BioBioPha
China
Product Name: Fumitremorgin C
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Purity: 98.0%
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Shanghai Jizhi Biochemical Technology Co., Ltd
China
Product Name: Fumitremorgin C
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Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: 5H,14H-Pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione,1,2,3,5a,6,11,12,14a-octahydro-9-methoxy-12-(2-methyl-1-propen-1-yl)-,(5aS,12S,14aS)-
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Purity: 98.0%
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118974-02-0

118974-02-0 structure

118974-02-0 structure

Name: Fumitremorgin C
Chemical Name: fumitremorgin C
CAS Number: 118974-02-0
Molecular Formula: C₂₂H₂₅N₃O₃
Molecular Weight: 379.452
Catalog: Natural product Alkaloid
Create Date: 2016-08-19 03:51:08
Modify Date: 2024-01-02 19:09:10
Fumitremorgin C is a potent and selective ABCG2/BRCP inhibitor.

Name	fumitremorgin C
Synonyms	fumitremorogin C (5aS,12S,14aS)-1,2,5a,6,11,12,14a-octahydro-9-methoxy-12-(2-methylprop-1-en-1-yl)-5H,14H-pyrrolo[1'',4'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione MFCD08702652 fumitremogin C 5H,14H-Pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione, 1,2,3,5a,6,11,12,14a-octahydro-9-methoxy-12-(2-methyl-1-propen-1-yl)-, (5aS,12S,14aS)- (5aS,12S,14aS)-9-methoxy-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione Fumitremorgin C (5aS,12S,14aS)-9-Methoxy-12-(2-methyl-1-propen-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione

Description	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.

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	solid
Vapour Pressure	0.0±1.9 mmHg at 25°C
Index of Refraction	1.676
Storage condition	2-8°C
Water Solubility	acetonitrile: 5 mg/mL, soluble

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Safety Phrases	S22-S24/25
RIDADR	NONH for all modes of transport
WGK Germany	3