Dioleoyl-3-trimethylammonium propane

Last updated
Dioleoyl-3-trimethylammonium propane
DOTAP.svg
Names
IUPAC name
2,3-Bis{[(Z)-octadec-9-enoyl]oxy}propyl-trimethylazanium
Other names
DOTAP
Identifiers
3D model (JSmol)
PubChem CID
UNII
  • InChI=1S/C42H80NO4/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-41(44)46-39-40(38-43(3,4)5)47-42(45)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,40H,6-19,24-39H2,1-5H3/q+1/b22-20-,23-21-
    Key: KWVJHCQQUFDPLU-YEUCEMRASA-N
  • CCCCCCCC/C=C\CCCCCCCC(=O)OCC(C[N+](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC
Properties
C42H80NO4+ (cation)
C42H80NO4Cl (chloride salt)
Molar mass 663.10 g/mol (cation)
698.56 g/mol (chloride salt)
AppearanceWhite 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]

Contents

Synthesis

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.

The di-sterate, sometimes referred to as Hamburg Esterquat (HEQ), CAS No: 220609-41-6 DiesterCl.png
The di-sterate, sometimes referred to as Hamburg Esterquat (HEQ), CAS No: 220609-41-6

Material intended for transfection is prepared similarly from high purity oleic acid.

Applications

Fabric softener

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]

Liposomal transfection agent

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]

Related Research Articles

Detergent surfactants with cleansing properties, even in dilute solutions

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.

Surfactant Substance that lowers the surface tension between a liquid and another material

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 Eighteen-carbon straight-chain fatty acid

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.

Liposome Composite structures made of phospholipids and may contain small amounts of other molecules

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Hair conditioner Hair care product

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 cation class of chemical molecules

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 Type of detergent used for cleaning laundry

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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 Chemical compound

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.

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References

  1. 1 2 Simberg, Dmitri; Weisman, Sarah; Talmon, Yeshayahu; Barenholz, Yechezkel (2004). "DOTAP (and Other Cationic Lipids): Chemistry, Biophysics, and Transfection;". Critical Reviews in Therapeutic Drug Carrier Systems. 21 (4): 257–317. doi:10.1615/CritRevTherDrugCarrierSyst.v21.i4.10. PMID   15638468.
  2. Rainer Höfer (2009). Sustainable Solutions for Modern Economies. Royal Society of Chemistry. pp. 387–. ISBN   978-1-84755-905-0.
  3. Jowsey, Ian R.; Kligman, Albert M.; White, Ian R.; Goossens, An; Basketter, David A. (March 2007). "Evidence That Two Alkyl Ester Quaternary Ammonium Compounds Lack Substantial Human Skin-Sensitizing Potential". Dermatitis. 18 (1): 32–39. doi:10.2310/6620.2007.06036. PMID   17303042. S2CID   36637867.