Distearoylphosphatidylcholine

Last updated
Distearoylphosphatidylcholine
Distearoylphosphatidylcholine-line.png
Names
Systematic IUPAC name
(2R)-2,3-Bis(octadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
Other names
1,2-distearoyl-sn-glycero-3-phosphocholine, DSPC, 18:0 PC
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.011.309 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 212-440-2
PubChem CID
UNII
  • InChI=1S/C44H88NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h42H,6-41H2,1-5H3/t42-/m1/s1
    Key: NRJAVPSFFCBXDT-HUESYALOSA-N
  • O=C(OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C)CCCCCCCCCCCCCCCCC
Properties
C44H88NO8P
Molar mass 790.161 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Distearoylphosphatidylcholine is a phosphatidylcholine, a kind of phospholipid. It is a natural constituent of cell membranes, eg. soybean phosphatidylcholines are mostly different 18-carbon phosphatidylcholines (including minority of saturated DSPC), and their hydrogenation results in 85% DSPC. [1] It can be used to prepare lipid nanoparticles which are used in mRNA vaccines, [2] [3] In particular, it forms part of the drug delivery system for the Moderna and Pfizer COVID-19 vaccines. [4] [5]


See also

Moderna COVID-19 vaccine nanoparticle ingredients
Others

Related Research Articles

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Phospholipids are a class of lipids whose molecule has a hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue. Marine phospholipids typically have omega-3 fatty acids EPA and DHA integrated as part of the phospholipid molecule. The phosphate group can be modified with simple organic molecules such as choline, ethanolamine or serine.

<span class="mw-page-title-main">Liposome</span> Composite structures made of phospholipids and may contain small amounts of other molecules

A liposome is a small artificial vesicle, spherical in shape, having at least one lipid bilayer. Due to their hydrophobicity and/or hydrophilicity, biocompatibility, particle size and many other properties, liposomes can be used as drug delivery vehicles for administration of pharmaceutical drugs and nutrients, such as lipid nanoparticles in mRNA vaccines, and DNA vaccines. Liposomes can be prepared by disrupting biological membranes.

<span class="mw-page-title-main">Drug delivery</span> Methods for delivering drugs to target sites

Drug delivery refers to approaches, formulations, manufacturing techniques, storage systems, and technologies involved in transporting a pharmaceutical compound to its target site to achieve a desired therapeutic effect. Principles related to drug preparation, route of administration, site-specific targeting, metabolism, and toxicity are used to optimize efficacy and safety, and to improve patient convenience and compliance. Drug delivery is aimed at altering a drug's pharmacokinetics and specificity by formulating it with different excipients, drug carriers, and medical devices. There is additional emphasis on increasing the bioavailability and duration of action of a drug to improve therapeutic outcomes. Some research has also been focused on improving safety for the person administering the medication. For example, several types of microneedle patches have been developed for administering vaccines and other medications to reduce the risk of needlestick injury.

<span class="mw-page-title-main">PEGylation</span> Chemical reaction

PEGylation is the process of both covalent and non-covalent attachment or amalgamation of polyethylene glycol polymer chains to molecules and macrostructures, such as a drug, therapeutic protein or vesicle, which is then described as PEGylated. PEGylation affects the resulting derivatives or aggregates interactions, which typically slows down their coalescence and degradation as well as elimination in vivo.

<span class="mw-page-title-main">Solid lipid nanoparticle</span> Novel drug delivery system

Lipid nanoparticles (LNPs) are nanoparticles composed of lipids. They are a novel pharmaceutical drug delivery system, and a novel pharmaceutical formulation. LNPs as a drug delivery vehicle were first approved in 2018 for the siRNA drug Onpattro. LNPs became more widely known in late 2020, as some COVID-19 vaccines that use RNA vaccine technology coat the fragile mRNA strands with PEGylated lipid nanoparticles as their delivery vehicle.

Biomagnetics is a field of biotechnology. It has actively been researched since at least 2004. Although the majority of structures found in living organisms are diamagnetic, the magnetic field itself, as well as magnetic nanoparticles, microstructures and paramagnetic molecules can influence specific physiological functions of organisms under certain conditions. The effect of magnetic fields on biosystems is a topic of research that falls under the biomagnetic umbrella, as well as the construction of magnetic structures or systems that are either biocompatible, biodegradable or biomimetic. Magnetic nanoparticles and magnetic microparticles are known to interact with certain prokaryotes and certain eukaryotes.

<span class="mw-page-title-main">Moderna</span> American biotechnology company

Nanoparticles for drug delivery to the brain is a method for transporting drug molecules across the blood–brain barrier (BBB) using nanoparticles. These drugs cross the BBB and deliver pharmaceuticals to the brain for therapeutic treatment of neurological disorders. These disorders include Parkinson's disease, Alzheimer's disease, schizophrenia, depression, and brain tumors. Part of the difficulty in finding cures for these central nervous system (CNS) disorders is that there is yet no truly efficient delivery method for drugs to cross the BBB. Antibiotics, antineoplastic agents, and a variety of CNS-active drugs, especially neuropeptides, are a few examples of molecules that cannot pass the BBB alone. With the aid of nanoparticle delivery systems, however, studies have shown that some drugs can now cross the BBB, and even exhibit lower toxicity and decrease adverse effects throughout the body. Toxicity is an important concept for pharmacology because high toxicity levels in the body could be detrimental to the patient by affecting other organs and disrupting their function. Further, the BBB is not the only physiological barrier for drug delivery to the brain. Other biological factors influence how drugs are transported throughout the body and how they target specific locations for action. Some of these pathophysiological factors include blood flow alterations, edema and increased intracranial pressure, metabolic perturbations, and altered gene expression and protein synthesis. Though there exist many obstacles that make developing a robust delivery system difficult, nanoparticles provide a promising mechanism for drug transport to the CNS.

mRNA vaccine Type of vaccine

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<span class="mw-page-title-main">COVID-19 vaccine</span> Vaccine against SARS-CoV-2

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<span class="mw-page-title-main">Moderna COVID-19 vaccine</span> RNA COVID-19 vaccine

The Moderna COVID‑19 vaccine, sold under the brand name Spikevax, is a COVID-19 vaccine developed by American company Moderna, the United States National Institute of Allergy and Infectious Diseases (NIAID), and the Biomedical Advanced Research and Development Authority (BARDA). Depending on the jurisdiction, it is authorized for use in people aged six months, twelve years, or eighteen years and older. It provides protection against COVID-19 which is caused by infection by the SARS-CoV-2 virus. It is designed to be administered as two or three 0.5 mL doses given by intramuscular injection at an interval of at least 28 days apart.

<span class="mw-page-title-main">Katalin Karikó</span> Hungarian-American biochemist (born 1955)

Katalin "Kati" Karikó is a Hungarian-American biochemist who specializes in ribonucleic acid (RNA)-mediated mechanisms, particularly in vitro-transcribed messenger RNA (mRNA) for protein replacement therapy. Karikó laid the scientific groundwork for mRNA vaccines, overcoming major obstacles and skepticism in the scientific community. Karikó received the Nobel Prize in Physiology or Medicine in 2023 for her work, along with American immunologist Drew Weissman.

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The Pfizer–BioNTech COVID-19 vaccine, sold under the brand name Comirnaty, is an mRNA-based COVID-19 vaccine developed by the German biotechnology company BioNTech. For its development, BioNTech collaborated with American company Pfizer to carry out clinical trials, logistics, and manufacturing. It is authorized for use in people to provide protection against COVID-19, caused by infection with the SARS-CoV-2 virus. The vaccine is given by intramuscular injection. It is composed of nucleoside-modified mRNA (modRNA) encoding a mutated form of the full-length spike protein of SARS-CoV-2, which is encapsulated in lipid nanoparticles. Initial advice indicated that vaccination required two doses given 21 days apart, but the interval was later extended to up to 42 days in the US, and up to four months in Canada.

<span class="mw-page-title-main">ALC-0315</span> Chemical compound

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<span class="mw-page-title-main">Drew Weissman</span> American physician and immunologist (born 1959)

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<span class="mw-page-title-main">Intracellular delivery</span> Scientific research area

Intracellular delivery is the process of introducing external materials into living cells. Materials that are delivered into cells include nucleic acids, proteins, peptides, impermeable small molecules, synthetic nanomaterials, organelles, and micron-scale tracers, devices and objects. Such molecules and materials can be used to investigate cellular behavior, engineer cell operations or correct a pathological function.

<span class="mw-page-title-main">Acuitas Therapeutics</span> Canadian biotechnology company

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References

  1. van Hoogevest P, Wendel A (2014). "The use of natural and synthetic phospholipids as pharmaceutical excipients". The European Journal of Lipid Science and Technology. 116 (9): 1088–1107. doi:10.1002/ejlt.201400219. PMC   4207189 . PMID   25400504.
  2. Puri A, Loomis K, Smith B, Lee JH, Yavlovich A, Heldman E, Blumenthal R (2009). "Lipid-based nanoparticles as pharmaceutical drug carriers: from concepts to clinic". Critical Reviews in Therapeutic Drug Carrier Systems. 26 (6): 523–80. doi:10.1615/critrevtherdrugcarriersyst.v26.i6.10. PMC   2885142 . PMID   20402623.
  3. Salvatori G, Luberto L, and Marra E (2020). "SARS-CoV-2 SPIKE PROTEIN: an optimal immunological target for vaccines". Journal of Translational Medicine. 18 (1): 222. doi: 10.1186/s12967-020-02392-y . PMC   7268185 . PMID   32493510.
  4. "Moderna COVID-19 Vaccine Standing Orders for Administering Vaccine to Persons 18 Years of Age and Older" (PDF). Centers for Disease Control and Prevention (CDC).
  5. "Pfizer-BioNTech COVID-19 Vaccine EUA Fact Sheet for Recipients and Caregivers". Food and Drug Administration (FDA). 29 June 2022.