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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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100 MG
$240.00
1 G
$956.00

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100 MG
$240.00
1 G
$956.00

About This Item

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

$240.00

Available to ship onApril 22, 2025Details

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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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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 [1].

Biochem/physiol Actions

DOPE in mixed membranes have been found to decrease fluorescence lifetime and increase acyl-chain order.[2] DOPE is an essential component of cationic liposomes designed to deliver DNA into gliosarcoma[3] and kidney[4] cell lines (gene therapy).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL7110
BCCL9573
BCCH8913
BCCJ6267
BCCJ6750

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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
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
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
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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