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DOCP

Name: DOCP
SKU: ACM1360461579
Rating: 5 (1 reviews)

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Catalog NumberACM1360461579

CAS Number1360461-57-9

CategoryPhospholipids

Synonyms

2-((2,3-Bis(oleoyloxy)propyl)dimethylammonio)ethyl hydrogen phosphate

Molecular Weight

772.09

Molecular Formula

C43H82NO8P

Purity

>99%

Appearance

Powder

Exact Mass

771.578

Hygroscopic

Light Sensitive

Percent Composition

C 66.89%, H 10.70%, N 1.81%, O 16.58%, P 4.01%

Stability

1 Year

Storage Temperature

-20 °C

Download COA Download MSDS

Case Study

Role of 2-((2,3-bis(oleoyloxy)propyl)dimethylammonio)ethyl hydrogen phosphate (DOCP) in Lipid Vesicle Self-Assembly on TiO2 and SiO2 Surfaces Mediated by Divalent Cations

Sut, Tun Naw, et al. Applied Materials Today 35 (2023): 101953.

This study investigates the role of 2-((2,3-bis(oleoyloxy)propyl)dimethylammonio)ethyl hydrogen phosphate (DOCP) in modulating lipid vesicle interactions with TiO2 and SiO2 surfaces, focusing on how divalent cations (Ca2+ and Mg2+) influence lipid self-assembly processes. Using quartz crystal microbalance-dissipation (QCM-D) and fluorescence recovery after photobleaching (FRAP), the researchers explored lipid vesicle adsorption and the formation of supported lipid bilayers (SLBs). Results showed that divalent cations inhibited the adsorption of 100 mol% DOCP lipid vesicles on both surfaces, while enabling SLB formation at lower concentrations (25 mol%) of DOCP. Specifically, Mg2+ on TiO2 disrupted SLB formation, while Ca2+ promoted SLB assembly on both surfaces. The study highlights the importance of ionic bridging interactions, suggesting that divalent cations play a critical role in regulating DOCP lipid vesicle self-assembly on oxide surfaces. These findings open avenues for controlling lipid membrane formation in nanotechnology applications, particularly in surface modification and biosensing.

The Hypoglycemic and Hypolipidemic Effects of 2-((2,3-bis(oleoyloxy)propyl)dimethylammonio)ethyl hydrogen phosphate (DOCP) in Streptozotocin-Induced Type 2 Diabetic Mice

Li, Chen, et al. Journal of Functional Foods 106 (2023): 105579.

This study explores the therapeutic potential of 2-((2,3-bis(oleoyloxy)propyl)dimethylammonio)ethyl hydrogen phosphate (DOCP) in managing type 2 diabetes using a streptozotocin-induced diabetic mouse model. DOCP (800 mg/kg) significantly reduced fasting blood glucose levels and improved insulin sensitivity in the diabetic mice after 35 days of treatment. The polysaccharide compound also enhanced serum insulin content, reduced insulin resistance, and lowered total cholesterol, triglyceride, and LDL-C concentrations. Additionally, DOCP exhibited notable antioxidant effects, increasing the total antioxidant capacity (T-AOC), superoxide dismutase (SOD) activity, and catalase (CAT) activity levels, thereby protecting liver and pancreas tissues from damage. The treatment also influenced intestinal flora, promoting the growth of beneficial bacteria such as Lactobacillus and Bifidobacteriaceae, contributing to improved gut health. On a molecular level, DOCP upregulated the expression of glucose metabolism-related genes like Glut2, Gck, Pklr, and Insr, while downregulating Caspase-3, which is involved in cell apoptosis. These findings suggest that DOCP may offer a multifaceted approach to managing type 2 diabetes and its complications, making it a promising candidate for use in functional foods or dietary supplements aimed at diabetes management.

Evaluation of DOCP in Charge Reversal Self-Emulsifying Drug Delivery Systems (SEDDS) for Enzyme-Activated Phosphate Release

Akkuş-Dağdeviren, Zeynep Burcu, et al. Journal of colloid and interface science 589 (2021): 532-544.

This study investigates the role of 2-((2,3-bis(oleoyloxy)propyl)dimethylammonio)ethyl hydrogen phosphate (DOCP) in self-emulsifying drug delivery systems (SEDDS) activated by intestinal alkaline phosphatase (IAP). DOCP-loaded SEDDS were characterized by their zeta potential changes upon IAP activation and phosphate release behavior. The results revealed that DOCP, alongside other phosphorylated surfactants, exhibited a moderate phosphate release upon IAP treatment. However, the release was less significant compared to other phosphates, such as nonylphenol monophosphate ester (PNPP) and C12-15 alcohol 3 ethoxylate phosphate ester (PME), which displayed more pronounced release and a charge reversal from negative to positive values.
In comparison with dipalmitoyl-sn-glycero-3-phosphatidic acid disodium salt (PA) and DOCP, the SEDDS showed safe cell viability profiles in Caco-2 cells, indicating low cytotoxicity. Phosphate release from DOCP-loaded SEDDS was observed on both isolated IAP and Caco-2 cells, though to a lesser extent than for PNPP or PME. The findings highlight the importance of the chemical structure of phosphate-bearing excipients in optimizing enzyme-sensitive systems for drug and gene delivery. DOCP's role in SEDDS, although less pronounced, still presents promising potential for future development of enzyme-activated, charge-reversal drug delivery systems.

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