U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C41H78NO8P
Molecular Weight 744.0337
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of 1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI

InChIKey=MWRBNPKJOOWZPW-NYVOMTAGSA-N
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

HIDE SMILES / InChI

Molecular Formula C41H78NO8P
Molecular Weight 744.0337
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 2
Optical Activity UNSPECIFIED

Gene therapy is expected to treat various incurable diseases including viral infections, autoimmune disorders, and cancers. Complexes of cationic liposomes with DNA are promising tools to deliver genetic information into cells for gene therapy and vaccines. Electrostatic interaction is thought to be the major force in lipid–DNA interaction, while lipid-base binding and the stability of cationic lipid–DNA complexes have been the subject of more debate in recent years. 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) forms heterogeneous liposomes with cationic lipids, which are used as delivery vehicles for therapeutic agents. DOPE is an essential component of cationic liposomes designed to deliver DNA into gliosarcoma and kidney cell lines (gene therapy). The order of stability of lipid–DNA complexation is DOTAP>DDAB>DOPE>Chol. Recently was discovered Lip-DOPE-MPL-GP2 formulation could be a promising vaccine and a therapeutic delivery system against HER2 positive cancers and merited further investigation.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Spacer structure and hydrophobicity influences transfection activity of novel polycationic gemini amphiphiles.
2017-08-01
DOTAP/DOPE ratio and cell type determine transfection efficiency with DOTAP-liposomes.
2015-10
Surface modification of tri-calcium phosphate nanoparticles by DOPE and/or anti-E6 antibody to enhance uptake of antisense of E6 mRNA.
2015-02-01
Thermodynamic analysis of binding and protonation in DOTAP/DOPE (1:1): DNA complexes using isothermal titration calorimetry.
2003-05-01
Evaluation and optimization of DNA delivery into gliosarcoma 9L cells by a cholesterol-based cationic liposome.
2002-08-31
Kidney-targeted liposome-mediated gene transfer in mice.
1997-05
Patents

Sample Use Guides

in mice: intravenous administration demonstrated that Man/DOPE complex was accumulated in the liver more efficiently and achieved a higher gene expression in the liver than Man/DOPC complex
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:13:49 GMT 2025
Edited
by admin
on Mon Mar 31 18:13:49 GMT 2025
Record UNII
JNP6V6AI0U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE
Common Name English
1,2-DI-(9Z-OCTADECENOYL)-SN-GLYCERO-3-PHOSPHOETHANOLAMINE
Preferred Name English
DOPE, R-
Common Name English
PE(18:1(9Z)/18:1(9Z))
Common Name English
DOPE, L-
Common Name English
Code System Code Type Description
CHEBI
84839
Created by admin on Mon Mar 31 18:13:49 GMT 2025 , Edited by admin on Mon Mar 31 18:13:49 GMT 2025
PRIMARY
FDA UNII
JNP6V6AI0U
Created by admin on Mon Mar 31 18:13:49 GMT 2025 , Edited by admin on Mon Mar 31 18:13:49 GMT 2025
PRIMARY
CAS
4004-05-1
Created by admin on Mon Mar 31 18:13:49 GMT 2025 , Edited by admin on Mon Mar 31 18:13:49 GMT 2025
PRIMARY
SMS_ID
100000163315
Created by admin on Mon Mar 31 18:13:49 GMT 2025 , Edited by admin on Mon Mar 31 18:13:49 GMT 2025
PRIMARY
CHEBI
74986
Created by admin on Mon Mar 31 18:13:49 GMT 2025 , Edited by admin on Mon Mar 31 18:13:49 GMT 2025
PRIMARY
EPA CompTox
DTXSID601029609
Created by admin on Mon Mar 31 18:13:49 GMT 2025 , Edited by admin on Mon Mar 31 18:13:49 GMT 2025
PRIMARY
PUBCHEM
9546757
Created by admin on Mon Mar 31 18:13:49 GMT 2025 , Edited by admin on Mon Mar 31 18:13:49 GMT 2025
PRIMARY
WIKIPEDIA
1,2-Dioleoyl-sn-glycerophosphoethanolamine
Created by admin on Mon Mar 31 18:13:49 GMT 2025 , Edited by admin on Mon Mar 31 18:13:49 GMT 2025
PRIMARY
MESH
C020888
Created by admin on Mon Mar 31 18:13:49 GMT 2025 , Edited by admin on Mon Mar 31 18:13:49 GMT 2025
PRIMARY