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Chemical Compound Review

CHEMBL1685065     [(2S,3S,5S,6R)-4-[[(2R)-2,3...

Synonyms: PtdIns[3,4,5]P, CHEBI:1175412, CMC_6566, CMC_9574, CMC_11403, ...
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Disease relevance of dipalmitolyphosphoinositol


High impact information on dipalmitolyphosphoinositol

  • Shallow gradients of chemoattractants, sensed by G protein-linked signaling pathways, elicit localized binding of PH domains specific for PI(3,4,5)P3 at sites on the membrane where rearrangements of the cytoskeleton and pseudopod extension occur [2].
  • Engagement of IL3-R and GM-CSF-R in these cells leads to increased and prolonged PI3'K-dependent PI(3,4,5)P3 accumulation and PKB activation [3].
  • High osmolarity did not affect phosphatidylinositol 3-kinase activity but led to a marked increase in PI(3,4,5)P3 and a decrease in PI(3,4)P2 formation after pervanadate stimulation, suggesting that hyperosmotic stress has an inhibitory effect on a phosphatidylinositol 5-phosphatase which converts PI(3,4,5)P3 into PI(3,4)P2 [4].
  • The PB region of Rac1 showed strong phospholipid interaction with PI(3)P, PI(4)P, PI(5)P, PI(3,4,5)P3, and phosphatidic acid, however, that of Rac2 did not [5].
  • Investigations in Dictyostelium discoideum and neutrophils have established that pleckstrin homology (PH) domain-containing proteins that bind to the PI3K products PI(3,4)P2 and PI(3,4,5)P3, such as CRAC (cytosolic regulator of adenylyl cyclase) and Akt/PKB, translocate specifically to the leading edge of chemotaxing cells [6].

Biological context of dipalmitolyphosphoinositol

  • Two phases of actin polymerization display different dependencies on PI(3,4,5)P3 accumulation and have unique roles during chemotaxis [7].
  • Although PI(3,4,5)P3 and PI(3,4)P2 are known to possibly activate a downstream molecule of PI3-kinase Akt in vitro, overexpression of WT-SHIP2 inhibited insulin-induced phosphorylation and activation of Akt [8].
  • AIMS/HYPOTHESIS: SHIP2 is a physiologically important negative regulator of insulin signalling hydrolysing the PI3-kinase product, PI(3,4,5)P3, which also has an impact on insulin resistance [9].
  • Exogenous PI(3,4,5)P3 (10 microM), the principal product of IGF-1-stimulated PI3K in 3T3-L1 preadipocytes, had a modest survival effect on its own, reducing cell death from 47.9 +/- 3.4% to 35.6 +/- 3.5% [10].
  • Moreover, pretreatment of the control nucleus with PI(3,4,5)P3 alone mimics the anti-apoptotic activity of NGF by selectively preventing apoptosis, for which nuclear Akt is required but not sufficient [11].

Anatomical context of dipalmitolyphosphoinositol


Associations of dipalmitolyphosphoinositol with other chemical compounds

  • Tyrosine phosphorylation of p110 did not alter its catalytic activity, and hydrogen peroxide stimulation did not cause an increase in the intrinsic PI3K activity; however, hydrogen peroxide stimulation did induce PI(3,4,5)P3 accumulation and activate Akt [14].

Gene context of dipalmitolyphosphoinositol


  1. PilT is required for PI(3,4,5)P3-mediated crosstalk between Neisseria gonorrhoeae and epithelial cells. Lee, S.W., Higashi, D.L., Snyder, A., Merz, A.J., Potter, L., So, M. Cell. Microbiol. (2005) [Pubmed]
  2. Tumor suppressor PTEN mediates sensing of chemoattractant gradients. Iijima, M., Devreotes, P. Cell (2002) [Pubmed]
  3. SHIP is a negative regulator of growth factor receptor-mediated PKB/Akt activation and myeloid cell survival. Liu, Q., Sasaki, T., Kozieradzki, I., Wakeham, A., Itie, A., Dumont, D.J., Penninger, J.M. Genes Dev. (1999) [Pubmed]
  4. Inactivation and dephosphorylation of protein kinase Balpha (PKBalpha) promoted by hyperosmotic stress. Meier, R., Thelen, M., Hemmings, B.A. EMBO J. (1998) [Pubmed]
  5. Isoform-specific membrane targeting mechanism of Rac during Fc gamma R-mediated phagocytosis: positive charge-dependent and independent targeting mechanism of Rac to the phagosome. Ueyama, T., Eto, M., Kami, K., Tatsuno, T., Kobayashi, T., Shirai, Y., Lennartz, M.R., Takeya, R., Sumimoto, H., Saito, N. J. Immunol. (2005) [Pubmed]
  6. The PI3K-mediated activation of CRAC independently regulates adenylyl cyclase activation and chemotaxis. Comer, F.I., Lippincott, C.K., Masbad, J.J., Parent, C.A. Curr. Biol. (2005) [Pubmed]
  7. Two phases of actin polymerization display different dependencies on PI(3,4,5)P3 accumulation and have unique roles during chemotaxis. Chen, L., Janetopoulos, C., Huang, Y.E., Iijima, M., Borleis, J., Devreotes, P.N. Mol. Biol. Cell (2003) [Pubmed]
  8. SH2-containing inositol phosphatase 2 negatively regulates insulin-induced glycogen synthesis in L6 myotubes. Sasaoka, T., Hori, H., Wada, T., Ishiki, M., Haruta, T., Ishihara, H., Kobayashi, M. Diabetologia (2001) [Pubmed]
  9. Inhibition of endogenous SHIP2 ameliorates insulin resistance caused by chronic insulin treatment in 3T3-L1 adipocytes. Sasaoka, T., Fukui, K., Wada, T., Murakami, S., Kawahara, J., Ishihara, H., Funaki, M., Asano, T., Kobayashi, M. Diabetologia (2005) [Pubmed]
  10. Phosphatidylinositol-3,4,5-trisphosphate is required for insulin-like growth factor 1-mediated survival of 3T3-L1 preadipocytes. Gagnon, A., Dods, P., Roustan-Delatour, N., Chen, C.S., Sorisky, A. Endocrinology (2001) [Pubmed]
  11. PIKE/nuclear PI 3-kinase signaling in preventing programmed cell death. Ye, K. J. Cell. Biochem. (2005) [Pubmed]
  12. Regulation of the actin cytoskeleton by PI(4,5)P2 and PI(3,4,5)P3. Hilpelä, P., Vartiainen, M.K., Lappalainen, P. Curr. Top. Microbiol. Immunol. (2004) [Pubmed]
  13. Temporal and spatial regulation of phosphoinositide signaling mediates cytokinesis. Janetopoulos, C., Borleis, J., Vazquez, F., Iijima, M., Devreotes, P. Dev. Cell (2005) [Pubmed]
  14. Implication of phosphatidylinositol 3-kinase membrane recruitment in hydrogen peroxide-induced activation of PI3K and Akt. Qin, S., Chock, P.B. Biochemistry (2003) [Pubmed]
  15. Targeting of OSBP-related protein 3 (ORP3) to endoplasmic reticulum and plasma membrane is controlled by multiple determinants. Lehto, M., Hynynen, R., Karjalainen, K., Kuismanen, E., Hyvärinen, K., Olkkonen, V.M. Exp. Cell Res. (2005) [Pubmed]
  16. The pleckstrin homology domain of Gab-2 is required for optimal interleukin-3 signalsome-mediated responses. Edmead, C.E., Fox, B.C., Stace, C., Ktistakis, N., Welham, M.J. Cell. Signal. (2006) [Pubmed]
  17. Nucleophosmin/B23, a multifunctional protein that can regulate apoptosis. Ye, K. Cancer Biol. Ther. (2005) [Pubmed]
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