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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Kristina Martinez et al.
Journal of lipid research, 54(3), 662-670 (2012-12-25)
Diacylglycerol kinases (DGK) convert diacylglycerol to phosphatidic acid, which has been reported to stimulate calcium release from the endoplasmic reticulum. Based on our published data showing that trans-10, cis-12 conjugated linoleic acid (t10,c12 CLA)-mediated intracellular calcium accumulation is linked to
Yoshihiko Kito et al.
American journal of physiology. Gastrointestinal and liver physiology, 298(5), G755-G763 (2010-02-20)
The relaxant effects of Rikkunshi-to (TJ-43), a gastroprotective herbal medicine, on rat gastric fundus were investigated. Experiments were carried out using standard tension and intracellular microelectrode recording techniques. During contraction induced by enprostil (0.5 microM), a prostaglandin E(2) analog, TJ-43
Ana M Laxalt et al.
The Journal of biological chemistry, 282(29), 21160-21168 (2007-05-11)
Nitric Oxide (NO) is a second messenger related to development and (a)biotic stress responses in plants. We have studied the role of NO in signaling during plant defense responses upon xylanase elicitation. Treatment of tomato cell cultures with the fungal
Neil J Holden et al.
Molecular medicine (Cambridge, Mass.), 17(11-12), 1242-1252 (2011-08-13)
Dysregulated release of neutrophil azurophilic granules causes increased tissue damage and amplified inflammation during autoimmune disease. Antineutrophil cytoplasmic antibodies (ANCAs) are implicated in the pathogenesis of small vessel vasculitis and promote adhesion and exocytosis in neutrophils. ANCAs activate specific signal
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