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Details

Stereochemistry ACHIRAL
Molecular Formula C5H13NO4P.Ca.Cl
Molecular Weight 257.666
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CALCIUM PHOSPHORYLCHOLINE CHLORIDE

SMILES

[Cl-].[Ca++].C[N+](C)(C)CCOP([O-])([O-])=O

InChI

InChIKey=ICVPTJCCKTXCDT-UHFFFAOYSA-L
InChI=1S/C5H14NO4P.Ca.ClH/c1-6(2,3)4-5-10-11(7,8)9;;/h4-5H2,1-3H3,(H-,7,8,9);;1H/q;+2;/p-2

HIDE SMILES / InChI

Description

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

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PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Male Wistar rats were treated with Phosphorylcholine, 200mg/kg as single IV injection.
Route of Administration: Intravenous
In Vitro Use Guide
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.