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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)

Quality Level

200

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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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
M Galdiero et al.
The Journal of infection, 46(2), 111-119 (2003-03-14)
In the present study a monocytic cell line, U937, was used to investigate the possible involvement of protein tyrosine kinases (NT-PTKs), protein kinase A (PKA) and protein kinase C (PKC) in cell signaling pathways following Salmonella enterica serovar Typhimurium porin
Y Jiang et al.
Biochemical pharmacology, 59(7), 763-772 (2000-03-16)
Diacylglycerol kinases (DGKs) attenuate diacylglycerol-induced protein kinase C activation during stimulated phosphatidylinositol turnover. This reaction also initiates phosphatidylinositol resynthesis. Two agents, 3-(2-(4-[bis-(4-fluorophenyl)methylene]-1-piperidinyl)ethyl)-2,3-dihydro -2-thioxo-4(1H)quinazolinone (R59949) and 6-(2-(4-[(4-fluorophenyl)phenylmethylene]-1-piperidinyl)ethyl)-7-m ethyl-5H-thiazolo(3,2-a)pyrimidin-5-one (R59022), inhibit diacylglycerol phosphorylation in several systems. To examine the mechanism of this
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, 20(16), 4262-4273 (2014)
Michelle A Blaskovich et al.
PloS one, 8(10), e78632-e78632 (2013-11-10)
Lysophosphatidic acid acyltransferase (LPAAT-β) is a phosphatidic acid (PA) generating enzyme that plays an essential role in triglyceride synthesis. However, LPAAT-β is now being studied as an important regulator of cell growth and differentiation and as a potential therapeutic target
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