| Field | Specification |
|---|---|
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C25H25N3O2S |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
NVP 231 is a potent, specific, reversible inhibitor of ceramide kinase (CerK) that competitively blocks the binding of ceramide to CerK, with an IC50 of 12 nM[1]. It induces cell apoptosis by increasing DNA fragmentation and cleavage of caspase-3 and caspase-9[2]. It is supplied as a white to off-white solid (C25H25N3O2S, MW 431.55) at 99.73% purity.
Physical & Chemical Properties
| CAS Number | 362003-83-6 |
|---|---|
| Molecular Formula | C25H25N3O2S |
| Molecular Weight | 431.55 g/mol |
| Purity | 99.73% |
| Appearance | Solid |
| Color | White to off-white |
| SMILES | O=C(C1(C[C@@H](C2)C3)C[C@@H]3C[C@@H]2C1)NC4=CC=C5N=C(NC(C6=CC=CC=C6)=O)SC5=C4 |
| Signaling Pathway | Apoptosis |
| Solubility | In Vitro: DMSO: ≥ 41 mg/mL (95.01 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) * "≥" means soluble, but saturation unknown. |
| Storage | Powder: -20°C, 3 years; 4°C, 2 years. In solvent: -80°C, 2 years; -20°C, 1 year. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Biological Activity
IC50 & Target
IC50: 12 nM (CerK); apoptosis[1][3]
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | ≥ 41 mg/mL (95.01 mM) | use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 2 years) or -20°C (up to 1 year); avoid repeated freeze-thaw cycles.
In Vivo
Choose the formulation that suits the animal model and route of administration; percentages are volume ratios of the final working solution. Start from a clear DMSO stock (see In Vitro above), add the co-solvents one at a time in the order listed, mixing after each addition, and prepare the working solution fresh on the day of dosing. If precipitation or phase separation occurs, gentle warming or sonication can help.
Protocol 1
| Composition | 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% saline |
|---|---|
| Result | ≥ 2.5 mg/mL (5.79 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.5 mg/mL (saturation not determined). For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 400 μL PEG300; then 50 μL Tween-80; then 450 μL saline to bring the volume to 1 mL. Saline: dissolve 0.9 g sodium chloride in ddH2O and make up to 100 mL. |
Protocol 2
| Composition | 10% DMSO + 90% (20% SBE-β-CD in saline) |
|---|---|
| Result | ≥ 2.5 mg/mL (5.79 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.5 mg/mL (saturation not determined). For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 900 μL 20% SBE-β-CD in saline. 20% SBE-β-CD in saline: dissolve 2 g SBE-β-CD powder in 10 mL saline until clear (4°C, store up to one week). |
Protocol 3
| Composition | 10% DMSO + 90% Corn Oil |
|---|---|
| Result | ≥ 2.5 mg/mL (5.79 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.5 mg/mL (saturation not determined). Use with caution if continuous dosing will exceed two weeks. For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 900 μL corn oil. |
Data provided by the manufacturer.
In Vitro
NVP-231 (0-500 nM; 24 hours) progressively lowers cellular CerK activity, measured by NBD-C1P formation, showing that NVP-231 is active in transfected cells. In this cellular system, CerK is inhibited with an IC50 of 59.70 ± 12 nM[3]. Cell viability decreases in a dose-dependent manner with NVP-231 (0-1000 nM; 48 hours), with IC50 values of 1 μM (MCF-7 cells) and 500 nM (NCI-H358 cells)[3]. In both cell lines, NVP-231 (1 μM; 24-72 hours) induces cleavage of caspase-3 and caspase-9. In MCF-7 cells, cleavage and activation of caspase-3 and caspase-9 peak at 24 hours and then fall again, whereas in NCI-H358 cells the cleavage continues throughout the 72 hours[3]. At 0-500 nM for 24 hours, NVP-231 upregulates cyclin B1 phosphorylation at Ser133 in a concentration-dependent manner and reduces CDK1 phosphorylation at Tyr15. Total CDK1 expression also declines with CerK inhibition[3].
Cell Viability Assay[3]
| Cell Line | MCF-7 cells; NCI-H358 cells |
|---|---|
| Concentration | 0 nM, 10 nM, 100 nM, 300 nM, 500 nM, 1000 nM |
| Incubation Time | 48 hours |
| Result | Reduced MCF-7 cells and NCI-H358 cells in a concentration manner. |
Apoptosis Analysis[3]
| Cell Line | MCF-7 cells; NCI-H358 cells |
|---|---|
| Concentration | 1000 nM |
| Incubation Time | 24-72 hours |
| Result | Increases caspase-3 and caspase-9 cleavage in MCF-7 and NCI-H358 cells. |
Western Blot Analysis[3]
| Cell Line | MCF-7 cells; NCI-H358 cells |
|---|---|
| Concentration | 0 nM, 100 nM, 300 nM, 500 nM |
| Incubation Time | 24 hours |
| Result | Decreased p-cyclin B1, p-CDK1 as a concentration manner. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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Ceramide kinase confers tamoxifen resistance in estrogen receptor-positive breast cancer by altering sphingolipid metabolism. Pharmacol Res 2023 Jan:187:106558. PMID: 36410675
Research Square Preprint. 2024 Oct 08.
Multiplexed single-cell lineage tracing of mitotic kinesin inhibitor resistance in glioblastoma. bioRxiv 2023 Sep 12:2023.09.09.557001. PMID: 37745469
