N-[2-(Benzoylamino)-6-benzothiazolyl]tricyclo[3.3.1.13,7]decane-1-carboxamide Chemical Properties

Melting point:

246-248 °C(Solv: isopropanol (67-63-0); water (7732-18-5))

Density 

1.398±0.06 g/cm3(Predicted)

storage temp. 

Store at +4°C

solubility 

DMSO: >10mg/mL

pka

9.09±0.70(Predicted)

form 

powder

color 

white to off-white

Stability:

Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.

InChI

InChI=1S/C25H25N3O2S/c29-22(18-4-2-1-3-5-18)28-24-27-20-7-6-19(11-21(20)31-24)26-23(30)25-12-15-8-16(13-25)10-17(9-15)14-25/h1-7,11,15-17H,8-10,12-14H2,(H,26,30)(H,27,28,29)

InChIKey

MVSSJPGNLQPWSW-UHFFFAOYSA-N

SMILES

C12(C(NC3C=C4SC(NC(=O)C5=CC=CC=C5)=NC4=CC=3)=O)CC3CC(CC(C3)C1)C2

Safety Information

WGK Germany 

nwg

N-[2-(Benzoylamino)-6-benzothiazolyl]tricyclo[3.3.1.13,7]decane-1-carboxamide Usage And Synthesis

Description

NVP-231 (362003-83-6) is a reversible inhibitor of ceramide kinase (IC50 = 12 nM).1 At 10 nM, it inhibited ceramide-1-phosphate formation by >50% and at 100 nM it completely inhibited its formation in cell culture.? NVP-231 was inactive against hSphK1/2, hPI3Ka, hPI4Kb, hVps34, hGCS, hSMS-1, CERT, and 500-fold less potent against hDAGKa.? NVP-231 inhibited breast and lung cancer cell proliferation via M phase arrest.2 It potently blocked cell migration and invasion in PANC-1 pancreatic cancer cells3 as well as MDA-MB-231 breast cancer cells4.

Uses

A ceramide kinase inhibitors that completely inhibits binding of ceramide to CerK and protects against C2-Cer-induced cell death.

storage

Store at +4°C

References

Graf et al. (2008), Targeting ceramide metabolism with a potent and specific ceramide kinase inhibitor; Mol. Pharmacol., 74 925 Pastukhov et al. (2014), The ceramide kinase inhibitor NVP-231 inhibits breast and lung cancer cell proliferation by inducing M phase arrest and subsequent cell death; Br. J. Pharmacol., 171 5829 Rivera et al. (2016), Ceramide-1-phosphate regulates cell migration and invasion of human pancreatic cancer cells; Biochem. Pharmacol., 102 107 Schwalm et al. (2020), Ceramide Kinase Is Upregulated in Metastatic Breast Cancer Cells and Contributes to Migration and Invasion by Activation of PI3-Kinase and Akt; Int. J. Mol. Sci., 21 1396

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