1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine

Synonym(s):DOPE;Dioleoyl phosphatidylethanolamine;PE(18:1(9Z)/18:1(9Z));(9Z)-9-Octadecenoic acid (1R)-1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester;L-β,γ-Dioleoyl-α-cephalin

CAS NO.：4004-05-1
Empirical Formula: C41H78NO8P
Molecular Weight: 744.05
MDL number: MFCD16621009
EINECS: 200-663-8
SAFETY DATA SHEET (SDS)
Update Date: 2024-07-26 17:49:17

1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine Structural

What is 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine?

Description

1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) is a neutral phospholipid and displays sensitivity towards pH change and has been used in the preparation of liposome and giant unilamellar vesicles (GUVs).
Phosphatidylethanolamine (PE) is formed primarily in the reaction of CDP-ethanolamine and diacylglycerol. PE is one of the major components of cell membranes in bacteria and in nervous system.

Chemical properties

Yellowish wax

The Uses of 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine

1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) forms heterogenous liposomes with N-[1-(2,3-dioleoyloxy)propyl]-N,N,N-trimethylammonium methylsulfate (DOTAP), which are used as delivery vehicles for therapeutic agents.

The Uses of 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine

1,2-Dioleoyl-sn-glycero-3-phosphatidylethanolamine (DOPE) is a synthetic analog of naturally-occurring PE containing 18:1 fatty acids at the sn-1 and sn-2 positions. DOPE can be used as an emulsifier to facilitate DNA-liposome complex transport across membranes. It is used in combination with cationic phospholipids to increase efficiency during DNA transfection studies as a non-viral method of gene delivery.

The Uses of 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine

18:1 (Δ9-Cis) PE (DOPE) has been used in the preparation of liposome for human uncoupling protein 1 (UCP1) reconstitution and for Caenorhabditis elegans autophagy related cysteine protease protein conjugation studies. It has also been used for the generation of giant unilamellar vesicles (GUVs) for septin induced deformation studies.

What are the applications of Application

1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine is a membrane phospholipid emulsifier to improve transfection of DNA

Definition

ChEBI: Dioleoyl phosphatidylethanolamine is a phosphatidylethanolamine in which the phosphatidyl acyl groups are both oleoyl.

General Description

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (18:1 (Δ9-Cis) PE (DOPE)) is a neutral phospholipid and displays sensitivity towards pH change. At acidic it is an inverted hexagonal micelle and transforms to spherical micelle at alkaline pH.

Biological Activity

DOPE in mixed membranes have been found to decrease fluorescence lifetime and increase acyl-chain order. DOPE is an essential component of cationic liposomes designed to deliver DNA into gliosarcoma and kidney cell lines (gene therapy).

Biochem/physiol Actions

storage

Store at -20°C

Properties of 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine

Melting point:	200°C(lit.)
Boiling point:	759.2±70.0 °C(Predicted)
Density	1.008±0.06 g/cm3(Predicted)
storage temp.	-20°C
solubility	DMSO: 31.25 mg/mL (42.00 mM)
form	lyophilized powder
pka	1.17±0.50(Predicted)
color	White to Light yellow
BRN	1718431

Safety information for 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine

Signal word	Danger
Pictogram(s)	Skull and Crossbones Acute Toxicity GHS06 Health Hazard GHS08
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H331:Acute toxicity,inhalation H336:Specific target organ toxicity,single exposure; Narcotic effects H351:Carcinogenicity H372:Specific target organ toxicity, repeated exposure H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P201:Obtain special instructions before use. P273:Avoid release to the environment. P302+P352:IF ON SKIN: wash with plenty of soap and water. P308+P313:IF exposed or concerned: Get medical advice/attention.