Page last updated: 2024-12-11

1,2-dielaidoylphosphatidylethanolamine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

1,2-Dilauroylphosphatidylethanolamine (DLPE) is a type of phospholipid, specifically a **phosphatidylethanolamine** with **lauroyl (C12) fatty acid chains** at both the sn-1 and sn-2 positions.

**Importance in Research:**

* **Membrane Model System:** DLPE is commonly used as a model lipid in research studies investigating membrane structure and function. Due to its well-defined structure and properties, it provides a controlled system for studying membrane properties like fluidity, permeability, and interactions with proteins and other molecules.
* **Drug Delivery:** DLPE's biocompatible and bio-degradable nature makes it a promising candidate for developing drug delivery systems. It can be used to encapsulate drugs, enhancing their solubility and bioavailability.
* **Cell Signaling:** Phosphatidylethanolamines, including DLPE, play a role in cellular signaling pathways. They can be modified by enzymes to generate signaling molecules like lysophosphatidylethanolamine, which are involved in processes like inflammation and cell death.
* **Lipidomics:** DLPE is a key component of cellular membranes and is studied in lipidomics research to understand the composition and dynamics of lipid profiles in different cell types and under various physiological conditions.
* **Biomaterials:** DLPE can be incorporated into biomaterials like liposomes and nanoparticles for drug delivery, gene therapy, and tissue engineering applications.
* **Biophysical Studies:** Due to its defined structure, DLPE is useful in studying the physicochemical properties of lipid membranes using techniques like X-ray diffraction and NMR spectroscopy.

**Overall, DLPE is a versatile and valuable tool for research in a variety of fields related to membrane biology, drug delivery, cell signaling, and biomaterials.**

1,2-dielaidoylphosphatidylethanolamine: RN given refers to (E,E)-isomer; member of a class of cationic lipid formulations called cytofectins [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5909904
CHEMBL ID2448912
SCHEMBL ID10028732
MeSH IDM0075154

Synonyms (18)

Synonym
1,2-dielaidoylphosphatidylethanolamine
CHEMBL2448912
SCHEMBL10028732
AKOS032949924
(e)-3-(((2-aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate
elaidin, 1,2-di-, dihydrogen phosphate, 2-aminoethyl ester
5pbf1dl6zo ,
dielaidoylphosphatidylethanolamine
unii-5pbf1dl6zo
16777-83-6
elaidin, 1,2-di-, 2-aminoethyl hydrogen phosphate
9-octadecenoic acid, 1-((((2-aminoethoxy)hydroxyphosphinyl)oxy)methyl)-1,2-ethanediyl ester, (e,e)-
1,2-dielaidoylphosphatidylethanolamine, (+/-)-
9-octadecenoic acid, 1,1'-(1-((((2-aminoethoxy)hydroxyphosphinyl)oxy)methyl)-1,2-ethanediyl) ester, (9e,9'e)-
depe, (+/-)-
HY-142993
(e)-3-(((2-aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyldioleate
CS-0374734

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" pH-sensitive immunoliposomes containing diphtheria fragment A were not toxic to nontarget diphtheria-resistant A31 cells or to nontarget diphtheria-sensitive Vero cells."( Cytotoxicity of diphtheria toxin A fragment to toxin-resistant murine cells delivered by pH-sensitive immunoliposomes.
Collins, D; Huang, L, 1987
)
0.27
" The toxic effect of cationic liposomes was very limited with uninfected cells, although concentrations of liposomes that were not toxic within a few days of treatment could cause toxicity at later times."( Human immunodeficiency virus type-1 (HIV-1) infection increases the sensitivity of macrophages and THP-1 cells to cytotoxicity by cationic liposomes.
Düzgüneş, N; Felgner, PL; Konopka, K; Pretzer, E, 1996
)
0.29

Compound-Compound Interactions

ExcerptReferenceRelevance
" We show here that the polycationic lipid DOSPER in combination with histone H1 was much more efficient in transfection of neonatal cardiomyocytes than DOSPER alone or other cationic lipids."( A new efficient method for transfection of neonatal cardiomyocytes using histone H1 in combination with DOSPER liposomal transfection reagent.
Böttger, M; Buchberger, B; Haberland, A; Kott, M; Morano, I; Zaitsev, S, 1998
)
0.3

Bioavailability

ExcerptReferenceRelevance
"Delivery activity of pH-sensitive 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE):cholesteryl hemisuccinate (CHEMS) liposomes was assessed as an in vitro intracellular carrier system to increase the bioavailability of depigmentation actives."( Enhanced depigmenting effects of N-glycosylation inhibitors delivered by pH-sensitive liposomes into HM3KO melanoma cells.
Chang, IS; Choi, H; Hwang, JS; Kim, J; Park, JY,
)
0.13
"The development of antisense oligonucleotides suitable for tumor targeting applications is hindered by low stability and bioavailability of oligonucleotides in vivo and by the absence of efficient and safe vectors for oligonucleotide delivery."( In vitro characterization of two novel biodegradable vectors for the delivery of radiolabeled antisense oligonucleotides.
Koslowsky, I; Lavasanifar, A; Mercer, J; Murray, D; Shahhosseini, S; von Guggenberg, E, 2010
)
0.36

Dosage Studied

ExcerptRelevanceReference
" Optimal dosage of injected DNA was from 30 to 70 micrograms per tumor."( Direct gene transfer to mouse melanoma by intratumor injection of free DNA.
Huang, L; Yang, JP, 1996
)
0.29
" Under these conditions, mRNA target reduction dose-response curves were also shifted to lower doses."( Transfection protocol for antisense oligonucleotides affects uniformity of transfection in cell culture and efficiency of mRNA target reduction.
Bennett, CF; Freier, S; Lollo, B; Peralta, ER; Reed, CA; Wenrich, LM; Wong, CA, 2005
)
0.33
" Successful reduction in the liposomal dosage was attained by employing GALA while maintaining a high transfection efficiency."( Unique features of a pH-sensitive fusogenic peptide that improves the transfection efficiency of cationic liposomes.
Futaki, S; Harashima, H; Kogure, K; Masui, Y; Nakamura, T; Nakase, I; Sugiura, Y, 2005
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID781325pKa (acid-base dissociation constant) as determined by Liao ref: J Chem Info Model 20092014Pharmaceutical research, Apr, Volume: 31, Issue:4
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (598)

TimeframeStudies, This Drug (%)All Drugs %
pre-199049 (8.19)18.7374
1990's320 (53.51)18.2507
2000's147 (24.58)29.6817
2010's74 (12.37)24.3611
2020's8 (1.34)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.16%)5.53%
Reviews5 (0.80%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other619 (99.04%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]