R 59949
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 461069

CAS#: 120166-69-0

Description: R 59949 is a Diacylglycerol kinase (DGK) inhibitor.


Chemical Structure

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R 59949
CAS# 120166-69-0

Theoretical Analysis

MedKoo Cat#: 461069
Name: R 59949
CAS#: 120166-69-0
Chemical Formula: C28H25F2N3OS
Exact Mass: 489.1686
Molecular Weight: 489.58
Elemental Analysis: C, 68.69; H, 5.15; F, 7.76; N, 8.58; O, 3.27; S, 6.55

Price and Availability

Size Price Availability Quantity
5.0mg USD 310.0 2 weeks
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Synonym: R 59949; R-59949; R59949;

IUPAC/Chemical Name: 3-(2-(4-(bis(4-fluorophenyl)methylene)piperidin-1-yl)ethyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

InChi Key: ZCNBZFRECRPCKU-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C1N(CCN2CC/C(CC2)=C(C3=CC=C(F)C=C3)\C4=CC=C(F)C=C4)C(NC5=C1C=CC=C5)=S

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 489.58 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Yang L, Xu Y, Li W, Yang B, Yu S, Zhou H, Yang C, Xu F, Wang J, Gao Y, Huang Y, Lu L, Liang X. Diacylglycerol kinase (DGK) inhibitor II (R59949) could suppress retinal neovascularization and protect retinal astrocytes in an oxygen-induced retinopathy model. J Mol Neurosci. 2015 May;56(1):78-88. doi: 10.1007/s12031-014-0469-2. Epub 2014 Dec 2. PubMed PMID: 25451596.

2: Tolan D, Conway AM, Pyne NJ, Pyne S. Sphingosine prevents diacylglycerol signaling to mitogen-activated protein kinase in airway smooth muscle. Am J Physiol. 1997 Sep;273(3 Pt 1):C928-36. PubMed PMID: 9316414.

3: Nakamura T, Kamishikiryo J, Morita T. Prazosin-stimulated release of hepatic triacylglyceride lipase from primary cultured rat hepatocytes is involved in the regulation of cAMP-dependent protein kinase through activation of the Ca(2+)/calmodulin-dependent protein kinase-II. Pharmacol Rep. 2016 Jun;68(3):649-53. doi: 10.1016/j.pharep.2016.02.001. Epub 2016 Feb 22. PubMed PMID: 27031052.

4: Torres-Ayuso P, Daza-Martín M, Martín-Pérez J, Ávila-Flores A, Mérida I. Diacylglycerol kinase α promotes 3D cancer cell growth and limits drug sensitivity through functional interaction with Src. Oncotarget. 2014 Oct 30;5(20):9710-26. PubMed PMID: 25339152; PubMed Central PMCID: PMC4259432.

5: Massart J, Zierath JR, Chibalin AV. A simple and rapid method to characterize lipid fate in skeletal muscle. BMC Res Notes. 2014 Jun 24;7:391. doi: 10.1186/1756-0500-7-391. PubMed PMID: 24962347; PubMed Central PMCID: PMC4089939.

6: de Chaffoy de Courcelles D, Roevens P, Van Belle H, Kennis L, Somers Y, De Clerck F. The role of endogenously formed diacylglycerol in the propagation and termination of platelet activation. A biochemical and functional analysis using the novel diacylglycerol kinase inhibitor, R 59 949. J Biol Chem. 1989 Feb 25;264(6):3274-85. PubMed PMID: 2536741.

7: Dominguez CL, Floyd DH, Xiao A, Mullins GR, Kefas BA, Xin W, Yacur MN, Abounader R, Lee JK, Wilson GM, Harris TE, Purow BW. Diacylglycerol kinase α is a critical signaling node and novel therapeutic target in glioblastoma and other cancers. Cancer Discov. 2013 Jul;3(7):782-97. doi: 10.1158/2159-8290.CD-12-0215. Epub 2013 Apr 4. PubMed PMID: 23558954; PubMed Central PMCID: PMC3710531.

8: Papp A, Hoyer J. PKC-dependent reduction of the acetylcholine-evoked inward Na current in Aplysia D-neurons: effect of injected PKC and PKC activators. Brain Res. 1996 Feb 5;708(1-2):123-7. PubMed PMID: 8720867.

9: Sato M, Liu K, Sasaki S, Kunii N, Sakai H, Mizuno H, Saga H, Sakane F. Evaluations of the selectivities of the diacylglycerol kinase inhibitors R59022 and R59949 among diacylglycerol kinase isozymes using a new non-radioactive assay method. Pharmacology. 2013;92(1-2):99-107. doi: 10.1159/000351849. Epub 2013 Aug 16. PubMed PMID: 23949095.

10: Kurohane Kaneko Y, Kobayashi Y, Motoki K, Nakata K, Miyagawa S, Yamamoto M, Hayashi D, Shirai Y, Sakane F, Ishikawa T. Depression of type I diacylglycerol kinases in pancreatic β-cells from male mice results in impaired insulin secretion. Endocrinology. 2013 Nov;154(11):4089-98. doi: 10.1210/en.2013-1356. Epub 2013 Sep 13. PubMed PMID: 24035999.

11: Marumo M, Nakano T, Takeda Y, Goto K, Wakabayashi I. Inhibition of thrombin-induced Ca²⁺ influx in platelets by R59949, an inhibitor of diacylglycerol kinase. J Pharm Pharmacol. 2012 Jun;64(6):855-61. doi: 10.1111/j.2042-7158.2012.01485.x. Epub 2012 Mar 12. PubMed PMID: 22571264.

12: Nakano T, Hozumi Y, Goto K, Wakabayashi I. Involvement of diacylglycerol kinase γ in modulation of iNOS synthesis in Golgi apparatus of vascular endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2012 Aug;385(8):787-95. doi: 10.1007/s00210-012-0760-0. Epub 2012 May 25. PubMed PMID: 22627682.

13: Kawaguchi M, Valencia JC, Namiki T, Suzuki T, Hearing VJ. Diacylglycerol kinase regulates tyrosinase expression and function in human melanocytes. J Invest Dermatol. 2012 Dec;132(12):2791-9. doi: 10.1038/jid.2012.261. Epub 2012 Aug 16. PubMed PMID: 22895365; PubMed Central PMCID: PMC3502659.

14: Deng XF, Mulay S, Varma DR. Role of Ca(2+)-independent PKC in alpha 1-adrenoceptor-mediated inotropic responses of neonatal rat hearts. Am J Physiol. 1997 Sep;273(3 Pt 2):H1113-8. PubMed PMID: 9321796.

15: Baldanzi G, Pietronave S, Locarno D, Merlin S, Porporato P, Chianale F, Filigheddu N, Cantelmo AR, Albini A, Graziani A, Prat M. Diacylglycerol kinases are essential for hepatocyte growth factor-dependent proliferation and motility of Kaposi's sarcoma cells. Cancer Sci. 2011 Jul;102(7):1329-36. doi: 10.1111/j.1349-7006.2011.01953.x. Epub 2011 May 18. PubMed PMID: 21477072.

16: Saadeh M, Ferrante TC, Kane A, Shirihai O, Corkey BE, Deeney JT. Reactive oxygen species stimulate insulin secretion in rat pancreatic islets: studies using mono-oleoyl-glycerol. PLoS One. 2012;7(1):e30200. doi: 10.1371/journal.pone.0030200. Epub 2012 Jan 17. PubMed PMID: 22272304; PubMed Central PMCID: PMC3260220.

17: Rodríguez-Liñares B, Walker T, Watson S. The diacylglycerol kinase inhibitor, R59949, potentiates secretion but not increased phosphorylation of a 47 kDalton protein in human platelets. Biochem Pharmacol. 1991 Mar 1;41(5):835-8. PubMed PMID: 1847818.

18: Fuchs B, Rupp M, Ghofrani HA, Schermuly RT, Seeger W, Grimminger F, Gudermann T, Dietrich A, Weissmann N. Diacylglycerol regulates acute hypoxic pulmonary vasoconstriction via TRPC6. Respir Res. 2011 Feb 4;12:20. doi: 10.1186/1465-9921-12-20. PubMed PMID: 21294865; PubMed Central PMCID: PMC3042943.

19: Shibata Y, Kawada-Matsuo M, Shirai Y, Saito N, Li D, Yamashita Y. Streptococcus mutans diacylglycerol kinase homologue: a potential target for anti-caries chemotherapy. J Med Microbiol. 2011 May;60(Pt 5):625-30. doi: 10.1099/jmm.0.026070-0. Epub 2011 Feb 11. PubMed PMID: 21317193.

20: Filigheddu N, Sampietro S, Chianale F, Porporato PE, Gaggianesi M, Gregnanin I, Rainero E, Ferrara M, Perego B, Riboni F, Baldanzi G, Graziani A, Surico N. Diacylglycerol kinase α mediates 17-β-estradiol-induced proliferation, motility, and anchorage-independent growth of Hec-1A endometrial cancer cell line through the G protein-coupled estrogen receptor GPR30. Cell Signal. 2011 Dec;23(12):1988-96. doi: 10.1016/j.cellsig.2011.07.009. Epub 2011 Jul 22. PubMed PMID: 21802511.

R 59949

5.0mg / USD 310.0