Page last updated: 2024-11-07

1,2-distearoylphosphatidylethanolamine

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

Description

1,2-distearoylphosphatidylethanolamine (DSP) is a synthetic phospholipid with two stearic acid chains attached to the glycerol backbone. It is commonly used in research as a model membrane component to study lipid bilayer properties and membrane protein interactions. DSP is known for its high melting temperature and its ability to form stable, tightly packed lipid bilayers. It is used in various applications, including liposome formulations for drug delivery, biocompatible coatings, and model systems for studying membrane fluidity and permeability. The high melting temperature of DSP makes it suitable for studying the effects of temperature on membrane structure and function. Its stability and well-defined structure make it a reliable tool for analyzing membrane protein interactions and lipid bilayer dynamics.'
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1,2-distearoylphosphatidylethanolamine: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1,2-distearoylphosphatidylethanolamine : A phosphatidylethanolamine in which the phosphatidyl acyl group at C-1 and C-2 is stearoyl. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID102547
CHEBI ID47764
SCHEMBL ID239308
MeSH IDM0114830

Synonyms (26)

Synonym
1,2-distearoylphosphatidylethanolamine
3-({[(2-aminoethyl)oxy](hydroxy)phosphoryl}oxy)propane-1,2-diyl dioctadecanoate
pe 18:0
octadecanoic acid, 1-((((2-aminoethoxy)hydroxyphosphinyl)oxy)methyl)-1,2-ethanediyl ester
CHEBI:47764
3-{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}propane-1,2-diyl dioctadecanoate
1-((((2-aminoethoxy)hydroxyphosphinyl)oxy)methyl)-1,2-ethanediyl octadecanoate
4537-76-2
D-7860
1,2-distearoyl-rac-glycero-3-phosphoethanolamine
[3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-octadecanoyloxypropyl] octadecanoate
distearoly-l-phosphatidylethanolamine
dc18pe
SCHEMBL239308
distearoylphosphatidylethanolamine
mfcd00036777
LVNGJLRDBYCPGB-UHFFFAOYSA-N
FT-0771986
3-(((2-aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl distearate
SY055932
STARBLD0009726
DTXSID80865952
mfcd00067452
SY327634
3-[[(2-aminoethoxy)(hydroxy)phosphoryl]oxy]propane-1,2-diyl distearate
pe 18:0_18:0

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" It was anticipated that the presence of this negative charge could have deleterious effects on liposome pharmacokinetic characteristics."( Comparison of different hydrophobic anchors conjugated to poly(ethylene glycol): effects on the pharmacokinetics of liposomal vincristine.
Bally, MB; Choi, LS; Cullis, PR; Lim, HJ; Mayer, LD; Saxon, D; Wang, Z; Webb, MS; Wong, FM, 1998
)
0.3
" The first dose resulted in a reduction in the circulation half-life of the second dose."( Accelerated clearance of a second injection of PEGylated liposomes in mice.
Ichihara, M; Ichikawa, T; Irimura, K; Ishida, T; Kiwada, H; Masuda, K, 2003
)
0.32
" A quantitative pharmacokinetic description of particulate drug forms requires serious adjustments in existing theoretical approaches, due to formulation size."( Pharmacokinetics of liposomes designed to carry glucocorticoids.
Hrynyk, R; Langner, M; Metselaar, B; Storm, G,
)
0.13
" In this study, the pharmacokinetic behavior of liposomes coated with the poly(amino acid) poly(hydroxyethyl-l-asparagine) (PHEA) was evaluated at low lipid doses and upon repeated administration in rats."( Pharmacokinetics of poly(hydroxyethyl-l-asparagine)-coated liposomes is superior over that of PEG-coated liposomes at low lipid dose and upon repeated administration.
Carstens, MG; Hennink, WE; Oussoren, C; Romberg, B; Snel, CJ; Storm, G, 2007
)
0.34
" The stealth liposomes were long-circulating showing a half-life time of 34."( Paclitaxel-loaded stealth liposomes: Development, characterization, pharmacokinetics, and biodistribution.
Meng, H; Xu, Y, 2016
)
0.43
" PEGylated liposomes decorated with folic acid have been investigated for several anticancer agents not only to extend plasma half-life but also for tumor targeting via folic acid receptors which overexpressed on tumor cell surface."( Gemcitabine-loaded Folic Acid Tagged Liposomes: Improved Pharmacokinetic and Biodistribution Profile.
Muddana Eswara, BR; Panduragaiah, VM; Sidramappa, MA; Unnam, S, 2019
)
0.51
" The comparative in vivo pharmacokinetic and biodistribution characteristics of radiolabeled (99mTc-labeled) plain GEM solution, and all liposomal formulations (conventional:CLs; stealth: SLs; folate targeted: FTLs) were evaluated in mice model."( Gemcitabine-loaded Folic Acid Tagged Liposomes: Improved Pharmacokinetic and Biodistribution Profile.
Muddana Eswara, BR; Panduragaiah, VM; Sidramappa, MA; Unnam, S, 2019
)
0.51

Compound-Compound Interactions

ExcerptReferenceRelevance
" The extraction procedure was combined with dispersive liquid-liquid microextraction for further preconcentration of the analytes for sensitive determination of the analytes followed by high performance liquid chromatography-diode array detector."( Determination of metronidazole and clarithromycin in plasma samples using surfactant-modified amorphous carbon-based DSPE combined with DLLME followed by HPLC.
Abbasalizadeh, A; Afshar Mogaddam, MR; Farajzadeh, MA; Javanbakht, F; Nemati, M, 2023
)
0.91

Bioavailability

ExcerptReferenceRelevance
" One way of prolonging the bioavailability of 99Tcm-MIBI is to use liposomes which do not affect its accumulation in tumour cells."( Uptake of liposome-encapsulated 99Tcm-MIBI by sensitive and multidrug-resistant tumour cell lines.
Benazzouz, F; Cordobes, MD; de Beco, V; Moretti, JL; Starzec, A, 1999
)
0.3
" With the aim of improving bioavailability and selectivity, the antiproliferative effects of free-, liposomed-, and immunoliposomed-curcumin and/or resveratrol formulations have been compared in two human breast cancer cell lines with different HER2 expression levels."( Immunoliposome encapsulation increases cytotoxic activity and selectivity of curcumin and resveratrol against HER2 overexpressing human breast cancer cells.
Barrajón-Catalán, E; Catania, A; Cicirata, F; Micol, V; Nicolosi, S, 2013
)
0.39
"RGD modified and PEGylated solid lipid nanoparticles loaded with puerarin (RGD/PEG-PUE-SLN) were developed to improve bioavailability of PUE, to prolong retention time in vivo and to enhance its protective effect on acute myocardial ischemia model."( RGD modified and PEGylated lipid nanoparticles loaded with puerarin: Formulation, characterization and protective effects on acute myocardial ischemia model.
Dong, Z; Du, Y; Guo, J; Lu, Q; Xing, X; Zhang, X, 2017
)
0.46
" In vivo pharmacokinetic study revealed noticeable enhancement of bioavailability and plasma circulation time of the drugs when encapsulated in the carrier system."( Folate receptor-targeted hybrid lipid-core nanocapsules for sequential delivery of doxorubicin and tanespimycin.
Choi, HG; Gautam, M; Gupta, B; Jeong, JH; Kim, JO; Lee, JS; Pathak, S; Poudel, BK; Regmi, S; Ruttala, HB; Yong, CS, 2017
)
0.46
" The biocompatible oral insulin formulation shows a high oral bioavailability of >40%, offers the possibility to fine tune insulin acting profiles and provides long-term safety, enabling the oral delivery of protein drugs."( Zwitterionic micelles efficiently deliver oral insulin without opening tight junctions.
Cao, Z; Du, H; Han, X; Lu, Y; Shi, Y; Song, B; Wang, K; Xie, J; Yang, C; Zhang, E; Zhu, H, 2020
)
0.56
" Yet, chronic treatments with anti-inflammatory agents, such as methotrexate (MTX), failed to modulate disease progression, possibly for the limited drug bioavailability and plaque deposition."( Modulating Lipoprotein Transcellular Transport and Atherosclerotic Plaque Formation in ApoE
Catelani, T; Cervadoro, A; Decuzzi, P; Di Francesco, V; Ferreira, MFMM; Gurgone, D; Maffia, P; Palomba, R, 2020
)
0.56
"Intrapulmonary delivery of these DSPE-PEG polymers significantly enhanced absorptions of poorly absorbed model drugs and did not induce serious damage to the pulmonary membranes of rats."( DSPE-PEG polymers for improving pulmonary absorption of poorly absorbed macromolecules in rats and relative mechanism.
Gao, Y; Liao, G; Long, Q; Sun, Y; Zhang, H, 2021
)
0.62
"Novelty statementIn this study, DSPE-PEG-OH and DSPE-PEG-SH polymers, two DSPE-PEG2000 conjugates with different terminal groups demonstrated significant promoting effects on the absorption of poorly absorbed macromolecular drugs after intrapulmonary delivery to rats, and did not induce serious damage to the pulmonary membranes of rats."( DSPE-PEG polymers for improving pulmonary absorption of poorly absorbed macromolecules in rats and relative mechanism.
Gao, Y; Liao, G; Long, Q; Sun, Y; Zhang, H, 2021
)
0.62
"DSPE-PEG polymer, as an excellent absorption enhancer, seems very promising in increasing oral bioavailability of berberine."( DSPE-PEG polymer enhanced berberine absorption specifically in the small intestine of rats through paracellular passway.
Gao, Y; Huxiao, L; Sun, J; Wang, S; Xu, Y; Zhang, H, 2023
)
0.91

Dosage Studied

ExcerptRelevanceReference
", saturation-type or Michaelis-Menten kinetics), with MPS uptake decreasing and % of injected dose in blood increasing as dose increased, over the entire dosage range."( Pharmacokinetics of stealth versus conventional liposomes: effect of dose.
Allen, TM; Hansen, C, 1991
)
0.28
" Mice dosed with LEH1 and LEH2 on Day +1 died rapidly from Listeria infection; but mice dosed with LEH2 lived significantly longer than did mice receiving LEH1."( Influence of steric stabilization of liposome-encapsulated hemoglobin on Listeria monocytogenes host defense.
Beissinger, RL; McCormick, DL; Sherwood, RL; Zheng, S, 1995
)
0.29
" We introduced here the development-process of liposomal formulations of polyene macrolide antibiotics, amphotericin B (AmB) and nystatin as injectable dosage forms."( Pharmaceutical design of the liposomal antimicrobial agents for infectious disease.
Maruyama, K; Moribe, K, 2002
)
0.31
" With the same dosage (2 mg."( [Preparation of long circulating mitoxantrone liposomes and its pharmacokinetics].
Duan, YS; Yu, BT; Zhang, ZR, 2002
)
0.31
" The two populations differ in their accumulation capacities, dosage and time constants."( Pharmacokinetics of liposomes designed to carry glucocorticoids.
Hrynyk, R; Langner, M; Metselaar, B; Storm, G,
)
0.13
" Although the mechanisms behind these observations are still not clear yet, the use of PHEA-liposomes appears beneficial when single low lipid doses and/or repeated dosing schedules are being applied."( Pharmacokinetics of poly(hydroxyethyl-l-asparagine)-coated liposomes is superior over that of PEG-coated liposomes at low lipid dose and upon repeated administration.
Carstens, MG; Hennink, WE; Oussoren, C; Romberg, B; Snel, CJ; Storm, G, 2007
)
0.34
" Therefore, DSPE-PEG-FA is considered as a proper stabilizer with active targeting effect for ACGs-NSps to reduce toxicity, enlarge the safe dosage range and apply in clinic for the treatment of folate-positive tumors."( Folate-targeting annonaceous acetogenins nanosuspensions: significantly enhanced antitumor efficacy in HeLa tumor-bearing mice.
Ao, H; Bi, D; Guo, Y; Han, M; Li, H; Li, Y; Wang, X, 2018
)
0.48
"Liposomal formulations have important therapeutic applications in anti-cancer treatments but current formulations suffer from serious side effects, high dosage requirements and prolonged treatment."( PEGylation and surface functionalization of liposomes containing drug nanocrystals for cell-targeted delivery.
Boyd, BJ; Clulow, AJ; de Campo, L; Gilbert, EP; Hawley, A; Li, T; Liu, Q; Manohar, M; Xiao, Y, 2019
)
0.51
" Thus, this study exhibited prospective potential of these DSPE-PEG polymers in developing into dosage forms with the aim to improve the poor bioavailability of some poorly absorbed macromolecular drugs."( DSPE-PEG polymers for improving pulmonary absorption of poorly absorbed macromolecules in rats and relative mechanism.
Gao, Y; Liao, G; Long, Q; Sun, Y; Zhang, H, 2021
)
0.62
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
phosphatidylethanolamine zwitterionThe zwitterion of a phosphatidylethanolamine compound formed by proton transfer from the phosphate to the primary amino group.
phosphatidylethanolamineA class of glycerophospholipids in which a phosphatidyl group is esterified to the hydroxy group of ethanolamine.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (266)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (0.75)18.7374
1990's32 (12.03)18.2507
2000's77 (28.95)29.6817
2010's132 (49.62)24.3611
2020's23 (8.65)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.30

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.30 (24.57)
Research Supply Index5.64 (2.92)
Research Growth Index5.95 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.30)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (1.07%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other278 (98.93%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]