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Details

Stereochemistry RACEMIC
Molecular Formula C42H80NO4.Cl
Molecular Weight 698.542
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of DOTAP CHLORIDE

SMILES

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

InChI

InChIKey=KSXTUUUQYQYKCR-LQDDAWAPSA-M
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-;

HIDE SMILES / InChI

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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Intracellular trafficking mechanism of cationic phospholipids including cationic liposomes in HeLa cells.
2014 Jul
B Cells Produce Type 1 IFNs in Response to the TLR9 Agonist CpG-A Conjugated to Cationic Lipids.
2017 Aug 1
Multifunctional peptide-lipid nanocomplexes for efficient targeted delivery of DNA and siRNA into breast cancer cells.
2017 Sep 1

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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
Created
by admin
on Sat Dec 16 10:55:30 GMT 2023
Edited
by admin
on Sat Dec 16 10:55:30 GMT 2023
Record UNII
3R78UC794Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOTAP CHLORIDE
Common Name English
DOTAP-Cl
Common Name English
N-(1-(2,3-DIOLEOYLOXY)PROPYL)-N,N,N-TRIMETHYLAMMONIUM CHLORIDE
Common Name English
1-PROPANAMINIUM, N,N,N-TRIMETHYL-2,3-BIS(((9Z)-1-OXO-9-OCTADECENYL)OXY)-, CHLORIDE (1:1))
Systematic Name English
(±)-DOTAP CHLORIDE
Common Name English
DOTAP CHLORIDE, (±)-
Common Name English
Code System Code Type Description
SMS_ID
300000039529
Created by admin on Sat Dec 16 10:55:30 GMT 2023 , Edited by admin on Sat Dec 16 10:55:30 GMT 2023
PRIMARY
PUBCHEM
11636182
Created by admin on Sat Dec 16 10:55:30 GMT 2023 , Edited by admin on Sat Dec 16 10:55:30 GMT 2023
PRIMARY
FDA UNII
3R78UC794Z
Created by admin on Sat Dec 16 10:55:30 GMT 2023 , Edited by admin on Sat Dec 16 10:55:30 GMT 2023
PRIMARY
CAS
132172-61-3
Created by admin on Sat Dec 16 10:55:30 GMT 2023 , Edited by admin on Sat Dec 16 10:55:30 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE