A fluorous biphase drug delivery system triggered by low frequency ultrasound: controlled release from perfluorous discoidal porous silicon particles

Liu, Jing; Li, Shuo; Liu, Lina; Zhu, Zhiling

doi:10.1039/d0na00324g

Cited by 8 publications

(6 citation statements)

References 69 publications

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“…Fluorous-containing amphiphiles are important for the formation of uniform nanoparticles, avoiding protein denaturation, efficient endocytosis and maintaining low cytotoxicity [17,18]. Several new fluorinated surfactants on the base of pyridinium salts were recently synthesized and studied as drug carriers and gene delivery systems with very promising results [19][20][21][22]. Herein, we report the synthesis and full characterization of new original synthetic lipid-like compounds: 3-(3,5-difluoro-3,5-bis((ethyloxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodide (4a) and 3-(3,5-difluoro-3,5-bis((nonyloxy)carbonyl)-2,6dioxoheptan-4-yl)-1-methylpyridin-1-ium iodide (4b).…”

Section: Resultsmentioning

confidence: 99%

“…Fluorouscontaining amphiphiles are important for the formation of uniform nanoparticles, avoiding protein denaturation, efficient endocytosis and maintaining low cytotoxicity [17,18]. Several new fluorinated surfactants on the base of pyridinium salts were recently synthesized and studied as drug carriers and gene delivery systems with very promising results [19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Evaluation of Self-Assembling Properties of 3-(3,5-Difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium Iodides

Pikun

Lacis

Sobolev

et al. 2022

Molbank

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A synthesis of 3-(3,5-difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodides with ethyl or nonyl ester groups at positions 3 and 5 was performed. Treatment of the corresponding 2’,6’-dimethyl-1’,4’-dihydro-[3,4’-bipyridine]-3’,5’-dicarboxylates with Selectfluor® followed by quaternization of pyridine moiety in the obtained dialkyl 2,4-diacetyl-2,4-difluoro-3-(pyridin-3-yl)pentanedioates with methyl iodide gave the desired 3-(3,5-difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodides. This type of compound would be useful as synthetic lipids for further development of the delivery systems. The obtained target compounds were fully characterized by 1H NMR, 19F NMR, 13C NMR, HRMS, IR and UV data. The estimation of self-assembling properties and characterization of the nanoparticles obtained by ethanol solution injection in an aqueous media were performed by dynamic light scattering (DLS) measurements. DLS measurement data showed that 3-(3,5-difluoro-3,5-bis((nonyloxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodide created liposomes with the average diameter of 300–400 nm and polydispersity index (PDI) value around 0.30–0.40, while 3-(3,5-difluoro-3,5-bis((ethyloxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodide formed a heterogeneous sample with PDI value 1, which was not prospective for delivery system development.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Self-Assembling Properties of 3-(3,5-Difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium Iodides

Pikun

Lacis

Sobolev

et al. 2022

Molbank

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“…The combination of its ease of synthesis, its small size, and the relative strength and mobility of the fluorous effect makes R F -DNA a powerful tool in the self-assembly arsenal of structural DNA nanotechnology and may prove to be useful in the formation of functional assemblies that span into the micron-scale. Furthermore, interfacing fluorous-directed assembly of DNA nanostructures with other components could provide a molecular blueprint to enhance the delivery of biological components to specific cell types. − …”

Section: Discussionmentioning

confidence: 99%

“…Furthermore, interfacing fluorous-directed assembly of DNA nanostructures with other components could provide a molecular blueprint to enhance the delivery of biological components to specific cell types. 29 − 31 …”

Section: Discussionmentioning

confidence: 99%

Fluorous-Directed Assembly of DNA Origami Nanostructures

et al. 2022

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An orthogonal, noncovalent approach to direct the assembly of higher-order DNA origami nanostructures is described. By incorporating perfluorinated tags into the edges of DNA origami tiles we control their hierarchical assembly via fluorous-directed recognition. When we combine this approach with Watson−Crick base-pairing we form discrete dimeric constructs in significantly higher yield (8x) than when either molecular recognition method is used in isolation. This integrated "catch-and-latch" approach, which combines the strength and mobility of the fluorous effect with the specificity of base-pairing, provides an additional toolset for DNA nanotechnology, one that enables increased assembly efficiency while requiring significantly fewer DNA sequences. As a result, our integration of fluorous-directed assembly into origami systems represents a cheap, atom-efficient means to produce discrete superstructures.

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“…; on the other hand, fluorination of stationary phase can improve the separation selectivity for fluorides through fluorinefluorine interaction. Fluorine-fluorine interaction is a noncovalent interaction between fluorine atoms, which has various functions such as adjusting crystal structure [32] and molecular structure [33], fluorinated drug delivery [34], fluoride extraction [35], etc. In analytical fields, fluorinated stationary phases or surfactants in HPLC [36,37], CEC [25,38], and micellar electrokinetic chromatography (MEKC) [39] have been reported to achieve the separation of fluorides through fluorine-fluorine interaction.…”

Section: Introductionmentioning

confidence: 99%

Fluorinated covalent‐organic polymers as stationary phase for analysis of organic fluorides by open‐tubular capillary electrochromatography

Sun

et al. 2023

J of Separation Science

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Fluorinated porous materials, which can provide specific fluorine-fluorine interaction, hold great promise for fluoride analysis. Here, a novel fluorinated covalent-organic polymer was prepared by using 2,4,6-tris(4-aminophenyl)-1,3,5-triazine and 2,3,5,6-tetrafluorotelephtal aldehyde as the precursors and introduced as stationary phase for open-tubular capillary electrochromatography. The as-synthesized fluorinated covalent-organic polymer and the modified capillary column were characterized by infrared spectroscopy, scanning electron microscopy, and energy dispersive X-ray spectrometry. Based on strong hydrophobic interaction and fluorine-fluorine interaction provided by fluorinated covalent-organic polymer coating layer, the modified column showed powerful separation selectivity toward hydrophobic compounds, organic fluorides, and fluorinated pesticides. Additionally, the fluorinated covalent-organic polymer with good porosity and regular shape was uniformly and tightly coated on the capillary inner wall. The obtained highest column efficiency could reach up to 1.2 × 10 5 plates⋅m −1 for fluorophenol. The loading capacity of the modified column can reach 141 pmol for trifluorotoluene. Besides, the relative standard deviations of retention times for intraday run (n = 5), interday run (n = 3), and between columns (n = 3) were all less than 2.55%. Significantly, this novel fluorinated material-based stationary phase shows great application potential in fluorides analysis.

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A fluorous biphase drug delivery system triggered by low frequency ultrasound: controlled release from perfluorous discoidal porous silicon particles

Abstract: A fluorous biphase drug delivery system (FB-DDS) trigged by low frequency ultrasound (LFUS) was developed for efficient delivery of fluorine containing pharmaceuticals.

Cited by 8 publications

References 69 publications

Synthesis and Evaluation of Self-Assembling Properties of 3-(3,5-Difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium Iodides

Synthesis and Evaluation of Self-Assembling Properties of 3-(3,5-Difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium Iodides

Fluorous-Directed Assembly of DNA Origami Nanostructures

Fluorinated covalent‐organic polymers as stationary phase for analysis of organic fluorides by open‐tubular capillary electrochromatography

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