Compounds > 1-thiohexadecyl-2-ethyl-glycero-3-phosphocholine
Page last updated: 2024-12-06

1-thiohexadecyl-2-ethyl-glycero-3-phosphocholine

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

Description

1-thiohexadecyl-2-ethyl-glycero-3-phosphocholine is a synthetic analog of **phosphatidylcholine**, a major phospholipid component of cell membranes.

Here's a breakdown of its structure and significance:

**Structure:**

* **Glycerol backbone:** The molecule is built around a glycerol backbone, a 3-carbon alcohol.
* **Fatty acid chains:** Two fatty acid chains are attached to the glycerol backbone.
* **Thioether linkage:** One of the fatty acid chains is a hexadecyl (C16) chain linked to glycerol through a sulfur atom, forming a thioether bond. This is the unique feature that distinguishes it from natural phosphatidylcholine.
* **Ethyl chain:** The second fatty acid chain is an ethyl group (C2H5).
* **Phosphocholine head group:** A phosphocholine group (PO4-CH2-CH2-N+(CH3)3) is attached to the glycerol backbone.

**Importance in research:**

1-thiohexadecyl-2-ethyl-glycero-3-phosphocholine is a valuable tool for researchers because:

* **Membrane mimicry:** It can act as a mimic for the phospholipid bilayer of cell membranes due to its similar structural properties.
* **Enhanced membrane permeability:** The thioether linkage increases the permeability of this compound across cell membranes compared to natural phosphatidylcholine.
* **Delivery vehicle:** This enhanced permeability makes it useful as a delivery vehicle for drugs, genes, and other molecules into cells.
* **Study of membrane interactions:** It allows researchers to study the interactions of various molecules with cell membranes in a controlled setting.
* **Biophysical studies:** It is used in biophysical studies to investigate the properties of lipid membranes and their interactions with other molecules.

**Applications:**

1-thiohexadecyl-2-ethyl-glycero-3-phosphocholine has applications in various fields, including:

* **Drug delivery:** Development of novel drug delivery systems to improve therapeutic efficacy.
* **Gene therapy:** Delivery of therapeutic genes into cells for genetic disorders.
* **Bioimaging:** Labeling with fluorescent dyes for imaging cellular processes.
* **Nanotechnology:** Building artificial membranes and nanocarriers for controlled drug release.

**Note:** While it is a valuable tool for research, further studies are required to evaluate its safety and potential toxicity in biological systems.

1-thiohexadecyl-2-ethyl-glycero-3-phosphocholine: RN given refers to hydroxide, inner salt, 4-oxide, (+-)-isomer; cpd without isomeric designation not available 4/88 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID73354
CHEMBL ID286705
MeSH IDM0155695

Synonyms (13)

Synonym
2-[(2-ethoxy-3-hexadecylsulfanyl-propoxy)-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium
cp-53(et-16s-oet)
103304-64-9
3,5-dioxa-9-thia-4-phosphapentacosan-1-aminium,7-ethoxy-4-hydroxy-n,n,n-trimethyl-,hydroxide,inner salt,4-oxide
CHEMBL286705
(2-ethoxy-3-hexadecylsulfanylpropyl) 2-(trimethylazaniumyl)ethyl phosphate
1-thiahexadecyl-2-ethyl-glycero-3-phosphocholine
1-thiohexadecyl-2-ethyl-glycero-3-phosphocholine
tegp
3,5-dioxa-9-thia-4-phosphapentacosan-1-aminium, 7-ethoxy-4-hydroxy-n,n,n-trimethyl-, hydroxide, inner salt, 4-oxide, (+-)-
1-mercaptohexadecyl-2-ethyl-glycero-3-phosphocholine
2-ethoxy-3-(hexadecylsulfanyl)propyl 2-(trimethylazaniumyl)ethyl phosphate
DTXSID10908321
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID41521Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-3 at 0.3 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID41514Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-1 at 10.0 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID82508Standard thymidine incorporation assay (TdR) was carried out for 48 hr and involved a 24-h pulse of [3H]- thymidine (n=3) and ID50 value was evaluated1993Journal of medicinal chemistry, Jul-09, Volume: 36, Issue:14
Synthesis of phosphocholine and quaternary amine ether lipids and evaluation of in vitro antineoplastic activity.
AID41394Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-1 at 0.0 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID41518Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-3 at 0.0 ug/mL,1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID41515Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-1 at 3.0 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID41519Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-3 at 0.03 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID89000In vitro inhibition of HIV-1 plaque formation1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
In vitro evaluation of phosphocholine and quaternary ammonium containing lipids as novel anti-HIV agents.
AID41397Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-1 at 0.3 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID89134Concentration of compound required to 50% growth inhibition of HIV-1 in CEM-SS cells1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Synthesis and evaluation of novel ether lipid nucleoside conjugates for anti-HIV-1 activity.
AID41396Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-1 at 0.1 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID82646Trypan blue exclusion assay (TB) was carried out for 48 hr and the in vitro ID50 value was evaluated in the HL-60 leukemic cell system (n=1)1993Journal of medicinal chemistry, Jul-09, Volume: 36, Issue:14
Synthesis of phosphocholine and quaternary amine ether lipids and evaluation of in vitro antineoplastic activity.
AID41520Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-3 at 0.1 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID89003Anti-HIV-1 activity against syncytial plaque formation1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Synthesis and evaluation of novel ether lipid nucleoside conjugates for anti-HIV-1 activity.
AID82641Standard thymidine incorporation assay (TdR) was carried out for 48 hr with an 8 hr pulse of [3H]- thymidine (TdR8) (n=3) and ID50 value was evaluated1993Journal of medicinal chemistry, Jul-09, Volume: 36, Issue:14
Synthesis of phosphocholine and quaternary amine ether lipids and evaluation of in vitro antineoplastic activity.
AID41522Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-3 at 1.0 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID41516Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-1 at 30.0 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID41525Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-3 at 30.0 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID41524Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-3 at 3.0 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID232296Differential selectivity measured as the ratio of CEM-SS cell growth IC50 vs HIV plaque formation IC50.1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
In vitro evaluation of phosphocholine and quaternary ammonium containing lipids as novel anti-HIV agents.
AID46608In vitro inhibition of CEM-SS cell growth by 50 %1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
In vitro evaluation of phosphocholine and quaternary ammonium containing lipids as novel anti-HIV agents.
AID41398Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-1 at 1.0 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID41523Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-3 at 10.0 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
AID41395Compound was evaluated for its effect on colony growth of human ovarian adenocarcinoma cell line BG-1 at 0.03 ug/mL1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of sulfur analogues of alkyl lysophospholipid and neoplastic cell growth inhibitory properties.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (33.33)18.7374
1990's4 (66.67)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.67

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 Index12.67 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.62 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.67)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
edelfosine
edelfosine: RN given refers to parent cpd. edelfosine : A racemate comprising equimolar amounts of (R)- and (S)-edelfosine.. 1-octadecyl-2-methylglycero-3-phosphocholine : A glycerophosphocholine that is glycero-3-phosphocholine substituted at positions 1 and 2 by octadecyl and methyl groups respectively.		2.8940glycerophosphocholine
methionine sulfoximine
methionine sulfoximine : A non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine .		1.9810methionine derivative;
non-proteinogenic alpha-amino acid;
sulfoximide
buthionine sulfoximine
Buthionine Sulfoximine: A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7). 2-amino-4-(S-butylsulfonimidoyl)butanoic acid : A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group carries an oxo, imino and butyl groups.. S-butyl-DL-homocysteine (S,R)-sulfoximine : A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.		1.9810diastereoisomeric mixture;
homocysteines;
non-proteinogenic alpha-amino acid;
sulfoximide		EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor;
ferroptosis inducer
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		2.3820azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
ilmofosine
ilmofosine: used in treatment of colonic adenocarcinoma in rats; structure given in first source; RN given refers to hydroxide inner salt		1.9810
3-octadecanamido-2-ethoxypropylphosphocholine
3-octadecanamido-2-ethoxypropylphosphocholine: anti-HIV agent; RN & structure given in first source		2.3820
cp 46665
CP 46665: immunomodulator; RN given refers to di-HCl		1.9710
perfosfamide
[no description available]		1.9710
piperidines
Piperidines: A family of hexahydropyridines.		1.9710
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		1.9810ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
didanosine
Didanosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.. didanosine : A purine 2',3'-dideoxyribonucleoside that is inosine in which the hydroxy groups at both the 2' and the 3' positions on the sugar moiety have been replaced by hydrogen. An antiviral drug, it is used as a medication to treat HIV/AIDS.		1.9710purine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor;
geroprotector;
HIV-1 reverse transcriptase inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 1210
[description not available]		01.9810
Adenocarcinoma, Basal Cell
[description not available]		01.9710
Cancer of Ovary
[description not available]		01.9710
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		01.9710
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		01.9710