F9054

Fumitremorgin C

From Neosartorya fischeri, breast cancer restance protein inhibitor, film

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

Properties

• Product Name: Fumitremorgin C, from Neosartorya fischeri, film
• biological source: Neosartorya fischeri
• Quality Segment: 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

Description

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).[1] It has also been used as an ABCG2 inhibitor to study its effects on lung cancer cells.[2][3]

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.

Selective inhibitor for the breast cancer resistance protein.

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)