A prodrug inhibitor of GPX4 and an inducer of ferroptosis
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Active Metabolite(s)
30784JKE-1674
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ML-210

Item No. 23282

Technical Information
Formal Name
[4-[bis(4-chlorophenyl)methyl]-1-piperazinyl](5-methyl-4-nitro-3-isoxazolyl)-methanone
CAS Number
1360705-96-9
Synonyms
  • DPI10
Molecular Formula
C22H20Cl2N4O4
Formula Weight
Purity
≥98%
Formulation
A crystalline solid
DMF: 10 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 2.5 mg/mlEthanol: slightly soluble
λmax
232 nm
SMILES
ClC1=CC=C(C(C2=CC=C(Cl)C=C2)N3CCN(C(C4=NOC(C)=C4[N+]([O-])=O)=O)CC3)C=C1
InChi Code
InChI=1S/C22H20Cl2N4O4/c1-14-20(28(30)31)19(25-32-14)22(29)27-12-10-26(11-13-27)21(15-2-6-17(23)7-3-15)16-4-8-18(24)9-5-16/h2-9,21H,10-13H2,1H3
InChi Key
VIBHJPDPEVVDTB-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    ML-210 is a prodrug inhibitor of GPX4 and an inducer of ferroptosis.1 ML-210 forms adducts with GPX4 in cells and inhibits GPX4 enzymatic activity in cell lysates but does not form adducts with recombinant human GPX4 or bind to GPX4 in a lysate-based cellular thermal shift assay (CETSA®) or a pull-down assay, indicating that a cellular transformation is required for its activity.1,2 In cells, ML-210 is converted to an active metabolite, JKE-1674 (Item No. 30784), which is then converted to a second active metabolite, JKE-1777.1 ML-210 (10 µM) induces the accumulation of cellular lipid hydroperoxides in LOX-IMVI human melanoma cells, an effect that can be blocked by the ferroptosis inhibitor ferrostatin-1 (Item No. 17729).1 It also induces ferroptotic cell death in LNCaP and androgen-independent LNCaP (LNCaP-AI) human prostate cancer cells, an effect that can be blocked by the ferroptosis inhibitors ferrostatin-1 or liproxstatin-1 (Item No. 17730).3 ML-210 selectively induces Ras-synthetic lethality in mutant RAS oncogene-expressing cells (IC50s = 71 and 272 nM in HRASG12V-expressing and wild-type RAS-expressing BJeH human fibroblasts, respectively).4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Eaton, J.K., Furst, L., Ruberto, R.A., et alSelective covalent targeting of GPX4 using masked nitrile-oxide electrophiles. Nat. Chem. Biol. 16(5), 497-506 (2020).

    2. Cheff, D.M., Huang, C., Scholzen, K.C., et alThe ferroptosis inducing compounds RSL3 and ML162 are not direct inhibitors of GPX4 but of TXNRD1. Redox Biol. 62, 102703 (2023).

    3. Zhao, R., Lv, Y., Feng, T., et alATF6α promotes prostate cancer progression by enhancing PLA2G4A-mediated arachidonic acid metabolism and protecting tumor cells against ferroptosis. Prostate 82(5), 617-629 (2022).

    4. Weïwer, M., Bittker, J.A., Lewis, T.A., et alDevelopment of small-molecule probes that selectively kill cells induced to express mutant RAS. Bioorg. Med. Chem. Lett. 22(4), 1822-1826 (2012).

    5. Viswanathan, V.S., Ryan, M.J., Dhruv, H.D., et alDependency of a therapy-resistant state of cancer cells on a lipid peroxidase pathway. Nature 547(7664), 453-457 (2017).

    Product Citations

    Nakamura, T., Hipp, C., Mourão, A.S.D., et alPhase separation of FSP1 promotes ferroptosis. Nature 619, 371-377 (2023).

    Xue, Q., Yan, D., Chen, X., et alCopper-dependent autophagic degradation of GPX4 drives ferroptosis. Autophagy (2023).

    ­Wang, F., Graham, E.T., Naowarojna, N., et alPALP: A rapid imaging technique for stratifying ferroptosis sensitivity in normal and tumor tissues in situ. Cell Chem. Bio. 29, 157-170 (2022).

    Mishima, E., Ito, J., Wu, Z., et alA non-canonical vitamin K cycle is a potent ferroptosis suppressor. Nature 608(7924), 778-783 (2022).

    Nagakannan, P., Islam, M.I., Conrad, M., et alCathepsin B is an excutioner of ferroptosis. Biochim. Biophys. Acta Mol. Cell Res. 1868(3), 118928 (2021).

    Wang, W., Green, M., Choi, J.E., et alCD8+ T cells regulate tumour ferroptosis during cancer immunotherapy. Nature 569(7755), 270-274 (2019).