Cucurbitacin I | CAS#2222-07-3

MedKoo Cat#: 525350 | Name: Cucurbitacin I

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Description:

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

Cucurbitacin I is a selective inhibitor of STAT3/JAK2 signaling.

Chemical Structure

Cucurbitacin I

CAS#2222-07-3

Theoretical Analysis

MedKoo Cat#: 525350

Name: Cucurbitacin I

CAS#: 2222-07-3

Chemical Formula: C30H42O7

Exact Mass: 514.2931

Molecular Weight: 514.66

Elemental Analysis: C, 70.01; H, 8.23; O, 21.76

Price and Availability

Size	Price	Availability
1mg	USD 350.00	2 Weeks
5mg	USD 750.00	2 Weeks
10mg	USD 1,250.00	2 Weeks

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Related CAS #

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Synonym

Cucurbitacin I; Elatericin B; JSI-124; JSI 124; JSI124; NSC 521777; NSC-521777; NSC521777;

IUPAC/Chemical Name

(8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione

InChi Key

NISPVUDLMHQFRQ-MKIKIEMVSA-N

InChi Code

InChI=1S/C30H42O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3/b12-11+/t17-,19-,20+,23+,27+,28-,29+,30+/m1/s1

SMILES Code

O=C(C(C)(C)C1=CC[C@@]2([H])[C@]3(C)C[C@@H](O)[C@H]([C@](C(/C=C/C(C)(O)C)=O)(O)C)[C@@]3(C)C4)C(O)=C[C@@]1([H])[C@]2(C)C4=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

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

Instruction

View handling instruction

Biological target:

Cucurbitacin I is a natural selective inhibitor of JAK2/STAT3, with potent anti-cancer activity.

In vitro activity:

JSI-124 (cucurbitacin I) at non-cytotoxic concentration (20 nM) can inhibit the IL-6/STAT3/NF-κB positive feedback loop in breast myofibroblasts, which enabled persistent inactivation of these cells. Interestingly, JSI-124 treatment suppressed the paracrine promotion of the epithelial-to-mesenchymal transition (EMT) process and the pro-migratory/-invasive and -proliferative effects of CAFs on breast cancer cells in vitro. Reference: Mol Carcinog. 2021 Apr;60(4):242-251. https://pubmed.ncbi.nlm.nih.gov/33621387/

In vivo activity:

Fig. 5A shows that, in the absence of cucurbitacin I, the growth of the 143B tumor was highly aggressive, but that treatment with 0.5 or 1.0 mg/kg of cucurbitacin I significantly and dose-dependently inhibited the tumor growth. Furthermore, treatment with 0.5 and 1.0 mg/kg of cucurbitacin I improved overall survival rate, and body weight significantly increased over time (Fig. 5B and C). Reference: Int J Oncol. 2016 Dec; 49(6): 2275–2284. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5117998/

	Solvent	mg/mL	mM
Solubility
	DMSO	36.7	71.35
	Ethanol	10.0	19.43

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 514.66 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. Al-Harbi B, Aboussekhra A. Cucurbitacin I (JSI-124)-dependent inhibition of STAT3 permanently suppresses the pro-carcinogenic effects of active breast cancer-associated fibroblasts. Mol Carcinog. 2021 Apr;60(4):242-251. doi: 10.1002/mc.23287. Epub 2021 Feb 23. PMID: 33621387. 2. Li R, Xiao J, Tang S, Lin X, Xu H, Han B, Yang M, Liu F. Cucurbitacin I induces apoptosis in ovarian cancer cells through oxidative stress and the p190B‑Rac1 signaling axis. Mol Med Rep. 2020 Sep;22(3):2545-2550. doi: 10.3892/mmr.2020.11327. Epub 2020 Jul 10. PMID: 32705204. 3. Oi T, Asanuma K, Matsumine A, Matsubara T, Nakamura T, Iino T, Asanuma Y, Goto M, Okuno K, Kakimoto T, Yada Y, Sudo A. STAT3 inhibitor, cucurbitacin I, is a novel therapeutic agent for osteosarcoma. Int J Oncol. 2016 Dec;49(6):2275-2284. doi: 10.3892/ijo.2016.3757. Epub 2016 Nov 3. PMID: 27840900; PMCID: PMC5117998. 4. Deng C, Zhang B, Zhang S, Duan C, Cao Y, Kang W, Yan H, Ding X, Zhou F, Wu L, Duan G, Shen S, Xu G, Zhang W, Chen M, Huang S, Zhang X, Lv Y, Ling T, Wang L, Zou X. Low nanomolar concentrations of Cucurbitacin-I induces G2/M phase arrest and apoptosis by perturbing redox homeostasis in gastric cancer cells in vitro and in vivo. Cell Death Dis. 2016 Feb 18;7(2):e2106. doi: 10.1038/cddis.2016.13. PMID: 26890145; PMCID: PMC5399186.

In vitro protocol:

In vivo protocol:

1. Oi T, Asanuma K, Matsumine A, Matsubara T, Nakamura T, Iino T, Asanuma Y, Goto M, Okuno K, Kakimoto T, Yada Y, Sudo A. STAT3 inhibitor, cucurbitacin I, is a novel therapeutic agent for osteosarcoma. Int J Oncol. 2016 Dec;49(6):2275-2284. doi: 10.3892/ijo.2016.3757. Epub 2016 Nov 3. PMID: 27840900; PMCID: PMC5117998. 2. Deng C, Zhang B, Zhang S, Duan C, Cao Y, Kang W, Yan H, Ding X, Zhou F, Wu L, Duan G, Shen S, Xu G, Zhang W, Chen M, Huang S, Zhang X, Lv Y, Ling T, Wang L, Zou X. Low nanomolar concentrations of Cucurbitacin-I induces G2/M phase arrest and apoptosis by perturbing redox homeostasis in gastric cancer cells in vitro and in vivo. Cell Death Dis. 2016 Feb 18;7(2):e2106. doi: 10.1038/cddis.2016.13. PMID: 26890145; PMCID: PMC5399186.

1: Kameyama H, Kudoh S, Hatakeyama J, Matuo A, Ito T. Significance of Stat3 Signaling in Epithelial Cell Differentiation of Fetal Mouse Lungs. Acta Histochem Cytochem. 2017 Feb 28;50(1):1-9. doi: 10.1267/ahc.16032. Epub 2017 Feb 23. PubMed PMID: 28386145; PubMed Central PMCID: PMC5374098. 2: Fiori GM, D'Agate S, Rocha A, Pereira AM, Pasqua OD, Lopes NP. Development and validation of a quantification method for cucurbitacins E and I in rat plasma: Application to population pharmacokinetic studies. J Pharm Biomed Anal. 2017 Feb 20. pii: S0731-7085(17)30363-1. doi: 10.1016/j.jpba.2017.02.021. [Epub ahead of print] PubMed PMID: 28274497. 3: Garg SM, Vakili MR, Molavi O, Lavasanifar A. Self-Associating Poly(ethylene oxide)-block-poly(α-carboxyl-ε-caprolactone) Drug Conjugates for the Delivery of STAT3 Inhibitor JSI-124: Potential Application in Cancer Immunotherapy. Mol Pharm. 2017 Mar 9. doi: 10.1021/acs.molpharmaceut.6b01119. [Epub ahead of print] PubMed PMID: 28221800. 4: Wu S, Zhu G, Ni Y, Zhang T, Jiang W. [Cucurbitacin I (JSI-124)-induced apoptosis of HepG2 cells via p53 signaling pathway]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2017 Jan;33(1):33-38. Chinese. PubMed PMID: 28031111. 5: Cui L, Bi J, Yan D, Ye X, Zheng M, Yu G, Wan X. JSI-124 inhibits IgE production in an IgE B cell line. Biochem Biophys Res Commun. 2017 Jan 29;483(1):669-673. doi: 10.1016/j.bbrc.2016.12.085. Epub 2016 Dec 14. PubMed PMID: 27988336. 6: Oi T, Asanuma K, Matsumine A, Matsubara T, Nakamura T, Iino T, Asanuma Y, Goto M, Okuno K, Kakimoto T, Yada Y, Sudo A. STAT3 inhibitor, cucurbitacin I, is a novel therapeutic agent for osteosarcoma. Int J Oncol. 2016 Dec;49(6):2275-2284. doi: 10.3892/ijo.2016.3757. Epub 2016 Nov 3. PubMed PMID: 27840900; PubMed Central PMCID: PMC5117998. 7: Wu Y, Chen H, Li R, Wang X, Li H, Xin J, Liu Z, Wu S, Jiang W, Zhu L. Cucurbitacin-I induces hypertrophy in H9c2 cardiomyoblasts through activation of autophagy via MEK/ERK1/2 signaling pathway. Toxicol Lett. 2016 Dec 15;264:87-98. doi: 10.1016/j.toxlet.2016.11.003. Epub 2016 Nov 9. PubMed PMID: 27836799. 8: Tang Y, Guo Q, Zhi Y, Jin X, Xia B, Guo S, Tian C, Zhang Y. [Role of CXCR4/STAT3 in mesenchymal stromal cell-mediated drug resistance of acute leukemia cells]. Zhonghua Xue Ye Xue Za Zhi. 2016 Feb;37(2):119-23. doi: 10.3760/cma.j.issn.0253-2727.2016.02.007. Chinese. PubMed PMID: 27014981. 9: Pan T, Zhong L, Wu S, Cao Y, Yang Q, Cai Z, Cai X, Zhao W, Ma N, Zhang W, Zhang H, Zhou J. 17β-Oestradiol enhances the expansion and activation of myeloid-derived suppressor cells via signal transducer and activator of transcription (STAT)-3 signalling in human pregnancy. Clin Exp Immunol. 2016 Jul;185(1):86-97. doi: 10.1111/cei.12790. Epub 2016 Apr 13. PubMed PMID: 26969967; PubMed Central PMCID: PMC4908292. 10: Cui Y, Sun S, Ren K, Quan M, Song Z, Zou H, Li D, Cao J. Reversal of liver cancer-associated stellate cell-induced stem-like characteristics in SMMC-7721 cells by 8-bromo-7-methoxychrysin via inhibiting STAT3 activation. Oncol Rep. 2016 May;35(5):2952-62. doi: 10.3892/or.2016.4637. Epub 2016 Feb 26. PubMed PMID: 26935885. 11: Deng C, Zhang B, Zhang S, Duan C, Cao Y, Kang W, Yan H, Ding X, Zhou F, Wu L, Duan G, Shen S, Xu G, Zhang W, Chen M, Huang S, Zhang X, Lv Y, Ling T, Wang L, Zou X. Low nanomolar concentrations of Cucurbitacin-I induces G2/M phase arrest and apoptosis by perturbing redox homeostasis in gastric cancer cells in vitro and in vivo. Cell Death Dis. 2016 Feb 18;7:e2106. doi: 10.1038/cddis.2016.13. PubMed PMID: 26890145; PubMed Central PMCID: PMC5399186. 12: Sari-Hassoun M, Clement MJ, Hamdi I, Bollot G, Bauvais C, Joshi V, Toma F, Burgo A, Cailleret M, Rosales-Hernández MC, Macias Pérez ME, Chabane-Sari D, Curmi PA. Cucurbitacin I elicits the formation of actin/phospho-myosin II co-aggregates by stimulation of the RhoA/ROCK pathway and inhibition of LIM-kinase. Biochem Pharmacol. 2016 Feb 15;102:45-63. doi: 10.1016/j.bcp.2015.12.013. Epub 2015 Dec 18. PubMed PMID: 26707799. 13: Nguyen BC, Taira N, Maruta H, Tawata S. Artepillin C and Other Herbal PAK1-blockers: Effects on Hair Cell Proliferation and Related PAK1-dependent Biological Function in Cell Culture. Phytother Res. 2016 Jan;30(1):120-7. doi: 10.1002/ptr.5510. Epub 2015 Nov 4. PubMed PMID: 26537230. 14: Park SY, Kim YH, Park G. Cucurbitacins attenuate microglial activation and protect from neuroinflammatory injury through Nrf2/ARE activation and STAT/NF-κB inhibition. Neurosci Lett. 2015 Nov 16;609:129-36. doi: 10.1016/j.neulet.2015.10.022. Epub 2015 Oct 22. PubMed PMID: 26472707. 15: Nguyen BC, Be Tu PT, Tawata S, Maruta H. Combination of immunoprecipitation (IP)-ATP_Glo kinase assay and melanogenesis for the assessment of potent and safe PAK1-blockers in cell culture. Drug Discov Ther. 2015 Aug;9(4):289-95. doi: 10.5582/ddt.2015.01041. PubMed PMID: 26370527. 16: Jeong MH, Kim SJ, Kang H, Park KW, Park WJ, Yang SY, Yang DK. Cucurbitacin I Attenuates Cardiomyocyte Hypertrophy via Inhibition of Connective Tissue Growth Factor (CCN2) and TGF- β/Smads Signalings. PLoS One. 2015 Aug 21;10(8):e0136236. doi: 10.1371/journal.pone.0136236. eCollection 2015. PubMed PMID: 26296085; PubMed Central PMCID: PMC4546681. 17: Hira SK, Mondal I, Bhattacharya D, Gupta KK, Manna PP. Downregulation of STAT3 phosphorylation enhances tumoricidal effect of IL-15-activated dendritic cell against doxorubicin-resistant lymphoma and leukemia via TNF-α. Int J Biochem Cell Biol. 2015 Oct;67:1-13. doi: 10.1016/j.biocel.2015.08.002. Epub 2015 Aug 5. PubMed PMID: 26255115. 18: Zhang CH, Guo FL, Xu GL, Jia WD, Ge YS. STAT3 activation mediates epithelial-to-mesenchymal transition in human hepatocellular carcinoma cells. Hepatogastroenterology. 2014 Jun;61(132):1082-9. PubMed PMID: 26158169. 19: Sun J, Xia F, Wang S, Wang KY, Chen JM, Tu PF. Structural elucidation of two new megastigmane glycosides from the leaves of Aquilaria sinensis. Chin J Nat Med. 2015 Apr;13(4):290-4. doi: 10.1016/S1875-5364(15)30016-9. PubMed PMID: 25908626. 20: Yuan G, Yan S, Xue H, Zhang P, Sun J, Li G. JSI-124 suppresses invasion and angiogenesis of glioblastoma cells in vitro. PLoS One. 2015 Mar 19;10(3):e0118894. doi: 10.1371/journal.pone.0118894. eCollection 2015. PubMed PMID: 25789853; PubMed Central PMCID: PMC4366361.