Fumitremorgin C

Names

[ Name ]:
Fumitremorgin C

[Synonym ]:
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

Biological Activity

[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.

[Related Small Molecules]

Ko 143 | elacridar | KS 176 | YHO-13177 | YHO-13351 | (S)-ML753286 | Zamicastat

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

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
acetonitrile: 5 mg/mL, soluble

MSDS

Click to get detail MSDS

Safety Information

[ 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

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