| Chemical & Physical Properties | |
|---|---|
| CAS Number | 118974-02-0 |
| Catalog No. | 2A-1177723 |
| Chinese Name | 烟曲霉素C, 来源于烟曲霉菌 |
| Synonyms | fumitremorogin C; MFCD08702652; fumitremogin C; Fumitremorgin C |
| Molecular Formula | C22H25N3O3 |
| Molecular Weight | 379.45 |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 642.9±55.0 °C at 760 mmHg |
| Melting Point | 259.5-260.5℃ |
| Appearance | film |
| Water Solubility | acetonitrile: 5 mg/mL, soluble |
| Storage Condition | Sealed in a cool, dry environment at 2-8 ºC |
| Application | Fumitremorgin C is a potent, selective ABCG2/BRCP inhibitor. |
| PubChem ID | 24724486 |
| MDL Number | MFCD08702652 |
| SMILES | COc1ccc2c3C[C@@H]4N([C@@H](\C=C(/C)C)c3[nH]c2c1)C(=O)[C@@H]5CCCN5C4=O |
| 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 |
| InChI Key | DBEYVIGIPJSTOR-FHWLQOOXSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12161501 |
| Hazard Symbols | transportation |
| MSDS | msds/178309_2_118974_02_0.pdf |
| Bioactivity | Fumitremorgin C is a potent and selective ABCG2/BRCP inhibitor. Related Catalog Signaling Pathways >> Membrane Transporter/Ion Channel >> BCRP Natural Products >> Alkaloid Research Areas >> Cancer 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]. Cell Assay Cells are treated with chemotherapeutic agent and the reversal agents Fumitremorgin C is added to cells (0.1 to 80 /UM). In parallel wells, cells are grown in the presence of the reversal agent alone. Following a 3-day growth period, cells are fixed in 10% trichloroacetic acid for 1 h and washed extensively with water, and cell-associated protein is stained using 0.1% SRB. Excess reagent is removed by washing plates in 5% acetic acid, the dye is solubilized in 10 mM Tris base, and absorbance is determined in a UV Max spectrophotometer at 540 nm. Cell survival is determined relative to control wells[1]. 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. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 642.9±55.0 °C at 760 mmHg Melting Point 259.5-260.5℃ Molecular Formula C22H25N3O3 Molecular Weight 379.452 Flash Point 342.6±31.5 °C Exact Mass 379.189606 PSA 65.64000 LogP 1.74 Appearance of Characters solid Vapour Pressure 0.0±1.9 mmHg at 25°C Index of Refraction 1.676 InChIKey DBEYVIGIPJSTOR-FHWLQOOXSA-N SMILES COc1ccc2c3c([nH]c2c1)C(C=C(C)C)N1C(=O)C2CCCN2C(=O)C1C3 Storage condition 2-8°C Water Solubility acetonitrile: 5 mg/mL, soluble |
| Use of | Properties Articles47 Name fumitremorgin C Synonym More Synonyms Fumitremorgin C Biological Activity Related Catalog Signaling Pathways >> Membrane Transporter/Ion Channel >> BCRP Natural Products >> Alkaloid Research Areas >> Cancer 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. Chemical & Physical Properties Molecular Formula C22H25N3O3 Exact Mass 379.189606 PSA 65.64000 Appearance of Characters solid Index of Refraction 1.676 InChIKey DBEYVIGIPJSTOR-FHWLQOOXSA-N |
| Transport Info | Product name: Purity: 97.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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