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D6182

Sigma-Aldrich

DOTAP chloride

≥98% (TLC), powder

Synonym(s):

N-[1-(2,3-Dioleoyloxy)propyl]-N,N,N-trimethylammonium chloride

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About This Item

Empirical Formula (Hill Notation):
C42H80ClNO4
CAS Number:
Molecular Weight:
698.54
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥98% (TLC)

form

powder

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H]C(C[N+](C)(C)C)(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O.[Cl-]

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-;

InChI key

KSXTUUUQYQYKCR-LQDDAWAPSA-M

Application

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.
Cationic liposome-forming compound for transfection of DNA, RNA and other negatively charged molecules into eukaryotic cells. Mixing DOTAP with DNA results in spontaneously formed stable complexes that can be directly added to cell culture medium. These complexes fuse with the cell membrane and release DNA into the cytoplasm. The cells are transfected efficiently without cytotoxic effects. Use approximately 5-10 μg DOTAP per μg DNA and approximately 10-20 μg DOTAP per mL cell culture medium. The optimal working concentration and transfection time depends in part on the cell line used, and the type of material (RNA, DNA, protein) loaded.

Biochem/physiol Actions

1,2-dioleoyloxy-3-(trimethylammonium)propane (DOTAP) chloride is useful in liposome preparation, without the use of helper lipid. DOTAP chloride is soluble in dimethyl sulfoxide (DMSO) and ethanol, this defines its function as a transfection agent.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A novel strategy for tumour therapy combining cell apoptosis and active immunity induced by caspy2, a zebrafish caspase
Liu L, et al.
Journal of Cellular and Molecular Medicine, 13(8b), 2271-2281 (2009)
A simplified direct lipid mixing lipoplex preparation: Comparison of liposomal-, dimethylsulfoxide-, and ethanol-based methods
Meisel JW and Gokel GW
Scientific Reports, 6, 27662-27662 (2016)
Ju-mei Zhao et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 22(12), 4272-4280 (2008-08-22)
The matrix (M) protein of vesicular stomatitis virus (VSV) plays a key role in inducing cell apoptosis during infection. To investigate whether M protein-mediated apoptosis could be used in cancer therapy, its cDNA was amplified and cloned into eukaryotic expression
Structurally distinct phosphatases CD45 and CD148 both regulate B cell and macrophage immunoreceptor signaling
Zhu JW, et al.
Immunity, 28(2), 183-196 (2008)

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