Skip to Content
MilliporeSigma
All Photos(1)

Documents

D5794

Sigma-Aldrich

Diacylglycerol Kinase Inhibitor II

solid

Synonym(s):

3-[2-[4-(bis(4-Fluorophenyl)methylene)-1-piperidinyl]ethyl]-2,3-dihydro-2-thioxo-4(1H)-quinazolinone, R59949

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C28H25F2N3OS
CAS Number:
120166-69-0
Molecular Weight:
489.58
MDL number:
MFCD00069258
UNSPSC Code:
41106300
PubChem Substance ID:
24278378
NACRES:
NA.77

biological source

synthetic (organic)

assay

≥97% (HPLC)

form

solid

color

pale yellow

mp

228-230  °C

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

Fc1ccc(cc1)\C(=C2\CCN(CCN3C(=S)Nc4ccccc4C3=O)CC2)c5ccc(F)cc5

InChI

1S/C28H25F2N3OS/c29-22-9-5-19(6-10-22)26(20-7-11-23(30)12-8-20)21-13-15-32(16-14-21)17-18-33-27(34)24-3-1-2-4-25(24)31-28(33)35/h1-12H,13-18H2,(H,31,35)

InChI key

ZCNBZFRECRPCKU-UHFFFAOYSA-N

Application

Diacylglycerol Kinase Inhibitor II has been used to determine tumor-induced inhibition with genetically modified cytotoxic T cells expressing chimeric antigen receptors (CAR). It has also been used to induce pAkt and PKR-like extracellular signal-regulated kinase (pErk) signals in T-cell acute lymphoblastic leukemia (T-ALL) cells.

Biochem/physiol Actions

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

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

T Kurz et al.
Cardiovascular research, 42(1), 48-56 (1999-08-06)
1,2-Diacylglycerol (1,2-DAG) and phosphatidic acid (PA) are produced by phospholipase C and D activity and play a key role as second messengers in receptor-mediated signal transduction. So far, little is known about alterations of endogenous 1,2-DAG and PA production during
Liquan Yang et al.
Molecular pharmacology, 78(1), 105-113 (2010-04-01)
We demonstrated recently that opioid-induced activation of phospholipase D2 (PLD2) enhances mu- (MOPr) and delta-opioid receptor endocytosis/recycling and thus reduces the development of opioid receptor desensitization and tolerance. However, the mechanistic basis for the PLD2-mediated induction of opioid receptor endocytosis
R W Erickson et al.
The Journal of biological chemistry, 274(32), 22243-22250 (1999-07-31)
The superoxide-generating neutrophil NADPH oxidase can be activated in cell-free reconstitution systems by several agonists, most notably arachidonic acid and the detergent sodium dodecyl sulfate. In this study, we show that both phosphatidic acids and diacylglycerols can serve separately as
X Du et al.
The Biochemical journal, 357(Pt 1), 275-282 (2001-06-21)
We have previously shown that unsaturated fatty acids amplify platelet-derived-growth-factor (PDGF)-induced protein kinase C (PKC) activation in vascular smooth-muscle cells (VSMCs). Diacylglycerol-induced PKC activation is normally terminated by diacylglycerol kinases (DGKs). We thus hypothesized that fatty acids act by inhibiting
Marylana Saadeh et al.
PloS one, 7(1), e30200-e30200 (2012-01-25)
Chronic exposure (24-72 hrs) of pancreatic islets to elevated glucose and fatty acid leads to glucolipoxicity characterized by basal insulin hypersecretion and impaired glucose-stimulated insulin secretion (GSIS). Our aim was to determine the mechanism for basal hypersecretion of insulin. We
View All Related Papers

Articles

Discover Bioactive Small Molecules for Kinase Phosphatase Biology

Discover Bioactive Small Molecules for Kinase Phosphatase Biology

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service