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Chemical Compound Review

DB00144     (2S)-2-amino-3-[[(2R)-2- butanoyloxy-3...

Synonyms: AC1O43S2, Phosphatidylserine, phosphatidyl-L-serine, LifeExtension PS Caps, O3-Phosphatidyl-L-serine, ...
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Disease relevance of Phosphatidylserine


Psychiatry related information on Phosphatidylserine


High impact information on Phosphatidylserine


Chemical compound and disease context of Phosphatidylserine


Biological context of Phosphatidylserine


Anatomical context of Phosphatidylserine


Associations of Phosphatidylserine with other chemical compounds


Gene context of Phosphatidylserine

  • ALA1 complements the deficiency in phosphatidylserine internalization into intact cells that is exhibited by the drs2 yeast mutant, and expression of ALA1 results in increased translocation of aminophospholipids in reconstituted yeast membrane vesicles [28].
  • However, cho1 yeast strains that are unable to synthesize PS do not phenocopy drs2 but instead transport proteins normally via the secretory pathway [29].
  • Therefore, whereas NBD-PS is a preferred substrate for Drs2p in vitro, endogenous PS is not an obligatory substrate in vivo for the role Drs2p plays in protein transport [29].
  • These data support a model for COAT-platelets where serotonin-derivatized procoagulant proteins interact with their respective receptors (eg, fibrinogen with glycoprotein IIb/IIIa or factor V with phosphatidylserine) as well as serotonin binding sites on fibrinogen and thrombospondin, resulting in a stable, multivalent complex on the cell surface [30].
  • Overexpression of cyclin E(276-395), but not of several other cyclin E mutants, specifically induced phosphatidylserine exposure and caspase activation in a dose-dependent manner, which were inhibited in Bcl-2-overexpressing cells or in the presence of zVAD-fmk [31].

Analytical, diagnostic and therapeutic context of Phosphatidylserine


  1. Exploring the mode-of-action of bioactive compounds by chemical-genetic profiling in yeast. Parsons, A.B., Lopez, A., Givoni, I.E., Williams, D.E., Gray, C.A., Porter, J., Chua, G., Sopko, R., Brost, R.L., Ho, C.H., Wang, J., Ketela, T., Brenner, C., Brill, J.A., Fernandez, G.E., Lorenz, T.C., Payne, G.S., Ishihara, S., Ohya, Y., Andrews, B., Hughes, T.R., Frey, B.J., Graham, T.R., Andersen, R.J., Boone, C. Cell (2006) [Pubmed]
  2. The introduction of poliovirus RNA into cells via lipid vesicles (liposomes). Wilson, T., Papahadjopoulos, D., Taber, R. Cell (1979) [Pubmed]
  3. Inhibition of VSV binding and infectivity by phosphatidylserine: is phosphatidylserine a VSV-binding site? Schlegel, R., Tralka, T.S., Willingham, M.C., Pastan, I. Cell (1983) [Pubmed]
  4. A receptor for phosphatidylserine-specific clearance of apoptotic cells. Fadok, V.A., Bratton, D.L., Rose, D.M., Pearson, A., Ezekewitz, R.A., Henson, P.M. Nature (2000) [Pubmed]
  5. A phospholipid derivative of cytosine arabinoside and its conversion to phosphatidylinositol by animal tissue. Raetz, C.R., Chu, M.Y., Srivastava, S., Turcotte, J.G. Science (1977) [Pubmed]
  6. Behavioral effects of phosphatidylserine in the aged Fischer 344 rat: amelioration of passive avoidance deficits without changes in psychomotor task performance. Corwin, J., Dean, R.L., Bartus, R.T., Rotrosen, J., Watkins, D.L. Neurobiol. Aging (1985) [Pubmed]
  7. Oral administration of soybean lecithin transphosphatidylated phosphatidylserine improves memory impairment in aged rats. Suzuki, S., Yamatoya, H., Sakai, M., Kataoka, A., Furushiro, M., Kudo, S. J. Nutr. (2001) [Pubmed]
  8. Reversal of scopolamine-induced amnesia by phosphatidylserine in rats. Zanotti, A., Valzelli, L., Toffano, G. Psychopharmacology (Berl.) (1986) [Pubmed]
  9. Double-blind cross-over study of phosphatidylserine vs. placebo in patients with early dementia of the Alzheimer type. Engel, R.R., Satzger, W., Günther, W., Kathmann, N., Bove, D., Gerke, S., Münch, U., Hippius, H. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology. (1992) [Pubmed]
  10. Effects of phosphatidylserine therapy in geriatric patients with depressive disorders. Maggioni, M., Picotti, G.B., Bondiolotti, G.P., Panerai, A., Cenacchi, T., Nobile, P., Brambilla, F. Acta psychiatrica Scandinavica. (1990) [Pubmed]
  11. Cell-surface calreticulin initiates clearance of viable or apoptotic cells through trans-activation of LRP on the phagocyte. Gardai, S.J., McPhillips, K.A., Frasch, S.C., Janssen, W.J., Starefeldt, A., Murphy-Ullrich, J.E., Bratton, D.L., Oldenborg, P.A., Michalak, M., Henson, P.M. Cell (2005) [Pubmed]
  12. Cloning and expression of multiple protein kinase C cDNAs. Knopf, J.L., Lee, M.H., Sultzman, L.A., Kriz, R.W., Loomis, C.R., Hewick, R.M., Bell, R.M. Cell (1986) [Pubmed]
  13. Identification of a factor that links apoptotic cells to phagocytes. Hanayama, R., Tanaka, M., Miwa, K., Shinohara, A., Iwamatsu, A., Nagata, S. Nature (2002) [Pubmed]
  14. Real-time imaging of apoptotic cell-membrane changes at the single-cell level in the beating murine heart. Dumont, E.A., Reutelingsperger, C.P., Smits, J.F., Daemen, M.J., Doevendans, P.A., Wellens, H.J., Hofstra, L. Nat. Med. (2001) [Pubmed]
  15. Activation of the alternative complement pathway by exposure of phosphatidylethanolamine and phosphatidylserine on erythrocytes from sickle cell disease patients. Wang, R.H., Phillips, G., Medof, M.E., Mold, C. J. Clin. Invest. (1993) [Pubmed]
  16. Nicotinamide: necessary nutrient emerges as a novel cytoprotectant for the brain. Maiese, K., Chong, Z.Z. Trends Pharmacol. Sci. (2003) [Pubmed]
  17. Phospholipids enhance the binding of peptides to class II major histocompatibility molecules. Roof, R.W., Luescher, I.F., Unanue, E.R. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  18. Membrane penetration of Sendai virus glycoproteins during the early stages of fusion with liposomes as determined by hydrophobic photoaffinity labeling. Novick, S.L., Hoekstra, D. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  19. Serine utilization as a precursor of phosphatidylserine and alkenyl-(plasmenyl)-, alkyl-, and acylethanolamine phosphoglycerides in cultured glioma cells. Xu, Z.L., Byers, D.M., Palmer, F.B., Spence, M.W., Cook, H.W. J. Biol. Chem. (1991) [Pubmed]
  20. Annexin-V imaging for noninvasive detection of cardiac allograft rejection. Narula, J., Acio, E.R., Narula, N., Samuels, L.E., Fyfe, B., Wood, D., Fitzpatrick, J.M., Raghunath, P.N., Tomaszewski, J.E., Kelly, C., Steinmetz, N., Green, A., Tait, J.F., Leppo, J., Blankenberg, F.G., Jain, D., Strauss, H.W. Nat. Med. (2001) [Pubmed]
  21. Molecular characterization of mitochondrial apoptosis-inducing factor. Susin, S.A., Lorenzo, H.K., Zamzami, N., Marzo, I., Snow, B.E., Brothers, G.M., Mangion, J., Jacotot, E., Costantini, P., Loeffler, M., Larochette, N., Goodlett, D.R., Aebersold, R., Siderovski, D.P., Penninger, J.M., Kroemer, G. Nature (1999) [Pubmed]
  22. Control of transmembrane lipid asymmetry in chromaffin granules by an ATP-dependent protein. Zachowski, A., Henry, J.P., Devaux, P.F. Nature (1989) [Pubmed]
  23. Inhibition of mast cell histamine secretion by N-substituteed derivatives of phosphatidylserine. Martin, T.W., Lagunoff, D. Science (1979) [Pubmed]
  24. Membrane and morphological changes in apoptotic cells regulated by caspase-mediated activation of PAK2. Rudel, T., Bokoch, G.M. Science (1997) [Pubmed]
  25. Transbilayer phospholipid asymmetry in Plasmodium knowlesi-infected host cell membrane. Gupta, C.M., Mishra, G.C. Science (1981) [Pubmed]
  26. NAD-induced T cell death: ADP-ribosylation of cell surface proteins by ART2 activates the cytolytic P2X7 purinoceptor. Seman, M., Adriouch, S., Scheuplein, F., Krebs, C., Freese, D., Glowacki, G., Deterre, P., Haag, F., Koch-Nolte, F. Immunity (2003) [Pubmed]
  27. Resistance to granzyme B-mediated cytochrome c release in Bak-deficient cells. Wang, G.Q., Wieckowski, E., Goldstein, L.A., Gastman, B.R., Rabinovitz, A., Gambotto, A., Li, S., Fang, B., Yin, X.M., Rabinowich, H. J. Exp. Med. (2001) [Pubmed]
  28. Chilling tolerance in Arabidopsis involves ALA1, a member of a new family of putative aminophospholipid translocases. Gomès, E., Jakobsen, M.K., Axelsen, K.B., Geisler, M., Palmgren, M.G. Plant Cell (2000) [Pubmed]
  29. Drs2p-coupled aminophospholipid translocase activity in yeast Golgi membranes and relationship to in vivo function. Natarajan, P., Wang, J., Hua, Z., Graham, T.R. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  30. Thrombospondin and fibrinogen bind serotonin-derivatized proteins on COAT-platelets. Szasz, R., Dale, G.L. Blood (2002) [Pubmed]
  31. Proteolytic cleavage of cyclin E leads to inactivation of associated kinase activity and amplification of apoptosis in hematopoietic cells. Mazumder, S., Gong, B., Chen, Q., Drazba, J.A., Buchsbaum, J.C., Almasan, A. Mol. Cell. Biol. (2002) [Pubmed]
  32. Evidence of lung surfactant abnormality in respiratory failure. Study of bronchoalveolar lavage phospholipids, surface activity, phospholipase activity, and plasma myoinositol. Hallman, M., Spragg, R., Harrell, J.H., Moser, K.M., Gluck, L. J. Clin. Invest. (1982) [Pubmed]
  33. Apoptosis induced by environmental stresses and amphotericin B in Candida albicans. Phillips, A.J., Sudbery, I., Ramsdale, M. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  34. Structural basis for autoantibody recognition of phosphatidylserine-beta 2 glycoprotein I and apoptotic cells. Cocca, B.A., Seal, S.N., D'Agnillo, P., Mueller, Y.M., Katsikis, P.D., Rauch, J., Weigert, M., Radic, M.Z. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  35. Intermembrane contact affects calcium binding to phospholipid vesicles. Ekerdt, R., Papahadjopoulos, D. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
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