Erastin

Erastin
Legal status
Legal status	Experimental;
Identifiers
	IUPAC name 2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone;
CAS Number	571203-78-6;
PubChem CID	11214940;
ChemSpider	9390002;
KEGG	C21478;
Chemical and physical data
Formula	C30H31ClN4O4
Molar mass	547.05 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1N(C2=CC=CC=C2OCC)C(C(C)N3CCN(C(COC4=CC=C(Cl)C=C4)=O)CC3)=NC5=CC=CC=C51;
	InChI 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; Key:BKQFRNYHFIQEKN-UHFFFAOYSA-N;

Erastin is a small molecule capable of initiating ferroptotic cell death.[1] Erastin binds and inhibits VDAC2 and VDAC3[2] and functionally inhibits the cystine-glutamate antiporter system Xc-.[3] Cells treated with erastin are deprived of cysteine and are unable to synthesize the antioxidant glutathione. Depletion of glutathione eventually leads to excessive lipid peroxidation and cell death.

References

Dixon SJ, Lemberg KM, Lamprecht MR, Skouta R, Zaitsev EM, Gleason CE, et al. (May 2012). "Ferroptosis: an iron-dependent form of nonapoptotic cell death". Cell. 149 (5): 1060–72. doi:10.1016/j.cell.2012.03.042. PMC 3367386. PMID 22632970.
Yagoda N, von Rechenberg M, Zaganjor E, Bauer AJ, Yang WS, Fridman DJ, et al. (June 2007). "RAS-RAF-MEK-dependent oxidative cell death involving voltage-dependent anion channels". Nature. 447 (7146): 864–8. Bibcode:2007Natur.447..865Y. doi:10.1038/nature05859. PMC 3047570. PMID 17568748.
Dixon SJ, Patel DN, Welsch M, Skouta R, Lee ED, Hayano M, et al. (May 2014). "Pharmacological inhibition of cystine-glutamate exchange induces endoplasmic reticulum stress and ferroptosis". eLife. 3: e02523. doi:10.7554/elife.02523. PMC 4054777. PMID 24844246.

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[1] Dixon SJ, Lemberg KM, Lamprecht MR, Skouta R, Zaitsev EM, Gleason CE, et al. (May 2012). "Ferroptosis: an iron-dependent form of nonapoptotic cell death". Cell. 149 (5): 1060–72. doi:10.1016/j.cell.2012.03.042. PMC 3367386. PMID 22632970.

[2] Yagoda N, von Rechenberg M, Zaganjor E, Bauer AJ, Yang WS, Fridman DJ, et al. (June 2007). "RAS-RAF-MEK-dependent oxidative cell death involving voltage-dependent anion channels". Nature. 447 (7146): 864–8. Bibcode:2007Natur.447..865Y. doi:10.1038/nature05859. PMC 3047570. PMID 17568748.

[3] Dixon SJ, Patel DN, Welsch M, Skouta R, Lee ED, Hayano M, et al. (May 2014). "Pharmacological inhibition of cystine-glutamate exchange induces endoplasmic reticulum stress and ferroptosis". eLife. 3: e02523. doi:10.7554/elife.02523. PMC 4054777. PMID 24844246.