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SML1414

Sigma-Aldrich

Liproxstatin-1

>98% (HPLC), powder, ferroptosis inhibitor

Synonym(s):

N-[(3-Chlorophenyl)methyl]-spiro[piperidine-4,2′(1′H)-quinoxalin]-3′-amine, N-[(3-chlorophenyl)methyl]spiro[4H-quinoxaline-3,4′-piperidine]-2-amine

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About This Item

Empirical Formula (Hill Notation):
C19H21ClN4
CAS Number:
950455-15-9
Molecular Weight:
340.85
MDL number:
MFCD14948691
UNSPSC Code:
12352200
PubChem Substance ID:
329825860
NACRES:
NA.77

product name

Liproxstatin-1, >98% (HPLC)

Quality Level

100

Assay

>98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

ClC1=CC(CNC2=NC3=CC=CC=C3NC24CCNCC4)=CC=C1

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)

InChI key

YAFQFNOUYXZVPZ-UHFFFAOYSA-N

Application

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Selenium utilization by GPX4 is required to prevent hydroperoxide-induced ferroptosis.
Ingold I, et al.
Cell, 172(3), 409-422 (2018)
Wen-Hsuan Yang et al.
Molecular cancer research : MCR, 18(1), 79-90 (2019-10-24)
Ovarian cancer is the deadliest gynecologic cancer. Despite recent advances, clinical outcomes remain poor, necessitating novel therapeutic approaches. To investigate metabolic susceptibility, we performed nutrigenetic screens on a panel of clear cell and serous ovarian cancer cells and identified cystine
Alejandra M Martinez et al.
FEBS open bio, 9(4), 582-593 (2019-04-16)
Ferroptosis is a form of regulated cell death that is driven by lethal accumulation of lipid peroxides upon inhibition of glutathione peroxidase 4 (GPx4). Deletion of the Gpx4 gene in mice revealed that neurons are sensitive to ferroptosis in vivo. However
Yilei Zhang et al.
Nature cell biology, 20(10), 1181-1192 (2018-09-12)
The roles and regulatory mechanisms of ferroptosis (a non-apoptotic form of cell death) in cancer remain unclear. The tumour suppressor BRCA1-associated protein 1 (BAP1) encodes a nuclear deubiquitinating enzyme to reduce histone 2A ubiquitination (H2Aub) on chromatin. Here, integrated transcriptomic
Ji-Yoon Lee et al.
Proceedings of the National Academy of Sciences of the United States of America, 117(51), 32433-32442 (2020-12-09)
Ferroptosis is an iron-dependent regulated necrosis mediated by lipid peroxidation. Cancer cells survive under metabolic stress conditions by altering lipid metabolism, which may alter their sensitivity to ferroptosis. However, the association between lipid metabolism and ferroptosis is not completely understood.
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