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Chemical Compound Review

PtdIns(3)P     [(1R,2R,3S,4R,5S,6S)-3- [[(2R)-2,3...

Synonyms: AG-L-65913, P3953_SIGMA, CMC_6572, CMC_9578, CTK8G0700, ...
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Disease relevance of dipalmitoylphosphoinositol


High impact information on dipalmitoylphosphoinositol

  • The PtdIns(3)P 5-kinase activity of Fab1p, which converts the product of the Vps34p PtdIns 3-kinase PtdIns(3)P into PtdIns(3,5)P2, also is required for cargo-selective sorting into the vacuole lumen [2].
  • Fab1p PtdIns(3)P 5-kinase function essential for protein sorting in the multivesicular body [2].
  • Specifically, certain FYVE domains bind PI(3)P whereas certain pleckstrin homology domains bind PI(3,4) P2 and/or PI(3,4,5) P3 [3].
  • Using this system, we biochemically dissect molecular events and signaling pathways involved in NADPH oxidase assembly and demonstrate specific roles for PKC delta, PI(3,4)P(2)/PI(3,4,5)P(3), and PI(3)P in the PMA-dependent intracellular activation process [4].
  • PtdIns(3)P binding by the FYVE domain of human early endosome autoantigen 1 (EEA1), a protein implicated in endosome fusion, involves two beta hairpins and an alpha helix [5].

Biological context of dipalmitoylphosphoinositol


Anatomical context of dipalmitoylphosphoinositol


Associations of dipalmitoylphosphoinositol with other chemical compounds

  • We find that the majority of the total pool of PtdIns(3)P which has been synthesized, but not PtdIns(4)P, requires transport to the vacuole in order to be turned over [15].
  • Moreover, our model can be used to predict the binding affinity of PI3-K-generated phospholipids and rationalize the specificity of the Akt PH domain for PI(3,4)P2, as opposed to other phospholipids such as PI(3)P and PI(3,4,5)P3 [16].

Gene context of dipalmitoylphosphoinositol

  • This rapid block in vacuolar protein sorting appears to be the result of loss of PtdIns 3-kinase activity since cellular PtdIns(3)P levels decrease dramatically in vps34 temperature-sensitive mutant cells that have been incubated at the nonpermissive temperature [17].
  • Analysis of a temperature-conditional allele of VPS15, in which a shift to the nonpermissive temperature leads to a decrease in cellular PtdIns(3)P levels, indicates that the loss of Vps15p function leads to a defect in activation of Vps34p [17].
  • Although myotubularin was thought to be a dual-specificity protein phosphatase, recent results indicate that it is primarily a lipid phosphatase, acting on phosphatidylinositol 3-monophosphate, and might be involved in the regulation of phosphatidylinositol 3-kinase (PI 3-kinase) pathway and membrane trafficking [18].
  • Here we show that mutations in VAM3 (vacuolar t-SNARE) and YPT7 (rab GTPase), which are required to direct protein and membrane delivery from prevacuolar endosomal compartments to the vacuole, dramatically increase/stabilize PtdIns(3)P levels in vivo by disrupting its turnover [15].
  • The prototypical SNX is sorting nexin-1 (SNX1), a protein that through its PX domain binds phosphatidylinositol 3-monophosphate [PtdIns(3)P] and phosphatidylinositol 3,5-bisphosphate [PtdIns(3,5)P(2)] [19].

Analytical, diagnostic and therapeutic context of dipalmitoylphosphoinositol


  1. The crystal structure of the PX domain from p40(phox) bound to phosphatidylinositol 3-phosphate. Bravo, J., Karathanassis, D., Pacold, C.M., Pacold, M.E., Ellson, C.D., Anderson, K.E., Butler, P.J., Lavenir, I., Perisic, O., Hawkins, P.T., Stephens, L., Williams, R.L. Mol. Cell (2001) [Pubmed]
  2. Fab1p PtdIns(3)P 5-kinase function essential for protein sorting in the multivesicular body. Odorizzi, G., Babst, M., Emr, S.D. Cell (1998) [Pubmed]
  3. Signalling through phosphoinositide 3-kinases: the lipids take centre stage. Leevers, S.J., Vanhaesebroeck, B., Waterfield, M.D. Curr. Opin. Cell Biol. (1999) [Pubmed]
  4. A novel assay system implicates PtdIns(3,4)P(2), PtdIns(3)P, and PKC delta in intracellular production of reactive oxygen species by the NADPH oxidase. Brown, G.E., Stewart, M.Q., Liu, H., Ha, V.L., Yaffe, M.B. Mol. Cell (2003) [Pubmed]
  5. Phosphatidylinositol 3-phosphate recognition by the FYVE domain. Kutateladze, T.G., Ogburn, K.D., Watson, W.T., de Beer, T., Emr, S.D., Burd, C.G., Overduin, M. Mol. Cell (1999) [Pubmed]
  6. The lipid phosphatase myotubularin is essential for skeletal muscle maintenance but not for myogenesis in mice. Buj-Bello, A., Laugel, V., Messaddeq, N., Zahreddine, H., Laporte, J., Pellissier, J.F., Mandel, J.L. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  7. A mammalian ortholog of Saccharomyces cerevisiae Vac14 that associates with and up-regulates PIKfyve phosphoinositide 5-kinase activity. Sbrissa, D., Ikonomov, O.C., Strakova, J., Dondapati, R., Mlak, K., Deeb, R., Silver, R., Shisheva, A. Mol. Cell. Biol. (2004) [Pubmed]
  8. Molecular Mechanism of Membrane Docking by the Vam7p PX Domain. Lee, S.A., Kovacs, J., Stahelin, R.V., Cheever, M.L., Overduin, M., Setty, T.G., Burd, C.G., Cho, W., Kutateladze, T.G. J. Biol. Chem. (2006) [Pubmed]
  9. The phosphoinositide kinase PIKfyve/Fab1p regulates terminal lysosome maturation in Caenorhabditis elegans. Nicot, A.S., Fares, H., Payrastre, B., Chisholm, A.D., Labouesse, M., Laporte, J. Mol. Biol. Cell (2006) [Pubmed]
  10. Complementary roles for CD19 and Bruton's tyrosine kinase in B lymphocyte signal transduction. Fujimoto, M., Poe, J.C., Satterthwaite, A.B., Wahl, M.I., Witte, O.N., Tedder, T.F. J. Immunol. (2002) [Pubmed]
  11. Dynamics of phosphoinositides in membrane retrieval and insertion. Czech, M.P. Annu. Rev. Physiol. (2003) [Pubmed]
  12. The phox homology (PX) domain-dependent, 3-phosphoinositide-mediated association of sorting nexin-1 with an early sorting endosomal compartment is required for its ability to regulate epidermal growth factor receptor degradation. Cozier, G.E., Carlton, J., McGregor, A.H., Gleeson, P.A., Teasdale, R.D., Mellor, H., Cullen, P.J. J. Biol. Chem. (2002) [Pubmed]
  13. Purification and characterization of human erythrocyte phosphatidylinositol 4-kinase. Phosphatidylinositol 4-kinase and phosphatidylinositol 3-monophosphate 4-kinase are distinct enzymes. Graziani, A., Ling, L.E., Endemann, G., Carpenter, C.L., Cantley, L.C. Biochem. J. (1992) [Pubmed]
  14. Phosphoinositide 3-phosphatase segregates from phosphatidylinositol 3-kinase in EGF-stimulated A431 cells and fails to in vitro hydrolyse phosphatidylinositol(3,4,5)trisphosphate. Payrastre, B., Gironcel, D., Plantavid, M., Mauco, G., Breton, M., Chap, H. FEBS Lett. (1994) [Pubmed]
  15. Phosphoinositide signaling and turnover: PtdIns(3)P, a regulator of membrane traffic, is transported to the vacuole and degraded by a process that requires lumenal vacuolar hydrolase activities. Wurmser, A.E., Emr, S.D. EMBO J. (1998) [Pubmed]
  16. Molecular modeling studies of the Akt PH domain and its interaction with phosphoinositides. Rong, S.B., Hu, Y., Enyedy, I., Powis, G., Meuillet, E.J., Wu, X., Wang, R., Wang, S., Kozikowski, A.P. J. Med. Chem. (2001) [Pubmed]
  17. Vesicle-mediated protein transport: regulatory interactions between the Vps15 protein kinase and the Vps34 PtdIns 3-kinase essential for protein sorting to the vacuole in yeast. Stack, J.H., DeWald, D.B., Takegawa, K., Emr, S.D. J. Cell Biol. (1995) [Pubmed]
  18. The myotubularin family: from genetic disease to phosphoinositide metabolism. Laporte, J., Blondeau, F., Buj-Bello, A., Mandel, J.L. Trends Genet. (2001) [Pubmed]
  19. Sorting nexin-1 mediates tubular endosome-to-TGN transport through coincidence sensing of high- curvature membranes and 3-phosphoinositides. Carlton, J., Bujny, M., Peter, B.J., Oorschot, V.M., Rutherford, A., Mellor, H., Klumperman, J., McMahon, H.T., Cullen, P.J. Curr. Biol. (2004) [Pubmed]
  20. The activation of nuclear phosphoinositide 3-kinase C2beta in all-trans-retinoic acid-differentiated HL-60 cells. Visnjić, D., Crljen, V., Curić, J., Batinić, D., Volinia, S., Banfić, H. FEBS Lett. (2002) [Pubmed]
  21. Sorting nexin 17, a non-self-assembling and a PtdIns(3)P high class affinity protein, interacts with the cerebral cavernous malformation related protein KRIT1. Czubayko, M., Knauth, P., Schlüter, T., Florian, V., Bohnensack, R. Biochem. Biophys. Res. Commun. (2006) [Pubmed]
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