Page last updated: 2024-12-11

1,2-dioleoylphosphatidylserine

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

Description

## 1,2-Dioleoylphosphatidylserine (DOPS): A Key Player in Membrane Research

**1,2-Dioleoylphosphatidylserine (DOPS)** is a type of phospholipid, a class of molecules that make up the cell membrane. It has a distinctive structure with two oleic acid chains (unsaturated fatty acids) attached to glycerol, a phosphate group, and a serine molecule. This specific structure gives DOPS unique properties that make it crucial in various research areas.

**Importance in Research:**

* **Cell Signaling:** DOPS is a critical component of the cell membrane and plays a key role in cell signaling processes. It interacts with various proteins, including enzymes and receptors, and influences their activity. This interaction can affect cell growth, differentiation, and apoptosis (programmed cell death).
* **Membrane Fusion:** DOPS is essential for membrane fusion, a process where two cell membranes merge. This is crucial for functions like exocytosis (release of substances from the cell) and endocytosis (uptake of substances by the cell). DOPS facilitates membrane fusion by interacting with other lipids and proteins, promoting the formation of the fusion pore.
* **Membrane Structure and Dynamics:** DOPS contributes to the structural integrity and fluidity of the cell membrane. Its negatively charged head group attracts positively charged molecules, affecting the electrostatic interactions within the membrane. This, in turn, influences membrane permeability, protein localization, and other membrane-related properties.
* **Model Systems:** DOPS is widely used in model systems to study membrane properties and interactions. Researchers use liposomes (artificial vesicles) composed of DOPS and other lipids to mimic cell membranes and investigate the behavior of proteins and other molecules in a controlled environment.
* **Drug Delivery:** DOPS is explored for its potential in drug delivery systems. Its negatively charged head group can interact with positively charged drugs, enabling encapsulation and targeted delivery to specific cells or tissues.

**Research Applications:**

* **Understanding Cell Communication:** Researchers use DOPS to investigate cell signaling pathways, particularly those involving proteins that interact with the cell membrane.
* **Studying Membrane Dynamics:** DOPS is essential for studying membrane fluidity, protein trafficking, and other dynamic processes within the cell membrane.
* **Developing New Therapies:** Researchers explore the potential of DOPS-based liposomes for drug delivery and targeted therapies for various diseases, including cancer.

**In Summary:**

1,2-Dioleoylphosphatidylserine is a fundamental phospholipid with significant implications in cell signaling, membrane fusion, and overall membrane structure and dynamics. Its unique properties make it an invaluable tool in research, aiding in understanding cellular processes and developing new therapeutic strategies.

1,2-dioleoylphosphatidylserine: RN given in first source; RN given refers to (R-(Z,Z))-isomer; RN for cpd without isomeric designation not available 6/90 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1,2-dioleoyl-sn-glycero-3-phospho-L-serine : A 3-sn-phosphatidyl L-serine in which the phosphatidyl acyl groups are both oleoyl. [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]

phosphatidylserine(18:1/18:1) : A 3-sn-phosphatidyl-L-serine in which the 1- and 2-acyl groups are octadecenoyl groups. [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 CID6438639
CHEMBL ID4165044
CHEBI ID60568
SCHEMBL ID203029
MeSH IDM0125516

Synonyms (45)

Synonym
LMGP03010030
dioleoyl phosphatidylserine
l-serine, 2,3-bis[(1-oxo-9-octadecenyl)oxy]propyl-2-t hydrogen phosphate (ester), [r-(z,z)]-
ps(18:1/18:1)
ps(18:1(9z)/18:1(9z))
1,2-di-(9z-octadecenoyl)-sn-glycero-3-phosphoserine
1,2-dioleoylphosphatidylserine
ps(36:2)
phosphatidylserine(36:2)
1,2-dioleoyl-sn-glycero-3-phospho-l-serine
18:1 ps (dops)
1,2-dioleoyl-sn-glycero-3-phosphoserine
dopse
1,2-dlps
phosphatidylserine(18:1/18:1)
ps(18:1omega9/18:1omega9)
CHEBI:60568 ,
phosphatidylserine(18:1omega9/18:1omega9)
70614-14-1
o-[({(2r)-2,3-bis[(9z)-octadec-9-enoyloxy]propyl}oxy)(hydroxy)phosphoryl]-l-serine
o-[(s)-({(2r)-2,3-bis[(9z)-octadec-9-enoyloxy]propyl}oxy)(hydroxy)phosphoryl]-l-serine
unii-kj401h4834
kj401h4834 ,
l-serine, 2,3-bis((1-oxo-9-octadecenyl)oxy)propyl hydrogen phosphate (ester), (r-(z,z))-
EPITOPE ID:140431
dops, r-
4,6,10-trioxa-5-phosphaoctacos-19-enoic acid, 2-amino-5-hydroxy-11-oxo-8-(((9z)-1-oxo-9-octadecen-1-yl)oxy)-, 5-oxide, (2s,8r,19z)-
SCHEMBL203029
dioleoylphosphatidylserine
4,6,10-trioxa-5-phosphaoctacos-19-enoic acid, 2-amino-5-hydroxy-11-oxo-8-[[(9z)-1-oxo-9-octadecen-1-yl]oxy]-, 5-oxide, (2s,8r,19z)-
ps(36:02)
ps(18:1n9/18:1n9)
ps(18:1w9/18:1w9)
phosphatidylserine(18:1n9/18:1n9)
pser(18:1n9/18:1n9)
1,2-dioleoyl-rac-glycero-3-phosphoserine
pser(18:1/18:1)
pser(18:1w9/18:1w9)
phosphatidylserine(18:1w9/18:1w9)
Q27127822
CHEMBL4165044
DTXSID701311823
ps(18:1_18:1)
PD131389
o-(((r)-2,3-bis(oleoyloxy)propoxy)(hydroxy)phosphoryl)-l-serine

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" dosing of saposin C-dioleoylphosphatidylserine showed no toxic effects in nontumor tissues."( Cancer-selective targeting and cytotoxicity by liposomal-coupled lysosomal saposin C protein.
Chu, Z; Cripe, TP; Mahller, YY; Qi, X; Stringer, KF; Witte, DP, 2009
)
0.35

Dosage Studied

ExcerptRelevanceReference
" dosing of saposin C-dioleoylphosphatidylserine showed no toxic effects in nontumor tissues."( Cancer-selective targeting and cytotoxicity by liposomal-coupled lysosomal saposin C protein.
Chu, Z; Cripe, TP; Mahller, YY; Qi, X; Stringer, KF; Witte, DP, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[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 (1)

ClassDescription
phosphatidylserine(18:1/18:1)A 3-sn-phosphatidyl-L-serine in which the 1- and 2-acyl groups are octadecenoyl groups.
[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]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1354852Activation of full length recombinant human His-tagged tissue factor expressed in Escherichia coli BL21(DE3)/recombinant factor 7a (unknown origin) assessed as induction of coagulant factor-10a production using S-2765 as substrate measured for 2 mins in p2018ACS medicinal chemistry letters, May-10, Volume: 9, Issue:5
Synthesis of Phosphatidylserine and Its Stereoisomers: Their Role in Activation of Blood Coagulation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (187)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (3.21)18.7374
1990's50 (26.74)18.2507
2000's55 (29.41)29.6817
2010's67 (35.83)24.3611
2020's9 (4.81)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.17

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 Index10.17 (24.57)
Research Supply Index5.24 (2.92)
Research Growth Index5.41 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.17)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (1.07%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other185 (98.93%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]