Page last updated: 2024-12-07

(3-dimyristyloxypropyl)(dimethyl)(hydroxyethyl)ammonium

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

(3-dimyristyloxypropyl)(dimethyl)(hydroxyethyl)ammonium is a **cationic lipid**, a type of molecule that has a positively charged head group and a long, hydrophobic tail. This specific lipid is known by the trade name **DOTAP** (**D**ioleoyl**T**ri**M**ethylammonium **A**ceto**P**hosphate).

**Why is DOTAP important for research?**

DOTAP plays a critical role in **gene delivery**, particularly for **non-viral gene therapy**. Here's why:

* **Lipid-based delivery systems:** DOTAP is a key component of **cationic liposomes**, which are tiny vesicles made of lipids that can encapsulate DNA or RNA. These liposomes act as delivery vehicles, transporting genetic material into cells.
* **Interactions with DNA:** DOTAP's positive charge interacts electrostatically with the negatively charged phosphate groups of DNA, forming stable complexes. This helps to protect the DNA from degradation and facilitate its entry into cells.
* **Cellular uptake:** Once the liposome-DNA complex reaches a cell, DOTAP helps the complex fuse with the cell membrane, allowing the genetic material to enter the cell's interior.

**Research Applications:**

DOTAP is used in various research areas, including:

* **Gene therapy:** DOTAP-based liposomes are used to deliver genes for treating genetic disorders, cancers, and infectious diseases.
* **Vaccines:** DOTAP can be incorporated into vaccines to enhance the delivery of antigens and stimulate immune responses.
* **Drug delivery:** DOTAP can be used to deliver therapeutic drugs to specific cells or tissues.
* **Bioimaging:** DOTAP-labeled molecules can be used to track the distribution of genetic material or other substances in cells and tissues.

**Advantages of DOTAP:**

* **High transfection efficiency:** DOTAP is known for its ability to deliver genetic material into cells effectively.
* **Versatility:** DOTAP can be used in various delivery systems and for a wide range of applications.
* **Biocompatibility:** DOTAP is generally well-tolerated by cells and organisms.

**Limitations of DOTAP:**

* **Toxicity:** While generally well-tolerated, DOTAP can cause some toxicity at high concentrations.
* **Limited stability:** DOTAP-based liposomes can be unstable in some formulations.
* **Off-target delivery:** DOTAP can sometimes deliver genetic material to unintended cells or tissues.

**Conclusion:**

DOTAP is a crucial molecule in non-viral gene delivery, enabling the effective transport of genetic material into cells for therapeutic and research purposes. It is an essential tool in advancing gene therapy and other biomedical fields. Ongoing research continues to optimize DOTAP-based delivery systems and explore its potential for a wide range of applications.

(3-dimyristyloxypropyl)(dimethyl)(hydroxyethyl)ammonium: a cationic lipid; RN refers to bromide salt [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID122191
SCHEMBL ID51215
MeSH IDM0231206

Synonyms (20)

Synonym
dmrie
pj9gnx9bop ,
dimyristyloxypropyl-3-dimethyl-hydroxyethyl ammonium
153312-64-2
unii-pj9gnx9bop
1-propanaminium, n-(2-hydroxyethyl)-n,n-dimethyl-2,3-bis(tetradecyloxy)-, bromide
(3-dimyristyloxypropyl)(dimethyl)(hydroxyethyl)ammonium
n-(2-hydroxyethyl)-n,n-dimethyl-2,3-bis(tetradecyloxy)-1-propanaminium bromide
SCHEMBL51215
1-propanaminium, n-(2-hydroxyethyl)-n,n-dimethyl-2,3-bis(tetradecyloxy)-, bromide (1:1)
dmrie-br
dmrie br
n-(2-hydroxyethyl)-n,n-dimethyl-2,3-bis(tetradecyloxy)-1-propaniminium bromide
(+/-)-n-(2-hydroxyethyl)-n,n-dimethyl-2,3-bis(tetradecyloxy)-1-propaniminium bromide
(+/-)-n-(2-hydroxyethyl)-n,n-dimethyl-2,3-bis(tetradecyloxy)-1-propanaminium bromide
WALUVDCNGPQPOD-UHFFFAOYSA-M
DTXSID30934728
n-(2-hydroxyethyl)-n,n-dimethyl-2,3-bis(tetradecyloxy)propan-1-aminium bromide
Q27286590
2,3-di(tetradecoxy)propyl-(2-hydroxyethyl)-dimethylazanium;bromide

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The toxic effect of cationic liposomes was very limited with uninfected cells, although concentrations of liposomes that were not toxic within a few days of treatment could cause toxicity at later times."( Human immunodeficiency virus type-1 (HIV-1) infection increases the sensitivity of macrophages and THP-1 cells to cytotoxicity by cationic liposomes.
Düzgüneş, N; Felgner, PL; Konopka, K; Pretzer, E, 1996
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (50)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's27 (54.00)18.2507
2000's22 (44.00)29.6817
2010's1 (2.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.11

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.11 (24.57)
Research Supply Index4.03 (2.92)
Research Growth Index4.14 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.11)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (5.77%)5.53%
Reviews4 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other45 (86.54%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]