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76548

Sigma-Aldrich

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

≥97.0% (TLC)

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))

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About This Item

Empirical Formula (Hill Notation):
C41H78NO8P
CAS Number:
4004-05-1
Molecular Weight:
744.03
Beilstein:
1718431
MDL number:
MFCD00057986
UNSPSC Code:
51191904
PubChem Substance ID:
329767176
NACRES:
NA.85

biological source

synthetic

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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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

Certificates of Analysis (COA)

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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
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
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
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
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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