Synthesis
6 mg of MAL-PEG(3000)-MMP2-COH was activated overnight in 5 mL of anhydrous chloroform/methanol/triethylamine solvent mixture (4.5:0.5:0.05 v/v) with a 20-fold molar excess of NHS/EDC (1:1 molar ratio). The activated MAL-PEG(3000)-MMP2-NHS was reacted with a 10-fold molar excess of DOPE for 2 h under nitrogen protection at 4°C. The reaction was purified on preparative aluminum TLC plates (silica gel 60 F254, 20 x 20 cm, Merck) using chloroform/methanol (4:1 v/v) as the mobile phase. The purified lyophilized residue was stored at −20°C to obtain the product 1,2-dioleoyl-SN-glycerol-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
Uses
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.
Uses
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.
Uses
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.
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
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).
