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950455-15-9

950455-15-9 Structure

950455-15-9 Structure
IdentificationBack Directory
[Name]

Liproxstatin-1
[CAS]

950455-15-9
[Synonyms]

CS-1656
Liproxstatin-1
Liproxstatin-1 USP/EP/BP
LIPROXSTATIN-1;LIPROXSTATIN1
N-(3-Chlorobenzyl)-1'H-spiro[piperidine-4,2'-quinoxalin]-3'-amine
N-[(3-chlorophenyl)methyl]spiro[4H-quinoxaline-3,4'-piperidine]-2-amine
N-[(3-chlorophenyl)methyl]-spiro[piperidine-4,2'(1'H)-quinoxalin]-3'-amine
N-[(3-chlorophenyl)methyl]-1'H-spiro[piperidine-4,2'-quinoxaline]-3'-amine
[Molecular Formula]

C19H21ClN4
[MDL Number]

MFCD14948691
[MOL File]

950455-15-9.mol
[Molecular Weight]

340.85
Chemical PropertiesBack Directory
[Boiling point ]

581.4±50.0 °C(Predicted)
[density ]

1.32±0.1 g/cm3(Predicted)
[storage temp. ]

-20°C
[solubility ]

Soluble in DMSO (15 mg/ml)
[form ]

powder
[pka]

9.45±0.40(Predicted)
[color ]

white to light brown
[Stability:]

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 month.
[InChI]

InChI=1S/C19H21ClN4/c20-15-5-3-4-14(12-15)13-22-18-19(8-10-21-11-9-19)24-17-7-2-1-6-16(17)23-18/h1-7,12,21,24H,8-11,13H2,(H,22,23)
[InChIKey]

YAFQFNOUYXZVPZ-UHFFFAOYSA-N
[SMILES]

N1CCC2(C(NCC3=CC=CC(Cl)=C3)=NC3=C(N2)C=CC=C3)CC1
Hazard InformationBack Directory
[Description]

Liproxstatin-1 is a ferroptosis inhibitor. It inhibits ferroptotic cell death (IC50 = 22 nM) and lipid peroxidation in mouse embryonic fibroblasts (MEFs) with an inducible knockdown of glutathione peroxidase 4 (Gpx4-/- MEFs) when used at a concentration of 50 nM. Liproxstatin-1 also inhibits ferroptosis induced by the ferroptosis-inducing agents L-buthionine sulphoximine (BSO), erastin (Item No. 17754), and (1S,3R)-RSL3 (Item No. 19288) in a concentration-dependent manner in MEFs, but does not inhibit necroptosis, apoptosis, or necrosis. It inhibits cell death and lipid peroxidation induced by (1S,3R)-RSL3 in human renal proximal tubule epithelial cells. Liproxstatin-1 (10 mg/kg) increases survival and decreases TUNEL+ kidney cells in inducible Gpx4-/- mice and reduces tissue injury in a mouse model of hepatic ischemia/reperfusion injury. It is also an antioxidant that inhibits autooxidation of lipids by trapping peroxyl radicals.
[Uses]

Liproxstatin-1 has been used as a cell death inhibitor in the cell viability assay and for the determination of lipid peroxidation.
[Definition]

ChEBI: Liproxstatin-1 is an azaspiro compound that is 1'H-spiro[piperidine-4,2'-quinoxaline] in which the hydrogen at position 3' is replaced by a (3-chlorobenzyl)amino group. It is a potent inhibitor of ferroptosis. It has a role as a ferroptosis inhibitor, a radical scavenger, an antioxidant and a cardioprotective agent. It is a member of monochlorobenzenes, a secondary amino compound, an azaspiro compound and an organic heterotricyclic compound.
[Biochem/physiol Actions]

Liproxstatin-1 is a potent inhibitor of ferroptosis, a non-apoptotic form of cell death characterized by iron-dependent accumulation of lethal lipid reactive oxygen species (ROS). Liproxstatin-1 suppressed ferroptosis in human cells and in an ischaemia/reperfusion-induced tissue injury model in mice. Knockout of glutathione peroxidase 4 (Gpx4) Has been shown to cause cell death by ferroptosis. Liproxstatin-1 was able to suppress ferroptosis in Gpx4 knock-out mice.
[in vivo]

Liproxstatin-1 (10 mg/kg, i.p.) suppresses ferroptosis in human cells, Gpx4 / kidney and in an ischaemia/reperfusion-induced tissue injury model[1].

[storage]

Store at -20°C
[References]

Angeli et al. (2014), Inactivation of the ferroptosis regulator Gpx4 triggers acute renal failure in mice; Nat. Chem. Biol. 16 1180 Feng et al. (2019), Liproxstatin-1 protects the mouse myocardium against ischemia/reperfusion injury by decreasing VDAC1 levels and restoring GPX4 levels; Biochem. Biophys. Res. Commun. 520 606 Zilka et al. (2017), On the mechanism of Cytoprotection by Ferrostatin-1 and Liproxstatin-1 and the Role of Lipid Peroxidation in Ferroptotic Cell Death; ACS Cent. Sci. 3 232
Spectrum DetailBack Directory
[Spectrum Detail]

Liproxstatin-1(950455-15-9)1HNMR
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