LY294002

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Contents

LY294002
LY294002.svg
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
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • 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,9-12H2 X mark.svgN
    Key: CZQHHVNHHHRRDU-UHFFFAOYSA-N X mark.svgN
  • 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,9-12H2
    Key: CZQHHVNHHHRRDU-UHFFFAOYAM
  • C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=CC=CC=C4
Properties
C19H17NO3
Molar mass 307.349 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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LY294002 is a morpholine-containing chemical compound that is a potent inhibitor of numerous proteins, and a strong inhibitor of phosphoinositide 3-kinases (PI3Ks). [1] It is generally considered a non-selective research tool, and should not be used for experiments aiming to target PI3K uniquely. [2]

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. [3] 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. [4]

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. [5]

LY294002 is also a BET inhibitor (e.g. of BRD2, BRD3, and BRD4). [6]

Application

Research

It has been shown that LY294002 administration has an additive effect on quercetin antiviral activity against hepatitis C virus. [7]

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: 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.
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