| Identification | Back Directory | [Name]
Erastin | [CAS]
571203-78-6 | [Synonyms]
Erastin
CS-1430
Erastin - CAS 571203-78-6 - Calbiochem
2-(1-(4-(2-(4-Chlorophenoxy)acetyl)piperazin-1-yl)ethyl)-3-(2-ethoxyphenyl)quinazolin-4(3H)-on
2-(1-(4-(2-(4-Chlorophenoxy)acetyl)piperazin-1-yl)ethyl)-3-(2-ethoxyphenyl)quinazolin-4(3H)-one
2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone
4(3H)-Quinazolinone, 2-[1-[4-[2-(4-chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-
2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone USP/EP/BP
2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-quinazolinone Erastin | [Molecular Formula]
C30H31ClN4O4 | [MDL Number]
MFCD09837984 | [MOL File]
571203-78-6.mol | [Molecular Weight]
547.06 |
| Chemical Properties | Back Directory | [Boiling point ]
721.9±70.0 °C(Predicted) | [density ]
1.28±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C | [solubility ]
DMSO: soluble5mg/mL, clear (warmed) | [form ]
White solid | [pka]
5.54±0.10(Predicted) | [color ]
white to beige | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | [CAS DataBase Reference]
571203-78-6 |
| Hazard Information | Back Directory | [Description]
Erastin, named for eradicator of RAS and small T (ST) antigen-expressing cells, is a ferroptosis inducer.1 It induces ferroptotic cell death in vitro, an effect that can be blocked by the ferroptosis inhibitors ciclopirox olamine, Trolox (Item No. 10011659), ferrostatin-1 (Item No. 17729), U-0126 (Item No. 70970), cycloheximide (Item No. 14126), and β-mercaptoethanol. Erastin (5 μM) inhibits cystine uptake by the system xc- cystine-glutamate transporter in HT-1080 fibrosarcoma and Calu-1 lung carcinoma cells and inhibits glutamate release in an enzyme-coupled fluorescence assay (EC50 = 1.2 μM). It also selectively induces cell death in cells expressing the SV40 small T oncoprotein and oncogenic Ras (IC50s = 1.25-5 μg/ml).2 | [Uses]
Erastin, named for eradicator of RAS and ST-expressing cells, is an irreversible antitumor agent that selectively kills cells expressing the small T oncoprotein and oncogenic Ras (IC50s = 1.25-5 μg/ml). It produces non-apoptotic tumor cell death by altering mitochondrial voltage-dependent anion channel gating, allowing cations to enter mitochondria and leading to release of oxidative species causing oxidative cell death.[Cayman Chemical] | [Definition]
ChEBI:Erastin is a member of the class of quinazolines that is quinazolin-4(3H)-one in which the hydrogens at positions 2 and 3 are replaced by 1-{4-[(4-chlorophenoxy)acetyl]piperazin-1-yl}ethyl and 2-ethoxyphenyl groups, respectively. It is an inhibitor of voltage-dependent anion-selective channels (VDAC2 and VDAC3) and a potent ferroptosis inducer. It has a role as a ferroptosis inducer, an antineoplastic agent and a voltage-dependent anion channel inhibitor. It is a member of quinazolines, a member of monochlorobenzenes, an aromatic ether, a N-acylpiperazine, a N-alkylpiperazine, a diether and a tertiary carboxamide. | [General Description]
Erastin is a cell-permeable piperazinyl-quinazolinone. It interacts with antiporter system Xc-. | [Biochem/physiol Actions]
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. | [storage]
Store at -20° C, unstable in solution, ready to use. | [References]
1) Dolma et al. (2003), Identification of genotype-selective antitumor agents using synthetic lethal chemical screening in engineered human tumor cells; Cancer Cell, 3 285
2) Dixon et al. (2014), Pharmacological inhibition of cysteine-glutamate exchange induces endoplasmic reticulum stress and ferroptosis; Elife, 3 e02523
3) Sato et al. (2018), The ferroptosis inducer erastin irreversibly inhibits system xc-and synergizes with cisplatin to increase cisplatin’s cytotoxicity in cancer cells; Sci. Rep., 8 968
4) Yagoda et al. (2007), RAS-RAF-MEK-dependent oxidative cell death involving voltage-dependent anion channels; Nature, 447 864 |
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