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Chemical Compound Review

diC8     (1-hydroxy-3-octanoyloxy- propan-2-yl)...

Synonyms: CHEMBL24609, AG-D-21789, AG-K-06720, CTK4A4899, DNC012656, ...
 
 
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Disease relevance of Dicaprylglyceride

 

High impact information on Dicaprylglyceride

  • Although a single dose of phorbol 12-myristate 13-acetate (PMA) allowed HL-60 cells to differentiate to macrophages, a single dose of membrane-permeant diacylglycerol (DAG), 1,2-dioctanoylglycerol (1,2-DiC8), was normally insufficient to differentiate these cells [2].
  • Another protein kinase C (PKC) activator, 1,2-dioctanoylglycerol (diC8), blocked 70-100% of sustained current when applied intracellularly or extracellularly at 5 microM, whereas extracellular application of ethylene glycol dioctanoate (5 microM), an analog reported not to stimulate PKC, inhibited only 14% of sustained current [3].
  • B-50 phosphorylation in nerve growth cones is stimulated by 4 beta-phorbol 12,13-dibutyrate (PDB) and 1,2-dioctanoylglycerol (DOG) in a concentration-dependent manner, but not by 4 alpha-phorbol 12,13-didecanoate (4 alpha-PDD) [4].
  • Phorbol 12-myristate 13-acetate and 1,2-dioctanoylglycerol induced the rapid phosphorylation of occludin in Madin-Darby canine kidney cells cultured in low extracellular calcium medium with a concomitant translocation of occludin to the regions of cell-cell contact [5].
  • Stimulation with 1,2-dioctanoylglycerol resulted in little translocation of PKC isoforms or p47phox, and in minimal oxidase activity [6].
 

Biological context of Dicaprylglyceride

 

Anatomical context of Dicaprylglyceride

  • We have now compared the effects of two related diterpenes (mezerein and 12-O-tetradecanoylphorbol-13-acetate) and two cell-permeable diacylglycerols (1-oleoyl-2-acetoylglycerol and 1,2-dioctanoylglycerol) on the induction of differentiation in HL-60 cells [9].
  • 1,2-Dioctanoylglycerol and phorbol esters which activate protein kinase C enhanced the Ca2+-dependent and Ca2+-independent secretion in digitonin-permeabilized PC12 cells [12].
  • Adenylate cyclase (ATP-pyrophosphate lyase (cyclizing); EC 4.6.1.1) in the human keratinocyte cell line SCC 12F was potentiated by 12-O-tetradecanoyl-phorbol-13-acetate (TPA), phorbol-12,13-diacetate, and 1,2-dioctanoylglycerol [13].
  • Ro 31-8425 inhibited superoxide generation in human neutrophils activated by both receptor stimuli (formyl-methionyl-leucylphenylalanine, opsonized zymosan, IgG and heat aggregated IgG) and post-receptor stimuli (1,2-dioctanoylglycerol and fluoride) [14].
  • To investigate the participation of protein kinase C (PKC) in this hormone-induced response, calcium uptake was measured in myocytes treated with PKC activators 12-O-tetradecanoyl phorbol 13-acetate (TPA, 50 nM) or 1,2-dioctanoyl-rac-glycerol (DOG, 50 microM) [15].
 

Associations of Dicaprylglyceride with other chemical compounds

 

Gene context of Dicaprylglyceride

  • In contrast, addition of a phospholipase C or a synthetic diacylglycerol (DG) analog, 1,2-dioctanoylglycerol, failed to enhance nuclear NF-kappa B binding despite large increases in cellular DG content [21].
  • Both the tumor promoter agent phorbol myristate acetate (PMA) and a diacylglycerol analog, 1,2-dioctanoylglycerol, induced a 2.7- and 2.5-fold increase in steady-state glucagon mRNA levels at 24 h, respectively [22].
  • At 2.0 mM extracellular Ca2+, PMA (10(-6) M) bryostatin-1 (10(-7) M), and 1,2-dioctanoylglycerol (3 x 10(-4) M) blunted the suppressive effects of high Ca2+ on secretion, thus stimulating PTH release 252 +/- 45%, 122 +/- 20%, and 485 +/- 95% over control levels, respectively [23].
  • Phorbol-12,13-dibutyrate and 1,2-dioctanoylglycerol, activators of protein kinase C (PKC) that stimulate DNA synthesis in serum-deprived Swiss 3T3 fibroblasts, induce histone H1 kinase activity associated with anti-cdc2 immunoprecipitates after a lag period of 15h, a time point close to G1/S boundary of the cell cycle in these cells [24].
  • In contrast, treatment with either TNF (1,000 U/ml for 15 min) or 1,2-dioctanoylglycerol (4 x 10(-5) M for 5 min), a diacylglycerol that activates PKC, resulted in translocation of fluorescence to the cell periphery; fine, punctate PKC-associated fluorescence was localized to the margins of cells [25].
 

Analytical, diagnostic and therapeutic context of Dicaprylglyceride

References

  1. Leukocyte chemoattraction by 1,2-diacylglycerol. Wright, T.M., Hoffman, R.D., Nishijima, J., Jakoi, L., Snyderman, R., Shin, H.S. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  2. Sustained activation of protein kinase C is essential to HL-60 cell differentiation to macrophage. Aihara, H., Asaoka, Y., Yoshida, K., Nishizuka, Y. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  3. Inhibition by bradykinin of voltage-activated barium current in a rat dorsal root ganglion cell line: role of protein kinase C. Boland, L.M., Allen, A.C., Dingledine, R. J. Neurosci. (1991) [Pubmed]
  4. Muscarinic receptor activation stimulates B-50/GAP43 phosphorylation in isolated nerve growth cones. Van Hooff, C.O., De Graan, P.N., Oestreicher, A.B., Gispen, W.H. J. Neurosci. (1989) [Pubmed]
  5. Protein kinase C regulates the phosphorylation and cellular localization of occludin. Andreeva, A.Y., Krause, E., Müller, E.C., Blasig, I.E., Utepbergenov, D.I. J. Biol. Chem. (2001) [Pubmed]
  6. Protein kinase C (PKC) isoforms translocate to Triton-insoluble fractions in stimulated human neutrophils: correlation of conventional PKC with activation of NADPH oxidase. Nixon, J.B., McPhail, L.C. J. Immunol. (1999) [Pubmed]
  7. Physiologic 1,2-diacylglycerol levels induce protein kinase C-independent translocation of a regulatory enzyme. Kolesnick, R.N., Hemer, M.R. J. Biol. Chem. (1990) [Pubmed]
  8. Protein kinase C-mediated bidirectional regulation of DNA synthesis, RB protein phosphorylation, and cyclin-dependent kinases in human vascular endothelial cells. Zhou, W., Takuwa, N., Kumada, M., Takuwa, Y. J. Biol. Chem. (1993) [Pubmed]
  9. Disparate effects of activators of protein kinase C on HL-60 promyelocytic leukemia cell differentiation. Morin, M.J., Kreutter, D., Rasmussen, H., Sartorelli, A.C. J. Biol. Chem. (1987) [Pubmed]
  10. Effects of polymyxin B on superoxide anion release and priming in human polymorphonuclear leukocytes. Aida, Y., Pabst, M.J., Rademacher, J.M., Hatakeyama, T., Aono, M. J. Leukoc. Biol. (1990) [Pubmed]
  11. Increased phospholipase C-catalyzed hydrolysis of phosphatidylinositol-4,5-bisphosphate and 1,2-sn-diacylglycerol content in psoriatic involved compared to uninvolved and normal epidermis. Fisher, G.J., Talwar, H.S., Baldassare, J.J., Henderson, P.A., Voorhees, J.J. J. Invest. Dermatol. (1990) [Pubmed]
  12. Catecholamine secretion from digitonin-treated PC12 cells. Effects of Ca2+, ATP, and protein kinase C activators. Peppers, S.C., Holz, R.W. J. Biol. Chem. (1986) [Pubmed]
  13. Modulation of adenylate cyclase in human keratinocytes by protein kinase C. Choi, E.J., Toscano, W.A. J. Biol. Chem. (1988) [Pubmed]
  14. A novel conformationally restricted protein kinase C inhibitor, Ro 31-8425, inhibits human neutrophil superoxide generation by soluble, particulate and post-receptor stimuli. Muid, R.E., Dale, M.M., Davis, P.D., Elliott, L.H., Hill, C.H., Kumar, H., Lawton, G., Twomey, B.M., Wadsworth, J., Wilkinson, S.E. FEBS Lett. (1991) [Pubmed]
  15. Involvement of protein kinase C in 1,25(OH)2-vitamin D3 regulation of calcium uptake by cultured myocytes. Marinissen, M.J., Selles, J., Boland, R. Cell. Signal. (1994) [Pubmed]
  16. Selective translocation of beta II-protein kinase C to the nucleus of human promyelocytic (HL60) leukemia cells. Hocevar, B.A., Fields, A.P. J. Biol. Chem. (1991) [Pubmed]
  17. The effect of alpha-adrenergic agents and protein kinase C activators on protein phosphorylation in isolated guinea pig hearts. Edes, I., Talosi, L., Kranias, E.G. Eur. Heart J. (1991) [Pubmed]
  18. Effects of Ca2+ ionophore A23187, 1,2-dioctanoylglycerol, and dibutyryl cAMP on the activity and expression of ornithine decarboxylase in guinea pig lymphocytes. Otani, S., Matsui-Yuasa, I., Goto, H., Morisawa, S. J. Biochem. (1990) [Pubmed]
  19. Cellular regulation of arachidonate mobilization and metabolism. Rosenthal, M.D., Rzigalinski, B.A., Blackmore, P.F., Franson, R.C. Prostaglandins Leukot. Essent. Fatty Acids (1995) [Pubmed]
  20. Calcium requirements for acetylcholine-induced contraction of cat esophageal circular muscle cells. Sohn, U.D., Chiu, T.T., Bitar, K.N., Hillemeier, C., Behar, J., Biancani, P. Am. J. Physiol. (1994) [Pubmed]
  21. Tumor necrosis factor activation of the sphingomyelin pathway signals nuclear factor kappa B translocation in intact HL-60 cells. Yang, Z., Costanzo, M., Golde, D.W., Kolesnick, R.N. J. Biol. Chem. (1993) [Pubmed]
  22. Glucagon gene transcription in an islet cell line is regulated via a protein kinase C-activated pathway. Philippe, J., Drucker, D.J., Habener, J.F. J. Biol. Chem. (1987) [Pubmed]
  23. The effects of protein kinase-C agonists on parathyroid hormone release and intracellular free Ca2+ in bovine parathyroid cells. Membreño, L., Chen, T.H., Woodley, S., Gagucas, R., Shoback, D. Endocrinology (1989) [Pubmed]
  24. Activators of protein kinase C induce p34cdc2 histone H1 kinase stimulation in Swiss 3T3 fibroblasts. Takuwa, N., Zhou, W., Kumada, M., Takuwa, Y. Biochem. Biophys. Res. Commun. (1992) [Pubmed]
  25. Tumor necrosis factor-alpha activates pulmonary artery endothelial protein kinase C. Ferro, T.J., Parker, D.M., Commins, L.M., Phillips, P.G., Johnson, A. Am. J. Physiol. (1993) [Pubmed]
  26. The effect of phorbol esters and diacylglycerol analogues on the basal phosphoinositide turnover in isolated guinea pig hearts. Edes, I., Kranias, E.G. Cardioscience. (1990) [Pubmed]
 
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