Misplaced Pages

LY294002

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

LY294002
Names
Preferred IUPAC name 2-(Morpholin-4-yl)-8-phenyl-4H-1-benzopyran-4-one
Other names 2-(4-Morpholinyl)-8-phenyl-4H-1-benzopyran-4-one
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
IUPHAR/BPS
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C19H17NO3/c21-17-13-18(20-9-11-22-12-10-20)23-19-15(7-4-8-16(17)19)14-5-2-1-3-6-14/h1-8,13H,9-12H2Key: CZQHHVNHHHRRDU-UHFFFAOYSA-N
  • InChI=1/C19H17NO3/c21-17-13-18(20-9-11-22-12-10-20)23-19-15(7-4-8-16(17)19)14-5-2-1-3-6-14/h1-8,13H,9-12H2Key: CZQHHVNHHHRRDU-UHFFFAOYAM
SMILES
  • C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=CC=CC=C4
Properties
Chemical formula C19H17NO3
Molar mass 307.349 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

LY294002 is a morpholine-containing chemical compound that is a potent inhibitor of numerous proteins, and a strong inhibitor of phosphoinositide 3-kinases (PI3Ks). It is generally considered a non-selective research tool, and should not be used for experiments aiming to target PI3K uniquely.

Two of these are the proto-oncogene serine/threonine-protein kinase (PIM1) and the phosphatidylinositol-4,5-bisphosphate 3-kinase P110 gamma|catalytic subunit gamma isoform. With an IC50 of 1.4 μM it is somewhat less potent than wortmannin, another well-known PI3 kinase inhibitor. However, LY294002 is a reversible inhibitor of PI3K whereas wortmannin acts irreversibly.

Application of LY294002 causes a substantial acceleration of MEPP frequency (150 μM) at the frog neuromuscular junction through a mechanism that is independent of intraterminal calcium. LY294002 causes the release of MEPPs through a perturbation of synaptotagmin function.

LY294002 is also a BET inhibitor (e.g. of BRD2, BRD3, and BRD4).

Application

Research

It has been shown that LY294002 administration has an additive effect on quercetin antiviral activity against hepatitis C virus.

References

  1. Maira SM, Stauffer F, Schnell C, García-Echeverría C (February 2009). "PI3K inhibitors for cancer treatment: where do we stand?". Biochemical Society Transactions. 37 (Pt 1): 265–272. doi:10.1042/BST0370265. PMID 19143644.
  2. Arrowsmith CH, Audia JE, Austin C, Baell J, Bennett J, Blagg J, et al. (August 2015). "The promise and peril of chemical probes". Nature Chemical Biology. 11 (8): 536–541. doi:10.1038/nchembio.1867. PMC 4706458. PMID 26196764.
  3. "LY294002". DrugBank. Retrieved 2009-09-25.
  4. Vlahos CJ, Matter WF, Hui KY, Brown RF (February 1994). "A specific inhibitor of phosphatidylinositol 3-kinase, 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one (LY294002)". The Journal of Biological Chemistry. 269 (7): 5241–5248. doi:10.1016/S0021-9258(17)37680-9. PMID 8106507.
  5. Searl TJ, Silinsky EM (December 2005). "LY 294002 inhibits adenosine receptor activation by a mechanism independent of effects on PI-3 kinase or casein kinase II". Purinergic Signalling. 1 (4): 389–394. doi:10.1007/s11302-005-0778-6. PMC 2096559. PMID 18404524.
  6. Dittmann A, Werner T, Chung CW, Savitski MM, Fälth Savitski M, Grandi P, et al. (February 2014). "The commonly used PI3-kinase probe LY294002 is an inhibitor of BET bromodomains". ACS Chemical Biology. 9 (2): 495–502. doi:10.1021/cb400789e. PMID 24533473.
  7. Pisonero-Vaquero S, García-Mediavilla MV, Jorquera F, Majano PL, Benet M, Jover R, et al. (March 2014). "Modulation of PI3K-LXRα-dependent lipogenesis mediated by oxidative/nitrosative stress contributes to inhibition of HCV replication by quercetin". Laboratory Investigation; A Journal of Technical Methods and Pathology. 94 (3): 262–274. doi:10.1038/labinvest.2013.156. PMID 24492281.
Categories: