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Details

Stereochemistry RACEMIC
Molecular Formula C42H80NO4
Molecular Weight 663.0889
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 2
Charge 1

SHOW SMILES / InChI
Structure of DOTAP

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)OCC(C[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI

InChIKey=KWVJHCQQUFDPLU-YEUCEMRASA-N
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-

HIDE SMILES / InChI

Molecular Formula C42H80NO4
Molecular Weight 663.0889
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 2
Optical Activity ( + / - )

Description

The DOTAP (N-[1-(2,3-Dioleoyloxy)propyl]-N,N,N-trimethylammonium methyl-sulfate) is a liposomal transfection reagent suitable for transient and stable transfection of mammalian cell lines with DNA (plasmids, bacmids) and modified nucleic acids (antisense oligonucleotides). Mixing DOTAP with DNA results in spontaneously formed stable complexes. These complexes can be added directly to the tissue culture medium. This method avoiding the cytotoxic effects commonly encountered with lipofection or others transfection methods. The recently published article described the ability of R-DOTAP stabilized microparticles (MP) to act as a carrier platform for antigens e.g. for cancer vaccination. It was investigated whether or not a combination of R-DOTAP and PLGA leads to a boosted adjuvant effect in dendritic cell maturation.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Freshly isolated CD34+ cells were resuspended in RPMI-1640 supplemented with the agents used to generate immunogenic dendritic cells. Immediately after treatment, cells were subjected to transfection using a predesigned siRNA targeting the CatS gene. The procedure, run in a 24-well plate format via triplicate tests, was implemented using a 25 nM final siRNA concentration. Each well-contained cells in a volume of 500 uL. The siRNAs were combined with DOTAP and maintained for 30 minutes at room temperature to form complexes. The mixture (50 uL) was then overlaid dropwise on the cell cultures. Following 4-hour incubation, 1.2 mL of RPMI-1640 containing 10% FCS and differentiating agents was added to each well. To ensure silencing of genes for the entire 14-day differentiation process, cells were centrifuged, resuspended in 500  L of cytokine-enriched culture medium and exposed to a second (day 3) and third (day 9) transfection round under the same experimental conditions.
Substance Class Chemical
Record UNII
MR86K0XRQP
Record Status Validated (UNII)
Record Version