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DOTMA (E-configuration chloride)

Alias: DOTMA; DOTMA (E-configuration chloride); 1,2-di-O-octadecenyl-3-trimethylammonium propane
Cat No.:V41367 Purity: ≥98%
DOTMA (E-configuration chloride) is atetra-methylated DOTA analog used as a non viral vector for gene therapy, in miRNA delivery system and promotes liposome-cell membrane interactions.
DOTMA (E-configuration chloride)
DOTMA (E-configuration chloride) Chemical Structure CAS No.: 104872-42-6
Product category: Liposome
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of DOTMA (E-configuration chloride):

  • DOTMA (Z-configuration chloride)
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Top Publications Citing lnvivochem Products
Product Description
DOTMA (E-configuration chloride) is a tetra-methylated DOTA analog used as a non viral vector for gene therapy, in miRNA delivery system and promotes liposome-cell membrane interactions. It is also used for cationic microbubble preparations, promotes liposome-cell membrane interactions. It has been used as a component in liposomes that can be used to encapsulate siRNA, microRNAs, and oligonucleotides and for gene transfection in vitro. It exhibits effective in vitro and in vivo gene transfection. DOTMA induces a positive charge on the liposomes and thus promotes efficient liposome- cell membrane interaction.
DOTMA (1,2-di-O-octadecenyl-3-trimethylammonium propane) is a cationic lipid widely used as a non-viral vector for gene therapy and transfection. It was one of the first cationic lipids developed for gene delivery applications. DOTMA forms stable cationic liposomes in solution and can be used for the cell transfection of DNA, RNA, oligonucleotides, anionic proteins, and small peptides. The positive charge on DOTMA liposomes promotes efficient interaction with negatively charged cell membranes and condenses anionic nucleic acids, facilitating cellular uptake. DOTMA-based liposomes are widely used for the delivery of plasmid DNA, mRNA, and siRNA to various cell lines.
Biological Activity I Assay Protocols (From Reference)
Targets
DOTMA is a cationic lipid used as a non-viral vector for gene therapy. Its mechanism of action involves electrostatic interaction between the positively charged DOTMA headgroup and negatively charged nucleic acids (DNA, RNA, siRNA, microRNA, oligonucleotides), forming stable lipoplexes. The positive charge on DOTMA liposomes also promotes efficient liposome-cell membrane interaction, facilitating cellular uptake. Once inside the cell, the lipoplexes must escape from endosomes to deliver their nucleic acid cargo into the cytoplasm. DOTMA is typically formulated into liposomes, often with a neutral "helper" lipid like DOPE (dioleoylphosphatidylethanolamine), to enhance transfection efficacy by facilitating endosomal escape.
ln Vitro
DOTMA exhibits effective in vitro and in vivo gene transfection. It induces a positive charge on liposomes, promoting efficient liposome-cell membrane interaction. The compound condenses anionic nucleic acids and promotes efficient interactions between the cell membrane and the liposome. DOTMA-based liposomes are widely used for the delivery of plasmid DNA, mRNA, and siRNA to a variety of cell lines. It has been used as a component in liposomes that can encapsulate siRNA, microRNAs, and oligonucleotides for gene transfection in vitro.
ln Vivo
DOTMA has shown good gene transfection effects both in vitro and in vivo. It is an effective transfection agent in vitro and in vivo. DOTMA-based liposomes have been used in anticancer vaccine research for the delivery of nucleic acids. The compound's ability to form stable complexes with nucleic acids supports its use in various gene delivery applications. It is well known for forming stable complexes with nucleic acids, supporting early development of liposomal transfection reagents.
Enzyme Assay
The activity of DOTMA is assessed in transfection efficiency assays using reporter genes such as luciferase or GFP. Cells are seeded in multi-well plates and transfected with DOTMA liposomes complexed with reporter plasmid DNA. Transfection efficiency is measured by quantifying reporter gene expression (luminescence or fluorescence) 24-48 hours post-transfection. Liposome formulations are prepared by mixing DOTMA with helper lipids (e.g., DOPE) in organic solvent, drying to form a lipid film, hydrating with buffer, and extruding to form uniform liposomes. Nucleic acids are complexed with liposomes at various charge ratios.
Cell Assay
Cellular assays for DOTMA involve transfecting various cell lines (e.g., HEK-293, CHO, HeLa) with nucleic acid cargo complexed with DOTMA liposomes. Cells are seeded in 96-well or 24-well plates and incubated with lipoplexes for 4-6 hours. The transfection medium is then replaced with complete growth medium. After 24-48 hours, transfection efficiency is assessed by measuring reporter gene expression (luciferase assay or GFP fluorescence) or by qPCR for specific gene targets. Cytotoxicity is assessed using MTT or LDH release assays. The optimal lipid-to-DNA ratio and formulation conditions are determined for each cell type.
Animal Protocol
In vivo transfection studies with DOTMA are typically performed in mouse models. Lipoplexes containing therapeutic nucleic acids (e.g., siRNA, mRNA, or plasmid DNA) are administered via intravenous, intraperitoneal, or intratumoral injection. Transgene expression or gene knockdown is assessed in target tissues by measuring protein levels (ELISA, Western blot) or mRNA levels (qPCR). Biodistribution studies are performed using labeled nucleic acids. Tumor growth inhibition is assessed in xenograft models for anticancer applications. The compound's in vivo gene transfection efficacy has been demonstrated in various models.
ADME/Pharmacokinetics
DOTMA has molecular formula C42H84NO4Cl and molecular weight 670.57. It is soluble in organic solvents and forms stable liposomes in aqueous solutions. The compound is typically formulated with helper lipids such as DOPE to enhance transfection efficiency. DOTMA is stable at -20°C for long-term storage. Its strong bilayer-forming and nucleic acid-binding capacity make it a foundational molecule in gene delivery research and liposome engineering.
Toxicity/Toxicokinetics
DOTMA is generally considered well-tolerated in vitro and in vivo at appropriate doses. However, as a cationic lipid, it may cause cytotoxicity at high concentrations due to membrane disruption. Cytotoxicity is typically assessed using standard cell viability assays (MTT, LDH release). The compound should be handled with appropriate laboratory safety precautions. In vivo, DOTMA liposomes may cause some inflammatory responses, which can be mitigated by optimizing formulation and dosing.
References

[1].Aime S, et al. Properties, solution state behavior, and crystal structures of chelates of DOTMA. Inorg Chem. 2011;50(17):7955-7965.

[2].Bhavsar D, et al. Translational siRNA therapeutics using liposomal carriers: prospects & challenges. Curr Gene Ther. 2012;12(4):315-332.

[3].Ren T, et al. Structural basis of DOTMA for its high intravenous transfection activity in mouse. Gene Ther. 2000;7(9):764-768.

Additional Infomation
DOTMA is one of the first cationic lipids used for gene transfection. It serves as a component in liposomes for encapsulating siRNA, microRNA, and oligonucleotides, and is also employed for in vitro gene transfection. DOTMA-based liposomes are widely used in anticancer vaccine research. The compound forms stable cationic liposomes in solution and can be used for the transfection of DNA, RNA, oligonucleotides, anionic proteins, and small peptides. DOTMA is a foundational molecule in gene delivery research and liposome engineering.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C42H84CLNO2
Molecular Weight
670.574872970581
Exact Mass
669.619
Elemental Analysis
C, 75.23; H, 12.63; Cl, 5.29; N, 2.09; O, 4.77
CAS #
104872-42-6
Related CAS #
104162-48-3 (Z-isomer chloride);122342-03-4 (Z-isomer cation);104872-42-6 (E-configuration chloride);717090-94-3 (E-isomer cation);
PubChem CID
6438350
Appearance
White to light yellow solid powder
Melting Point
35-38℃
LogP
13.971
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
37
Heavy Atom Count
46
Complexity
608
Defined Atom Stereocenter Count
0
SMILES
[Cl-].O(CCCCCCCC/C=C\CCCCCCCC)C(COCCCCCCCC/C=C\CCCCCCCC)C[N+](C)(C)C
InChi Key
LDGWQMRUWMSZIU-LQDDAWAPSA-M
InChi Code
InChI=1S/C42H84NO2.ClH/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-44-41-42(40-43(3,4)5)45-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2;/h20-23,42H,6-19,24-41H2,1-5H3;1H/q+1;/p-1/b22-20-,23-21-;
Chemical Name
2,3-bis[(Z)-octadec-9-enoxy]propyl-trimethylazanium;chloride
Synonyms
DOTMA; DOTMA (E-configuration chloride); 1,2-di-O-octadecenyl-3-trimethylammonium propane
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~12.5 mg/mL (~18.64 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.73 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 2.5 mg/mL (3.73 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (3.73 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.4913 mL 7.4563 mL 14.9127 mL
5 mM 0.2983 mL 1.4913 mL 2.9825 mL
10 mM 0.1491 mL 0.7456 mL 1.4913 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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