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Chemical Compound Review

phosphocholine     trimethyl-(2- phosphonooxyethyl)azanium

Synonyms: CHOP, AG-H-34675, CHEBI:18132, HMDB01565, AC1L1AJH, ...
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Disease relevance of choline phosphate

  • Vaccinated mice developed a high titer of antibody to phosphorylcholine, which is known to protect against infection with Streptococcus pneumoniae [1].
  • Haemophilus influenzae undergoes phase variation in expression of the phosphorylcholine (ChoP) epitope, a structure present on several invasive pathogens residing in the human respiratory tract [2].
  • The many binding studies of monoclonal immunoglobulin (Ig) produced by plasmacytomas have found no universally common binding properties, but instead, groups of plasmacytomas with specific antigen-binding activities to haptens such as phosphorylcholine, dextrans, fructofuranans, or dinitrophenyl [3].
  • Elicitation of delayed-type hypersensitivity to phosphorylcholine by monoclonal anti-idiotypic antibodies in an allogeneic environment [4].
  • Studies with another monoclonal IgA antibody-containing antigen-binding activity to phosphorylcholine also demonstrated the ability of IgA antibody to cause acute lung injury in the rat [5].

Psychiatry related information on choline phosphate

  • In addition, the binding of labeled MOPC-167 to anti-A48 Id antibodies was not inhibited by PC but was inhibited by A48 and 3-76-42 MAb bearing A48, UPC-10 non-antigen-inhibitable idiotopes [6].
  • At early stages of Alzheimer's disease, phosphomonoesters (PMEs) including phosphocholine (P-choline) are present at elevated levels [7].
  • Six patients with vascular dementia had lower choline and elevated phosphocholine levels, when compared to controls, but normal levels of GPCh [8].
  • The new procedure, which used p-toulenesulfonate instead of 2-bromoethyl phosphorylcholine, not only reduced the reaction time but also allowed the reaction to proceed under mild conditions [9].

High impact information on choline phosphate


Chemical compound and disease context of choline phosphate


Biological context of choline phosphate


Anatomical context of choline phosphate


Associations of choline phosphate with other chemical compounds


Gene context of choline phosphate

  • Neutral sphingomyelinases sphingomyelin phosphodiesterase (SMPD)2 and -3 hydrolyze sphingomyelin to phosphocholine and ceramide. smpd2 is expressed ubiquitously, and smpd3 is expressed predominantly in neurons of the CNS [35].
  • In contrast, the lower concentration of 10 micromol/L U0126 for 40 hours had no significant effect on either P-ERK1/ 2 or phosphocholine levels in MDA-MB-231 cells [36].
  • Thus, phosphocholine has potential as a noninvasive pharmacodynamic marker for monitoring MAPK signaling blockade [36].
  • C-reactive protein (CRP), the major human acute-phase plasma protein, binds to phosphocholine (PCh) residues present in pneumococcal C-polysaccharide (PnC) of Streptococcus pneumoniae and to PCh exposed on damaged and apoptotic cells [37].
  • Immunomodulation via novel use of TLR4 by the filarial nematode phosphorylcholine-containing secreted product, ES-62 [38].

Analytical, diagnostic and therapeutic context of choline phosphate


  1. Monoclonal idiotope vaccine against Streptococcus pneumoniae infection. McNamara, M.K., Ward, R.E., Kohler, H. Science (1984) [Pubmed]
  2. Phosphorylcholine on the lipopolysaccharide of Haemophilus influenzae contributes to persistence in the respiratory tract and sensitivity to serum killing mediated by C-reactive protein. Weiser, J.N., Pan, N., McGowan, K.L., Musher, D., Martin, A., Richards, J. J. Exp. Med. (1998) [Pubmed]
  3. Restricted immunoglobulin variable region (Ig V) gene expression accompanies secondary rearrangements of light chain Ig V genes in mouse plasmacytomas. Diaw, L., Siwarski, D., Coleman, A., Kim, J., Jones, G.M., Dighiero, G., Huppi, K. J. Exp. Med. (1999) [Pubmed]
  4. Elicitation of delayed-type hypersensitivity to phosphorylcholine by monoclonal anti-idiotypic antibodies in an allogeneic environment. Arnold, B., Wallich, R., Hämmerling, G.J. J. Exp. Med. (1982) [Pubmed]
  5. Acute lung injury in rat caused by immunoglobulin A immune complexes. Johnson, K.J., Wilson, B.S., Till, G.O., Ward, P.A. J. Clin. Invest. (1984) [Pubmed]
  6. Idiotype-antiidiotype regulation. IV. Expression of common regulatory idiotopes on fructosan-binding and non-fructosan-binding monoclonal immunoglobulin. Goldberg, B., Paul, W.E., Bona, C.A. J. Exp. Med. (1983) [Pubmed]
  7. Elevated phosphocholine and phosphatidylcholine following rat entorhinal cortex lesions. Geddes, J.W., Panchalingam, K., Keller, J.N., Pettegrew, J.W. Neurobiol. Aging (1997) [Pubmed]
  8. Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Walter, A., Korth, U., Hilgert, M., Hartmann, J., Weichel, O., Hilgert, M., Fassbender, K., Schmitt, A., Klein, J. Neurobiol. Aging (2004) [Pubmed]
  9. Simplified methods for the synthesis of 2-hexadecanoylthio-1-ethylphosphorylcholine and for the determination of phospholipase A2 activity. Bhat, M.K., Mueller-Harvey, I., Sumner, I.G., Goodenough, P.W. Biochim. Biophys. Acta (1993) [Pubmed]
  10. Chimeric immunoglobulin-T cell receptor proteins form functional receptors: implications for T cell receptor complex formation and activation. Goverman, J., Gomez, S.M., Segesman, K.D., Hunkapiller, T., Laug, W.E., Hood, L. Cell (1990) [Pubmed]
  11. Antibody diversity: somatic hypermutation of rearranged VH genes. Kim, S., Davis, M., Sinn, E., Patten, P., Hood, L. Cell (1981) [Pubmed]
  12. Streptococcus pneumoniae anchor to activated human cells by the receptor for platelet-activating factor. Cundell, D.R., Gerard, N.P., Gerard, C., Idanpaan-Heikkila, I., Tuomanen, E.I. Nature (1995) [Pubmed]
  13. Phosphorylcholine acts as a Ca2+-dependent receptor molecule for lymphocyte perforin. Tschopp, J., Schäfer, S., Masson, D., Peitsch, M.C., Heusser, C. Nature (1989) [Pubmed]
  14. Inhibition of phosphorylcholine binding to antibodies using synthetic peptides. Lai, E.H., Kabat, E.A., Meienhofer, J., Heimer, E.P., Olson, A.J., Lerner, R. Nature (1987) [Pubmed]
  15. Acetyl glyceryl ether phosphorylcholine (AGEPC). A putative mediator of cardiac anaphylaxis in the guinea pig. Levi, R., Burke, J.A., Guo, Z.G., Hattori, Y., Hoppens, C.M., McManus, L.M., Hanahan, D.J., Pinckard, R.N. Circ. Res. (1984) [Pubmed]
  16. Molecular causes of the aberrant choline phospholipid metabolism in breast cancer. Glunde, K., Jie, C., Bhujwalla, Z.M. Cancer Res. (2004) [Pubmed]
  17. Alterations of choline phospholipid metabolism in ovarian tumor progression. Iorio, E., Mezzanzanica, D., Alberti, P., Spadaro, F., Ramoni, C., D'Ascenzo, S., Millimaggi, D., Pavan, A., Dolo, V., Canevari, S., Podo, F. Cancer Res. (2005) [Pubmed]
  18. Detection of increased choline compounds with proton nuclear magnetic resonance spectroscopy subsequent to malignant transformation of human prostatic epithelial cells. Ackerstaff, E., Pflug, B.R., Nelson, J.B., Bhujwalla, Z.M. Cancer Res. (2001) [Pubmed]
  19. "Nonspecific" immunoenhancing T cells in tumor-bearing mice include anti-idiotypic subsets. Behforouz, N., Eardley, D.D., Cerny, J. J. Immunol. (1983) [Pubmed]
  20. Assembly of a functional immunoglobulin Fv fragment in Escherichia coli. Skerra, A., Plückthun, A. Science (1988) [Pubmed]
  21. Phosphorylcholine-specific helper T cells in mice with an X-linked defect of antibody production to the same hapten. Kaplan, R.B., Quintáns, J. J. Exp. Med. (1979) [Pubmed]
  22. Interleukin 4 receptor signaling in human monocytes and U937 cells involves the activation of a phosphatidylcholine-specific phospholipase C: a comparison with chemotactic peptide, FMLP, phospholipase D, and sphingomyelinase. Ho, J.L., Zhu, B., He, S., Du, B., Rothman, R. J. Exp. Med. (1994) [Pubmed]
  23. Analysis of a T cell receptor gene as a target of the somatic hypermutation mechanism. Hackett, J., Stebbins, C., Rogerson, B., Davis, M.M., Storb, U. J. Exp. Med. (1992) [Pubmed]
  24. A new neuronal marker identified by phosphorylcholine-binding myeloma proteins. Hooghe-Peters, E.L., Fowlkes, B.J., Hooghe, R.J. Nature (1979) [Pubmed]
  25. IgG antibodies to phosphorylcholine exhibit more diversity than their IgM counterparts. Gearhart, P.J., Johnson, N.D., Douglas, R., Hood, L. Nature (1981) [Pubmed]
  26. Expression of phosphorylcholine-specific B cells during murine development. Sigal, N.H., Pickard, A.R., Metcalf, E.S., Gearhart, P.J., Klinman, N.R. J. Exp. Med. (1977) [Pubmed]
  27. Monoclonal antibodies against protease-sensitive pneumococcal antigens can protect mice from fatal infection with Streptococcus pneumoniae. McDaniel, L.S., Scott, G., Kearney, J.F., Briles, D.E. J. Exp. Med. (1984) [Pubmed]
  28. Subpopulations of B cells distinguished by cell surface expression of Ia antigens. Correlation of Ia and idiotype during activation by cloned Ia-restricted T cells. Bottomly, K., Jones, B., Kaye, J., Jones, F. J. Exp. Med. (1983) [Pubmed]
  29. A critical role of natural immunoglobulin M in immediate defense against systemic bacterial infection. Boes, M., Prodeus, A.P., Schmidt, T., Carroll, M.C., Chen, J. J. Exp. Med. (1998) [Pubmed]
  30. Alteration of clonal profile. III. T15 ontogenetic advantages are not sufficient for establishing idiotypic dominance in adoptive transfer. Quan, Z.S., Quintáns, J. J. Exp. Med. (1981) [Pubmed]
  31. Induction of idiotype-specific suppressor T cells with antigen/antibody complexes. Caulfield, M.J., Luce, K.J., Proffitt, M.R., Cerny, J. J. Exp. Med. (1983) [Pubmed]
  32. The xipotl mutant of Arabidopsis reveals a critical role for phospholipid metabolism in root system development and epidermal cell integrity. Cruz-Ramírez, A., López-Bucio, J., Ramírez-Pimentel, G., Zurita-Silva, A., Sánchez-Calderon, L., Ramírez-Chávez, E., González-Ortega, E., Herrera-Estrella, L. Plant Cell (2004) [Pubmed]
  33. Uptake of free choline by isolated perfused rat liver. Zeisel, S.H., Story, D.L., Wurtman, R.J., Brunengraber, H. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  34. Neisseria gonorrhoeae type IV pili undergo multisite, hierarchical modifications with phosphoethanolamine and phosphocholine requiring an enzyme structurally related to lipopolysaccharide phosphoethanolamine transferases. Aas, F.E., Egge-Jacobsen, W., Winther-Larsen, H.C., Løvold, C., Hitchen, P.G., Dell, A., Koomey, M. J. Biol. Chem. (2006) [Pubmed]
  35. Neutral sphingomyelinase 2 (smpd3) in the control of postnatal growth and development. Stoffel, W., Jenke, B., Blöck, B., Zumbansen, M., Koebke, J. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  36. Magnetic resonance spectroscopy monitoring of mitogen-activated protein kinase signaling inhibition. Beloueche-Babari, M., Jackson, L.E., Al-Saffar, N.M., Workman, P., Leach, M.O., Ronen, S.M. Cancer Res. (2005) [Pubmed]
  37. A C-reactive protein mutant that does not bind to phosphocholine and pneumococcal C-polysaccharide. Agrawal, A., Simpson, M.J., Black, S., Carey, M.P., Samols, D. J. Immunol. (2002) [Pubmed]
  38. Immunomodulation via novel use of TLR4 by the filarial nematode phosphorylcholine-containing secreted product, ES-62. Goodridge, H.S., Marshall, F.A., Else, K.J., Houston, K.M., Egan, C., Al-Riyami, L., Liew, F.Y., Harnett, W., Harnett, M.M. J. Immunol. (2005) [Pubmed]
  39. Molecular structures of cytidine-5'-diphosphate and cytidine-5'-diphospho-choline, and their role in intermidiary metabolism. Viswamitra, M.A., Seshadri, T.P., Post, M.L., Kennard, O. Nature (1975) [Pubmed]
  40. Antigen binding and idiotype analysis of antibodies obtained after electroporation of heavy and light chain genes encoding phosphocholine-specific antibodies: a model for T15-idiotype dominance. Kenny, J.J., Moratz, C.M., Guelde, G., O'Connell, C.D., George, J., Dell, C., Penner, S.J., Weber, J.S., Berry, J., Claflin, J.L. J. Exp. Med. (1992) [Pubmed]
  41. Continuous anti-interleukin 10 antibody administration depletes mice of Ly-1 B cells but not conventional B cells. Ishida, H., Hastings, R., Kearney, J., Howard, M. J. Exp. Med. (1992) [Pubmed]
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