CAS 120166-69-0|R59949
| Common Name | R59949 | ||
|---|---|---|---|
| CAS Number | 120166-69-0 | Molecular Weight | 489.57900 |
| Density | 1.36g/cm3 | Boiling Point | 637.1ºC at 760mmHg |
| Molecular Formula | C28H25F2N3OS | Melting Point | / |
| MSDS | ChineseUSA | Flash Point | 339.1ºC |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | 3-[2-[4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl]ethyl]-2-sulfanylidene-1H-quinazolin-4-one |
|---|---|
| Synonym | More Synonyms |
R59949 BiologicalActivity
| Description | R59949 is a pan diacylglycerol kinase (DGK) inhibitor with an IC50 of 300 nM. R59949 strongly inhibits the activity of type I DGK α and γ and moderately attenuates the activity of type II DGK θ and κ. R59949 activates protein kinase C (PKC) by enhancing the levels of the endogenous ligand diacyl glycerol[1][2][3]. |
|---|---|
| Related Catalog | Signaling Pathways >>Epigenetics >>PKCResearch Areas >>CancerSignaling Pathways >>TGF-beta/Smad >>PKC |
| In Vitro | In the presence of R59949, vasopressin- as well as collagen-induced release reaction and aggregation was strongly increased, independently of the formation of arachidonate metabolites[1]. In THP‐1 monocytes, R59949 attenuates CCL2‐evoked Ca2+ signalling with a half‐maximal concentration of 8.6 μM[2]. R59949 inhibits inducible nitric oxide production through decreasing transplasmalemmal L-arginine uptake in vascular smooth muscle cells[4]. |
| References | [1]. de Chaffoy de Courcelles D, et al. The role of endogenously formed diacylglycerol in the propagation and termination of platelet activation. A biochemical and functional analysis using the novel diacylglycerol kinase inhibitor, R 59 949. J Biol Chem. 1989;264(6):3274-3285. [2]. Day P, et al. Inhibitors of DAG metabolism suppress CCR2 signalling in human monocytes. Br J Pharmacol. 2019;176(15):2736-2749. [3]. Meinhardt G, et al. Effect of novel modulators of protein kinase C activity upon chemotherapy-induced differentiation and apoptosis in myeloid leukemic cells. Anticancer Drugs. 2002;13(7):725-733. [4]. Shimomura T, et al. R59949, a diacylglycerol kinase inhibitor, inhibits inducible nitric oxide production through decreasing transplasmalemmal L-arginine uptake in vascular smooth muscle cells. Naunyn Schmiedebergs Arch Pharmacol. 2017;390(2):207-214. |
Chemical & Physical Properties
| Density | 1.36g/cm3 |
|---|---|
| Boiling Point | 637.1ºC at 760mmHg |
| Molecular Formula | C28H25F2N3OS |
| Molecular Weight | 489.57900 |
| Flash Point | 339.1ºC |
| Exact Mass | 489.16900 |
| PSA | 73.12000 |
| LogP | 5.87310 |
| Vapour Pressure | 3.94E-16mmHg at 25°C |
| Index of Refraction | 1.688 |
| InChIKey | ZCNBZFRECRPCKU-UHFFFAOYSA-N |
| SMILES | O=c1c2ccccc2[nH]c(=S)n1CCN1CCC(=C(c2ccc(F)cc2)c2ccc(F)cc2)CC1 |
| Storage condition | -20°C |
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H315-H319-H335 |
| Precautionary Statements | P261-P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xi |
| Risk Phrases | R36/37/38 |
| Safety Phrases | S26-S36 |
| RIDADR | NONH for all modes of transport |
Articles33
More Articles| Diacylglycerol kinase α promotes 3D cancer cell growth and limits drug sensitivity through functional interaction with Src. Oncotarget 5(20) , 9710-26, (2014) Diacylglycerol kinase (DGK)α converts diacylglycerol to phosphatidic acid. This lipid kinase sustains survival, migration and invasion of tumor cells, with no effect over untransformed cells, suggesti... | |
| Insulin action on polyunsaturated phosphatidic acid formation in rat brain: an "in vitro" model with synaptic endings from cerebral cortex and hippocampus. Neurochem. Res. 34(7) , 1236-48, (2009) The highly efficient formation of phosphatidic acid from exogenous 1-stearoyl-2-arachidonoyl-sn-glycerol (SAG) in rat brain synaptic nerve endings (synaptosomes) from cerebral cortex and hippocampus i... | |
| Effect of novel modulators of protein kinase C activity upon chemotherapy-induced differentiation and apoptosis in myeloid leukemic cells. Anticancer Drugs 13(7) , 725-33, (2002) Modulation of protein kinase C (PKC) activity has been demonstrated to either prevent or enhance drug-induced apoptosis in various tissue types. We tested four novel modulators of PKC activity in comp... |
Synonyms
| MFCD00069258 |
| Diacylglycerol Kinase Inhibitor II |
