Elesclomol
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MedKoo CAT#: 201210

CAS#: 488832-69-5 (free base)

Description: Elesclomol, also known as STA-4783, is a HSP-90 Inhibitor, and is a small-molecule bis(thio-hydrazide amide) with oxidative stress induction, pro-apoptotic, and potential antineoplastic activities. Elesclomol induces oxidative stress, creating high levels of reactive oxygen species (ROS), such as hydrogen peroxide, in both cancer cells and normal cells. Because tumor cells have elevated levels of ROS compared to normal cells, the increase in oxidative stress beyond baseline levels elevates ROS beyond sustainable levels, exhausting tumor cell antioxidant capacity, which may result in the induction of the mitochondrial apoptosis pathway.

Chemical Structure

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Elesclomol
CAS# 488832-69-5 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 201210
Name: Elesclomol
CAS#: 488832-69-5 (free base)
Chemical Formula: C19H20N4O2S2
Exact Mass: 400.10
Molecular Weight: 400.520
Elemental Analysis: C, 56.98; H, 5.03; N, 13.99; O, 7.99; S, 16.01

Price and Availability

Size Price Availability Quantity
10mg USD 90 Ready to ship
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 450 Ready to ship
200mg USD 750 Ready to ship
500mg USD 1650 Ready to ship
1g USD 2950 Ready to ship
2g USD 5250 Ready to ship
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Related CAS #: 488832-69-5 (free base)   874477-51-7 (disodium)  

Synonym: STA4783; STA-4783; STA 4783, Elesclomol.

IUPAC/Chemical Name: N'1,N'3-dimethyl-N'1,N'3-di(phenylcarbonothioyl)malonohydrazide

InChi Key: BKJIXTWSNXCKJH-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(NN(C)C(C1=CC=CC=C1)=S)CC(NN(C)C(C2=CC=CC=C2)=S)=O

Appearance: 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: >5 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:

Biological target: Elesclomol (STA-4783) is a novel potent oxidative stress inducer that elicits pro-apoptosis events among tumor cells.
In vitro activity: Treatment of cancer cells in vitro with elesclomol resulted in the rapid generation of reactive oxygen species (ROS) and the induction of a transcriptional gene profile characteristic of an oxidative stress response. Inhibition of oxidative stress by the antioxidant N-acetylcysteine blocked the induction of gene transcription by elesclomol. In addition, N-acetylcysteine blocked drug-induced apoptosis, indicating that ROS generation is the primary mechanism responsible for the proapoptotic activity of elesclomol. Excessive ROS production and elevated levels of oxidative stress are critical biochemical alterations that contribute to cancer cell growth. Thus, the induction of oxidative stress by elesclomol exploits this unique characteristic of cancer cells by increasing ROS levels beyond a threshold that triggers cell death. Reference: Mol Cancer Ther. 2008 Aug;7(8):2319-27. http://mct.aacrjournals.org/cgi/pmidlookup?view=long&pmid=18723479
In vivo activity: To investigate the impact of elesclomol on HS formation, the rabbit ear HS model was established. We created 6 full-thickness circular wounds on the ventral surface of each ear (Fig. 4A). The wounds were observed on days 5 to 7, and scar hyperplasia peaked after approximately 21 days. As shown in Fig. 4C, the wound areas on the rabbit ears in the no-treatment and vehicle groups consisted of prominent skin tissue with a tough texture, light red bulges, and hard areas. In contrast, the wound areas in the elesclomol group (0.2 mg elesclomol per wound area) appeared flatter and softer with a near-normal color. HE-stained sections of rabbit ear tissue collected 35 days after wounding showed numerous fibroblasts in the blank control and vehicle groups, along with abundant fibroblast proliferation and coarsely arranged collagen fibers (Fig. 4D). In contrast, the tissues from the elesclomol group were flatter and had a significantly smaller cross-sectional wound area. These findings were consistent with the overall wound appearance (Fig. 4C). In addition, Masson's trichrome staining was performed, which stained the collagen fibers blue, and the cells interspersed between the collagen fibers light gray. Masson stained images showed that, in the elesclomol group, the collagen fibers were arranged regularly and loosely, while in the blank-control and vehicle groups, the fibers were disordered, dense, and even formed spiral-like tangles (Fig. 4E). Analysis of the Masson-stained images showed that elesclomol treatment reduced the SEI (Fig. 4F), which is considered to be the most objective criterion for assessing scar formation. Reference: EBioMedicine. 2020 Apr;54:102715. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/32251998/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 20.0 49.90

Preparing Stock Solutions

The following data is based on the product molecular weight 400.52 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.

Recalculate based on batch purity %
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:
In vitro protocol: 1. Feng Y, Wu JJ, Sun ZL, Liu SY, Zou ML, Yuan ZD, Yu S, Lv GZ, Yuan FL. Targeted apoptosis of myofibroblasts by elesclomol inhibits hypertrophic scar formation. EBioMedicine. 2020 Apr;54:102715. doi: 10.1016/j.ebiom.2020.102715. Epub 2020 Apr 3. PMID: 32251998; PMCID: PMC7132150. 2. Guthrie LM, Soma S, Yuan S, Silva A, Zulkifli M, Snavely TC, Greene HF, Nunez E, Lynch B, De Ville C, Shanbhag V, Lopez FR, Acharya A, Petris MJ, Kim BE, Gohil VM, Sacchettini JC. 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. PMID: 32381719; PMCID: PMC7304446.
In vivo protocol: 1. Feng Y, Wu JJ, Sun ZL, Liu SY, Zou ML, Yuan ZD, Yu S, Lv GZ, Yuan FL. Targeted apoptosis of myofibroblasts by elesclomol inhibits hypertrophic scar formation. EBioMedicine. 2020 Apr;54:102715. doi: 10.1016/j.ebiom.2020.102715. Epub 2020 Apr 3. PMID: 32251998; PMCID: PMC7132150. 2. Guthrie LM, Soma S, Yuan S, Silva A, Zulkifli M, Snavely TC, Greene HF, Nunez E, Lynch B, De Ville C, Shanbhag V, Lopez FR, Acharya A, Petris MJ, Kim BE, Gohil VM, Sacchettini JC. 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. PMID: 32381719; PMCID: PMC7304446.

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1: Zheng P, Zhou C, Lu L, Liu B, Ding Y. Elesclomol: a copper ionophore targeting mitochondrial metabolism for cancer therapy. J Exp Clin Cancer Res. 2022 Sep 12;41(1):271. doi: 10.1186/s13046-022-02485-0. PMID: 36089608; PMCID: PMC9465867.


2: Gao W, Huang Z, Duan J, Nice EC, Lin J, Huang C. Elesclomol induces copper- dependent ferroptosis in colorectal cancer cells via degradation of ATP7A. Mol Oncol. 2021 Dec;15(12):3527-3544. doi: 10.1002/1878-0261.13079. Epub 2021 Sep 15. PMID: 34390123; PMCID: PMC8637554.


3: Li Y, Yang J, Zhang Q, Xu S, Sun W, Ge S, Xu X, Jager MJ, Jia R, Zhang J, Fan X. Copper ionophore elesclomol selectively targets GNAQ/11-mutant uveal melanoma. Oncogene. 2022 Jul;41(27):3539-3553. doi: 10.1038/s41388-022-02364-0. Epub 2022 Jun 13. PMID: 35697803.


4: Tsvetkov P, Coy S, Petrova B, Dreishpoon M, Verma A, Abdusamad M, Rossen J, Joesch-Cohen L, Humeidi R, Spangler RD, Eaton JK, Frenkel E, Kocak M, Corsello SM, Lutsenko S, Kanarek N, Santagata S, Golub TR. Copper induces cell death by targeting lipoylated TCA cycle proteins. Science. 2022 Mar 18;375(6586):1254-1261. doi: 10.1126/science.abf0529. Epub 2022 Mar 17. Erratum in: Science. 2022 Apr 22;376(6591):eabq4855. PMID: 35298263; PMCID: PMC9273333.


5: Guthrie LM, Soma S, Yuan S, Silva A, Zulkifli M, Snavely TC, Greene HF, Nunez E, Lynch B, De Ville C, Shanbhag V, Lopez FR, Acharya A, Petris MJ, Kim BE, Gohil VM, Sacchettini JC. 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. PMID: 32381719; PMCID: PMC7304446.


6: Guo B, Yang F, Zhang L, Zhao Q, Wang W, Yin L, Chen D, Wang M, Han S, Xiao H, Xing N. Cuproptosis Induced by ROS Responsive Nanoparticles with Elesclomol and Copper Combined with αPD-L1 for Enhanced Cancer Immunotherapy. Adv Mater. 2023 Jun;35(22):e2212267. doi: 10.1002/adma.202212267. Epub 2023 Apr 2. PMID: 36916030.


7: Buccarelli M, D'Alessandris QG, Matarrese P, Mollinari C, Signore M, Cappannini A, Martini M, D'Aliberti P, De Luca G, Pedini F, Boe A, Biffoni M, Pallini R, Ricci-Vitiani L. Elesclomol-induced increase of mitochondrial reactive oxygen species impairs glioblastoma stem-like cell survival and tumor growth. J Exp Clin Cancer Res. 2021 Jul 12;40(1):228. doi: 10.1186/s13046-021-02031-4. PMID: 34253243; PMCID: PMC8273992.


8: Tsvetkov P, Detappe A, Cai K, Keys HR, Brune Z, Ying W, Thiru P, Reidy M, Kugener G, Rossen J, Kocak M, Kory N, Tsherniak A, Santagata S, Whitesell L, Ghobrial IM, Markley JL, Lindquist S, Golub TR. Mitochondrial metabolism promotes adaptation to proteotoxic stress. Nat Chem Biol. 2019 Jul;15(7):681-689. doi: 10.1038/s41589-019-0291-9. Epub 2019 May 27. Erratum in: Nat Chem Biol. 2019 Jun 4;: PMID: 31133756; PMCID: PMC8183600.


9: Gao J, Wu X, Huang S, Zhao Z, He W, Song M. Novel insights into anticancer mechanisms of elesclomol: More than a prooxidant drug. Redox Biol. 2023 Sep 17;67:102891. doi: 10.1016/j.redox.2023.102891. Epub ahead of print. PMID: 37734229; PMCID: PMC10518591.


10: Huo S, Wang Q, Shi W, Peng L, Jiang Y, Zhu M, Guo J, Peng D, Wang M, Men L, Huang B, Lv J, Lin L. ATF3/SPI1/SLC31A1 Signaling Promotes Cuproptosis Induced by Advanced Glycosylation End Products in Diabetic Myocardial Injury. Int J Mol Sci. 2023 Jan 14;24(2):1667. doi: 10.3390/ijms24021667. PMID: 36675183; PMCID: PMC9862315.


11: Zulkifli M, Spelbring AN, Zhang Y, Soma S, Chen S, Li L, Le T, Shanbhag V, Petris MJ, Chen TY, Ralle M, Barondeau DP, Gohil VM. FDX1-dependent and independent mechanisms of elesclomol-mediated intracellular copper delivery. Proc Natl Acad Sci U S A. 2023 Mar 7;120(10):e2216722120. doi: 10.1073/pnas.2216722120. Epub 2023 Feb 27. PMID: 36848556; PMCID: PMC10013847.


12: Yang W, Wang Y, Huang Y, Yu J, Wang T, Li C, Yang L, Zhang P, Shi L, Yin Y, Tao K, Li R. 4-Octyl itaconate inhibits aerobic glycolysis by targeting GAPDH to promote cuproptosis in colorectal cancer. Biomed Pharmacother. 2023 Mar;159:114301. doi: 10.1016/j.biopha.2023.114301. Epub 2023 Jan 25. PMID: 36706634.


13: Zheng H, Liu H, Li H, Dou W, Wang J, Zhang J, Liu T, Wu Y, Liu Y, Wang X. Characterization of stem cell landscape and identification of stemness-relevant prognostic gene signature to aid immunotherapy in colorectal cancer. Stem Cell Res Ther. 2022 Jun 9;13(1):244. doi: 10.1186/s13287-022-02913-0. PMID: 35681225; PMCID: PMC9185878.


14: Gohil VM. Repurposing elesclomol, an investigational drug for the treatment of copper metabolism disorders. Expert Opin Investig Drugs. 2021 Jan;30(1):1-4. doi: 10.1080/13543784.2021.1840550. Epub 2020 Nov 5. PMID: 33081534; PMCID: PMC7855837.


15: Feng Y, Wu JJ, Sun ZL, Liu SY, Zou ML, Yuan ZD, Yu S, Lv GZ, Yuan FL. Targeted apoptosis of myofibroblasts by elesclomol inhibits hypertrophic scar formation. EBioMedicine. 2020 Apr;54:102715. doi: 10.1016/j.ebiom.2020.102715. Epub 2020 Apr 3. PMID: 32251998; PMCID: PMC7132150.


16: Yuan S, Korolnek T, Kim BE. Oral Elesclomol Treatment Alleviates Copper Deficiency in Animal Models. Front Cell Dev Biol. 2022 Apr 1;10:856300. doi: 10.3389/fcell.2022.856300. PMID: 35433682; PMCID: PMC9010564.


17: Garza NM, Swaminathan AB, Maremanda KP, Zulkifli M, Gohil VM. Mitochondrial copper in human genetic disorders. Trends Endocrinol Metab. 2023 Jan;34(1):21-33. doi: 10.1016/j.tem.2022.11.001. Epub 2022 Nov 23. PMID: 36435678; PMCID: PMC9780195.


18: Schulz V, Basu S, Freibert SA, Webert H, Boss L, Mühlenhoff U, Pierrel F, Essen LO, Warui DM, Booker SJ, Stehling O, Lill R. Functional spectrum and specificity of mitochondrial ferredoxins FDX1 and FDX2. Nat Chem Biol. 2023 Feb;19(2):206-217. doi: 10.1038/s41589-022-01159-4. Epub 2022 Oct 24. PMID: 36280795.


19: Qu Y, Wang J, Sim MS, Liu B, Giuliano A, Barsoum J, Cui X. Elesclomol, counteracted by Akt survival signaling, enhances the apoptotic effect of chemotherapy drugs in breast cancer cells. Breast Cancer Res Treat. 2010 Jun;121(2):311-21. doi: 10.1007/s10549-009-0470-6. Epub 2009 Jul 16. PMID: 19609669.


20: Kirshner JR, He S, Balasubramanyam V, Kepros J, Yang CY, Zhang M, Du Z, Barsoum J, Bertin J. 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. PMID: 18723479.