Merck
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850725P

Avanti

18:1 (Δ9-Cis) PE (DOPE)

Avanti Polar Lipids

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Synonym(s):
1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine; DOPE; PE(18:1(9Z)/18:1(9Z)); 110635, DOPE
Empirical Formula (Hill Notation):
C41H78NO8P
CAS Number:
Molecular Weight:
744.03
NACRES:
NA.25

description

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

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 g (850725P-1g)
pkg of 2 × 100 mg (850725P-200mg)
pkg of 5 × 100 mg (850725P-500mg)
pkg of 1 × 25 mg (850725P-25mg)

manufacturer/tradename

Avanti Polar Lipids

application(s)

advanced drug delivery

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@@](COP([O-])(OCC[NH3+])=O)(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O

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-/t39-/m1/s1

InChI key

MWRBNPKJOOWZPW-NYVOMTAGSA-N

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

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850725P

18:1 (Δ9-Cis) PE (DOPE)

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

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

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

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18:1 (Δ9-Cis) PC (DOPC)

form

powder

form

liquid

form

liquid

form

powder

packaging

pkg of 1 × 1 g (850725P-1g), pkg of 2 × 100 mg (850725P-200mg), pkg of 5 × 100 mg (850725P-500mg), pkg of 1 × 25 mg (850725P-25mg)

packaging

pkg of 1 × 2.5 mL (850725C-25mg), pkg of 2 × 20 mL (850725C-1g), pkg of 2 × 4 mL (850725C-200mg), pkg of 5 × 4 mL (850725C-500mg)

packaging

pkg of 1 × 2.5 mL (850375C-25mg), pkg of 2 × 20 mL (850375C-1g), pkg of 2 × 4 mL (850375C-200mg), pkg of 5 × 4 mL (850375C-500mg)

packaging

pkg of 1 × 1 g (850375P-1g), pkg of 2 × 100 mg (850375P-200mg), pkg of 5 × 100 mg (850375P-500mg), pkg of 1 × 25 mg (850375P-25mg)

manufacturer/tradename

Avanti Polar Lipids

manufacturer/tradename

Avanti Polar Lipids

manufacturer/tradename

Avanti Polar Lipids

manufacturer/tradename

Avanti Polar Lipids

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

General description

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (18:1 (Δ9-Cis) PE (DOPE)) is a neutral phospholipid and displays sensitivity towards pH change. At acidic it is an inverted hexagonal micelle and transforms to spherical micelle at alkaline pH.

Application

18:1 (Δ9-Cis) PE (DOPE) has been used in the preparation of liposome for human uncoupling protein 1 (UCP1) reconstitution and for Caenorhabditis elegans autophagy related cysteine protease protein conjugation studies. It has also been used for the generation of giant unilamellar vesicles (GUVs) for septin induced deformation studies.

Biochem/physiol Actions

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (18:1 (Δ9-Cis) PE (DOPE)) forms a stable lipid layer and rapidly fuses with endosomal lipid bilayer. DOPE in combination with 1,2-dioleoyl-3-trimethylammonium-propane (DOTAP) has high in vitro transfection efficiency.

Packaging

20 mL Clear Glass Screw Cap Vial (850725P-1g)
5 mL Clear Glass Sealed Ampule (850725P-200mg)
5 mL Clear Glass Sealed Ampule (850725P-25mg)
5 mL Clear Glass Sealed Ampule (850725P-500mg)

also commonly purchased with this product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Sigma-Aldrich

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The role of the helper lipid dioleoylphosphatidylethanolamine (DOPE) for DNA transfection cooperating with a cationic lipid bearing ethylenediamine
Mochizuki S, et al.
Biochimica et Biophysica Acta - Biomembranes, 1828(2), 412-418 (2013)
Autophagy impairment mediated by S-nitrosation of ATG4B leads to neurotoxicity in response to hyperglycemia
Li Y, et al.
Autophagy, 13(7), 1145-1160 (2017)
Specific interaction of the human mitochondrial uncoupling protein 1 with free long-chain fatty acid
Zhao L, et al.
Structure, 25(9), 1371-1379 (2017)
Exploring the correlation between lipid packaging in lipoplexes and their transfection efficacy
Moghaddam B, et al.
Pharmaceutics, 3(4), 848-864 (2011)
Membrane reshaping by micrometric curvature sensitive septin filaments
Beber A, et al.
Nature Communications, 10(1), 420-420 (2019)

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