Erastin

Last updated
Erastin
Erastin Structure.svg
Legal status
Legal status
  • Experimental
Identifiers
  • 2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
Formula C30H31ClN4O4
Molar mass 547.05 g·mol−1
3D model (JSmol)
  • O=C1N(C2=CC=CC=C2OCC)C(C(C)N3CCN(C(COC4=CC=C(Cl)C=C4)=O)CC3)=NC5=CC=CC=C51
  • 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 activates voltage-dependent anion channels (VDAC) by reversing tubulin's inhibition on VDAC2 and VDAC3, [2] and functionally inhibits the cystine-glutamate antiporter enzyme SLC7A11 [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.

Erastin was first described in 2003. Its name is short for "eradicator of RAS and ST-expressing cells". [4]

References

  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): 1060–1072. 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): 864–868. 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.
  4. ↑ Dolma S, Lessnick SL, Hahn WC, Stockwell BR (March 2003). "Identification of genotype-selective antitumor agents using synthetic lethal chemical screening in engineered human tumor cells". Cancer Cell. 3 (3): 285–296. doi: 10.1016/S1535-6108(03)00050-3 . PMID   12676586.
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