This article is about the functional group derived fromphosphocholine. For the class of phospholipids that incorporate choline as a headgroup, seephosphatidylcholine.
Phosphorylcholine (abbreviatedChoP) is thehydrophilic polar head group of somephospholipids, which is composed of a negatively charged phosphate bonded to a small, positively chargedcholine group. Phosphorylcholine is part of theplatelet-activating factor; thephospholipidphosphatidylcholine andsphingomyelin, the only phospholipid of themembrane that is not built with a glycerol backbone.[1] Treatment of cell membranes, like those ofRBCs, by certain enzymes, like somephospholipase A2, renders the phosphorylcholine moiety exposed to the external aqueous phase, and thus accessible for recognition by theimmune system.[2] Antibodies against phosphorylcholine are naturally occurring autoantibodies that are created by CD5+/B-1 B cells and are referred to as non-pathogenicautoantibodies.[3]
Ininterventional cardiology, phosphorylcholine is used as a synthetic polymer-basedcoating, applied todrug-eluting stents, to prevent the occurrence ofcoronary arteryrestenosis.[4] The first application of this approach for use of stents evolved from efforts by Hayward, Chapmanet al., who showed that the phosphorylcholine component of the outer surface of theerythrocytebilayer was non-thrombogenicity.[5] Until 2002, over 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.[6]
Drug-eluting stents (DES) are used by interventional cardiologists, operating on patients withcoronary artery disease. The stent is inserted into the artery via aballoon angioplasty. This will dilate the diameter of the coronary artery and keep it fixed in this phase so that more blood flows through the artery without the risk of blood clots (atherosclerosis).[7]
Phosphorylcholine is used as the polymer-based coating of a DES because its molecular design improves surface biocompatibility and lowers the risk of causing inflammation orthrombosis. Polymer coatings of stents that deliver the anti-proliferative drugZotarolimus to the arterial vessel wall are components of these medical devices. For targeted local delivery of Zotarolimus to the artery, the drug is incorporated into amethacrylate-based copolymer that includes a synthetic form of phosphorylcholine. This use ofbiomimicry, or the practice of using polymers that occur naturally in biology, provides a coating with minimal thrombus deposition and no adverse clinical effect on late healing of the arterial vessel wall. Not only is the coating non-thrombogenic, but it also exhibits other features that should be present when applying such a material to a medical device for long-term implantation. These include durability, neutrality to the chemistry of the incorporated drug and ability forsterilization using standard methods which do not affect drug structure or efficiency[citation needed]
^Karp, Gerald (2010).Cell and molecular biology: concepts and experiments (6 ed.). Hoboken, NJ: John Wiley. pp. 48, 123.ISBN978-0-470-48337-4.OCLC432406854.
^Beckmann, E.; Bach, M. A.; et al. (1984). "Phosphorylcholine on isologous red blood cells induces polyclonal but not anti-phosphorylcholine plaque-forming cells in mice".Eur J Immunol.14 (7):595–598.doi:10.1002/eji.1830140703.PMID6378644.S2CID37626179.
^Hardy, Richard (2008). "Chapter 7: B Lymphocyte Development and Biology". In Paul, William (ed.).Fundamental Immunology (Book) (6th ed.). Philadelphia: Lippincott Williams & Wilkins. pp. 237–269.ISBN978-0-7817-6519-0.
^J.A. Hayward and D. Chapman, Biomembrane surfaces as models for polymer design: the potential for haemocompatibility, Biomaterials 5 (1984), pp. 135–142.https://doi.org/10.1016/0142-9612(84)90047-4 Retrieved on 2009-02-09
^A.L. Lewis, L.A. Tolhurst and P.W. Stratford, Analysis of a phosphorylcholine-based polymer coating on a coronary stent pre- and post-implantation, Biomaterials 23 (2002), pp. 1697–1706.https://dx.doi.org/10.1016/S0142-9612(01)00297-6 Retrieved on 2009-02-09
^A. L. Lewis, P. W. Stratford, A. L. Lewis, R. T. Freeman, L. Hughes, R. P. Redman, L. A. Tolhurst and T. A. Vick, Abstracts of UKSB 1st Annual Conference, July 2000.https://doi.org/10.1023%2FA%3A1012803503667 Retrieved on 2009-02-09
