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Chemical Compound Review

AC1NRAI3     [(2R)-1-[[3-[[(2R)-2,3...

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Disease relevance of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid


Psychiatry related information on [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid


High impact information on [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid


Chemical compound and disease context of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid


Biological context of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid


Anatomical context of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid


Associations of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid with other chemical compounds

  • A significant increase in functional affinity for purified megalin was observed when beta2-glycoprotein-I was bound to the acidic phospholipids, phosphatidylserine and cardiolipin [25].
  • In addition to a cardiolipin that has previously been reported [McAuley, K. E., Fyfe, P. K., Ridge, J. P., Isaacs, N. W., Cogdell, R. J. & Jones, M. R. (1999) Proc. Natl. Acad. Sci. USA 96, 14706-14711], two other major lipids of the cell membrane are found, a phosphatidylcholine and a glucosylgalactosyl diacylglycerol [26].
  • Specific rabbit anti-cardiolipin (anti-CL) antibodies were used to investigate the hypothesis that cardiolipin, associated with mitochondrial membrane proteins, binds C1 and facilitates activation of the complement cascade following reperfusion of ischemic myocardium [27].
  • Circulating autoantibodies to oxidized cardiolipin correlate with isoprostane F(2alpha)-VI levels and the extent of atherosclerosis in ApoE-deficient mice: modulation by vitamin E [28].
  • The effect of cholic acid on both cardiolipin-mediated Na+ partition and Na+ translocation across the chloroform phase showed a marked dependence on pH, being greater at pH 7.4.(ABSTRACT TRUNCATED AT 250 WORDS)[29]

Gene context of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid

  • Translational regulation of nuclear gene COX4 expression by mitochondrial content of phosphatidylglycerol and cardiolipin in Saccharomyces cerevisiae [30].
  • In mice lacking alpha-synuclein (Snca-/-), total brain steady-state mass of the mitochondria-specific phospholipid, cardiolipin, is reduced 22% and its acyl side chains show a 51% increase in saturated FAs and a 25% reduction in essential n-6, but not n-3, polyunsaturated FAs [31].
  • tBid interaction with cardiolipin primarily orchestrates mitochondrial dysfunctions and subsequently activates Bax and Bak [32].
  • Phosphatidylglycerophosphate synthase catalyzes the committed step in the synthesis of the mitochondrial phospholipid cardiolipin [33].
  • Interestingly, the growth defect of isc1Delta strains resembled that of pgs1Delta strains, lacking the committed step in the synthesis of phosphatidylglycerol (PG) and cardiolipin (CL), which were shown to activate Isc1p in vitro [34].

Analytical, diagnostic and therapeutic context of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid


  1. Antibody to cardiolipin as a predictor of fetal distress or death in pregnant patients with systemic lupus erythematosus. Lockshin, M.D., Druzin, M.L., Goei, S., Qamar, T., Magid, M.S., Jovanovic, L., Ferenc, M. N. Engl. J. Med. (1985) [Pubmed]
  2. Lupus anticoagulant activity of autoimmune antiphospholipid antibodies is dependent upon beta 2-glycoprotein I. Roubey, R.A., Pratt, C.W., Buyon, J.P., Winfield, J.B. J. Clin. Invest. (1992) [Pubmed]
  3. Cardiolipin antibodies in survivors of myocardial infarction. Cortellaro, M., Cofrancesco, E., Boschetti, C. Lancet (1993) [Pubmed]
  4. Cholestasis confers resistance to the rat liver mitochondrial permeability transition. Lieser, M.J., Park, J., Natori, S., Jones, B.A., Bronk, S.F., Gores, G.J. Gastroenterology (1998) [Pubmed]
  5. Monoclonal anticardiolipin antibodies derived from mice with experimental lupus erythematosus: characterization and the induction of a secondary antiphospholipid syndrome. Sthoeger, Z.M., Tartakovsky, B., Bentwich, Z., Mozes, E. J. Clin. Immunol. (1993) [Pubmed]
  6. Content and fatty acid composition of cardiolipin in the brain of patients with Alzheimer's disease. Guan, Z.Z., Söderberg, M., Sindelar, P., Edlund, C. Neurochem. Int. (1994) [Pubmed]
  7. Absence of antibodies to cardiolipin in patients with Huntington's chorea, Sydenhams chorea and acute rheumatic fever. Asherson, R.A., Hughes, G.R., Gledhill, R., Quinn, N.P. J. Neurol. Neurosurg. Psychiatr. (1988) [Pubmed]
  8. Deficiency in CD22, a B cell-specific inhibitory receptor, is sufficient to predispose to development of high affinity autoantibodies. O'Keefe, T.L., Williams, G.T., Batista, F.D., Neuberger, M.S. J. Exp. Med. (1999) [Pubmed]
  9. Polyspecific monoclonal lupus autoantibodies reactive with both polynucleotides and phospholipids. Lafer, E.M., Rauch, J., Andrzejewski, C., Mudd, D., Furie, B., Furie, B., Schwartz, R.S., Stollar, B.D. J. Exp. Med. (1981) [Pubmed]
  10. Cardiolipin provides specificity for targeting of tBid to mitochondria. Lutter, M., Fang, M., Luo, X., Nishijima, M., Xie, X., Wang, X. Nat. Cell Biol. (2000) [Pubmed]
  11. Properties of an acid phosphatase in pulmonary surfactant. Benson, B.J. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  12. Phospholipid in the hexagonal II phase is immunogenic: evidence for immunorecognition of nonbilayer lipid phases in vivo. Rauch, J., Janoff, A.S. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  13. Pharmacological, toxicological, and therapeutic evaluation in mice of doxorubicin entrapped in cardiolipin liposomes. Rahman, A., White, G., More, N., Schein, P.S. Cancer Res. (1985) [Pubmed]
  14. An IgG antiprothrombin antibody enhances prothrombin binding to damaged endothelial cells and shortens plasma coagulation times. Zhao, Y., Rumold, R., Zhu, M., Zhou, D., Ahmed, A.E., Le, D.T., Hahn, B.H., Woods, V.L., Chen, P.P. Arthritis Rheum. (1999) [Pubmed]
  15. Saturated fatty acid-induced apoptosis in MDA-MB-231 breast cancer cells. A role for cardiolipin. Hardy, S., El-Assaad, W., Przybytkowski, E., Joly, E., Prentki, M., Langelier, Y. J. Biol. Chem. (2003) [Pubmed]
  16. The superoxide dismutase mimetic MnTBAP prevents Fas-induced acute liver failure in the mouse. Malassagne, B., Ferret, P.J., Hammoud, R., Tulliez, M., Bedda, S., Trébéden, H., Jaffray, P., Calmus, Y., Weill, B., Batteux, F. Gastroenterology (2001) [Pubmed]
  17. Autoimmunity to cardiolipin in infectious mononucleosis. Misra, R., Venables, P.J., Watkins, R.P., Maini, R.N. Lancet (1987) [Pubmed]
  18. Recurrent miscarriage. II: Clinical associations, causes, and management. Stirrat, G.M. Lancet (1990) [Pubmed]
  19. Non-bilayer lipids are required for efficient protein transport across the plasma membrane of Escherichia coli. Rietveld, A.G., Koorengevel, M.C., de Kruijff, B. EMBO J. (1995) [Pubmed]
  20. Evidence for multiple mechanisms of polyclonal T cell activation in murine lupus. Singh, R.R., Hahn, B.H., Tsao, B.P., Ebling, F.M. J. Clin. Invest. (1998) [Pubmed]
  21. Activation of cultured vascular endothelial cells by antiphospholipid antibodies. Simantov, R., LaSala, J.M., Lo, S.K., Gharavi, A.E., Sammaritano, L.R., Salmon, J.E., Silverstein, R.L. J. Clin. Invest. (1995) [Pubmed]
  22. Polypeptide and phospholipid composition of the membrane of rat liver peroxisomes: comparison with endoplasmic reticulum and mitochondrial membranes. Fujiki, Y., Fowler, S., Shio, H., Hubbard, A.L., Lazarow, P.B. J. Cell Biol. (1982) [Pubmed]
  23. Antibodies to endothelial cells in borderline hypertension. Frostegård, J., Wu, R., Gillis-Haegerstrand, C., Lemne, C., de Faire, U. Circulation (1998) [Pubmed]
  24. Structural details of an interaction between cardiolipin and an integral membrane protein. McAuley, K.E., Fyfe, P.K., Ridge, J.P., Isaacs, N.W., Cogdell, R.J., Jones, M.R. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  25. beta2-glycoprotein-I (apolipoprotein H) and beta2-glycoprotein-I-phospholipid complex harbor a recognition site for the endocytic receptor megalin. Moestrup, S.K., Schousboe, I., Jacobsen, C., Leheste, J.R., Christensen, E.I., Willnow, T.E. J. Clin. Invest. (1998) [Pubmed]
  26. Interactions between lipids and bacterial reaction centers determined by protein crystallography. Camara-Artigas, A., Brune, D., Allen, J.P. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  27. Cardiolipin-protein complexes and initiation of complement activation after coronary artery occlusion. Rossen, R.D., Michael, L.H., Hawkins, H.K., Youker, K., Dreyer, W.J., Baughn, R.E., Entman, M.L. Circ. Res. (1994) [Pubmed]
  28. Circulating autoantibodies to oxidized cardiolipin correlate with isoprostane F(2alpha)-VI levels and the extent of atherosclerosis in ApoE-deficient mice: modulation by vitamin E. Praticò, D., Tangirala, R.K., Hörkkö, S., Witztum, J.L., Palinski, W., FitzGerald, G.A. Blood (2001) [Pubmed]
  29. Phospholipids and bile acids as diffusional carriers of Na+ across nonpolar media. Accatino, L., Gavilan, P. Hepatology (1988) [Pubmed]
  30. Translational regulation of nuclear gene COX4 expression by mitochondrial content of phosphatidylglycerol and cardiolipin in Saccharomyces cerevisiae. Su, X., Dowhan, W. Mol. Cell. Biol. (2006) [Pubmed]
  31. Mitochondrial lipid abnormality and electron transport chain impairment in mice lacking alpha-synuclein. Ellis, C.E., Murphy, E.J., Mitchell, D.C., Golovko, M.Y., Scaglia, F., Barceló-Coblijn, G.C., Nussbaum, R.L. Mol. Cell. Biol. (2005) [Pubmed]
  32. tBid interaction with cardiolipin primarily orchestrates mitochondrial dysfunctions and subsequently activates Bax and Bak. Gonzalvez, F., Pariselli, F., Dupaigne, P., Budihardjo, I., Lutter, M., Antonsson, B., Diolez, P., Manon, S., Martinou, J.C., Goubern, M., Wang, X., Bernard, S., Petit, P.X. Cell Death Differ. (2005) [Pubmed]
  33. Regulation of phosphatidylglycerophosphate synthase by inositol in Saccharomyces cerevisiae is not at the level of PGS1 mRNA abundance. Zhong, Q., Greenberg, M.L. J. Biol. Chem. (2003) [Pubmed]
  34. The phosphatidylglycerol/cardiolipin biosynthetic pathway is required for the activation of inositol phosphosphingolipid phospholipase C, Isc1p, during growth of Saccharomyces cerevisiae. Vaena de Avalos, S., Su, X., Zhang, M., Okamoto, Y., Dowhan, W., Hannun, Y.A. J. Biol. Chem. (2005) [Pubmed]
  35. Modifications of anionic-lipid domains preceding membrane fusion in guinea pig sperm. Bearer, E.L., Friend, D.S. J. Cell Biol. (1982) [Pubmed]
  36. Specific roles of protein-phospholipid interactions in the yeast cytochrome bc1 complex structure. Lange, C., Nett, J.H., Trumpower, B.L., Hunte, C. EMBO J. (2001) [Pubmed]
  37. The nature of the inhibition of 4,7-dioxobenzothiazole derivatives on mitochondrial ubiquinol-cytochrome c reductase. Yang, F.D., Yu, L., Yu, C.A. J. Biol. Chem. (1989) [Pubmed]
  38. A chimeric antibody with the human gamma1 constant region as a putative standard for assays to detect IgG beta2-glycoprotein I-dependent anticardiolipin and anti-beta2-glycoprotein I antibodies. Ichikawa, K., Tsutsumi, A., Atsumi, T., Matsuura, E., Kobayashi, S., Hughes, G.R., Khamashta, M.A., Koike, T. Arthritis Rheum. (1999) [Pubmed]
  39. Mitochondrial contact sites. Lipid composition and dynamics. Ardail, D., Privat, J.P., Egret-Charlier, M., Levrat, C., Lerme, F., Louisot, P. J. Biol. Chem. (1990) [Pubmed]
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