End-chain fluorination of polyesters favors perfluorooctyl bromide encapsulation into echogenic PEGylated nanocapsules

Houvenagel, Sophie; Picheth, Guilherme Fadel; Dejean, Camille; Brûlet, Annie; Chennevière, Alexis; Couture, Olivier; Huang, Nicolas; Moine, Laurence; Tsapis, Nicolas

doi:10.1039/c7py00400a

Cited by 14 publications

(45 citation statements)

References 49 publications

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“…Furthermore, methylene protons of CH 2 -C=O group and methine proton of CH-F 2 group appeared at 4.57 ppm (b), and 5.93-6.15 ppm (a) were attributed to OFP moieties [9,21]. On the other hand, as can be seen in 19 F-NMR spectra of F-PCLs, the peaks of CHF 2 , CHF 2 -CF 2 , CHF 2 -CF 2 -CF 2 , CHF 2 -CF 2 -CF 2 -CF 2 groups seemed at -137,28 ppm (w), -130.02 ppm (x), -125,37 ppm (y) and -119,74 ppm (z), respectively, coming from OFP moieties supported the formation of targeted fluorinated polymers [26]. Also, molecular weights of F-PCLs were firstly estimated 1 H-NMR analysis using the areas of the all signed peaks on the spectra and found to be as 8500 and 12 800 g•mol -1 for F-PCL 24 h and F-PCL 48 h, respectively, assuming that all polymer chains have the same length and possess a fluorinated end group through Equation (2):(2)…”

Section: Resultsmentioning

confidence: 88%

Synthesis, properties and enzymatic biodegradation behavior of fluorinated poly(ε-caprolactone)s

Açık¹

2020

Express Polym. Lett.

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This study reports on the synthesis of new fluoro functionalized poly(ε-caprolactone)s (F-PCLs) via ring-opening polymerization (ROP) of ε-caprolactone (ε-CL) for different time intervals (24 and 48 h.) by using 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (OFP) as an initiator. The structure and properties of F-PCLs are investigated by Fourier-transform infrared (FT-IR), proton and fluorine 19 nuclear magnetic resonance (1 H-NMR and 19 F-NMR) spectroscopies, gel permeation chromatography (GPC), energy dispersive scanning electron microscopy (SEM-EDS), atomic force microscopy (AFM), water contact angle (WCA) measurements, thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC). Enzymatic degradation experiments are also conducted to study the biodegradation behavior of terminal F-PCLs. Experimental observations obtained by 1 H-NMR, 19 F-NMR and GPC indicate that higher reaction time leads to the formation of higher fluorinated repeating units in F-PCLs. This observation is confirmed by results of SEM-EDS, AFM, WCA, DSC and TGA analyses, respectively. Based on the biodegradability study of F-PCLs in degradation solutions in the presence and absence of porcine pancreatic lipase, it can observed that utilization of more extended time in the ROP reaction medium decreases the biodegradation of resulting polymer. With the obtained features, biodegradable F-PCLs might have potential applications, particularly in the fields of drug delivery and tissue engineering, requiring improved thermal but lower wettability properties.

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Section: Resultsmentioning

confidence: 88%

Synthesis, properties and enzymatic biodegradation behavior of fluorinated poly(ε-caprolactone)s

Açık¹

2020

Express Polym. Lett.

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“…Nonetheless, none of the polymers was able to decrease the interfacial tension compared to the solvent itself regardless the end-group chemistry or the length of the fluorinated end-group. ), a conformational rearrangement based on the higher solubility of the polymeric chains within the solvents may hide the fluorinated groups inside the PLA coil, hindering an effective interaction with the PFH phase 19 .…”

Section: Polymers Dynamicsmentioning

confidence: 99%

“…The insets (left) exhibit the CF 3 resonance in a mixed system of polymer and perfluorohexane. 19 F peak assignment is indicated in the top of each image.…”

Section: Polymers Dynamicsmentioning

confidence: 99%

“…Recent reports describe the use of capsules containing PFOB to provide in vivo 19 F-MRI or ultrasound detection and also passively deliver chemotherapeutics to cancer cells [5][6][7][8][9] . Similar formulations use PFH as an active core for its lower boiling point, as it favors liquid-to-gas transition by acoustic and thermal stimuli, allowing real-time ultrasonic imaging as well as localized drug-release [10][11][12] .…”

Section: Introductionmentioning

confidence: 99%

“…Several groups have turned to the use of fluorinated surfactants or lipids to improve PFCs encapsulation [15][16][17] . Literature also reports the functionalization of polymer with fluorinated end-groups to favor interactions with PFCs 11,14,[18][19][20][21][22][23][24] . It was previously demonstrated that a wide range of fluorinated end-groups linked to the PLA chainfrom C 3 F 7 to C 13 F 27increased the entrapment of PFCs into nanocapsules, resulting in more efficient acoustic responses 14,19 .…”

Section: Introductionmentioning

confidence: 99%

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Impact of Polylactide Fluorinated End-Group Lengths and Their Dynamics on Perfluorohexane Microcapsule Morphology

et al. 2019

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We have synthesized polylactide (PLA) polymers containing five distinct lengths of fluorinated end-groups (from C 3 F 7 to C 13 F 27). The influence of fluorinated end-groups length and their dynamics in chlorinated solvents (chloroform and dichloromethane) was investigated as a function of the presence of perfluohexane (PFH) and related to the morphology of capsules of PFH obtained using these fluorinated polylactides. 19 F spin-spin relaxation time (T 2) measurements revealed a reduced mobility of the fluorinated units with dependency on fluorinated chain length in the order C 3 F 7 >C 8 F 17 >C 13 F 27. The presence of perfluorohexane (PFH) led to a further decrease on the segmental mobility, indicating the existence of fluorous interactions. The T 2 relaxation time of the CF 3 resonance of PLA-C 3 F 7 decreased from 540±50 ms in CDCl 3 to 81±15 ms after the addition of PFH. Due to these fluorous interactions, PLA polymers containing short fluorinated groups (C 3 F 7 and C 6 F 13) led to microcapsules with core-shell morphologies, whereas those formulated with long F-units (C 8 F 17 , C 11 F 23 and C 13 F 27) favored the formation of multinucleated capsules as observed by confocal microscopy.

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Echogenicity enhancement by end-fluorinated polylactide perfluorohexane nanocapsules: Towards ultrasound-activable nanosystems

et al. 2017

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We have synthesized novel fluorinated polyesters and formulated them into nanocapsules of perfluorohexane as ultrasound contrast agents. This nanosystem has been thoroughly characterized by several techniques and we show that fluorination of the biodegradable polymer favors the encapsulation of perfluorohexane without producing further reduction of cell viability. Contrary to nanocapsules of perfluoroctyl bromide formulated with the fluorinated polymers [32], the presence of the fluorinated moieties leads to an increase of echogenicity that is dependent of the length of the fluorinated moiety. Morevover, the ability of nanocapsules to explode when submitted to focused ultrasound also depends on the length of the fluorinated chain. These results pave the way to theranostic perfluorohexane nanocapsules co-encapsulating a drug for precision delivery using focused ultrasound.

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End-chain fluorination of polyesters favors perfluorooctyl bromide encapsulation into echogenic PEGylated nanocapsules

Abstract: Fluorination of polyesters favors the encapsulation efficiency of perfluorooctyl bromide into nanocapsules.

Cited by 14 publications

References 49 publications

Synthesis, properties and enzymatic biodegradation behavior of fluorinated poly(ε-caprolactone)s

Synthesis, properties and enzymatic biodegradation behavior of fluorinated poly(ε-caprolactone)s

Impact of Polylactide Fluorinated End-Group Lengths and Their Dynamics on Perfluorohexane Microcapsule Morphology

Echogenicity enhancement by end-fluorinated polylactide perfluorohexane nanocapsules: Towards ultrasound-activable nanosystems

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