Erastin

Names

[ Name ]:
Erastin

[Synonym ]:
2-[1-[4-[2-(4-chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone
2-(1-{4-[(4-Chlorophenoxy)acetyl]-1-piperazinyl}ethyl)-3-(2-ethoxyphenyl)-4(3H)-quinazolinone
s7242
2-(1-{4-[2-(4-chloro-phenoxy)-acetyl]-piperazin-1-yl}-ethyl)-3-(2-ethoxy-phenyl)-3H-quinazolin-4-one
2-(1-{4-[(4-chlorophenoxy)acetyl]piperazin-1-yl}ethyl)-3-(2-ethoxyphenyl)quinazolin-4(3H)-one
4(3H)-Quinazolinone, 2-[1-[4-[2-(4-chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-
Erastin

Biological Activity

[Description]:

Erastin is a ferroptosis activator.

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Ferroptosis

Research Areas >> Cancer

[In Vitro]

Erastin triggers oxidative, iron-dependent cell death. Treatment of NRAS-mutant HT-1080 fibrosarcoma cells with the RSL molecule erastin (10 µM) results in a time-dependent increase in cytosolic and lipid ROS beginning at 2 hours[1]. Cell death triggered by erastin is significantly inhibited by antioxidants (e.g., α-tocopherol, butylated hydroxytoluene, and β-carotene) and iron chelators (e.g., deferoxamine), suggesting that ROS- and iron-dependent signaling is required for erastin-induced ferroptosis. Erastin can directly bind to VDAC2/3 in BJeLR cells. Knockdown of VDAC2 and VDAC3, but not VDAC1, leads to erastin resistance. Erastin has the ability to reduce glutathione level by directly inhibiting cystine/glutamate antiporter system Xc− activity, with activation of the ER stress response[2]. Erastin potently inhibits HT-29 cell survival. Erastin shows a dose-dependent effect, and 30 μM of erastin displays the most dramatic effect[3].

[In Vivo]

Intraperitoneal injection of erastin at well-tolerated doses dramatically inhibits HT-29 xenograft growth in severe combined immunodeficient mice[3].

[Cell Assay]

To test erastin’s activity on colorectal cancer cell survival, HT-29 cells are treated with increasing concentrations of erastin (0.1–30 μM). MTT assay was performed[3].

[Animal admin]

Mice: Mice are treated daily with 10 or 30 mg/kg body weight of erastin (intraperitoneal injection, for 4 weeks) or vehicle control (Saline). Tumor volumes are calculated. Mice body weights are also recorded every week[3].

[References]

[1]. Dixon SJ, et al. Ferroptosis: an iron-dependent form of nonapoptotic cell death. Cell. 2012 May 25;149(5):1060-72.

[2]. Xie Y, et al. Ferroptosis: process and function. Cell Death Differ. 2016 Mar;23(3):369-79.

[3]. Huo H, et al. Erastin Disrupts Mitochondrial Permeability Transition Pore (mPTP) and Induces Apoptotic Death of Colorectal Cancer Cells. PLoS One. 2016 May 12;11(5):e0154605.

[Related Small Molecules]

Ferrostatin-1 | Liproxstatin-1 | Piperazine Erastin | FIN 56 | CA3(CIL56)

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
721.9±70.0 °C at 760 mmHg

[ Molecular Formula ]:
C₃₀H₃₁ClN₄O₄

[ Molecular Weight ]:
547.044

[ Flash Point ]:
390.4±35.7 °C

[ Exact Mass ]:
546.203369

[ PSA ]:
76.90000

[ LogP ]:
4.75

[ Appearance of Characters ]:
white to beige

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.634

[ Storage condition ]:
−20°C

[ Water Solubility ]:
DMSO: soluble5mg/mL, clear (warmed)

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310 + P330

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T

[ Risk Phrases ]:
25

[ Safety Phrases ]:
45

[ RIDADR ]:
UN 2811 6.1/PG 3

Articles

HSPB1 as a novel regulator of ferroptotic cancer cell death.

Oncogene 34(45) , 5617-25, (2015)

Ferroptosis is an iron-dependent form of non-apoptotic cell death, but its molecular mechanism remains largely unknown. Here, we demonstrate that heat shock protein beta-1 (HSPB1) is a negative regula...

Sensitization of acute lymphoblastic leukemia cells for LCL161-induced cell death by targeting redox homeostasis.

Biochem. Pharmacol. 105 , 14-22, (2016)

Disturbed redox homeostasis with both elevated reactive oxygen species (ROS) levels and antioxidant defense mechanisms has been reported in acute lymphoblastic leukemia (ALL). We therefore hypothesize...

Glutathione peroxidase 4 prevents necroptosis in mouse erythroid precursors.

Blood 127 , 139-48, (2016)

Maintaining cellular redox balance is vital for cell survival and tissue homoeostasis because imbalanced production of reactive oxygen species (ROS) may lead to oxidative stress and cell death. The an...