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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

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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 Code

11 - Combustible Solids

WGK

WGK 3

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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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
Costin N Antonescu et al.
Molecular biology of the cell, 21(16), 2944-2952 (2010-06-25)
Clathrin-mediated endocytosis (CME) is the main route of internalization of receptor-ligand complexes. Relatively little is known about the role of specific lipids in CME, in particular that of phosphatidic acid (PA). We examined the effect of altering cellular PA levels
RasGRP1 overexpression in T-ALL increases basal nucleotide exchange on Ras rendering the Ras/PI3K/Akt pathway responsive to protumorigenic cytokines
Ksionda O, et al.
Oncogene, 35(28), 3658-3658 (2016)
Elisa Temes et al.
The Journal of biological chemistry, 280(25), 24238-24244 (2005-04-26)
Hypoxia-inducible factors (HIF) are heterodimeric (alpha/beta) transcription factors that play a fundamental role in cellular adaptation to low oxygen tension. In the presence of oxygen, the HIF-alpha subunit becomes hydroxylated at specific prolyl residues by prolyl hydroxylases. This post-translational modification
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
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