1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE

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

Structure Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23092705 | https://www.ncbi.nlm.nih.gov/pubmed/28645658 | https://www.ncbi.nlm.nih.gov/pubmed/29045460

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

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: DNA Sources: https://www.ncbi.nlm.nih.gov/pubmed/19103664	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Kidney-targeted liposome-mediated gene transfer in mice.	1997 May	9274719
Evaluation and optimization of DNA delivery into gliosarcoma 9L cells by a cholesterol-based cationic liposome.	2002 Aug 31	12175922
Surface modification of tri-calcium phosphate nanoparticles by DOPE and/or anti-E6 antibody to enhance uptake of antisense of E6 mRNA.	2015 Feb 1	25601794
DOTAP/DOPE ratio and cell type determine transfection efficiency with DOTAP-liposomes.	2015 Oct	26112463
Spacer structure and hydrophobicity influences transfection activity of novel polycationic gemini amphiphiles.	2017 Aug 1	28645658

Patents

Sample Use Guides

In Vivo Use Guide

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 `Fri Dec 15 15:56:17 GMT 2023` Edited by `admin` on `Fri Dec 15 15:56:17 GMT 2023`
Record UNII	JNP6V6AI0U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE

Common Name

English

DOPE, R-

Common Name

English

PE(18:1(9Z)/18:1(9Z))

Common Name

English

1,2-DI-(9Z-OCTADECENOYL)-SN-GLYCERO-3-PHOSPHOETHANOLAMINE

Common Name

English

DOPE, L-

Common Name

English

Code System Code Type Description

CHEBI

84839