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Safety Information

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

F9054-250UG-PW:
F9054-BULK:
F9054-250UG:
F9054-VAR:

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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Ross D Cranston et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 64(5), 614-620 (2016-12-18)
Human immunodeficiency virus (HIV) disproportionately affects men who have sex with men (MSM) and transgender women (TGW). Safe and acceptable topical HIV prevention methods that target the rectum are needed. MTN-017 was a phase 2, 3-period, randomized sequence, open-label, expanded
Christopher W Peterson et al.
PLoS pathogens, 14(4), e1006956-e1006956 (2018-04-20)
Autologous transplantation and engraftment of HIV-resistant cells in sufficient numbers should recapitulate the functional cure of the Berlin Patient, with applicability to a greater number of infected individuals and with a superior safety profile. A robust preclinical model of suppressed
Chien-Yu Cheng et al.
Infection and drug resistance, 11, 849-859 (2018-06-13)
Increasing trends of resistance-associated mutations (RAMs) to non-nucleoside reverse-transcriptase inhibitors (nNRTIs) have raised concerns about the effectiveness of the regimens in the national HIV treatment programs in resource-limited countries. We aimed to retrospectively investigate the incidence and patterns of emergent
H P M Natukunda et al.
South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde, 107(11), 965-975 (2017-12-22)
Studies investigating symptoms associated with combination antiretroviral therapy (cART) use among adolescents in resource-limited settings are rare beyond clinical trials. Identifying adolescents at risk of non-adherence is imperative for HIV/AIDS programming and controlling the epidemic in this key population. To
Jose I Bernardino et al.
PloS one, 14(1), e0209911-e0209911 (2019-01-29)
Comparison of changes in body composition, adipokines and inflammatory markers after initial therapy with a nucleos(t)ide reverse transcriptase inhibitor (N(t)RTI)- sparing or containing regimen are scarce. Randomised Clinical Trial. This is the body composition substudy of NEAT 001/ANRS 143, a
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