1,2-dioleoyl-3-trimethylammonium-propane (chloride salt) - CAS 132172-61-3

Catalog number: BRH-003

1,2-dioleoyloxy-3-(trimethylammonium)propane (DOTAP) chloride has been used for the preparation of cationic liposome and liposome-DNA complex. It has also been used to assess tumor necrosis factor α (TNF-α) production.

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Ordering Information

Catalog Number	Size	Price	Stock	Quantity
BRH-003	5 g	$1999	In stock

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Synonyms

Dotap chloride; DOTAP-Cl; DOTAP (chloride); 1-Propanaminium, N,N,N-trimethyl-2,3-bis[[(9Z)-1-oxo-9-octadecenyl]oxy]-, chloride (1:1); 1,2-Dioleoyl-3-trimethylammonium-propane, Chloride; (+/-)-Dotap chloride; Dotap chloride, (+/-)-; N-(1-(2,3-Dioleoyloxy)propyl)-N,N,N-trimethylammonium chloride; (2,3-dioleoyloxy-propyl)-trimethylammonium-chloride; 18:1 TAP (DOTAP), 1,2-dioleoyl-3-trimethylammonium-propane (chloride salt), chloroform; DOTAP Chloride; N,N,N-Trimethyl-2,3-bis[[(9Z)-1-oxo-9-octadecenyl]oxy]-1-propanaminium; 2,3-di(octadec-9-enoyloxy)propyl-trimethylazanium

CAS

132172-61-3

IUPAC Name

2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl-trimethylazanium;chloride

Molecular Weight

698.54

Molecular Formula

C42H80ClNO4

Canonical SMILES

CCCCCCCCC=CCCCCCCCC(=O)OCC(C[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC.[Cl-]

InChI

InChI=1S/C42H80NO4.ClH/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;1H/q+1;/p-1/b22-20-,23-21-;

InChIKey

KSXTUUUQYQYKCR-LQDDAWAPSA-M

Melting Point

35-38 °C

Purity

>98% by HPLC

Solubility

Slightly soluble in Chloroform, Methanol.

Appearance

Light Yellow or White Waxy Solid

Storage

-20 °C under inert atmosphere

Chemical Structure:

Reference Reading

1. X-ray Absorption Spectroscopy and Spectromicroscopy of Supported Lipid Bilayers

Jonathan D West, Yujie Zhu, Sokunthearath Saem, Jose Moran-Mirabal, Adam P Hitchcock. J Phys Chem B. 2017 May 4;121(17):4492-4501. doi: 10.1021/acs.jpcb.7b02646.

The C 1s, O 1s, and N 1s X-ray absorption spectra of three lipid species, 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), and 1,2-dioleoyl-3-trimethylammonium-propane (chloride salt) (DOTAP), have been recorded using transmission detection in a scanning transmission X-ray microscope. The spectra are presented on an absolute intensity scale (i.e., optical density per nm) to allow their use as reference standards for spectromicroscopic analysis of supported lipid bilayers. Examples of C 1s based spectromicroscopic mapping of saturated and unsaturated domains in dry lipid bilayers of DOPC and DSPC at several compositions are presented. The results are compared with fluorescence microscopy of the same area. Challenges for extending this work to studies of wet lipid bilayers interacting with antimicrobial peptides are discussed.

2. Progress in the development of lipopolyplexes as efficient non-viral gene delivery systems

Mehdi Rezaee, Reza Kazemi Oskuee, Hooriyeh Nassirli, Bizhan Malaekeh-Nikouei. J Control Release. 2016 Aug 28;236:1-14. doi: 10.1016/j.jconrel.2016.06.023.

Efficient gene therapy is mainly dependent on the gene transfer capability of gene delivery vectors. Non-viral vectors have become the research interest of many researchers because these vectors are safer than viral vectors. Acquiring the advantages of both polyplexes and lipoplexes, the lipopolyplex (LPP) is a ternary nanocomplex composed of cationic liposome, polycation, and nucleic acid. Considering the polycationic component, ternary complexes (LPPs) are divided into cationic polymer-based LPPs and cationic peptide-based LPPs. Considering the capability of rational design, LPP is an interesting field of research to design a more potent nucleic acid carrier. With the promising transfection activity and safety observed in the LPPs, many researchers have formulated various types of lipids and polycations to achieve an efficient and safe carrier for gene therapy. Here we provide a review on the designed LPPs for efficient delivery of different nucleic acids such as plasmid DNA, siRNA, shRNA, and DNA vaccines.

3. Doxorubicin liposomes as an investigative model to study the skin permeation of nanocarriers

Cedar H A Boakye, Ketan Patel, Mandip Singh. Int J Pharm. 2015 Jul 15;489(1-2):106-16. doi: 10.1016/j.ijpharm.2015.04.059.

The objectives of this study were to develop an innovative investigative model using doxorubicin as a fluorophore to evaluate the skin permeation of nanocarriers and the impact of size and surface characteristics on their permeability. Different doxorubicin-loaded liposomes with mean particle size 600 nm were restricted within the stratum corneum. DOTAP (p<0.01) and CY5 (p<0.05) liposomes demonstrated significant permeation into the skin than DOPA and PEG liposomes. Tape stripping significantly (p<0.01) enhanced the skin permeation of doxorubicin liposomes but TAT-decorated doxorubicin liposomes permeated better (p<0.005). Blockage of the hair follicles resulted in significant reduction in the extent and intensity of fluorescence observed within the skin layers. Overall, doxorubicin liposomes proved to be an ideal fluorophore-based model. The hair follicles were the major route utilized by the liposomes to permeate skin. Surface charge and particle size played vital roles in the extent of permeation.