Ferrostatin-1 (Fer-1) Chemical Properties

Boiling point:

437.3±35.0 °C(Predicted)

Density 

1.150±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: soluble10mg/mL, clear

pka

4.78±0.11(Predicted)

form 

powder

color 

purple to brown

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.

InChI

InChI=1S/C15H22N2O2/c1-2-19-15(18)11-8-9-14(13(16)10-11)17-12-6-4-3-5-7-12/h8-10,12,17H,2-7,16H2,1H3

InChIKey

UJHBVMHOBZBWMX-UHFFFAOYSA-N

SMILES

C(OCC)(=O)C1=CC=C(NC2CCCCC2)C(N)=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2922498590

Ferrostatin-1 (Fer-1) Usage And Synthesis

Description

Ferrostatin-1 (347174-05-4) inhibits ferroptosis (EC50=60 nM), an iron-dependent form of nonapoptotic cell death.1?Potent inhibitor of ferroptosis in cancer cells and glutamate-induced cell death in organotypic rat brain slices.1?Blocks the cytotoxic effects of sorafenib in hepatocellular carcinoma cells.2?Ferrostatin-1 inhibits oxidative lipid damage and cell death in diverse disease models3 and prevents apoptosis of renal proximal tubular cells induced by reactive oxygen species4.

Uses

Ferrostatin-1 (Fer-1) is a potent and selective inhibitor of ferroptosis.

Definition

ChEBI: Ferrostatin-1 is an ethyl ester resulting from the formal condensation of the carboxy group of 3-amino-4-(cyclohexylamino)benzoic acid with ethanol. It is a potent inhibitor of ferroptosis, a distinct non-apoptotic form of cell death caused by lipid peroxidation. It is also a radical-trapping antioxidant and has the ability to reduce the accumulation of lipid peroxides and chain-carrying peroxyl radicals. It has a role as a ferroptosis inhibitor, a radiation protective agent, an antioxidant, a radical scavenger, an antifungal agent and a neuroprotective agent. It is a substituted aniline, an ethyl ester and a primary arylamine.

Biochem/physiol Actions

Ferrostatin-1 is an active radical-trapping antioxidant that traps peroxyl radicals, and thus serves as a potential inhibitor of ferroptosis. Ferroptosis is considered as regulated necrosis, which differs from apoptosis and autophagy. Ferrostatin-1 is known to show protective effects against Huntington′s disease and also prevents neurotoxicity induced by glutamate in cellular models.

Synthesis

General procedure for the synthesis of ethyl 3-amino-4-(cyclohexylamino)benzoate from ethyl 4-(cyclohexylamino)-3-nitrobenzoate: the nitro derivative (24.28 g, 83 mmol) was dissolved in methanol (150 mL) and 20% Pd(OH)2/carbon catalyst (200 mg) was added. The hydrogenation reaction was carried out under hydrogen atmosphere at 1 atmosphere for 3 days. Upon completion of the reaction, the catalyst was removed by filtration followed by evaporation of the solvent under reduced pressure to afford the target product ethyl 3-amino-4-(cyclohexylamino)benzoate (21.72 g, 100% yield) as a dark purple solid.

storage

Store at +4°C

References

[1] SCOTT J DIXON. Ferroptosis: an iron-dependent form of nonapoptotic cell death.[J]. Cell, 2012, 149 5: 1060-1072. DOI:10.1016/j.cell.2012.03.042
[2] CHRISTOPHE LOUANDRE. Iron-dependent cell death of hepatocellular carcinoma cells exposed to sorafenib[J]. International Journal of Cancer, 2013, 133 7: 1732-1742. DOI:10.1002/ijc.28159
[3] RACHID SKOUTA. Ferrostatins Inhibit Oxidative Lipid Damage and Cell Death in Diverse Disease Models[J]. Journal of the American Chemical Society, 2014, 136 12: 4551-4556. DOI:10.1021/ja411006a
[4] GRAZYNA NOWAK  Ruben M  Sridharan Soundararajan. Protein kinase C-α interaction with iHSP70 in mitochondria promotes recovery of mitochondrial function after injury in renal proximal tubular cells.[J]. American Journal of Physiology-renal Physiology, 2013, 305 5: F764-76. DOI:10.1152/ajprenal.00061.2013

Ferrostatin-1 (Fer-1)(347174-05-4)Related Product Information

• Rapamycin
• Astemizole
• SU 4312
• GF109203X
• Fludarabine
• ABT-199
• SB 431542
• PD 0325901
• Erastin
• Z-VAD-FMK