Cyclotriphosphazene, a scaffold for  19 F MRI contrast agents

Önal, Emel; Zhang, Cheng; Davarcı, Derya; İşçi, Ümit; Pilet, Guillaume; Whittaker, Andrew K.; Dumoulin, Fabienne

doi:10.1016/j.tetlet.2017.12.032

Cited by 16 publications

(5 citation statements)

References 17 publications

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“…The synthetic details and characterization data for the copolymers are shown in the experimental section and Table S1. [25][26][27][28][29][30][31][32][33][34] Fig. 1a illustrates the chemical structures of PFPE polymer (EO10-PFPE) and control polymer (EO10-CTRL).…”

Section: Resultsmentioning

confidence: 99%

Ultra-stable all-solid-state sodium metal batteries enabled by perfluoropolyether-based electrolytes

et al. 2022

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Rechargeable batteries paired with sodium (Na)-metal anodes are considered as one of the most promising high energy and low-cost energy storage systems. However, the use of highly reactive Na metal and the formation of Na dendrites during battery operation have caused signi cant safety concerns, especially when highly ammable liquid electrolytes are used. Herein, we design and develop a solventfree solid polymer electrolytes (SPEs) based on a per uoropolyether (PFPE) terminated polyethylene glycol (PEG)-based block copolymer for safe and stable all-solid-state Na-metal batteries. Compared with traditional poly(ethylene oxide) (PEO) or PEG SPEs, our results suggest that block copolymer design allows for the formation of self-assembled microstructures leading to high storage modulus at elevated temperatures with the PEG domains providing transport channels even at high salt concentration (EO/Na + = 8:2). Moreover, it is demonstrated that the incorporation of PFPE segments enhances the Na + transference number of the electrolyte to 0.46 at 80 o C. Finally, the proposed SPE exhibits highly stable symmetric cell cycling performance with high current density (0.5 mA cm -2 and 1.0 mAh cm -2 , up to 1300 hours). The assembled all-solid-state Na-metal batteries with Na 3 V 2 (PO 4 ) 3 cathode demonstrate outstanding rate performance, high capacity retention and long-term charge/discharge stability (CE = 99.91%) after more than 900 cycles.

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Section: Resultsmentioning

confidence: 99%

Ultra-stable all-solid-state sodium metal batteries enabled by perfluoropolyether-based electrolytes

et al. 2022

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“…Importantly, the absence of endogenous 19 F MR signal in the body, and the reported linear relationship between fluorine concentration and resulting MRI signal intensity means that quantitative imaging experiments can be conducted. [5][6][7] Measurement of the number of imaging agent molecules or particles within a particular imaging volume element is often highly challenging for imaging agents based on paramagnetic ions or particles.…”

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High F-Content Perfluoropolyether-Based Nanoparticles for Targeted Detection of Breast Cancer by ¹⁹F Magnetic Resonance and Optical Imaging

et al. 2018

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Two important challenges in the field of F magnetic resonance imaging (MRI) are the maintenance of high fluorine content without compromising imaging performance, and effective targeting of small particles to diseased tissue. To address these challenges, we have developed a series of perfluoropolyether (PFPE)-based hyperbranched (HBPFPE) nanoparticles with attached peptide aptamer as targeting ligands for specific in vivo detection of breast cancer with highF MRI sensitivity. A detailed comparison of the HBPFPE nanoparticles (NPs) with the previously reported trifluoroethyl acrylate (TFEA)-based polymers demonstrates that the mobility of fluorinated segments of the HBPFPE nanoparticles is significantly enhanced (F T > 80 ms vs 31 ms), resulting in superior MR imaging sensitivity. Selective targeting was confirmed by auto- and pair correlation analysis of fluorescence microscopy data, in vitro immunofluorescence, in vivo F MRI, ex vivo fluorescence andF NMR. The results highlight the high efficiency of aptamers for targeting and the excellent sensitivity of the PFPE moieties for F MRI. Of relevance to in vivo applications, the PFPE-based polymers exhibit much faster clearance from the body than the previously introduced perfluorocarbon emulsions ( t ∼ 20 h vs up to months). Moreover, the aptamer-conjugated NPs show significantly higher tumor-penetration, demonstrating the potential of these imaging agents for therapeutic applications. This report of the synthesis of polymeric aptamer-conjugated PFPE-based F MRI CAs with high fluorine content (∼10 wt %) demonstrates that these NPs are exciting candidates for detecting diseases with high imaging sensitivity.

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“…Despite being absent in most biological systems, fluorine has been widely used to tailor the properties and behavior of molecules and particles for biomedical applications. − The substitution of hydrogen with fluorine can improve cellular uptake and subsequently facilitate the crossing of intracellular bilayers, thus increasing the therapeutic efficacy of certain drugs. ,− Molecules containing fluorine have hydrophobic and lipophobic characteristics and tend to form aggregates in aqueous solutions. As such, long-term stability and well-controlled aggregation under physiological conditions are significant challenges. − For example, high contents of fluorine may facilitate enhanced cellular uptake but can lead to low stability in aqueous solutions and the formation of large aggregates.…”

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Tuning of the Aggregation Behavior of Fluorinated Polymeric Nanoparticles for Improved Therapeutic Efficacy

et al. 2020

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Incorporation of fluorinated moieties in polymeric nanoparticles has been shown in many instances to increase their uptake by living cells and, hence, has proven to be a useful approach to enhancing delivery to cells. However, it remains unclear how incorporation of fluorine affects critical transport processes, such as interactions with membranes, intracellular transport, and tumor penetration. In this study, we investigate the influence of fluorine on transport properties using a series of rationally designed poly(oligo(ethylene glycol) methyl ether acrylate)-block-perfluoropolyether (poly(OEGA) m -PFPE) copolymers. Copolymers with different fluorine contents were prepared and exhibit aggregate in solution in a manner dependent on the fluorine content. Doxorubicin-conjugated poly(OEGA)20-PFPE nanoparticles with lower fluorine content exist in solution as unimers, leading to greater exposure of hydrophobic PFPE segments to the cell surface. This, in turn, results in greater cellular uptake, deeper tumor penetration, as well as enhanced therapeutic efficacy compared to that with the micelle-state nanoaggregates (poly(OEGA)10-PFPE and poly(OEGA)5-PFPE) with higher fluorine content but with less PFPE exposed to the cell membranes. Our results demonstrate that the aggregation behavior of these fluorinated polymers plays a critical role in internalization and transport in living cells and 3D spheroids, providing important design criteria for the preparation of highly effective delivery agents.

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Cyclotriphosphazene, a scaffold for 19 F MRI contrast agents

Cited by 16 publications

References 17 publications

Ultra-stable all-solid-state sodium metal batteries enabled by perfluoropolyether-based electrolytes

Ultra-stable all-solid-state sodium metal batteries enabled by perfluoropolyether-based electrolytes

High F-Content Perfluoropolyether-Based Nanoparticles for Targeted Detection of Breast Cancer by ¹⁹F Magnetic Resonance and Optical Imaging

Tuning of the Aggregation Behavior of Fluorinated Polymeric Nanoparticles for Improved Therapeutic Efficacy

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Cyclotriphosphazene, a scaffold for 19 F MRI contrast agents

Cited by 16 publications

References 17 publications

Ultra-stable all-solid-state sodium metal batteries enabled by perfluoropolyether-based electrolytes

Ultra-stable all-solid-state sodium metal batteries enabled by perfluoropolyether-based electrolytes

High F-Content Perfluoropolyether-Based Nanoparticles for Targeted Detection of Breast Cancer by 19F Magnetic Resonance and Optical Imaging

Tuning of the Aggregation Behavior of Fluorinated Polymeric Nanoparticles for Improved Therapeutic Efficacy

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High F-Content Perfluoropolyether-Based Nanoparticles for Targeted Detection of Breast Cancer by ¹⁹F Magnetic Resonance and Optical Imaging