A DGK inhibitor
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R-59-022

Item No. 16772

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-[2-[4-[(4-fluorophenyl)phenylmethylene]-1-piperidinyl]ethyl]-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one
CAS Number
93076-89-2
Synonyms
  • Diacylglycerol Kinase Inhibitor I
Molecular Formula
C27H26FN3OS
Formula Weight
459.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS(pH7.2) (1:2): 0.25 mg/mlDMSO: 5 mg/mlEthanol: 5 mg/ml
λmax
228, 324 nm
SMILES
FC1=CC=C(/C(C2=CC=CC=C2)=C3CCN(CCC4=C(C)N=C(SC=C5)N5C4=O)CC\3)C=C1
InChi Code
InChI=1S/C27H26FN3OS/c1-19-24(26(32)31-17-18-33-27(31)29-19)13-16-30-14-11-22(12-15-30)25(20-5-3-2-4-6-20)21-7-9-23(28)10-8-21/h2-10,17-18H,11-16H2,1H3
InChi Key
MFVJXLPANKSLLD-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    R-59-022 is an inhibitor of DGK (IC50 = 2.8 µM).1 This results in increased DAG-dependent PKC activity and potentiates aggregation of thrombin-stimulated platelets.1,2 R-59-022 also blocks vascular contraction induced by the thromboxane analog U-46619 (Item No. 16450).3 At 10 µM, R-59-022 induces apoptosis in glioblastoma cells without being toxic to non-cancerous cells.4 It inhibits DGK-θ in vitro at concentrations below 1 µM and blocks DGK-θ activity in vivo.5 R-59-022 also inhibits A. thaliana DGK2 (IC50 = 50 µM) and suppresses root growth but does not affect DGK7 at 50 µM.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. de Chaffoy de Courcelles, D.C., Roevens, P., and Van Belle, H. R 59 022, a diacylglycerol kinase inhibitor. Its effect on diacylglycerol and thrombin-induced C kinase activation in the intact platelet. The Journal of Biological Chemisty 260(29), 15762-15770 (1985).

    2. Nunn, D.L., and Watson, S.P. A diacylglycerol kinase inhibitor, R59022, potentiates secretion by and aggregation of thrombin-stimulated human platelets. Biochem. J. 243(3), 809-813 (1987).

    3. Nobe, K., Miyatake, M., Nobe, H., et al. Novel diacylglycerol kinase inhibitor selectively suppressed an U46619-induced enhancement of mouse portal vein contraction under high glucose conditions. Br. J. Pharmacol. 143(1), 166-179 (2004).

    4. Dominguez, C.L., Floyd, D.H., Xiao, A., et al. Diacylglycerol kinase a is a critical signaling node and novel therapeutic target in glioblastoma and other cancers. Cancer Discov. 3(7), 782-797 (2013).

    5. Tu-Sekine, B., Goldschmidt, H., Petro, E., et al. Diacylglycerol kinase θ: Regulation and stability. Adv. Biol. Regul. 53(1), 118-126 (2013).

    6. Gómez-Merino, F.C., Arana-Ceballos, F.A., Trejo-Téllez, L.I., et al. Arabidopsis AtDGK7, the smallest member of plant diacylglycerol kinases (DGKs), displays unique biochemical features and saturates at low substrate concentration: The DGK inhibitor R59022 differentially affects AtDGK2 and AtDGK7 activity in vitro and alters plant growth and development. The Journal of Biological Chemisty 280(41), 34888-34899 (2005).