1,2-dioleoyl-3-trimethylammonium-propane (methyl sulfate salt)
Need Assistance?
  • US & Canada:
    +
  • UK: +

1,2-dioleoyl-3-trimethylammonium-propane (methyl sulfate salt)

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

1,2-dioleoyl-3-trimethylammonium-propane (methyl sulfate salt) is a liposome formulation for cationic lipid DOTAP. DOTAP can be used for the efficiency of DNA transfection, including yeast artificial chromosomes (YAC) transfection to eukaryotic cells used in transient or stable gene expression, and also suitable for efficient will other negatively charged molecules, such as RNA, oligonucleotides, and glutamic acid, the ribosome protein (RNP) complex, and protein, transferred to the study sample of mammalian cells.

Category
Peptide Synthesis Reagents
Catalog number
BAT-006359
CAS number
144189-73-1
Molecular Formula
C43H83NO8S
Molecular Weight
774.20
1,2-dioleoyl-3-trimethylammonium-propane (methyl sulfate salt)
IUPAC Name
2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl-trimethylazanium;methyl sulfate
Synonyms
DOTAP Transfection Reagent; DOTAP-MS; n-(2,3-dioleoyloxy-1-propyl) trimethylammonium methyl sulfate; N,N,N-Trimethyl-2,3-bis(oleoyloxy)propan-1-aminium methyl sulfate; DOTAP methosulfate; 18:1 TAP (DOTAP, MS Salt), 1,2-dioleoyl-3-trimethylammonium-propane (methyl sulfate salt), chloroform; 18:1 TAP (DOTAP, MS Salt), 1,2-dioleoyl-3-trimethylammonium-propane (methyl sulfate salt), Powder; DOTAP Liposomal Transfection Reagent, N-[1-(2,3-Dioleoyloxy)propyl]-N,N,N-trimethylammonium methyl-sulfate
Related CAS
113669-21-9 (free base)
Appearance
Solid
Purity
98%
Storage
- 20 °C, keep away from light and store in a dry place. Stored under Nitrogen.
InChI
InChI=1S/C42H80NO4.CH4O4S/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;1-5-6(2,3)4/h20-23,40H,6-19,24-39H2,1-5H3;1H3,(H,2,3,4)/q+1;/p-1/b22-20-,23-21-;
InChI Key
RSMRWWHFJMENJH-LQDDAWAPSA-M
Canonical SMILES
CCCCCCCCC=CCCCCCCCC(=O)OCC(C[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC.COS(=O)(=O)[O-]
1. Cationic amphiphiles and the solubilization of cholesterol crystallites in membrane bilayers
Carlos R Benatti, M Teresa Lamy, Richard M Epand Biochim Biophys Acta. 2008 Apr;1778(4):844-53. doi: 10.1016/j.bbamem.2007.12.011. Epub 2007 Dec 23.
Cationic amphiphiles used for transfection can be incorporated into biological membranes. By differential scanning calorimetry (DSC), cholesterol solubilization in phospholipid membranes, in the absence and presence of cationic amphiphiles, was determined. Two different systems were studied: 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC)+cholesterol (1:3, POPC:Chol, molar ratio) and 1-palmitoyl-2-oleoyl-sn-glycero-3-[phospho-l-serine] (POPS)+cholesterol (3:2, POPS:Chol, molar ratio), which contain cholesterol in crystallite form. For the zwitterionic lipid POPC, cationic amphiphiles were tested, up to 7 mol%, while for anionic POPS bilayers, which possibly incorporate more positive amphiphiles, the fractions used were higher, up to 23 mol%. 1,2-dioleoyl-3-trimethylammonium-propane (DOTAP) and DOTAP in methyl sulfate salt form (DOTAPmss) were found to cause a small decrease on the enthalpy of the cholesterol transition of pure cholesterol aggregates, possibly indicating a slight increase on the cholesterol solubilization in POPC vesicles. With the anionic system POPS:Chol, the cationic amphiphiles dramatically change the cholesterol crystal thermal transition, indicating significant changes in the cholesterol aggregates. For structural studies, phospholipids spin labeled at the 5th or 16th carbon atoms were incorporated. In POPC, at the bilayer core, the cationic amphiphiles significantly increase the bilayer packing, decreasing the membrane polarity, with the cholesterol derivative 3 beta-[N-(N',N'-dimethylaminoethane)-carbamoyl]-cholesterol (DC-chol) displaying a stronger effect. In POPS and POPS:Chol, DC-chol was also found to considerably increase the bilayer packing. Hence, exogenous cationic amphiphiles used to deliver nucleic acids to cells can change the bilayer packing of biological membranes and alter the structure of cholesterol crystals, which are believed to be the precursors to atherosclerotic lesions.
2. The role of fibronectin in pulmonary gene transfer following intravenous administration of lipoplex in mice
Naoki Yoshikawa, Shintaro Fumoto, Mikiro Nakashima, Kenta Shimokawa, Hirotaka Miyamoto, Koyo Nishida Biol Pharm Bull. 2013;36(11):1807-13. doi: 10.1248/bpb.b13-00500.
We analyzed the effect of serum and fibronectin on pulmonary transgene expression after intravenous injection of cationic liposome-plasmid DNA (pDNA) complex (lipoplex) in mice. 1,2-Dioleoyl-3-trimethylammonium-propane (DOTAP) methyl sulfate salt/cholesterol lipoplex was incubated with several serum components for 5 min at 37°C prior to injection. We analyzed pulmonary transgene expression and pulmonary accumulation of lipoplex. While interaction with serum did not decrease pulmonary transgene expression, interaction with heat-inactivated serum did decrease it. Moreover, interaction with fibronectin enhanced pulmonary transgene expression. Inhibition of the binding of fibronectin to integrin decreased pulmonary transgene expression after injection of untreated lipoplex. We found that pulmonary accumulation of lipoplex changed depending on the kind of interacting serum components after injection. Furthermore, interaction with fibronectin increased pulmonary accumulation of lipoplex. Interaction with serum was required for pulmonary gene transfer following intravenous injection of lipoplex. Fibronectin appears to be a particularly critical component. Furthermore, the binding of fibronectin interacting with lipoplex to integrin was an important mechanism for pulmonary transgene expression.
Online Inquiry
Verification code
Inquiry Basket