## 1,2-dibutyrylphosphatidylcholine (diC4PC)
**1,2-dibutyrylphosphatidylcholine (diC4PC)** is a synthetic analog of phosphatidylcholine (PC), a major phospholipid found in cell membranes. It differs from naturally occurring PC in two key ways:
1. **Shortened Fatty Acid Chains:** diC4PC has **butyryl** groups (four-carbon chains) attached to the glycerol backbone instead of the longer fatty acid chains found in natural PC.
2. **Synthetic Origin:** It's not naturally found in biological systems and is synthesized in the lab.
**Why is diC4PC important for research?**
This molecule has emerged as a valuable tool in research due to its unique properties:
* **Membrane Permeability:** The short butyryl chains make diC4PC **more permeable through cell membranes** compared to natural PC. This allows it to bypass normal membrane transport mechanisms and enter cells more readily.
* **Signaling Mimicry:** diC4PC can **mimic the signaling effects** of certain natural PC metabolites like diacylglycerol (DAG) and phosphatidic acid (PA).
* **Specific Cellular Targets:** Due to its structure, diC4PC is particularly effective at **activating certain signaling pathways**, such as the protein kinase C (PKC) pathway, which is crucial for cell growth, differentiation, and apoptosis.
* **Versatile Research Tool:** diC4PC is used in various research settings, including:
* **Studying cell signaling pathways:** Helps elucidate the role of specific pathways in various cellular processes.
* **Developing new drugs:** Its ability to target specific pathways makes it a potential lead compound for developing drugs targeting diseases like cancer and inflammation.
* **Investigating membrane dynamics:** Its unique membrane permeability properties allow researchers to study membrane transport and fluidity.
**Limitations of diC4PC:**
* **Short-Lived Effects:** Due to its rapid metabolism, the effects of diC4PC are typically transient.
* **Off-target Effects:** diC4PC can activate other pathways besides PKC, which can complicate research.
* **Toxicity:** While generally safe at low concentrations, diC4PC can be toxic at higher doses.
**Overall, 1,2-dibutyrylphosphatidylcholine is a powerful tool in research, providing insights into cellular signaling pathways, membrane dynamics, and potential therapeutic targets.** Its unique properties and versatility make it a valuable resource for researchers in various fields.
1,2-dibutyrylphosphatidylcholine: RN given refers to (R)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 193375 |
| CHEBI ID | 186468 |
| SCHEMBL ID | 416182 |
| MeSH ID | M0107091 |
| Synonym |
|---|
| pc(4:0/4:0) |
| butyrin, 1,2-di-, di-h phosphate, ester with choline, inner salt |
| dibutanoyllecithin |
| dibutyryl lecithin |
| 1,2-dibutyryl-sn-glycero-3-phosphocholine |
| LMGP01011222 |
| choline, hydroxide, dihydrogen phosphate, inner salt, ester with 1,2-dibutyrin, l- |
| 1,2-dibutyrylphosphatidylcholine |
| 3355-26-8 |
| [(2r)-2,3-di(butanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate |
| CHEBI:186468 |
| dic4pc |
| unii-kb699dh10e |
| dibutyryl-lecithin |
| 1,2-dibutyroyl-sn-glycero-3-phosphocholine |
| l-alpha-dibutyroylglycero-3-phosphatidylcholine |
| 3,5,9-trioxa-4-phosphatridecan-1-aminium, 4-hydroxy-n,n,n-trimethyl-10-oxo-7-(1-oxobutoxy)-, hydroxide, inner salt, 4-oxide, (r)- |
| kb699dh10e , |
| dibutyryl-pc |
| l-.alpha.-dibutyroylglycero-3-phosphatidylcholine |
| 3,5,9-trioxa-4-phosphatridecan-1-aminium, 4-hydroxy-n,n,n-trimethyl-10-oxo-7-(1-oxobutoxy)-, inner salt, 4-oxide, (7r)- |
| 1,2-dibutryl-sn-glycero-3-phosphorylcholine |
| 1,2-dibutryl-sn-glycero-3-phosphocholine |
| SCHEMBL416182 |
| 3,5,9-trioxa-4-phosphatridecan-1-aminium, 4-hydroxy-n,n,n-trimethyl-10-oxo-7-(1-oxobutoxy)-, inner salt, 4-oxide, (r)- |
| (r)-2,3-bis(butyryloxy)propyl (2-(trimethylammonio)ethyl) phosphate |
| 04:0 pc, 1,2-dibutyryl-sn-glycero-3-phosphocholine, powder |
| Q27282161 |
| DTXSID00955182 |
| 2,3-bis(butanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate |
| CS-0451229 |
| (r)-2,3-bis(butyryloxy)propyl(2-(trimethylammonio)ethyl)phosphate |
| Class | Description |
|---|---|
| 1,2-diacyl-sn-glycero-3-phosphocholine | The conjugate base of a 1,2-diacyl-sn-glycero-3-phosphocholine compound formed by deprotonation of the phosphate OH group. |
| [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] | |
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 2 (40.00) | 18.7374 |
| 1990's | 2 (40.00) | 18.2507 |
| 2000's | 1 (20.00) | 29.6817 |
| 2010's | 0 (0.00) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (12.74) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 5 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||