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F9054

Sigma-Aldrich

Fumitremorgin C

from Neosartorya fischeri, film

Synonym(s):

FTC

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About This Item

Empirical Formula (Hill Notation):
C22H25N3O3
CAS Number:
118974-02-0
Molecular Weight:
379.45
MDL number:
MFCD08702652
UNSPSC Code:
12161501
PubChem Substance ID:
24724486
NACRES:
NA.77

biological source

Neosartorya fischeri

Quality Level

200

form

film

solubility

acetonitrile: soluble 5 mg/mL
methanol: soluble 5 mg/mL
DMSO: soluble
chloroform: soluble

antibiotic activity spectrum

fungi

shipped in

wet ice

storage temp.

2-8°C

SMILES string

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

General description

Chemical structure: indol derivative

Application

Fumitremorgin C has been used as adenosine triphosphate (ATP)-binding cassette superfamily G member 2 (ABCG2) inhibitor to study its effects on the cell viability of mouse neural stem/progenitor cells (NSPCs). It has also been used as an ABCG2 inhibitor to study its effects on lung cancer cells.

Biochem/physiol Actions

Fumitremorgin C (FTC) is a fungal toxin of the diketopiperazines family of compounds. In mammalian cells, FTC is tremorgenic and causes cell cycle arrest. Fumitremorgin C has been shown to reverse resistance to doxorubicin, mitoxantrane, and topotecan in non-Pgp (P-glyco­protein), non-MRP (multidrug resistance protein) multidrug-resistance (MDR) cells. This reversal of resistance is associated with an increase in drug accumulation. Fumitremorgin C is a specific, selective, and potent inhibitor at micromolar concentrations of the breast cancer resistant protein (BCRP/ABCG2), an ABC transporter associated with chemotherapy resistance. FTC, in combination with mitoxantrone, can be used for the detection of ABCG2 functional activity in several cell lines.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Packaging

Store desiccated at 2-8 °C. Under these conditions, the product is stable for 2 years. A solution in DMSO is stable for 2 months at 2-8 °C.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jacob D Estes et al.
Nature medicine, 23(11), 1271-1276 (2017-10-03)
In the quest for a functional cure or the eradication of HIV infection, it is necessary to know the sizes of the reservoirs from which infection rebounds after treatment interruption. Thus, we quantified SIV and HIV tissue burdens in tissues
Stefanie J Vaccher et al.
PloS one, 12(9), e0185398-e0185398 (2017-09-28)
In Australia, pre-exposure prophylaxis (PrEP) is targeted to individuals at high risk for HIV infection. We describe the HIV risk profile and characteristics of PRELUDE participants, and evaluate the population validity of the sample in representing high-risk gay and bisexual
Johan O Paulsson et al.
The Journal of pathology, 250(2), 183-194 (2019-10-18)
The genetics underlying thyroid cancer dedifferentiation is only partly understood and has not yet been characterised using comprehensive pan-genomic analyses. We investigated a unique case with synchronous follicular thyroid carcinoma (FTC), poorly differentiated thyroid carcinoma (PDTC), and anaplastic thyroid carcinoma
Jean-Michel Molina et al.
The New England journal of medicine, 373(23), 2237-2246 (2015-12-02)
Antiretroviral preexposure prophylaxis has been shown to reduce the risk of human immunodeficiency virus type 1 (HIV-1) infection in some studies, but conflicting results have been reported among studies, probably due to challenges of adherence to a daily regimen. We
A van Loevezijn et al.
Bioorganic & medicinal chemistry letters, 11(1), 29-32 (2001-01-05)
A library of 42 diastereoisomeric mixtures of fumitremorgin-type indolyl diketopiperazines, prepared by parallel solid-phase synthesis, was screened for Breast Cancer Resistance Protein inhibitory activity and compared with GF120918. Demethoxy-fumitremorgin C was synthesized by solid-phase techniques and tested as well. Structure-activity
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