||
| SMILES | CC(=CC1C2=C(CC3N1C(=O)C4CCCN4C3=O)C5=C(N2)C=C(C=C5)OC)C | ||
| Standard InChIKey | DBEYVIGIPJSTOR-FHWLQOOXSA-N | ||
| Standard InChI | InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3/t17-,18-,19-/m0/s1 | ||
| 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. |
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| 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. |
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| 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. | ||
| Description | 1. Fumitremorgin C is a potent and specific chemosensitizing agent in cell lines selected for resistance to mitoxantrone that do not overexpress P-glycoprotein or multidrug resistance protein. 2. Fumitremorgin C reverses multidrug resistance in cells transfected with the breast cancer resistance protein. 3. Fumitremorgin C shows an antibacterial activity against Staphylococcus aureus, methicillin-resistant S. aureus, and multidrug-resistant S. aureus. 4. Fumitremorgin C shows cytotoxic activity against HCT-116 tumour cell line. |
| Targets | Antifection | P-gp |
Fumitremorgin C Dilution Calculator
Fumitremorgin C Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.6354 mL | 13.177 mL | 26.3539 mL | 52.7079 mL | 65.8848 mL |
| 5 mM | 0.5271 mL | 2.6354 mL | 5.2708 mL | 10.5416 mL | 13.177 mL |
| 10 mM | 0.2635 mL | 1.3177 mL | 2.6354 mL | 5.2708 mL | 6.5885 mL |
| 50 mM | 0.0527 mL | 0.2635 mL | 0.5271 mL | 1.0542 mL | 1.3177 mL |
| 100 mM | 0.0264 mL | 0.1318 mL | 0.2635 mL | 0.5271 mL | 0.6588 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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Fumitremorgin C is a potent and selective ABCG2/BRCP inhibitor.
In Vitro:Multidrug resistance (MDR) is a major problem in cancer chemotherapy. Fumitremorgin C is extremely effective in reversing resistance to mitoxantrone, doxorubicin, and topotecan in multidrug-selected cell lines. In MCF-7/mtxR (a mitoxantroneselected cell line), fumitremorgin C reverses mitoxantrone resistance (114-fold) and doxorubicin resistance (3-fold). Fumitremorgin C (5/AM)significantly potentiates the toxicity of mitoxantrone (93-fold), doxorubicin (26-fold), and topotecan (24-fold) in S1M1-3.2 cells. Reversal of resistance is associated with an increase in drug accumulation. Fumitremorgin C does not reverse drug resistance in cells with elevated expression of Pgp or MRP[1]. Fumitremorgin C almost completely reverses resistance mediated by BCRP in vitro and is a pharmacological probe for the expression and molecular action of this transporter. Fumitremorgin C also enhances the toxicity of mitoxantrone and topotecan in vector-transfected MCF-7 cells (2.5–5.6 fold). It reduces the IC50 of topotecan in BCRP-overexpressing cells below that observed in the untreated vector-transfected cells. [2].
References:
[1]. Rabindran SK, et al. Reversal of a novel multidrug resistance mechanism in human colon carcinoma cells by fumitremorgin C. Cancer Res. 1998 Dec 15;58(24):5850-8.
[2]. Rabindran SK, et al. Fumitremorgin C reverses multidrug resistance in cells transfected with the breast cancer resistance protein. Cancer Res. 2000 Jan 1;60(1):47-50.
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Fumitremorgin C reverses multidrug resistance in cells transfected with the breast cancer resistance protein.[Pubmed:10646850]
Cancer Res. 2000 Jan 1;60(1):47-50.
Fumitremorgin C (FTC) is a potent and specific chemosensitizing agent in cell lines selected for resistance to mitoxantrone that do not overexpress P-glycoprotein or multidrug resistance protein. The gene encoding a novel transporter, the breast cancer resistance protein (BCRP), was recently found to be overexpressed in a mitoxantrone-selected human colon cell line, S1-M1-3.2, which was used to identify FTC. Because the drug-selected cell line may contain multiple alterations contributing to the multidrug resistance phenotype, we examined the effect of FTC on MCF-7 cells transfected with the BCRP gene. We report that FTC almost completely reverses resistance mediated by BCRP in vitro and is a pharmacological probe for the expression and molecular action of this transporter.
Cytotoxic compounds from the marine-derived fungus Aspergillus sp. recovered from the sediments of the Brazilian coast.[Pubmed:25532964]
Nat Prod Res. 2015;29(16):1545-50.
A fungal strain of Aspergillus sp. (BRF 030) was isolated from the sediments collected in the northeast coast of Brazil, and the cytotoxic activity of its secondary metabolites was investigated against HCT-116 tumour cell line. The cytotoxicity-guided fractionation of the extracts from this fungus cultured in potato-dextrose-sea water for 14 days at room temperature yielded the hetero-spirocyclic gamma-lactams pseurotin A (1), pseurotin D (2) and pseurotin FD-838 (7), the alkaloids Fumitremorgin C (5), 12,13-dihydroxy Fumitremorgin C (6), methylsulochrin (4) and bis(dethio)bis(methylthio)gliotoxin (3). Among them, Fumitremorgin C (5) and 12,13-dihydroxy Fumitremorgin C (6) were the most active. The cytotoxic activities of the extracts from Aspergillus sp. grown from 7 to 28 days were investigated, and they were associated with the kinetic production of the compounds. The most active extracts (14 and 21 days) were those with the highest relative concentrations of the compounds Fumitremorgin C (5) and 12,13-dihydroxy Fumitremorgin C (6).
Reversal of a novel multidrug resistance mechanism in human colon carcinoma cells by fumitremorgin C.[Pubmed:9865745]
Cancer Res. 1998 Dec 15;58(24):5850-8.
We selected a human colon carcinoma cell line in increasing concentrations of mitoxantrone to obtain a resistant subline, S1-M1-3.2, with the following characteristics: profound resistance to mitoxantrone; significant cross-resistance to doxorubicin, bisantrene, and topotecan; and very low levels of resistance to Taxol, vinblastine, colchicine, and camptothecin. This multidrug resistance (MDR) phenotype, which was not reversed by verapamil or another potent P-glycoprotein (Pgp) inhibitor, CL 329,753, was dependent, in part, upon an energy-dependent drug efflux mechanism. Pgp and the multidrug resistance protein (MRP) were not elevated in the resistant cells relative to the drug-sensitive parent, suggesting that resistance was mediated by a novel pathway of drug transport. A cell-based screen with S1-M1-3.2 cells was used to identify agents capable of circumventing this non-Pgp, non-MRP MDR. One of the active agents identified was a mycotoxin, Fumitremorgin C. This molecule was extremely effective in reversing resistance to mitoxantrone, doxorubicin, and topotecan in multidrug-selected cell lines showing this novel phenotype. Reversal of resistance was associated with an increase in drug accumulation. The compound did not reverse drug resistance in cells with elevated expression of Pgp or MRP. We suggest that Fumitremorgin C is a highly selective chemosensitizing agent for the resistance pathway we have identified and can be used as a specific pharmacological probe to distinguish between the diverse resistance mechanisms that occur in the MDR cell.
