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D5919

Sigma-Aldrich

Diacylglycerol Kinase Inhibitor I

solid

Synonym(s):

6-[2-[4-[(4-Fluorophenyl)phenylmethylene]-1-piperidin­yl]ethyl]-7-methyl-5H-thiazolo-[3,2-a]-pyrimidin-5-one, R59022

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About This Item

Empirical Formula (Hill Notation):
C27H26FN3OS
CAS Number:
93076-89-2
Molecular Weight:
459.58
MDL number:
MFCD00055114
UNSPSC Code:
41106300
PubChem Substance ID:
24893986
NACRES:
NA.77

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

solid

color

pale yellow

solubility

0.1 M HCl: slightly soluble
0.1 M NaOH: slightly soluble
DMSO: soluble
H2O: insoluble
ethanol: soluble
ethyl acetate: soluble

storage temp.

−20°C

SMILES string

CC1=C(CCN2CCC(\CC2)=C(\c3ccccc3)c4ccc(F)cc4)C(=O)N5C=CSC5=N1

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

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General description

Diacylglycerol Kinase Inhibitor I prevents the formation of foreign body giant cell (FBGC). It inhibits the phosphorylation of diacylglycerol to phosphatidic acid. Diacylglycerol Kinase Inhibitor I functions as a serotonin (5-HT) receptor (5-HTR) antagonist. It stimulates apoptosis and autophagy in neuronal cell line NG108-15.

Application

Diacylglycerol Kinase Inhibitor I has been used as an inhibitor to study suppression of T cell function using advanced generation human CAR (chimeric antigen receptors) T cells.

Biochem/physiol Actions

Diacylglycerol kinase inhibitor. Inhibits formation of [38P]1-Oleoxyl-2-acetylglyceryl-3-phosphoric acid (OAPA) in red blood cell membranes: IC50 = 3.3 μM.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Activation of phospholipase C and protein kinase C has little involvement in ADP-induced primary aggregation of human platelets: effects of diacylglycerols, the diacylglycerols, the diacylglycerol kinase inhibitor R59022, staurosporine and okadaic acid
Packham MA, et al.
The Biochemical Journal, 290(3), 849-856 (1993)
Toshiaki Sawatani et al.
Journal of pharmacological sciences, 140(2), 178-186 (2019-07-08)
The role of type I diacylglycerol kinases (DGKs) in the regulation of insulin secretion was investigated in MIN6 β-cells. In intracellular Ca2+ concentration ([Ca2+]i) measurement experiments, 1 μM R59949, a type I DGK inhibitor, and 10 μM DiC8, a diacylglycerol (DAG) analog
Eric Ruelland et al.
Plant physiology, 130(2), 999-1007 (2002-10-12)
The signaling events generated by a cold exposure are poorly known in plants. We were interested in checking the possible activation of enzymes of the phosphoinositide signaling pathway in response to a temperature drop. In Arabidopsis suspension cells labeled with
Amy K McNally et al.
The American journal of pathology, 163(3), 1147-1156 (2003-08-26)
Multinucleated foreign body giant cells (FBGCs) form by monocyte-derived macrophage fusion on implanted biomedical devices and are believed to mediate oxidative damage to biomaterial surfaces. Our in vitro system of human macrophage culture and interleukin (IL)-4-induced FBGC formation was developed
Multifactorial T-cell hypofunction that is reversible can limit the efficacy of chimeric antigen receptor-transduced human T cells in solid tumors
Moon EK, et al.
Clinical Cancer Research, 197-201 (2014)
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