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DOCPe

Name: DOCPe
SKU: ACM1360461580
Rating: 5 (1 reviews)

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Catalog NumberACM1360461580

CAS Number1360461-58-0

CategoryPhospholipids

Synonyms

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

Molecular Weight

800.14

Molecular Formula

C45H86NO8P

Purity

>99%

Appearance

Powder

Exact Mass

799.609

Hygroscopic

Light Sensitive

Percent Composition

C 67.55%, H 10.83%, N 1.75%, O16.00%, P3.87%

Stability

1 Year

Storage Temperature

-20 °C

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Case Study

DOCPe for Liposome Preparation and Its Role in Regulating Fusion Behavior on TiO₂ Surfaces

Wang, Feng, and Juewen Liu. Journal of the American Chemical Society 137.36 (2015): 11736-11742.

In this study, 2-((2,3-bis(oleoyloxy)propyl)dimethylammonio)ethyl ethyl phosphate (DOCPe) was evaluated as a structural lipid component in liposome preparation and its influence on lipid-surface interactions was systematically investigated. Liposomes composed of DOCPe were fabricated via a standard thin-film hydration and extrusion method, yielding nanoscale vesicles (~100 nm) suitable for interfacial studies. Fluorescently labeled and calcein-loaded liposomes were further prepared to assess membrane fusion behavior upon interaction with TiO₂ nanoparticles.
Compared with analogous lipid systems such as DOPC and DOCP, DOCPe exhibited a markedly different interfacial response. Notably, no fluorescence enhancement was observed upon exposure to TiO₂ nanoparticles, indicating the absence of liposome rupture or fusion. This behavior contrasts with DOCP systems, where exposed phosphate groups facilitate strong coordination interactions with TiO₂, promoting membrane disruption and supported lipid bilayer formation.
Mechanistically, the presence of a small ethyl capping group on the phosphate moiety in DOCPe introduces steric and electronic constraints that hinder direct phosphate-titanium coordination. This modification effectively suppresses surface-induced fusion, despite maintaining the overall amphiphilic architecture required for liposome formation.
These findings highlight the critical role of headgroup accessibility and chemical structure in dictating lipid-surface interactions. DOCPe serves as a valuable model compound for tuning interfacial stability in lipid-based nanocarriers, offering potential applications in controlled drug delivery systems where prevention of premature membrane fusion is essential.

DOCPe for Investigating Lipid Bilayer Formation on TiO₂ and SiO₂ Biointerfaces

Wang, Xiaoshun, et al. Langmuir 35.5 (2018): 1672-1681.

This study examines the application of 2-((2,3-bis(oleoyloxy)propyl)dimethylammonio)ethyl ethyl phosphate (DOCPe) as a model neutral lipid to elucidate the mechanisms governing supported lipid bilayer (SLB) formation on TiO₂ and SiO₂ surfaces. DOCPe liposomes were prepared via thin-film hydration followed by extrusion, yielding uniform nanoscale vesicles suitable for interfacial analysis.
Compared with anionic counterparts such as DOCP and DOPS, DOCPe demonstrated distinct adsorption and fusion behavior governed primarily by surface chemistry and pH. On SiO₂, DOCPe formed stable SLBs at both acidic (pH 3) and physiological (pH 7) conditions, confirming that electrostatic neutrality favors bilayer formation on negatively charged oxide surfaces. In contrast, on TiO₂, DOCPe formed SLBs only under acidic conditions, indicating that protonation and enhanced van der Waals interactions are required to compensate for the lack of strong coordination bonding.
Mechanistically, the ethyl-capped phosphate group in DOCPe limits direct coordination with TiO₂, in contrast to DOCP, which exhibits strong phosphate-titanium interactions and forms robust SLBs across a wide pH range. This structural modification reduces binding affinity and renders DOCPe-mediated bilayers more sensitive to environmental conditions.
Overall, DOCPe serves as a critical probe for decoupling electrostatic and coordination effects in lipid-oxide interactions. Its well-defined behavior provides valuable insights for designing tunable biointerfaces in biosensing, nanofabrication, and lipid-based drug delivery systems, where controlled membrane assembly and stability are essential.

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