WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406144
CAS#: 362003-83-6
Description: NVP-231 is a potent, specific, and reversible CerK inhibitor that competitively inhibits binding of ceramide to CerK. NVP-231 is active in the low nanomolar range on purified as well as cellular CerK and abrogates phosphorylation of ceramide, resulting in decreased endogenous C1P levels. When combined with another ceramide metabolizing inhibitor, such as tamoxifen, NVP-231 synergistically increased ceramide levels and reduced cell growth. Therefore, NVP-231 represents a novel and promising compound for controlling ceramide metabolism that may provide insight into CerK physiological function.
MedKoo Cat#: 406144
Name: NVP-231
CAS#: 362003-83-6
Chemical Formula: C25H25N3O2S
Exact Mass: 431.16675
Molecular Weight: 431.55
Elemental Analysis: C, 69.58; H, 5.84; N, 9.74; O, 7.41; S, 7.43
Synonym: NVP231; NVP 231; NVP-231
IUPAC/Chemical Name: N -[2-(Benzoylamino)-6-benzothiazolyl]tricyclo[3.3.1.13,7]decane-1-carboxamide
InChi Key: MVSSJPGNLQPWSW-UHFFFAOYSA-N
InChi Code: 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)
SMILES Code: O=C(C1(C2)C[C@H]3C[C@@H]2C[C@H](C3)C1)NC4=CC=C5N=C(NC(C6=CC=CC=C6)=O)SC5=C4
1: Pastukhov O, Schwalm S, Zangemeister-Wittke U, Fabbro D, Bornancin F, Japtok L, Kleuser B, Pfeilschifter J, Huwiler A. 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. 2014 Dec;171(24):5829-44. doi: 10.1111/bph.12886. PubMed PMID: 25134723; PubMed Central PMCID: PMC4290720.
2: Pastukhov O, Schwalm S, Römer I, Zangemeister-Wittke U, Pfeilschifter J, Huwiler A. Ceramide kinase contributes to proliferation but not to prostaglandin E2 formation in renal mesangial cells and fibroblasts. Cell Physiol Biochem. 2014;34(1):119-33. doi: 10.1159/000362989. Epub 2014 Jun 16. PubMed PMID: 24977486.
3: Niwa S, Graf C, Bornancin F. Ceramide kinase deficiency impairs microendothelial cell angiogenesis in vitro. Microvasc Res. 2009 May;77(3):389-93. doi: 10.1016/j.mvr.2009.01.006. Epub 2009 Feb 6. PubMed PMID: 19323974.
4: Graf C, Rovina P, Bornancin F. A secondary assay for ceramide kinase inhibitors based on cell growth inhibition by short-chain ceramides. Anal Biochem. 2009 Jan 1;384(1):166-9. doi: 10.1016/j.ab.2008.09.008. Epub 2008 Sep 14. PubMed PMID: 18831956.
5: Graf C, Klumpp M, Habig M, Rovina P, Billich A, Baumruker T, Oberhauser B, Bornancin F. Targeting ceramide metabolism with a potent and specific ceramide kinase inhibitor. Mol Pharmacol. 2008 Oct;74(4):925-32. doi: 10.1124/mol.108.048652. Epub 2008 Jul 8. PubMed PMID: 18612076.
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