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76548

Sigma-Aldrich

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

≥97.0% (TLC)

Synonyme(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

Formule empirique (notation de Hill):
C41H78NO8P
Numéro CAS:
4004-05-1
Poids moléculaire :
744.03
Numéro Beilstein :
1718431
Numéro MDL:
MFCD00057986
Code UNSPSC :
51191904
ID de substance PubChem :
329767176
Nomenclature NACRES :
NA.85

Source biologique

synthetic

Pureté

≥97.0% (TLC)

Forme

solid

Groupe fonctionnel

amine

Type de lipide

phosphoglycerides

Température de stockage

−20°C

Chaîne SMILES 

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-

Clé InChI

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 .

Actions biochimiques/physiologiques

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).

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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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