Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H14NO4P |
| Molecular Weight | 183.1427 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[N+](C)(C)CCOP(O)([O-])=O
InChI
InChIKey=YHHSONZFOIEMCP-UHFFFAOYSA-N
InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)
DescriptionCurator's Comment: The description was created based on several sources, including
http://www.hmdb.ca/metabolites/HMDB01565 | https://www.ncbi.nlm.nih.gov/pubmed/11922473 | https://www.ncbi.nlm.nih.gov/pubmed/10203703 | https://www.ncbi.nlm.nih.gov/pubmed/5808301
Curator's Comment: The description was created based on several sources, including
http://www.hmdb.ca/metabolites/HMDB01565 | https://www.ncbi.nlm.nih.gov/pubmed/11922473 | https://www.ncbi.nlm.nih.gov/pubmed/10203703 | https://www.ncbi.nlm.nih.gov/pubmed/5808301
Phosphorylcholine (ChoP) is a small zwitterionic amino alcohol, which is composed of a negatively charged phosphate bonded to a small, positively charged choline group. Phosphorylcholine is the precursor metabolite of choline in the glycine, serine, and threonine metabolism pathways and in intermediate between choline and cytidine-diphosphate choline in the glycerophospholipid metabolism pathway. Phosphorylcholine is an interesting compound from an immunologic point of view, being an immunodominant determinant of pneumococcal teichoic acids and also a major prerequisite for proinflammatory effects of PAF and PAF-like lipids where PC is a common denominator. PC is also a component of some bacteria, apoptotic cells, and OxLDL, which, if exposed, is immunogenic. PC has several properties that could in principle both promote and protect against disease, depending on the pathogen and type of inflammatory reaction. In the field of interventional cardiology, phosphorylcholine is used as a synthetic polymer-based coating, applied to drug-eluting stents, to prevent the occurrence of coronary artery restenosis. To date, more than 120,000 Phosphorylcholine-coated stents have been implanted in patients with no apparent deleterious effect in the long term compared to bare metal stent technologies
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Phosphatidylethanolamine N-methyltransferase (PEMT) knockout mice have hepatic steatosis and abnormal hepatic choline metabolite concentrations despite ingesting a recommended dietary intake of choline. | 2003-03-15 |
|
| Biosynthesis of phosphatidylcholine in bacteria. | 2003-03 |
|
| Quantitative HRMAS proton total correlation spectroscopy applied to cultured melanoma cells treated by chloroethyl nitrosourea: demonstration of phospholipid metabolism alterations. | 2003-02 |
|
| In vivo and in vitro MR spectroscopic profile of central neurocytomas. | 2003-02 |
|
| Quantitative detection of C-reactive protein using phosphocholine-labelled enzyme or microspheres. | 2003-01-15 |
|
| Choline head groups stabilize the matrix loop regions of the ATP/ADP carrier ScAAC2. | 2003-01-03 |
|
| Structural elucidation of zwitterionic carbohydrates derived from glycosphingolipids of the porcine parasitic nematode Ascaris suum. | 2003-01-01 |
|
| The fine structure of Caenorhabditis elegans N-glycans. | 2002-12-20 |
|
| An improved method for assaying phosphocholine and glycerophosphocholine in mouse tissue. | 2002-12-17 |
|
| Choline transport in Leishmania major promastigotes and its inhibition by choline and phosphocholine analogs. | 2002-12-07 |
|
| Peptide conformational changes induced by tryptophan-phosphocholine interactions in a micelle. | 2002-12-05 |
|
| Evolution of catalytic antibody repertoire in autoimmune mice. | 2002-11-01 |
|
| Real-time changes in 1H and 31P NMR spectra of malignant human mammary epithelial cells during treatment with the anti-inflammatory agent indomethacin. | 2002-11 |
|
| Inhibition of CTP:phosphocholine cytidylyltransferase by C(2)-ceramide and its relationship to apoptosis. | 2002-11 |
|
| Binding of C-reactive protein to modified low-density-lipoprotein particles: identification of cholesterol as a novel ligand for C-reactive protein. | 2002-10-15 |
|
| Biochemical correlates of thiazolidinedione-induced adipocyte differentiation by high-resolution magic angle spinning NMR spectroscopy. | 2002-10 |
|
| Phosphomonoester concentrations differ between chronic lymphocytic leukemia cells and normal human lymphocytes. | 2002-10 |
|
| Use of radiolabelled choline as a pharmacodynamic marker for the signal transduction inhibitor geldanamycin. | 2002-09-23 |
|
| Phosphorylation of Saccharomyces cerevisiae choline kinase on Ser30 and Ser85 by protein kinase A regulates phosphatidylcholine synthesis by the CDP-choline pathway. | 2002-09-20 |
|
| Quantitation of choline and its metabolites in tissues and foods by liquid chromatography/electrospray ionization-isotope dilution mass spectrometry. | 2002-09-15 |
|
| A C-reactive protein mutant that does not bind to phosphocholine and pneumococcal C-polysaccharide. | 2002-09-15 |
|
| Rapid transbilayer movement of the fluorescent sterol dehydroergosterol in lipid membranes. | 2002-09 |
|
| Identification of cellular sections with imaging mass spectrometry following freeze fracture. | 2002-08-15 |
|
| The inhibitory effect of C-reactive protein on bacterial phosphorylcholine platelet-activating factor receptor-mediated adherence is blocked by surfactant. | 2002-08-01 |
|
| In vivo brain (31)P-MRS: measuring the phospholipid resonances at 4 Tesla from small voxels. | 2002-08 |
|
| NMR and pattern recognition studies on liver extracts and intact livers from rats treated with alpha-naphthylisothiocyanate. | 2002-07-01 |
|
| Structure-activity relationships of alkylphosphocholine derivatives: antineoplastic action on brain tumor cell lines in vitro. | 2002-07 |
|
| Breakdown of choline-containing phospholipids in rat brain during severe weight loss. | 2002-06-21 |
|
| Increased choline kinase activity in human breast carcinomas: clinical evidence for a potential novel antitumor strategy. | 2002-06-20 |
|
| Protection from Streptococcus pneumoniae infection by C-reactive protein and natural antibody requires complement but not Fc gamma receptors. | 2002-06-15 |
|
| The three-dimensional structure of calcium-depleted human C-reactive protein from perfectly twinned crystals. | 2002-06 |
|
| Protein encapsulation in liposomes: efficiency depends on interactions between protein and phospholipid bilayer. | 2002-05-10 |
|
| Regulation of platelet adhesion by oxidized lipoproteins and oxidized phospholipids. | 2002-05 |
|
| Changes of plasma free choline and choline-containing compounds' concentrations and choline loss during hemodialysis in ESRD patients. | 2002-05 |
|
| Beneficial effects of synthetic phospholipid polymer, poly(2-methacryloyloxyethyl phosphorylcholine-co-n-butyl methacrylate), on stratum corneum function. | 2002-05 |
|
| Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of amphoteric glycolipid analogues from the porcine nematode, Ascaris suum. | 2002-05 |
|
| Molecular and biochemical characterization of a cold-regulated phosphoethanolamine N-methyltransferase from wheat. | 2002-05 |
|
| Diethanolamine induces hepatic choline deficiency in mice. | 2002-05 |
|
| Transbilayer movement of fluorescent phospholipid analogues in the cytoplasmic membrane of Escherichia coli. | 2002-04-30 |
|
| Detection of polyol accumulation in a new ovarian carcinoma cell line, CABA I: a(1)H NMR study. | 2002-04-08 |
|
| Metabolic markers of breast cancer: enhanced choline metabolism and reduced choline-ether-phospholipid synthesis. | 2002-04-01 |
|
| The M603 idiotype is lost in the response to phosphocholine in terminal deoxynucleotidyl transferase-deficient mice. | 2002-04 |
|
| Perturbations in choline metabolism cause neural tube defects in mouse embryos in vitro. | 2002-04 |
|
| Apoptosis is associated with triacylglycerol accumulation in Jurkat T-cells. | 2002-03-18 |
|
| Melanoma tumors acquire a new phospholipid metabolism phenotype under cystemustine as revealed by high-resolution magic angle spinning proton nuclear magnetic resonance spectroscopy of intact tumor samples. | 2002-03-15 |
|
| Interactions of cyclosporines with lipid membranes as studied by solid-state nuclear magnetic resonance spectroscopy and high-sensitivity titration calorimetry. | 2002-03 |
|
| A calorimetric study of phosphocholine membranes mixed with desmopressin and its diacylated prodrug derivative (DPP). | 2002-02-21 |
|
| Intrathecal administration of liposomal neostigmine prolongs analgesia in mice. | 2002-01 |
|
| Inhibition of phosphatidylcholine synthesis is associated with excitotoxic cell death in cerebellar granule cell cultures. | 2002 |
|
| Glycosylated molecular variants of C-reactive proteins from the major carp Catla catla in fresh and polluted aquatic environments. | 2001-07 |
Patents
Sample Use Guides
Male Wistar rats were treated with Phosphorylcholine, 200mg/kg as single IV injection.
Route of Administration:
Intravenous
Red blood cells from BALB/c mice (MRBC) were either conjugated with PC (Phosphorylcholine), 2,4,6-trinitrophenyl (TNP) or treated with phospholipase A2 (PLA2) to expose PC on the cell membrane (determined by hemagglutination with the anti-PC myeloma HOPC8). When BALB/c mice were immunized i.v. with the conjugated or enzyme-treated MRBC, a significant polyclonal antibody response occurred (p less than 0.05) using PC-MRBC or PLA2-treated MRBC, but not with TNP-MRBC or sham-treated MRBC. No anti-PC or anti-MRBC immunoglobulin-secreting cells developed after immunization. Repeated immunization with PC-MRBC resulted in similar levels of protein A PFC after each immunization but no anti-PC, anti-MRBC or anti-PC-MRBC PFC.
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SUBSTANCE RECORD
