| Identification | Back Directory | [Name]
2-(3,4-Dihydroxy-benzylidene)-benzofuran-3-one, Sphingosine Kinase Inhibitor V | [CAS]
24418-86-8 | [Synonyms]
SKI V
Sphingosine Kinase Inhibitor V
2-(3,4-Dihydroxy-benzylidene)-benzofuran-3-one
(2Z)-2-(3,4-dihydroxybenzylidene)-1-benzofuran-3(2H)-one
3(2H)-Benzofuranone, 2-[(3,4-dihydroxyphenyl)methylene]-
(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-1-benzofuran-3-one
2-(3,4-Dihydroxy-benzylidene)-benzofuran-3-one, Sphingosine Kinase Inhibitor V | [Molecular Formula]
C15H10O4 | [MDL Number]
MFCD07772193 | [MOL File]
24418-86-8.mol | [Molecular Weight]
254.24 |
| Chemical Properties | Back Directory | [Boiling point ]
493.2±45.0 °C(Predicted) | [density ]
1.489±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO: 250 mg/mL (983.32 mM) | [form ]
Solid | [pka]
8.99±0.10(Predicted) | [color ]
Light yellow to yellow |
| Hazard Information | Back Directory | [Uses]
SKI V is a noncompetitive and potent non-lipid sphingosine kinase (SPHK; SK) inhibitor with an IC50 of 2 μM for GST-hSK. SKI V potently inhibits PI3K with an IC50 of 6 μM for hPI3k. SKI V decreases formation of the mitogenic second messenger sphingosine-1-phosphate (S1P). SKI V induces apoptosis and has antitumor activity[1][2]. | [Definition]
ChEBI: 3',4'-dihydroxyaurone is a hydroxyaurone that is aurone which is substituted by hydroxy groups at the 3' and 4' positions; major species at pH 7.3. It shows inhibitory activity against several isoforms of the histone deacetylase complex (HDAC). It has a role as an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a hydroxyaurone and a member of catechols. It is functionally related to a 2',3,4-trihydroxy-trans-chalcone. | [Biological Activity]
SKI V is a non-competitive, potent non-lipid sphingosine kinase (SPHK; SK) inhibitor with IC50 of 2 μM against GST-hSK. SKI V potently inhibits PI3K with IC50 of 6 μM for hPI3k. SKI V reduces the formation of the mitotic second messenger sphingosine-1-phosphate (S1P). SKI V induces apoptosis and has antitumor activity. | [in vivo]
SKI V (75 mg/kg; ip; days 1, 5, 9, 15) significantly lowers tumor growth (>50% decreased at day 18) than control animals. | Animal Model: | 6-8 weeks old BALB/c female mice with JC mammary adenocarcinoma cells | | Dosage: | 75 mg/kg | | Administration: | < td class="col2"> IP; days 1, 5, 9, 15 | Result: | Tumor growth was significantly lower (>50% decreased at day 18) than tumor growth in control animals. | | [target]
IC50: 2 μM (GST-hSK), 6 μM (hPI3k) and 80 μM (ERK2) | [References]
[1] French KJ, et al. Discovery and evaluation of inhibitors of human sphingosine kinase. Cancer Res. 2003 Sep 15;63(18):5962-9. PMID:14522923
[2] French KJ, et al. Antitumor activity of sphingosine kinase inhibitors. J Pharmacol Exp Ther. 2006 Aug;318(2):596-603. DOI:10.1124/jpet.106.101345 |
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