Page last updated: 2024-12-04

1-hexadecyl-2-methoxyglycero-3-phosphocholine

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

Description

1-hexadecyl-2-methoxyglycero-3-phosphocholine, also known as **hexadecyl-GPC (C16:0-GPC)**, is a synthetic analog of **phosphatidylcholine (PC)**, a major component of cell membranes.

Here's a breakdown of its structure and why it's important in research:

**Structure:**

* **1-hexadecyl:** This refers to a saturated fatty acid chain with 16 carbon atoms (hexadecanoic acid) attached to the glycerol molecule at the first position (sn-1).
* **2-methoxy:** This indicates a methoxy group (CH3O-) attached to the glycerol molecule at the second position (sn-2).
* **Glycero-3-phosphocholine:** This refers to the backbone of the molecule: glycerol with a phosphate group (PO4) attached to the third position (sn-3) and a choline molecule (N(CH3)3OH) linked to the phosphate group.

**Importance in Research:**

C16:0-GPC is an important research tool because it offers several advantages compared to natural PC:

* **Defined structure:** Unlike natural PC which has a complex mixture of fatty acids, C16:0-GPC has a single, well-defined structure. This makes it easier to study its specific effects in various experiments.
* **Enhanced stability:** C16:0-GPC is more stable than natural PC due to the presence of the methoxy group, which prevents degradation by lipases.
* **Improved solubility:** C16:0-GPC is more soluble in water than natural PC, making it easier to work with in aqueous solutions.

**Research Applications:**

C16:0-GPC has been investigated in various research areas, including:

* **Membrane biology:** Studying the role of PC in membrane structure and function.
* **Drug delivery:** Developing drug carriers that can effectively deliver therapeutic agents across cell membranes.
* **Neurological disorders:** Investigating the potential of C16:0-GPC as a therapeutic agent for conditions like Alzheimer's disease and Parkinson's disease.
* **Cancer research:** Studying the effects of C16:0-GPC on cancer cell growth and metastasis.
* **Cell signaling:** Exploring the role of C16:0-GPC in various signaling pathways.

**Overall, C16:0-GPC is a valuable research tool due to its defined structure, stability, and solubility. Its applications span various fields of research, making it a crucial compound for understanding cellular processes and developing novel therapies.**

1-hexadecyl-2-methoxyglycero-3-phosphocholine: RN given refers to hydroxide inner salt (R)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID127599
CHEMBL ID313574
SCHEMBL ID5497164
MeSH IDM0143452

Synonyms (20)

Synonym
CHEMBL313574
rac-1-hexadecyl 2-methyl phosphatidylcholine
1-hexadecyl-2-methoxyglycero-3-phosphocholine
(2r)-3-(hexadecyloxy)-2-methoxypropyl 2-(trimethylammonio)ethyl phosphate
78858-44-3
[(2r)-3-hexadecoxy-2-methoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
3,5,9-trioxa-4-phosphapentacosan-1-aminium, 4-hydroxy-7-methoxy-n,n,n-trimethyl-, hydroxide, inner salt, 4-oxide, (r)-
amg-pc
hd-mo-gpc
et16-ome
et-16-och3
1-o-hexadecyl-2-o-methylglycero-3-phosphocholine
SCHEMBL5497164
2-o-methyl paf c-16
RZNRKXGAJMGLIM-RUZDIDTESA-N
HMS3648N20
(r)-3-(hexadecyloxy)-2-methoxypropyl 2-(trimethylammonio)ethyl phosphate
3-(hexadecyloxy)-2-methoxypropyl 2-(trimethylazaniumyl)ethyl phosphate
DTXSID701000084
PD020920
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID218112Compound was evaluated for WEHI-3B cell viability after 48 hour at a concentration of 1.25 uM of compound was reported.1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID218115Compound was evaluated for WEHI-3B cell viability after 48 hour at a concentration of 30 uM of compound was reported.1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID219581Antineoplastic activity against X63/OMIL3 cell line in which [3H]thymidine was incorporated into DNA1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID218107Compound was evaluated for WEHI-3B cell viability after 24 hour at a concentration of 10 uM of compound was reported.1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID218110Compound was evaluated for WEHI-3B cell viability after 24 hour at a concentration of 5 uM of compound was reported.1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID218106Compound was evaluated for WEHI-3B cell viability after 24 hour at a concentration of 1.25 uM of compound was reported.1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID218113Compound was evaluated for WEHI-3B cell viability after 48 hour at a concentration of 10 uM of compound was reported.1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID44637Antineoplastic activity against C653 cell line in which [3H]-thymidine was incorporated into DNA1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID218109Compound was evaluated for WEHI-3B cell viability after 24 hour at a concentration of 30 uM of compound was reported.1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID218114Compound was evaluated for WEHI-3B cell viability after 48 hour at a concentration of 2.5 uM of compound was reported.1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID166071Antineoplastic activity against R6X-B15 cell line in which [3H]thymidine was incorporated into DNA1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID218111Compound was evaluated for WEHI-3B cell viability after 48 hour at a concentration of 0 uM of compound was reported.1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID218108Compound was evaluated for WEHI-3B cell viability after 24 hour at a concentration of 2.5 uM of compound was reported.1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID218116Compound was evaluated for WEHI-3B cell viability after 48 hour at a concentration of 5 uM of compound was reported.1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID218105Compound was evaluated for WEHI-3B cell viability after 24 hour at a concentration of 0 uM of compound was reported.1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
AID217955Antineoplastic activity against WEHI 3B cell line in which [3H]thymidine was incorporated into DNA1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis and antineoplastic properties of ether-linked thioglycolipids.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (28.57)18.7374
1990's4 (57.14)18.2507
2000's1 (14.29)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]

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]