Synthesis and ring-opening polymerisation of a new alkyne-functionalised glycolide towards biocompatible amphiphilic graft copolymers

Coumes, Fanny; Darcos, Vincent; Domurado, Dominique; Li, Suming; Coudane, Jean

doi:10.1039/c3py00375b

Cited by 45 publications

(63 citation statements)

References 51 publications

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“…Moreover, when the concentration of the mPEG-b-poly(Tyr) 25 -g-NB micelle was above the CMC, the maximum peak of the fluorescence emission spectra underwent a blue shift from 622 nm at concentration of 0.01 mg ml À1 to 608 nm at concentration of 0.2 mg ml À1 . Similar blue shift can also be found in the fluorescence emission spectra of mPEG-b-poly(Tyr) 50 -g-NB micelle.…”

Section: Synthesis and Characterization Of Block Copolymerssupporting

confidence: 68%

“…Note that the average size determined by SEM was smaller than that determined from DLS analysis, which was most likely led by shrinkage of the PEG shell upon drying. [50][51][52][53] Meanwhile, mPEG-b-poly(Tyr) 50 -g-NB formed micelles with number-average hydrodynamic diameter of 259.7 nm and polydispersity of 0.079 ( Fig. 5(b)).…”

Section: Synthesis and Characterization Of Block Copolymersmentioning

confidence: 99%

“…Two kinds of mPEG-b-poly(Tyr) with different hydrophobic chain length, namely mPEG-b-poly(Tyr) 25 and mPEG-b-poly(Tyr) 50 , were obtained at the monomer to initiator ratio of 25 and 50, respectively. The structures of the corresponding copolymer were determined by 1 H NMR and FT-IR, which were in accordance with those reported in literature 43 and 44.…”

Section: Synthesis and Characterization Of Block Copolymersmentioning

confidence: 99%

“…For light-responsive experiments, the mPEG-b-poly(Tyr) 25 -g-NB or mPEG-b-poly(Tyr) 50 -g-NB micelles were irradiated with UV light at 365 nm. The micelles (0.2 mg ml À1 ) were exposed to UV light for 60 min.…”

Section: Photo-responsiveness Experimentsmentioning

confidence: 99%

“…This figure is available in colour online at wileyonlinelibrary.com/ journal/pat Figure 7. Photo-controlled release of the micelles: fluorescence emission spectra of mPEG-b-poly(Tyr) 25 -g-NB (a), fluorescence emission spectra of mPEG-b-poly(Tyr) 50 -g-NB (b), and the photo-controlled NR release profiles in aqueous solution (c). This figure is available in colour online at wileyonlinelibrary.com/journal/pat hydrophobic o-NB esters to hydrophilic carboxylic acid.…”

mentioning

confidence: 99%

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Photo‐responsive amphiphilic poly(α‐hydroxy acids) with pendent o‐nitrobenzyl ester constructed via copper‐catalyzed azide‐alkyne cycloaddition reaction

Liu

Niu

et al. 2015

Polymers for Advanced Techs

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Photo-responsive block copolymer mPEG-b-poly(Tyr)-g-NB was prepared by introduction of o-nitrobenzyl ester group into the side chain of amphiphilic poly(ethylene glycol)-b-poly(α-hydroxy acids) (mPEG-b-poly(Tyr)) containing pendent alkynyl group via copper-catalyzed azide-alkyne cycloaddition reaction. The amphiphilic mPEG-bpoly(Tyr) was synthesized via the ring-opening polymerization of O-carboxyanhydrides, with monomethoxy poly (ethylene glycol) (mPEG) as macroinitiator. The molecular structure, self-assembly, and photo-controlled release of the obtained mPEG-b-poly(Tyr)-g-NB were thoroughly investigated. mPEG-b-poly(Tyr)-g-NB could self-assemble into spherical micelles in water and showed disassembly under UV light irradiation, which was demonstrated by means of UV-vis spectroscopy, scan electron microscopes, and dynamic light scattering measurement. Fluorescence emission measurements demonstrated that Nile red, encapsulated by micelles, can be released upon UV irradiation. This study provides a convenient way to construct smart poly(α-hydroxy acids)-based nanocarriers for controlled release of hydrophobic drugs.

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Section: Synthesis and Characterization Of Block Copolymerssupporting

confidence: 68%

Section: Synthesis and Characterization Of Block Copolymersmentioning

confidence: 99%

Section: Synthesis and Characterization Of Block Copolymersmentioning

confidence: 99%

Section: Photo-responsiveness Experimentsmentioning

confidence: 99%

mentioning

confidence: 99%

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Photo‐responsive amphiphilic poly(α‐hydroxy acids) with pendent o‐nitrobenzyl ester constructed via copper‐catalyzed azide‐alkyne cycloaddition reaction

Liu

Niu

et al. 2015

Polymers for Advanced Techs

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New Routes to Tailor‐Made Polyesters

Fukushima

Fujiwara

2017

Polymers for Biomedicine

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Ring‐Opening Polymerization of a New Diester Cyclic Dimer of Mandelic and Glycolic Acid: An Efficient Synthesis Method for Derivatives of Amorphous Polyglycolide with High T_g

Nakajima

Loos

Ishizu

et al. 2018

Macromol. Rapid Commun.

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In this study, poly(mandelate-co-glycolate) (PMG), a modified polyglycolide (PGL), is prepared by ring-opening polymerization (ROP) of L-3-phenyl-1,4-dioxane-2,5-dione (PDD); the cyclic dimer of biobased mandelic acid and glycolic acid. The resulting polymer shows an increased glass transition temperature (T ) due to the incorporation of phenyl groups in the chain. High molecular weight PMG is obtained by bulk ROP at 150 °C, and it exhibits a glassy amorphous state with enhanced thermal properties such as a T being 35 °C higher than conventional PGL. PDD is also copolymerized with glycolide (GL) and lactide (LA), resulting in poly(mandelate-co-glycolate/glycolate) ((P(MG/GL)) with GL and poly(mandelate-co-glycolate/lactide) ((P(MG/LA)) with LA. The thermal properties of P(MG/GL) and P(MG/LA) are found to be distinctly different from PMG and conventional PGL and polylactide, and they are tunable with a changing molar ratio of PDD, GL, and LA. Therefore, PDD opens an elegant way to control and tailor the properties of biobased polyesters.

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Synthesis and ring-opening polymerisation of a new alkyne-functionalised glycolide towards biocompatible amphiphilic graft copolymers

Cited by 45 publications

References 51 publications

Photo‐responsive amphiphilic poly(α‐hydroxy acids) with pendent o‐nitrobenzyl ester constructed via copper‐catalyzed azide‐alkyne cycloaddition reaction

Photo‐responsive amphiphilic poly(α‐hydroxy acids) with pendent o‐nitrobenzyl ester constructed via copper‐catalyzed azide‐alkyne cycloaddition reaction

New Routes to Tailor‐Made Polyesters

Ring‐Opening Polymerization of a New Diester Cyclic Dimer of Mandelic and Glycolic Acid: An Efficient Synthesis Method for Derivatives of Amorphous Polyglycolide with High T_g

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Synthesis and ring-opening polymerisation of a new alkyne-functionalised glycolide towards biocompatible amphiphilic graft copolymers

Cited by 45 publications

References 51 publications

Photo‐responsive amphiphilic poly(α‐hydroxy acids) with pendent o‐nitrobenzyl ester constructed via copper‐catalyzed azide‐alkyne cycloaddition reaction

Photo‐responsive amphiphilic poly(α‐hydroxy acids) with pendent o‐nitrobenzyl ester constructed via copper‐catalyzed azide‐alkyne cycloaddition reaction

New Routes to Tailor‐Made Polyesters

Ring‐Opening Polymerization of a New Diester Cyclic Dimer of Mandelic and Glycolic Acid: An Efficient Synthesis Method for Derivatives of Amorphous Polyglycolide with High Tg

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Product

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Ring‐Opening Polymerization of a New Diester Cyclic Dimer of Mandelic and Glycolic Acid: An Efficient Synthesis Method for Derivatives of Amorphous Polyglycolide with High T_g