CAS 2222-07-3|Cucurbitacin I

Introduction：Basic information about CAS 2222-07-3|Cucurbitacin I, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Cucurbitacin I BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Synonyms

Common Name	Cucurbitacin I
CAS Number	2222-07-3	Molecular Weight	514.650
Density	1.3±0.1 g/cm3	Boiling Point	716.9±60.0 °C at 760 mmHg
Molecular Formula	C₃₀H₄₂O₇	Melting Point	148-150ºC
MSDS	Chinese	Flash Point	401.3±29.4 °C

Names

Name	cucurbitacin I
Synonym	More Synonyms

Cucurbitacin I BiologicalActivity

Description	Cucurbitacin I is a natural selective inhibitor of JAK2/STAT3, with potent anti-cancer activity.
Related Catalog	Signaling Pathways >>JAK/STAT Signaling >>STATSignaling Pathways >>Stem Cell/Wnt >>STATResearch Areas >>CancerNatural Products >>Terpenoids and Glycosides
Target	JAK2 STAT3
In Vitro	Exposure of the COLO205 cells to Cucurbitacin I significantly decreases cell viability. The anticancer activity of Cucurbitacin I is accomplished by downregulating p-STAT3 and MMP-9 expression[1]. PE-induced cell enlargement and upregulation of ANF and β-MHC are significantly suppressed by pretreatment of the cardiomyocytes with Cucurbitacin I. Notably, Cucurbitacin I also impaires connective tissue growth factor (CTGF) and MAPK signaling, pro-hypertrophic factors, as well as TGF-β/Smad signaling, the important contributing factors to fibrosis[2]. Incubation of the Seax cell line with the Jak/Stat3 inhibitor Cucurbitacin I result in a time- and concentration-dependent decrease of P-Stat3 and Stat3. In freshly isolated Sz cells (n=3), Cucurbitacin I induces a concentration-dependent decrease in Stat3 expression whereas P-Stat3 is undetectable. Finally, incubation of freshly isolated Sz cells (n=4) with 30 μM Cucurbitacin I for 6 hours induces apoptosis in the large majority (73-91%) of tumor cells[3].
In Vivo	No major side effects are noted throughout the study. It is shown that average tumor volumes at the end of the study are as follows: control, 616 mm3 (±130); CQ, 580 mm3 (±107); Cucurbitacin I, 346mm3 (±79); and combination, 220mm3 (±62). The differences in tumor volume between the Cucurbitacin I and control, combination and control, and combination and Cucurbitacin I arms are significant. Furthermore, combination-treated tumors exhibit a significantly lower average tumor weight at study termination than the control. Moreover, there was no effect on the body weights of mice[4].
Animal Admin	Mice[4] BALB/c nude (nu/nu) female mice are used. U251 cells (5×106 cells in 50 μL of serum-free DMEM) are inoculated subcutaneously into the right flank of 5-week-old female mice after acclimatization for a week. Tumor growth is measured daily with calipers. When the tumors reach a mean volume of 90-120 mm3, animals are randomized into groups. In the first experiment, 16 mice are randomly assigned to Cucurbitacin I (1 mg/kg/day in 20% DMSO in PBS) or drug vehicle control (20% DMSO in PBS) and dosed intraperitoneally with 100 μL of vehicle or drug once daily for 18 days, whereas, in the second, 20 mice are assigned to four groups. Control animals receive 20% DMSO in PBS vehicle, whereas treated animals are injected with Cucurbitacin I (1 mg/kg/day) in 20% DMSO in PBS, CQ (25 mg/kg/day) in 20% DMSO in PBS, and Cucurbitacin I (1 mg/kg/day) plus CQ (25 mg/kg/day) in 20% DMSO in PBS and dosed intraperitoneally with 100 μL of vehicle or drug once daily for 15 days[4].
References	[1]. Song J, et al. Cucurbitacin I inhibits cell migration and invasion and enhances chemosensitivity in colon cancer. Oncol Rep. 2015 Apr;33(4):1867-71. [2]. Jeong MH, et al. 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. [3]. van Kester MS, et al. Cucurbitacin I inhibits Stat3 and induces apoptosis in Sézary cells. J Invest Dermatol. 2008 Jul;128(7):1691-5. [4]. Yuan G, et al. Cucurbitacin I induces protective autophagy in glioblastoma in vitro and in vivo. J Biol Chem. 2014 Apr 11;289(15):10607-19.

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Boiling Point	716.9±60.0 °C at 760 mmHg
Melting Point	148-150ºC
Molecular Formula	C₃₀H₄₂O₇
Molecular Weight	514.650
Flash Point	401.3±29.4 °C
Exact Mass	514.293030
PSA	132.13000
LogP	2.06
Vapour Pressure	0.0±5.2 mmHg at 25°C
Index of Refraction	1.594
InChIKey	NISPVUDLMHQFRQ-MKIKIEMVSA-N
SMILES	CC(C)(O)C=CC(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(C=C(O)C(=O)C4(C)C)C3(C)C(=O)CC12C
Storage condition	−20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RC6200000

CHEMICAL NAME :: 19-Nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22- trione, 9-methyl-2,16,20,25- tetrahydroxy-

CAS REGISTRY NUMBER :: 2222-07-3

LAST UPDATED :: 199007

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C30-H42-O7

MOLECULAR WEIGHT :: 514.72

WISWESSER LINE NOTATION :: L E5 B666 CV OV LU PUTJ B1 E1 FXQ1&V1U1XQ1&1 GQ I1 N1 N1 PQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CHTPBA Chimica Therapeutica. (Paris, France) V.1-8, 1965-73. For publisher information, see EJMCA5. Volume(issue)/page/year: 4,459,1969

Safety Information

Hazard Codes	T+:Verytoxic;
Risk Phrases	R28
Safety Phrases	S28-S36/37-S45
RIDADR	UN 2811
RTECS	RC6200000

Synonyms

2,16,20,26-Tetrahydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,24-triene-1,11,23-trione

CUCURBITACIN I

Estra-1,5-diene-3,11-dione, 17-(1,6-dihydroxy-1,5-dimethyl-3-oxo-4-hexen-1-yl)-2,16-dihydroxy-4,4,9,14-tetramethyl-

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