Merck
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76548

Sigma-Aldrich

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

≥97.0% (TLC)

All Photos(1)
Synonym(s):
(9Z)-9-Octadecenoic acid (1R)-1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester, 1,2-Di(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine, 3-sn-Phosphatidylethanolamine, 1,2-dideoyl, L-β,γ-Dioleoyl-α-cephalin, DOPE, Dioleoyl phosphatidylethanolamine, PE(18:1(9Z)/18:1(9Z))
Empirical Formula (Hill Notation):
C41H78NO8P
CAS Number:
4004-05-1
Molecular Weight:
744.03
Beilstein:
1718431
MDL number:
MFCD00057986
PubChem Substance ID:
329767176
NACRES:
NA.85

biological source

synthetic

Quality Level

200

Assay

≥97.0% (TLC)

form

solid

functional group

amine

lipid type

phosphoglycerides

storage temp.

−20°C

SMILES string

CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI

1S/C41H78NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,39H,3-16,21-38,42H2,1-2H3,(H,45,46)/b19-17-,20-18-

InChI key

MWRBNPKJOOWZPW-CLFAGFIQSA-N

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1 of 4

This Item
P122342490850725P
1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine ≥97.0% (TLC)

Sigma-Aldrich

76548

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

L-α-Phosphatidylethanolamine, dioleoyl ≥99% (GC), ≥98% (TLC), lyophilized powder

Sigma-Aldrich

P1223

L-α-Phosphatidylethanolamine, dioleoyl

1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine ≥99.0% (10 mg phospholipid per ml CHCl3, TLC)

Sigma-Aldrich

42490

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

18:1 (Δ9-Cis) PE (DOPE) Avanti Polar Lipids

Avanti

850725P

18:1 (Δ9-Cis) PE (DOPE)

assay

≥97.0% (TLC)

assay

≥98% (TLC), ≥99% (GC)

assay

≥99.0% (10 mg phospholipid per ml CHCl3, TLC)

assay

>99% (TLC)

form

solid

form

lyophilized powder

form

liquid

form

powder

functional group

amine

functional group

phospholipid

functional group

phospholipid

functional group

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

lipid type

phosphoglycerides

lipid type

phosphoglycerides

lipid type

phosphoglycerides

lipid type

cardiolipins
phospholipids

Application

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 .

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).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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1,2-Distearoyl-sn-glycero-3-phosphocholine ≥99%

Sigma-Aldrich

P1138

1,2-Distearoyl-sn-glycero-3-phosphocholine

18:1 (Δ9-Cis) PC (DOPC) Avanti Polar Lipids

Avanti

850375P

18:1 (Δ9-Cis) PC (DOPC)

18:1 TAP (DOTAP) Avanti Polar Lipids

Avanti

890890P

18:1 TAP (DOTAP)

USP

USP

1535744

Phosphatidylethanolamine

Cholesteryl hemisuccinate

Sigma-Aldrich

C6512

Cholesteryl hemisuccinate

D Lesage et al.
Biochimica et biophysica acta, 1564(2), 393-402 (2002-08-15)
This paper reports results concerning the transfection of gliosarcoma cells 9L using an original cholesterol-based cationic liposome as carrier. This cationic liposome was prepared from triethyl aminopropane carbamoyl cholesterol (TEAPC-Chol) and a helper lipid, dioleoyl phosphatidyl ethanolamine (DOPE). The used
Keisuke Shintou et al.
Biophysical journal, 93(11), 3900-3906 (2007-08-21)
The effect of 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) in mixed membranes with 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) on interaction with a class A amphipathic peptide, Ac-DWLKAFYDKVAEKLKEAF-NH(2) (Ac-18A-NH(2)), was investigated. The fluorescence lifetime of 2-(9-anthroyloxy)stearic acid and (2)H NMR spectra were used to evaluate the penetration of
Marco Scarzello et al.
Biophysical journal, 88(3), 2104-2113 (2004-12-23)
Two double-tailed pyridinium cationic amphiphiles, differing only in the degree of unsaturation of the alkyl chains, have been selected for a detailed study of their aggregation behavior, under conditions employed for transfection experiments. The transfection efficiencies of the two molecules
L W Lai et al.
Gene therapy, 4(5), 426-431 (1997-05-01)
To develop gene therapy targeted to the kidney, we compared three different routes of liposome-mediated gene delivery to the kidney in mice, ie intra-renal-pelvic, intra-renal-arterial, and intra-renal-parenchymal injections. A plasmid construct, pCMV beta gal, containing a cytomegalovirus (CMV) immediate-early gene
Antonio A M Gasperini et al.
Langmuir : the ACS journal of surfaces and colloids, 31(11), 3308-3317 (2015-03-03)
This work presents a study of the association between low molecular weight hyaluronic acid (16 kDa HA) and cationic liposomes composed of egg phosphatidylcholine (EPC), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), and 1,2-dioleoyl-3-trimethylammonium-propane (DOTAP). The cationic liposome/HA complexes were evaluated to determine their mesoscopic
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