3-[3-(4-Methoxyphenyl)-1-oxo-2-propen-1-yl]-4-phenyl-2(1H)-quinolinone

Product Name3-[3-(4-Methoxyphenyl)-1-oxo-2-propen-1-yl]-4-phenyl-2(1H)-quinolinone
CAS1402830-75-4
MFC25H19NO3
MW381.42
EINECS802-692-7
MOL File1402830-75-4.mol

Chemical Properties

Melting point	228-230 °C(Solvent: Ethanol)
Boiling point	629.248±55.00 °C(Press: 760.00 Torr)(predicted)
Density	1.245±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
storage temp.	-20°C
solubility	DMSO: soluble20mg/mL, clear
form	powder
pka	10.189±0.70(predicted)
color	white to beige

Safety Information

Hazard Codes	Xn
Risk Statements	22
WGK Germany	3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Ceranib-2 is a ceramidase inhibitor that inhibits ceramidase activity (IC₅₀ = 28 μM in SKOV3 cells). It also increases intracellular accumulation of various ceramides, including C14 ceramide , C24 ceramide , C26 ceramide, and C26:1 ceramide, and total ceramide levels and decreases levels of dihydrosphingosine, sphingosine, and sphingosine-1-phosphate in SKOV3 cells. In vivo, ceranib-2 (20 and 50 mg/kg, i.p.) reduces tumor volume in a JC mammary adenocarcinoma mouse syngeneic tumor model.

Uses

Ceranib-2 is a potent and nonlipid ceramidase inhibitor that inhibits cellular ceramidase activity with an IC50 of 28 μM in SKOV3 cells. Ceranib-2 induces the accumulation of multiple ceramide species, decreases levels of sphingosine and sphingosine-1-phosphate (S1P), and induces cell apoptosis. Anticancer activity[1][2].

in vivo

Ceranib-2 (20-50 mg/kg; intraperitoneal injection; daily for 5 days per week; for 3 weeks; female Balb/c mice) treatment delays tumor growth in a syngeneic tumor model without hematologic suppression or overt signs of toxicity^[1].
Intraperitoneal administration of 50 mg/kg Ceranib-2 results in progressive increases in its circulating levels, reaching a peak plasma concentration of approximately 40 μM at the 2 hr time point. Ceranib-2 appears to be cleared with a half-life of less than 2 hr^[1].

Animal Model:	Female Balb/c mice injected with JC murine mammary adenocarcinoma cells^[1]
Dosage:	20 mg/kg or 50 mg/kg
Administration:	Intraperitoneal injection; daily for 5 days per week; for 3 weeks
Result:	Delayed tumor growth in a syngeneic tumor model.

References

[1] Draper JM, et al. Discovery and evaluation of inhibitors of human ceramidase. Mol Cancer Ther. 2011 Nov;10(11):2052-61. DOI:10.1158/1535-7163.MCT-11-0365
[2] Kus G, et al. Induction of apoptosis in prostate cancer cells by the novel ceramidase inhibitor ceranib-2. In Vitro Cell Dev Biol Anim. 2015 Nov;51(10):1056-63. DOI:10.1007/s11626-015-9932-9

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