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E7781

Sigma-Aldrich

Erastin

≥98% (HPLC), powder, antitumor agent

Synonyme(s) :

2-[1-[4-[2-(4-chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone

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About This Item

Formule empirique (notation de Hill):
C30H31ClN4O4
Numéro CAS:
571203-78-6
Poids moléculaire :
547.04
Numéro MDL:
MFCD09837984
Code UNSPSC :
12352200
ID de substance PubChem :
329799073
Nomenclature NACRES :
NA.77

product name

Erastin, ≥98% (HPLC)

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 5 mg/mL, clear (warmed)

Température de stockage

−20°C

Chaîne SMILES 

CCOc1ccccc1N2C(=O)c3ccccc3N=C2C(C)N4CCN(CC4)C(=O)COc5ccc(Cl)cc5

InChI

1S/C30H31ClN4O4/c1-3-38-27-11-7-6-10-26(27)35-29(32-25-9-5-4-8-24(25)30(35)37)21(2)33-16-18-34(19-17-33)28(36)20-39-23-14-12-22(31)13-15-23/h4-15,21H,3,16-20H2,1-2H3

Clé InChI

BKQFRNYHFIQEKN-UHFFFAOYSA-N

Informations sur le gène

human ... hRas(3265)
mouse ... hRas(15461)
rat ... hRas(293621)

Description générale

Erastin is a cell-permeable piperazinyl-quinazolinone. It interacts with antiporter system Xc-.

Application

Erastin has been used:
  • as a positive control for inducing ferroptosis in hepatic stellate cell (HSC)
  • to induce ferroptosis and in transferrin internalization assay of human fibrosarcoma HT1080 cells
  • to induce ferroptosis of muscle-derived cell lines

Actions biochimiques/physiologiques

Erastin is an antitumor agent selective for tumor cells bearing oncogenic RAS (i.e. HRAS, KRAS). Erastin produces ferroptosis, a non-apoptotic tumor cell death, by altering mitochondrial voltage-dependent anion channel (VDAC) gating allowing cations to enter mitochondria and leading to release of oxidative species causing oxidative cell death.

Caractéristiques et avantages

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Nicholas Yagoda et al.
Nature, 447(7146), 864-868 (2007-06-15)
Therapeutics that discriminate between the genetic makeup of normal cells and tumour cells are valuable for treating and understanding cancer. Small molecules with oncogene-selective lethality may reveal novel functions of oncoproteins and enable the creation of more selective drugs. Here
Sonam Dolma et al.
Cancer cell, 3(3), 285-296 (2003-04-05)
We used synthetic lethal high-throughput screening to interrogate 23,550 compounds for their ability to kill engineered tumorigenic cells but not their isogenic normal cell counterparts. We identified known and novel compounds with genotype-selective activity, including doxorubicin, daunorubicin, mitoxantrone, camptothecin, sangivamycin
The ferroptosis inducer erastin promotes proliferation and differentiation in human peripheral blood mononuclear cells
Wang D, et al.
Biochemical and Biophysical Research Communications, 503(3), 1689-1695 (2018)
Cell growth potential drives ferroptosis susceptibility in rhabdomyosarcoma and myoblast cell lines
Codenotti S, et al.
Journal of Cancer Research and Clinical Oncology, 144(9), 1717-1730 (2018)
Antonio Bruni et al.
Cell death & disease, 9(6), 595-595 (2018-05-24)
Human islet transplantation has been hampered by donor cell death associated with the islet preparation procedure before transplantation. Regulated necrosis pathways are biochemically and morphologically distinct from apoptosis. Recently, ferroptosis was identified as a non-apoptotic form of iron-dependent regulated necrosis
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