Erastin | CAS#571203-78-6 | antitumor

MedKoo Cat#: 406290 | Name: Erastin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Erastin is an antitumor agent selective for tumor cells bearing oncogenic RAS (i.e. HRAS, KRAS). Erastin produces 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. Erastin blocks and reverses mitochondrial depolarization after microtubule destabilizers in intact cells and antagonized tubulin-induced VDAC blockage in planar bilayers. Reversal of tubulin-VDAC interaction by erastin antagonizes Warburg metabolism and restores oxidative mitochondrial metabolism.

Chemical Structure

Erastin

CAS#571203-78-6

Theoretical Analysis

MedKoo Cat#: 406290

Name: Erastin

CAS#: 571203-78-6

Chemical Formula: C30H31ClN4O4

Exact Mass: 546.2034

Molecular Weight: 547.04

Elemental Analysis: C, 65.87; H, 5.71; Cl, 6.48; N, 10.24; O, 11.70

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,350.00	Ready to ship
500mg	USD 2,850.00	Ready to ship
1g	USD 3,850.00	Ready to ship
2g	USD 6,450.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Erastin

IUPAC/Chemical Name

2-(1-(4-(2-(4-chlorophenoxy)acetyl)piperazin-1-yl)ethyl)-3-(2-ethoxyphenyl)quinazolin-4(3H)-one

InChi Key

BKQFRNYHFIQEKN-UHFFFAOYSA-N

InChi Code

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

SMILES Code

O=C1N(C2=CC=CC=C2OCC)C(C(N3CCN(C(COC4=CC=C(Cl)C=C4)=O)CC3)C)=NC5=C1C=CC=C5

Appearance

white solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#BBC40420

QC Data

View QC data: current batch, Lot#BBC40420

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Erastin is a ferroptosis inducer which binds and inhibits voltage-dependent anion channels (VDAC2/VDAC3).

In vitro activity:

The radiosensitizing effects of erastin on HeLa and NCI-H1975 cells were evaluated (Fig 3). The treatment with a combination of erastin and X-ray irradiation significantly decreased the survival of both the cancer cell lines (two-way ANOVA, p < 0.0001 for treatment with erastin and p < 0.0001 for X-ray irradiation in both the HeLa and NCI-H1975 cells) (Fig 3). The 10% lethal doses (D10) for the X-irradiated HeLa cells with and without treatment with erastin were 10.24 and 8.10 Gy, respectively (sensitizer enhancement ratio [SER] = 1.27). Similarly, the D10 values for the X-irradiated NCI-H1975 cells with and without treatment with erastin were 6.11 and 4.42 Gy, respectively (SER = 1.38). Reference: PLoS One. 2019 Dec 4;14(12):e0225931. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6892486/

In vivo activity:

For in vivo studies, NCI-H1975 cells were transplanted in the left shoulder of nude mice, and then radiosensitizing effect of erastin and glutathione concentration in the cancer were evaluated. The group administered with both erastin treatment and radiotherapy showed significant tumor growth suppression, while the group administered with erastin or radiotherapy alone showed no tumor growth suppression (Fig 4A). The values of tumor volume (mean ± S.E) at 14 days after irradiation were 1753.84 ± 288.67 mm3 for Control, 1738.52 ± 309.95 mm3 for X-ray alone, 1719.07 ± 203.13 mm3 for erastin alone, and 1079.89 ± 227.84 mm3 for erastin + X-ray. Furthermore, a glutathione quantification assay revealed that the intratumoral glutathione concentrations in erastin-treated tumors were significantly lower than those in nontreated tumors (Fig 4B). Reference: PLoS One. 2019 Dec 4;14(12):e0225931. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6892486/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	18.28
	DMSO	14.9	27.16
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.46
	Water	0.5	0.91

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 547.04 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Shibata Y, Yasui H, Higashikawa K, Miyamoto N, Kuge Y. Erastin, a ferroptosis-inducing agent, sensitized cancer cells to X-ray irradiation via glutathione starvation in vitro and in vivo. PLoS One. 2019 Dec 4;14(12):e0225931. doi: 10.1371/journal.pone.0225931. PMID: 31800616; PMCID: PMC6892486. 2. Oh BM, Lee SJ, Park GL, Hwang YS, Lim J, Park ES, Lee KH, Kim BY, Kwon YT, Cho HJ, Lee HG. Erastin Inhibits Septic Shock and Inflammatory Gene Expression via Suppression of the NF-κB Pathway. J Clin Med. 2019 Dec 14;8(12):2210. doi: 10.3390/jcm8122210. PMID: 31847346; PMCID: PMC6947339.

In vitro protocol:

In vivo protocol:

1: Yang Y, Luo M, Zhang K, Zhang J, Gao T, Connell DO, Yao F, Mu C, Cai B, Shang Y, Chen W. Nedd4 ubiquitylates VDAC2/3 to suppress erastin-induced ferroptosis in melanoma. Nat Commun. 2020 Jan 23;11(1):433. doi: 10.1038/s41467-020-14324-x. PMID: 31974380; PMCID: PMC6978386. 2: Wang L, Liu Y, Du T, Yang H, Lei L, Guo M, Ding HF, Zhang J, Wang H, Chen X, Yan C. ATF3 promotes erastin-induced ferroptosis by suppressing system Xc. Cell Death Differ. 2020 Feb;27(2):662-675. doi: 10.1038/s41418-019-0380-z. Epub 2019 Jul 4. PMID: 31273299; PMCID: PMC7206049. 3: Zhao Y, Li Y, Zhang R, Wang F, Wang T, Jiao Y. The Role of Erastin in Ferroptosis and Its Prospects in Cancer Therapy. Onco Targets Ther. 2020 Jun 11;13:5429-5441. doi: 10.2147/OTT.S254995. PMID: 32606760; PMCID: PMC7295539. 4: Li Y, Zeng X, Lu D, Yin M, Shan M, Gao Y. Erastin induces ferroptosis via ferroportin-mediated iron accumulation in endometriosis. Hum Reprod. 2021 Mar 18;36(4):951-964. doi: 10.1093/humrep/deaa363. PMID: 33378529. 5: Zhang Y, Tan H, Daniels JD, Zandkarimi F, Liu H, Brown LM, Uchida K, O'Connor OA, Stockwell BR. Imidazole Ketone Erastin Induces Ferroptosis and Slows Tumor Growth in a Mouse Lymphoma Model. Cell Chem Biol. 2019 May 16;26(5):623-633.e9. doi: 10.1016/j.chembiol.2019.01.008. Epub 2019 Feb 21. PMID: 30799221; PMCID: PMC6525071. 6: Yu M, Gai C, Li Z, Ding D, Zheng J, Zhang W, Lv S, Li W. Targeted exosome- encapsulated erastin induced ferroptosis in triple negative breast cancer cells. Cancer Sci. 2019 Oct;110(10):3173-3182. doi: 10.1111/cas.14181. Epub 2019 Oct 3. PMID: 31464035; PMCID: PMC6778638. 7: Liu M, Fan Y, Li D, Han B, Meng Y, Chen F, Liu T, Song Z, Han Y, Huang L, Chang Y, Cao P, Nakai A, Tan K. Ferroptosis inducer erastin sensitizes NSCLC cells to celastrol through activation of the ROS-mitochondrial fission-mitophagy axis. Mol Oncol. 2021 Aug;15(8):2084-2105. doi: 10.1002/1878-0261.12936. Epub 2021 Mar 17. PMID: 33675143; PMCID: PMC8334255. 8: Dixon SJ, Lemberg KM, Lamprecht MR, Skouta R, Zaitsev EM, Gleason CE, Patel DN, Bauer AJ, Cantley AM, Yang WS, Morrison B 3rd, Stockwell BR. Ferroptosis: an iron-dependent form of nonapoptotic cell death. Cell. 2012 May 25;149(5):1060-72. doi: 10.1016/j.cell.2012.03.042. PMID: 22632970; PMCID: PMC3367386. 9: Zhou HH, Chen X, Cai LY, Nan XW, Chen JH, Chen XX, Yang Y, Xing ZH, Wei MN, Li Y, Wang ST, Liu K, Shi Z, Yan XJ. Erastin Reverses ABCB1-Mediated Docetaxel Resistance in Ovarian Cancer. Front Oncol. 2019 Dec 19;9:1398. doi: 10.3389/fonc.2019.01398. PMID: 31921655; PMCID: PMC6930896. 10: Liang Z, Wu Q, Wang H, Tan J, Wang H, Gou Y, Cao Y, Li Z, Zhang Z. Silencing of lncRNA MALAT1 facilitates erastin-induced ferroptosis in endometriosis through miR-145-5p/MUC1 signaling. Cell Death Discov. 2022 Apr 11;8(1):190. doi: 10.1038/s41420-022-00975-w. PMID: 35399101; PMCID: PMC8995383. 11: Bao Z, Hua L, Ye Y, Wang D, Li C, Xie Q, Wakimoto H, Gong Y, Ji J. MEF2C silencing downregulates NF2 and E-cadherin and enhances Erastin-induced ferroptosis in meningioma. Neuro Oncol. 2021 Dec 1;23(12):2014-2027. doi: 10.1093/neuonc/noab114. PMID: 33984142; PMCID: PMC8643460. 12: Liu Y, Huang P, Li Z, Xu C, Wang H, Jia B, Gong A, Xu M. Vitamin C Sensitizes Pancreatic Cancer Cells to Erastin-Induced Ferroptosis by Activating the AMPK/Nrf2/HMOX1 Pathway. Oxid Med Cell Longev. 2022 Jul 19;2022:5361241. doi: 10.1155/2022/5361241. PMID: 35915609; PMCID: PMC9338737. 13: Yan R, Xie E, Li Y, Li J, Zhang Y, Chi X, Hu X, Xu L, Hou T, Stockwell BR, Min J, Zhou Q, Wang F. The structure of erastin-bound xCT-4F2hc complex reveals molecular mechanisms underlying erastin-induced ferroptosis. Cell Res. 2022 Jul;32(7):687-690. doi: 10.1038/s41422-022-00642-w. Epub 2022 Mar 29. PMID: 35352032; PMCID: PMC9253326. 14: Ye F, Chai W, Xie M, Yang M, Yu Y, Cao L, Yang L. HMGB1 regulates erastin- induced ferroptosis via RAS-JNK/p38 signaling in HL-60/NRASQ61L cells. Am J Cancer Res. 2019 Apr 1;9(4):730-739. PMID: 31105999; PMCID: PMC6511643. 15: Chen X, Kang R, Kroemer G, Tang D. Broadening horizons: the role of ferroptosis in cancer. Nat Rev Clin Oncol. 2021 May;18(5):280-296. doi: 10.1038/s41571-020-00462-0. Epub 2021 Jan 29. PMID: 33514910. 16: Bai YT, Chang R, Wang H, Xiao FJ, Ge RL, Wang LS. ENPP2 protects cardiomyocytes from erastin-induced ferroptosis. Biochem Biophys Res Commun. 2018 Apr 30;499(1):44-51. doi: 10.1016/j.bbrc.2018.03.113. Epub 2018 Mar 20. PMID: 29551679. 17: Xu C, Ni S, Xu N, Yin G, Yu Y, Zhou B, Zhao G, Wang L, Zhu R, Jiang S, Wang Y. Theaflavin-3,3'-Digallate Inhibits Erastin-Induced Chondrocytes Ferroptosis via the Nrf2/GPX4 Signaling Pathway in Osteoarthritis. Oxid Med Cell Longev. 2022 Nov 17;2022:3531995. doi: 10.1155/2022/3531995. PMID: 36439689; PMCID: PMC9691334. 18: Chen C, Xie B, Li Z, Chen L, Chen Y, Zhou J, Ju S, Zhou Y, Zhang X, Zhuo W, Yang J, Mao M, Xu L, Wang L. Fascin enhances the vulnerability of breast cancer to erastin-induced ferroptosis. Cell Death Dis. 2022 Feb 14;13(2):150. doi: 10.1038/s41419-022-04579-1. PMID: 35165254; PMCID: PMC8844358. 19: Lee H, Zandkarimi F, Zhang Y, Meena JK, Kim J, Zhuang L, Tyagi S, Ma L, Westbrook TF, Steinberg GR, Nakada D, Stockwell BR, Gan B. Energy-stress- mediated AMPK activation inhibits ferroptosis. Nat Cell Biol. 2020 Feb;22(2):225-234. doi: 10.1038/s41556-020-0461-8. Epub 2020 Feb 6. PMID: 32029897; PMCID: PMC7008777. 20: Shintoku R, Takigawa Y, Yamada K, Kubota C, Yoshimoto Y, Takeuchi T, Koshiishi I, Torii S. Lipoxygenase-mediated generation of lipid peroxides enhances ferroptosis induced by erastin and RSL3. Cancer Sci. 2017 Nov;108(11):2187-2194. doi: 10.1111/cas.13380. Epub 2017 Sep 15. PMID: 28837253; PMCID: PMC5666033.