Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H14NO4P |
| Molecular Weight | 183.1427 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| 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 |
|---|---|---|
| Glycosylated molecular variants of C-reactive proteins from the major carp Catla catla in fresh and polluted aquatic environments. | 2001 Jul |
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| An improved method for assaying phosphocholine and glycerophosphocholine in mouse tissue. | 2001 Sep-Oct |
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| Inhibition of phosphatidylcholine synthesis is associated with excitotoxic cell death in cerebellar granule cell cultures. | 2002 |
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| The M603 idiotype is lost in the response to phosphocholine in terminal deoxynucleotidyl transferase-deficient mice. | 2002 Apr |
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| Perturbations in choline metabolism cause neural tube defects in mouse embryos in vitro. | 2002 Apr |
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| Metabolic markers of breast cancer: enhanced choline metabolism and reduced choline-ether-phospholipid synthesis. | 2002 Apr 1 |
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| Transbilayer movement of fluorescent phospholipid analogues in the cytoplasmic membrane of Escherichia coli. | 2002 Apr 30 |
|
| Detection of polyol accumulation in a new ovarian carcinoma cell line, CABA I: a(1)H NMR study. | 2002 Apr 8 |
|
| In vivo brain (31)P-MRS: measuring the phospholipid resonances at 4 Tesla from small voxels. | 2002 Aug |
|
| The inhibitory effect of C-reactive protein on bacterial phosphorylcholine platelet-activating factor receptor-mediated adherence is blocked by surfactant. | 2002 Aug 1 |
|
| Identification of cellular sections with imaging mass spectrometry following freeze fracture. | 2002 Aug 15 |
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| The fine structure of Caenorhabditis elegans N-glycans. | 2002 Dec 20 |
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| Peptide conformational changes induced by tryptophan-phosphocholine interactions in a micelle. | 2002 Dec 5 |
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| A calorimetric study of phosphocholine membranes mixed with desmopressin and its diacylated prodrug derivative (DPP). | 2002 Feb 21 |
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| Intrathecal administration of liposomal neostigmine prolongs analgesia in mice. | 2002 Jan |
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| Structure-activity relationships of alkylphosphocholine derivatives: antineoplastic action on brain tumor cell lines in vitro. | 2002 Jul |
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| NMR and pattern recognition studies on liver extracts and intact livers from rats treated with alpha-naphthylisothiocyanate. | 2002 Jul 1 |
|
| The three-dimensional structure of calcium-depleted human C-reactive protein from perfectly twinned crystals. | 2002 Jun |
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| Protection from Streptococcus pneumoniae infection by C-reactive protein and natural antibody requires complement but not Fc gamma receptors. | 2002 Jun 15 |
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| Increased choline kinase activity in human breast carcinomas: clinical evidence for a potential novel antitumor strategy. | 2002 Jun 20 |
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| Breakdown of choline-containing phospholipids in rat brain during severe weight loss. | 2002 Jun 21 |
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| Interactions of cyclosporines with lipid membranes as studied by solid-state nuclear magnetic resonance spectroscopy and high-sensitivity titration calorimetry. | 2002 Mar |
|
| 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 Mar 15 |
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| Apoptosis is associated with triacylglycerol accumulation in Jurkat T-cells. | 2002 Mar 18 |
|
| Regulation of platelet adhesion by oxidized lipoproteins and oxidized phospholipids. | 2002 May |
|
| Changes of plasma free choline and choline-containing compounds' concentrations and choline loss during hemodialysis in ESRD patients. | 2002 May |
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| Beneficial effects of synthetic phospholipid polymer, poly(2-methacryloyloxyethyl phosphorylcholine-co-n-butyl methacrylate), on stratum corneum function. | 2002 May |
|
| Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of amphoteric glycolipid analogues from the porcine nematode, Ascaris suum. | 2002 May |
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| Molecular and biochemical characterization of a cold-regulated phosphoethanolamine N-methyltransferase from wheat. | 2002 May |
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| Diethanolamine induces hepatic choline deficiency in mice. | 2002 May |
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| Protein encapsulation in liposomes: efficiency depends on interactions between protein and phospholipid bilayer. | 2002 May 10 |
|
| Real-time changes in 1H and 31P NMR spectra of malignant human mammary epithelial cells during treatment with the anti-inflammatory agent indomethacin. | 2002 Nov |
|
| Inhibition of CTP:phosphocholine cytidylyltransferase by C(2)-ceramide and its relationship to apoptosis. | 2002 Nov |
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| Evolution of catalytic antibody repertoire in autoimmune mice. | 2002 Nov 1 |
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| Choline transport in Leishmania major promastigotes and its inhibition by choline and phosphocholine analogs. | 2002 Nov-Dec |
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| Biochemical correlates of thiazolidinedione-induced adipocyte differentiation by high-resolution magic angle spinning NMR spectroscopy. | 2002 Oct |
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| Phosphomonoester concentrations differ between chronic lymphocytic leukemia cells and normal human lymphocytes. | 2002 Oct |
|
| Binding of C-reactive protein to modified low-density-lipoprotein particles: identification of cholesterol as a novel ligand for C-reactive protein. | 2002 Oct 15 |
|
| Rapid transbilayer movement of the fluorescent sterol dehydroergosterol in lipid membranes. | 2002 Sep |
|
| Quantitation of choline and its metabolites in tissues and foods by liquid chromatography/electrospray ionization-isotope dilution mass spectrometry. | 2002 Sep 15 |
|
| A C-reactive protein mutant that does not bind to phosphocholine and pneumococcal C-polysaccharide. | 2002 Sep 15 |
|
| Phosphorylation of Saccharomyces cerevisiae choline kinase on Ser30 and Ser85 by protein kinase A regulates phosphatidylcholine synthesis by the CDP-choline pathway. | 2002 Sep 20 |
|
| Use of radiolabelled choline as a pharmacodynamic marker for the signal transduction inhibitor geldanamycin. | 2002 Sep 23 |
|
| Quantitative HRMAS proton total correlation spectroscopy applied to cultured melanoma cells treated by chloroethyl nitrosourea: demonstration of phospholipid metabolism alterations. | 2003 Feb |
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| In vivo and in vitro MR spectroscopic profile of central neurocytomas. | 2003 Feb |
|
| Structural elucidation of zwitterionic carbohydrates derived from glycosphingolipids of the porcine parasitic nematode Ascaris suum. | 2003 Jan 1 |
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| Quantitative detection of C-reactive protein using phosphocholine-labelled enzyme or microspheres. | 2003 Jan 15 |
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| Choline head groups stabilize the matrix loop regions of the ATP/ADP carrier ScAAC2. | 2003 Jan 3 |
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| Biosynthesis of phosphatidylcholine in bacteria. | 2003 Mar |
|
| Phosphatidylethanolamine N-methyltransferase (PEMT) knockout mice have hepatic steatosis and abnormal hepatic choline metabolite concentrations despite ingesting a recommended dietary intake of choline. | 2003 Mar 15 |
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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645-84-1
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SUBSTANCE RECORD
