SM-102
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SM-102
SM-102 is a synthetic amino lipid which is used in combination with other lipids to form lipid nanoparticles. These are used for the delivery of mRNA-based vaccines, and in particular SM-102 forms part of the drug delivery system for the Moderna COVID-19 vaccine. Lipid nanoparticles are an extension of earlier RNA transfection methods such as cationic liposomes. Such systems are needed to protect the delicate mRNA molecules and shuttle them into cells without the immune system destroying them first. The nanoparticles enter the cells by triggering receptor-mediated endocytosis. Ionisable lipids like SM-102 hold a relatively (/ close to) neutral charge at physiological pH but are positively charged within the nanoparticle (the amine group is protonated to form an ammonium cation). This allows them to bind to the negatively charged backbone of mRNA. The rest of the nanoparticle is formed from PEGylated lipids, which help stabilize the particle, and phospholipids and cholesterol ...
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Lipid Nanoparticle
Lipid-based nanoparticles are very small spherical particles composed of lipids. They are a novel pharmaceutical drug delivery system (part of nanoparticle drug delivery), and a novel pharmaceutical formulation. There are many subclasses of lipid-based nanoparticles such as: lipid nanoparticles (LNPs), solid lipid nanoparticles (SLNs), and nanostructured lipid carriers (NLCs). Sometimes the term "LNP" describes all lipid-based nanoparticles. In specific applications, LNPs describe a specific type of lipid-based nanoparticle, such as the LNPs used for the mRNA vaccine. Using LNPs for drug delivery was first approved in 2018 for the siRNA drug Onpattro. LNPs became more widely known late in 2020, as some COVID-19 vaccines that use RNA vaccine technology coat the fragile mRNA strands with PEGylated lipid nanoparticles as their delivery vehicle (including both the Moderna and the Pfizer–BioNTech COVID-19 vaccines). Characteristics A lipid nanoparticle is typically spheri ...
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Moderna COVID-19 Vaccine
The Moderna COVID19 vaccine, sold under the brand name Spikevax, is a COVID-19 vaccine developed by the 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 humans aged six months, twelve years, or eighteen years and older. It provides protection against COVID-19, which is caused by infection by the Severe acute respiratory syndrome coronavirus 2, SARS-CoV-2 virus. It is designed to be administered in two or three 0.5-Litre#SI prefixes applied to the litre, mL doses given by intramuscular injection, primarily into the deltoid muscle, at an interval of at least 28 days apart. The World Health Organization advises an eight-week interval between doses to optimize efficacy. Additional booster doses are approved in some regions to maintain immunity. Clinical trials and real-world data have demonst ...
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DMG-PEG 2000
DMG-PEG 2000 is a synthetic lipid formed by the PEGylation of myristoyl diglyceride. It is used to manufacture lipid nanoparticles that are used in mRNA vaccines, and in particular forms part of the drug delivery system for the Moderna COVID-19 vaccine. See also ;Moderna COVID-19 vaccine nanoparticle ingredients * Distearoylphosphatidylcholine * SM-102 *Cholesterol Cholesterol is the principal sterol of all higher animals, distributed in body Tissue (biology), tissues, especially the brain and spinal cord, and in Animal fat, animal fats and oils. Cholesterol is biosynthesis, biosynthesized by all anima ... References {{Reflist Excipients Polyethers Polymers ...
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Distearoylphosphatidylcholine
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. It can be used to prepare lipid nanoparticles which are used in mRNA vaccines, In particular, it forms part of the drug delivery system for the Moderna and Pfizer COVID-19 vaccines. See also ;Moderna COVID-19 vaccine nanoparticle ingredients *SM-102 *DMG-PEG 2000 ;Others * Stearic acid, contributing stearoyl- group * Phosphocholine Phosphocholine is an intermediate in the synthesis of phosphatidylcholine in tissues. Phosphocholine is made in a reaction, catalyzed by choline kinase, that converts ATP and choline into phosphocholine and ADP. Phosphocholine is a molecule ... References {{reflist Phosphatidylcholines ...
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Lipid
Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology. Lipids are broadly defined as hydrophobic or amphiphilic small molecules; the amphiphilic nature of some lipids allows them to form structures such as vesicles, multilamellar/ unilamellar liposomes, or membranes in an aqueous environment. Biological lipids originate entirely or in part from two distinct types of biochemical subunits or "building-blocks": ketoacyl and isoprene groups. Using this approach, lipids may be divided into eight categories: fatty acyls, glycerolipids, glycerophospholipids, sphingolipids, saccharolipids, and polyketides (derived from condensatio ...
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Lipids
Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins (such as vitamins Vitamin A, A, Vitamin D, D, Vitamin E, E and Vitamin K, K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, lipid signaling, signaling, and acting as structural components of cell membranes. Lipids have applications in the Cosmetic industry, cosmetic and Food industry, food industries, and in nanotechnology. Lipids are broadly defined as Hydrophobe, hydrophobic or Amphiphile, amphiphilic small molecules; the amphiphilic nature of some lipids allows them to form structures such as vesicle (biology), vesicles, multilamellar/unilamellar liposomes, or membranes in an aqueous environment. Biological lipids originate entirely or in part from two distinct types of biochemical subunits or "building-blocks": :wikt:ketoacyl, ketoacyl and isoprene groups. Using this approach, lipids may be divided into eight catego ...
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Tertiary Amines
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of electrons. Amines can also exist as hetero cyclic compounds. Aniline is the simplest aromatic amine, consisting of a benzene ring bonded to an amino group. Amines are classified into three types: primary (1°), secondary (2°), and tertiary (3°) amines. Primary amines (1°) contain one alkyl or aryl substituent and have the general formula RNH2. Secondary amines (2°) have two alkyl or aryl groups attached to the nitrogen atom, with the general formula R2NH. Tertiary amines (3°) contain three substituent groups bonded to the nitrogen atom, and are represented by the formula R3N. The functional group present in primary amines is called the amino group. Classification of amines Amines can be classified according to the nature and number o ...
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ALC-0315
ALC-0315 ( 4-hydroxybutyl)azanediyli(hexane-6,1-diyl) bis(2-hexyldecanoate)) is a synthetic lipid. A colorless oily material, it has attracted attention as a component of the SARS-CoV-2 vaccine, BNT162b2, from BioNTech and Pfizer. Specifically, it is one of four components that form lipid nanoparticles (LNPs), which encapsulate and protect the otherwise fragile mRNA that is the active ingredient in these drugs. These nanoparticles promote the uptake of therapeutically effective nucleic acids such as oligonucleotides or mRNA both ''in vitro'' and ''in vivo''. Below physiological pH, ALC-0315 becomes protonated at the nitrogen atom, yielding an ammonium cation that is attracted to the messenger RNA (mRNA), which is anionic. Synthesis The preparation of ALC-0315 was first described in a patent application to lipid nanoparticles by Acuitas Therapeutics in 2017. The final step is a reductive amination reaction in which 4-aminobutanol is condensed with a lipid aldehyde, using sodium ...
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Ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distinctive functional group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. amides), but not according to the IUPAC. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Lactones are cyclic carboxylic esters; naturally occurring lactones are mainly 5- and 6-membered ring lactones. Lactones contribute to the aroma of fruits, butter, cheese, vegetables like celery and other foods. Esters can be formed from oxoacids (e.g. esters of acetic acid, carbonic acid ...
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Amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of electrons. Amines can also exist as hetero cyclic compounds. Aniline is the simplest aromatic amine, consisting of a benzene ring bonded to an amino group. Amines are classified into three types: primary (1°), secondary (2°), and tertiary (3°) amines. Primary amines (1°) contain one alkyl or aryl substituent and have the general formula RNH2. Secondary amines (2°) have two alkyl or aryl groups attached to the nitrogen atom, with the general formula R2NH. Tertiary amines (3°) contain three substituent groups bonded to the nitrogen atom, and are represented by the formula R3N. The functional group present in primary amines is called the amino group. Classification of amines Amines can be classified according to the nature and number o ...
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Alkylation
Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with alkene, olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents. Nucleophilic alkylating agents Nucleophilic alkylating agents deliver the equivalent of an alkyl anion (carbanion). The formal "alkyl anion" attacks an electrophile, forming a new covalent bond ...
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Moderna
Moderna, Inc. ( ) is an American pharmaceutical and biotechnology company based in Cambridge, Massachusetts, that focuses on RNA therapeutics, primarily mRNA vaccines. These vaccines use a copy of a molecule called messenger RNA (mRNA) to carry instructions for proteins to produce an immune response. The company's name is derived from the terms "modified", "RNA", and "modern". The company's commercial products are the Moderna COVID-19 vaccine, marketed as Spikevax and a RSV vaccine, marketed as Mresvia. The company has 44 treatment and vaccine candidates, of which 37 have entered clinical trials. Candidates include possible vaccines for influenza, HIV, Epstein–Barr virus, the Nipah virus, chikungunya, human metapneumovirus, varicella zoster virus, as well as a cytomegalovirus vaccine, a Zika virus vaccine funded by the Biomedical Advanced Research and Development Authority, and three cancer vaccines. History Moderna was founded in 2010 by Derrick Rossi, Timothy A. Springer, ...
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