Names | |
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IUPAC name 2,3-Bis{[(Z)-octadec-9-enoyl]oxy}propyl-trimethylazanium | |
Other names DOTAP | |
Identifiers | |
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3D model (JSmol) | |
PubChem CID | |
UNII |
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Properties | |
C42H80NO4+ (cation) C42H80NO4Cl (chloride salt) | |
Molar mass | 663.10 g/mol (cation) 698.56 g/mol (chloride salt) |
Appearance | White solid (chloride salt) |
Soluble (chloride salt) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
1,2-Dioleoyl-3-trimethylammonium propane (often abbreviated DOTAP or 18:1TAP) is a di-chain, or gemini, cationic surfactant. It is most commonly encountered as an active ingredient in certain fabric softeners. The pure material can also be used for the liposomal-transfection of DNA, RNA and other negatively charged molecules. [1]
The commercial material used for fabric softening is formed by the di-esterification of 2,3-epoxypropyltrimethylammoniumchloride (EPTAC) with partially hydrogenated palm oil and as such contains a mixture of fatty acid tails; palmitic (saturated C16), stearic (saturated C18), oleic (monounsaturated C18) and linoleic (polyunsaturated C18). In practice the saturated di-sterate compound tend to be the major component of these mixtures.
Material intended for transfection is prepared similarly from high purity oleic acid.
It was originally introduced into European markets during the 1990s due to concerns over the environmental effects of DODAC, which was the principle softener used at the time. [2] The main difference was the incorporation of cleavable ester groups intended to accelerate its biodegradation. It is a superior softener to di- and triethanolamine based softeners but suffers from an increased tendency to hydrolyse. Small patch test studies have not shown any clear evidence of it acting is a skin irritant. [3]
DOTAP is a cationic surfactant and is able to form stable cationic liposomes in solution, these readily absorb DNA and other negatively charged organic compounds. The DNA laden liposomes can then be added directly to cell culture medium, where they will combine with the cell membrane and release their payload into the cell. [1]
A detergent is a surfactant or a mixture of surfactants with cleansing properties in dilute solutions. These substances are usually alkylbenzene sulfonates, a family of compounds that are similar to soap but are more soluble in hard water, because the polar sulfonate is less likely than the polar carboxylate to bind to calcium and other ions found in hard water.
Surfactants are compounds that lower the surface tension between two liquids, between a gas and a liquid, or between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming agents, or dispersants.
Stearic acid ( STEER-ik, stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. The triglyceride derived from three molecules of stearic acid is called stearin.
Transfection is the process of deliberately introducing naked or purified nucleic acids into eukaryotic cells. It may also refer to other methods and cell types, although other terms are often preferred: "transformation" is typically used to describe non-viral DNA transfer in bacteria and non-animal eukaryotic cells, including plant cells. In animal cells, transfection is the preferred term as transformation is also used to refer to progression to a cancerous state (carcinogenesis) in these cells. Transduction is often used to describe virus-mediated gene transfer into eukaryotic cells.
A liposome is a spherical vesicle having at least one lipid bilayer. The liposome can be used as a drug delivery vehicle for administration of nutrients and pharmaceutical drugs, such as lipid nanoparticles in mRNA vaccines, and DNA vaccines. Liposomes can be prepared by disrupting biological membranes.
Hair conditioner is a hair care product used to improve the feel, appearance and manageability of hair. Its main purpose is to reduce friction between strands of hair to allow smoother brushing or combing, which might otherwise cause damage to the scalp. Various other benefits are often advertised, such as hair repair, strengthening, or a reduction in split ends.
Quaternary ammonium cations, also known as quats, are positively charged polyatomic ions of the structure NR+
4, R being an alkyl group or an aryl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.
A fabric softener is a conditioner that is typically applied to laundry during the rinse cycle in a washing machine to reduce harshness in clothes that are dried in air after machine washing. In contrast to laundry detergents, fabric softeners may be regarded as a kind of after-treatment laundry aid.
Laundry detergent, or washing powder, is a type of detergent used for cleaning laundry. Laundry detergent is manufactured in powder and liquid form.
Cationic liposomes are structures that are made of positively charged lipids and are increasingly being researched for use in gene therapy due to their favorable interactions with negatively charged DNA and cell membranes. In 1987, Philip Felgner published the first approach to using cationic lipids to transfect DNA into cells, based on his research into cationic lipids at Syntex from 1982 to 1988. Upon interacting with negatively charged DNA, cationic liposomes form clusters of aggregated vesicles. At a critical density the DNA is condensed and becomes encapsulated within a lipid bilayer, although it is possible that the liposomes bind along the surface of the DNA, retaining its shape. They are also able to interact with negatively charged cell membranes more readily than classical liposomes. Fusion between cationic vesicles and cell surfaces can deliver the DNA directly across the plasma membrane. This process bypasses the endosomal-lysosomal route which leads to degradation of anionic liposome formulations.
Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor.
Lipofectamine or Lipofectamine 2000 is a common transfection reagent, produced and sold by Invitrogen, used in molecular and cellular biology. It is used to increase the transfection efficiency of RNA or plasmid DNA into in vitro cell cultures by lipofection. Lipofectamine contains lipid subunits that can form liposomes in an aqueous environment, which entrap the transfection payload, e.g. DNA plasmids.
Magnetofection is a simple and highly efficient transfection method that uses magnetic fields to concentrate particles containing nucleic acid into the target cells. This method attempts to unite the advantages of the popular biochemical and physical transfection methods in one system while excluding their inconveniences. Magnetofection is commercialized by OZ Biosciences and is registered as a trademark.
Reverse transfection is a technique for the transfer of genetic material into cells. As DNA is printed on a glass slide for the transfection process to occur before the addition of adherent cells, the order of addition of DNA and adherent cells is reverse that of conventional transfection. Hence, the word “reverse” is used.
Magnet-assisted transfection is a transfection method which uses magnetic interactions to deliver DNA into target cells. Nucleic acids are associated with magnetic nanoparticles, and magnetic fields drive the nucleic acid-particle complexes into target cells, where the nucleic acids are released.
Solid lipid nanoparticles, or 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.
Paint has four major components: pigments, binders, solvents, and additives. Pigments serve to give paint its color, texture, toughness, as well as determining if a paint is opaque or not. Common white pigments include titanium dioxide and zinc oxide. Binders are the film forming component of a paint as it dries and affects the durability, gloss, and flexibility of the coating. Polyurethanes, polyesters, and acrylics are all examples of common binders. The solvent is the medium in which all other components of the paint are dissolved and evaporates away as the paint dries and cures. The solvent also modifies the curing rate and viscosity of the paint in its liquid state. There are two types of paint: solvent-borne and water-borne paints. Solvent-borne paints use organic solvents as the primary vehicle carrying the solid components in a paint formulation, whereas water-borne paints use water as the continuous medium. The additives that are incorporated into paints are a wide range of things which impart important effects on the properties of the paint and the final coating. Common paint additives are catalysts, thickeners, stabilizers, emulsifiers, texturizers, biocides to fight bacterial growth, etc.
Gene therapy utilizes the delivery of DNA into cells, which can be accomplished by several methods, summarized below. The two major classes of methods are those that use recombinant viruses and those that use naked DNA or DNA complexes.
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.
Nanoparticle drug delivery systems are engineered technologies that use nanoparticles for the targeted delivery and controlled release of therapeutic agents. The modern form of a drug delivery system should minimize side-effects and reduce both dosage and dosage frequency. Recently, nanoparticles have aroused attention due to their potential application for effective drug delivery.