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P1223

Sigma-Aldrich

L-α-Phosphatidylethanolamine, dioleoyl

≥99% (GC), ≥98% (TLC), lyophilized powder

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Synonym(s):
1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine, (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:
24898174
NACRES:
NA.25

biological source

synthetic

Quality Level

200

Assay

≥98% (TLC)
≥99% (GC)

form

lyophilized powder

functional group

phospholipid

lipid type

phosphoglycerides

shipped in

ambient

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 .
Forms liposomes with DC-cholesterol that can be used to efficiently transfect several mammalian cell lines.

Packaging

Packaged under Argon.

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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Juliette Fedry et al.
PLoS biology, 16(8), e2006357-e2006357 (2018-08-14)
HAPLESS2 (HAP2) is a broadly conserved, gamete-expressed transmembrane protein that was shown recently to be structurally homologous to viral class II fusion proteins, which initiate fusion with host cells via insertion of fusion loops into the host membrane. However, the
Miriam Stoeber et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(50), E8069-E8078 (2016-11-12)
Caveolae are invaginated plasma membrane domains involved in mechanosensing, signaling, endocytosis, and membrane homeostasis. Oligomers of membrane-embedded caveolins and peripherally attached cavins form the caveolar coat whose structure has remained elusive. Here, purified Cavin1 60S complexes were analyzed structurally in
Jiao Wang et al.
Scientific reports, 8(1), 10795-10795 (2018-07-19)
P4-ATPases are a subfamily of P-type ATPases that flip phospholipids across membranes to generate lipid asymmetry, a property vital to many cellular processes. Mutations in several P4-ATPases have been linked to severe neurodegenerative and metabolic disorders. Most P4-ATPases associate with
Tatjana Michel et al.
Molecular therapy. Nucleic acids, 8, 459-468 (2017-09-18)
Synthetically modified mRNA is a unique bioactive agent, ideal for use in therapeutic applications, such as cancer vaccination or treatment of single-gene disorders. In order to facilitate mRNA transfections for future therapeutic applications, there is a need for the delivery
Yoshiki Moriizumi et al.
Scientific reports, 8(1), 11757-11757 (2018-08-08)
We developed a novel hybrid cell reactor system via functional fusion of single Escherichia coli protoplast cells, that are deficient in cell wall and expose plasma membrane, with arrayed lipid bilayer chambers on a device in order to incorporate the
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