Elesclomol Chemical Properties

Density 

1.313

storage temp. 

Store at -20°C

solubility 

insoluble in H2O; ≥20.15 mg/mL in DMSO; ≥5.68 mg/mL in EtOH with gentle warming and ultrasonic

form 

solid

pka

7.99±0.70(Predicted)

color 

Light yellow to yellow

InChI

InChI=1S/C19H20N4O2S2/c1-22(18(26)14-9-5-3-6-10-14)20-16(24)13-17(25)21-23(2)19(27)15-11-7-4-8-12-15/h3-12H,13H2,1-2H3,(H,20,24)(H,21,25)

InChIKey

BKJIXTWSNXCKJH-UHFFFAOYSA-N

SMILES

C1=CC(C(=S)N(C)NC(=O)CC(=O)NN(C)C(=S)C2C=CC=CC=2)=CC=C1

Elesclomol Usage And Synthesis

Uses

Elesclomol (STA-4783) is a potent copper ionophore and promotes copper-dependent cell death (cuproptosis). Elesclomol specifically binds ferredoxin 1 (FDX1) α2/α3 helices and β5 strand. Elesclomol inhibits FDX1-mediated Fe-S cluster biosynthesis. Elesclomol is an oxidative stress inducer that induces cancer cell apoptosis. Elesclomol is a reactive oxygen species (ROS) inducer. Elesclomol can be used for Menkes and associated disorders of hereditary copper deficiency research[1][2][3][4].

Definition

ChEBI: A carbohydrazide obtained by formal condensation of the carboxy groups of malonic acid with the hydrino groups of two molar equivalents of N-methylbenzenecarbothiohydrazide

Biological Activity

elesclomol (also known as sta-4783), originally identified in a cell-based phenotypic screen for proapoptotic activity, is a novel small-molecule that potently induces apoptosis of cancer cells through the rapid generation of reactive oxygen species (ros) and the induction of unmanageable levels of oxidative stress. elesclomol exhibits autitumor activity against a broad spectrum of types of cancer cell in human tumor xengograft models due to its excessive ros production and elevated levels of oxidative stress leading to the death of cancer cells. elesclomol is currently being studies as a novel cancer therapeutic, in which it has demonstrated ability to prolong progression-free survival in study subjects.ronald k. blackman, kahlin cheung-ong, marinella gebbia, david a. proia, suqin he, jane kepros, aurelie jonneaux, philippe marchetti, jerome kluza, patricia e. rao, yumiko wada, guri giaever, corey nislow. mitochondrial electron transport is the cellular target of the oncology drug elesclomol. plos one 2012; 7(1): e29798jessica r. kirshner, suqin he, vishwasenani balasubramanyam, jane kepros, chin-yu yang, mei zhang, zhenjian du, james barsoum, and john bertin. elesclomol induces cancer cell apoptosis through oxidative stress. mol cancer ther 2008; 7:2319-2327

in vivo

target

HSP70

References

[1] Peter Tsvetkov, et al. Copper induces cell death by targeting lipoylated TCA cycle proteins. Science. 2022 Mar 18;375(6586):1254-1261. DOI:10.1126/science.abf0529
[2] Peter Tsvetkov, et al. Mitochondrial metabolism promotes adaptation to proteotoxic stress. Nat Chem Biol. 2019 Jul;15(7):681-689. DOI:10.1038/s41589-019-0291-9
[3] Kirshner JR, et al. Elesclomol induces cancer cell apoptosis through oxidative stress. Mol Cancer Ther. 2008 Aug;7(8):2319-27. DOI:10.1158/1535-7163.MCT-08-0298
[4] Liam M Guthrie, et al. Elesclomol alleviates Menkes pathology and mortality by escorting Cu to cuproenzymes in mice. Science. 2020 May 8;368(6491):620-625. DOI:10.1126/science.aaz8899
[5] Bair JS, et al. Chemistry and biology of deoxynyboquinone, a potent inducer of cancer cell death. J Am Chem Soc. 2010 Apr 21;132(15):5469-7 DOI:10.1021/ja100610m

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