“Clickable” polymersomes

Opsteen, Joost A.; Brinkhuis, René P.; Teeuwen, Rosalie L. M.; Löwik, Dennis W. P. M.; Hest, Jan C. M. van

doi:10.1039/b704568a

Cited by 198 publications

(214 citation statements)

References 30 publications

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“…Since most polymersomes are destabilized in the presence of organic solvents, it is a prerequisite to perform this click chemistry conjugation reaction in aqueous media. Click chemistry with polymersomes in aqueous solution was introduced by van Hest and co-workers using poly(styrene)-block-poly(acrylic acid) (PS-b-PAA) diblock copolymers with terminal azide groups ( Figure 4) [32]. Different ligands, such as an alkyne bearing fluorescent dansyl probe, biotin and eGFP, have been conjugated to preformed polymersomes.…”

Section: Aminementioning

confidence: 99%

“…The state of the art in terms of common conjugation chemistry that fulfills all or some of these requirements is summarized in Table 1. [26,29] Horseradish peroxidase [26] and an azidofunctionalized Candida antarctica Lipase B [29] Azide Alkyne 1,4-disubstituted 1,2,3-triazole PBD-b-PEG [30,31], PS-b-PAA [32] Mannose functional polyester dendron [30,31], dansyl probe [32], biotin [32], eGFP [32] Biotin Streptavidin Biotin-Streptavidin interaction PBD-b-PEG and PEG-b-PEE [33], PMOXA-b-PDMS-b-PMOXA [17,20,34,35] Superavidin-coated microspheres [33], antibody [36], polyguanylic acid [20,34], streptavidin-modified glass surface [17], fluorescently labeled avidin [33,35] …”

Section: Conjugation To Preformed Polymersomesmentioning

confidence: 99%

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Functionalization of Block Copolymer Vesicle Surfaces

et al. 2011

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Abstract:In dilute aqueous solutions certain amphiphilic block copolymers self-assemble into vesicles that enclose a small pool of water with a membrane. Such polymersomes have promising applications ranging from targeted drug-delivery devices, to biosensors, and nanoreactors. Interactions between block copolymer membranes and their surroundings are important factors that determine their potential biomedical applications. Such interactions are influenced predominantly by the membrane surface. We review methods to functionalize block copolymer vesicle surfaces by chemical means with ligands such as antibodies, adhesion moieties, enzymes, carbohydrates and fluorophores. Furthermore, surface-functionalization can be achieved by self-assembly of polymers that carry ligands at their chain ends or in their hydrophilic blocks. While this review focuses on the strategies to functionalize vesicle surfaces, the applications realized by, and envisioned for, such functional polymersomes are also highlighted.

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Section: Aminementioning

confidence: 99%

Section: Conjugation To Preformed Polymersomesmentioning

confidence: 99%

Functionalization of Block Copolymer Vesicle Surfaces

et al. 2011

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“…[9][10][11] One of the great advantages of this concept was for example the possibility to combine homopolymers preliminary prepared by various living polymerization techniques, such as ringopening polymerization (ROP), ring-opening metathesis polymerization (ROMP), cationic polymerization, nitroxide-mediated radical polymerization (NMP), atom transfer radical polymerization (ATRP), and reversible addition fragmentation chain transfer polymerization (RAFT). Thus, various orthogonal and efficient coupling reactions such as thiol-ene or thiol-ene based Michael addition reactions, [12][13] and Diels-Alder reactions 14 were successfully carried out.…”

Section: Introductionmentioning

confidence: 99%

Well‐defined poly(oxazoline)‐b‐poly(acrylate) amphiphilic copolymers: From synthesis by polymer–polymer coupling to self‐organization in water

Guillerm

Monge

Lapinte

et al. 2012

J. Polym. Sci. A Polym. Chem.

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In this contribution, we report on the self assembly in water of original amphiphilic poly(2-methyl-2-oxazoline)-b-poly(tert-butyl acrylate) copolymers, synthesized by copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction. For such purpose, polyoxazoline (poly(2-methyl-2-oxazoline)) and polyacrylate (poly(tert-butyl acrylate)) are first prepared by cationic ring-opening polymerization (CROP) and atom transfer radical polymerization (ATRP), respectively. Well-defined polymeric building blocks, ω-N 3 -P(t-BA) and -alkyne-P(MOx), bearing reactive chain end groups, are accurately characterized by MALDI-Tof spectroscopy. Then, P(MOx) n -b-P(t-BA) m are achieved by polymer-polymer coupling and are fully characterized by DOSY NMR and size exclusion chromatography, demonstrating the obtaining of pure amphiphilic copolymers. Consequently, the latter lead to the formation in water of well-defined monodisperse spherical micelles (R H = 40-60 nm) which are studied by fluorescence spectroscopy, SLS, AFM and TEM.

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“…It was shown that six-membered ring carbonates react with amines as nucleophiles at room temperature. It is also known that copper-(I) catalysed click-reactions work at room temperature [32][33][34]. So these functional groups are perfect for connecting two building blocks without heating.…”

Section: Coupling Reaction Using the Orthogonal Coupler 3amentioning

confidence: 99%

Synthesis and characterization of functional six-membered ring carbonates for the preparation of orthogonal couplers

2011

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On the basis of commercially available trimethylolpropane (TMP) three six-membered ring carbonates were prepared, substituted with reactive side groups: a chloroformate (2a), an imidazolyl carbamate (2b) and a phenyl carbonate (2c). Their synthesis and characterizations are described and compared to known ring carbonates with reactive side groups. Starting from 2a-c orthogonal couplers 3a and 3b were synthesized for conversion under mild reaction conditions. In a model reaction 2-azidoethyl 2-N-acetylamino-2-deoxy--D-glucopyranose and tertbutyl-N-(3-aminopropyl) carbamate were linked with coupler 3a via a 1,3-dipolar cycloaddition and a nucleophilic ring-opening reaction. This coupling principle can be used for the preparation of multifunctional polymers or surface coatings at ambient conditions.

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“Clickable” polymersomes

Abstract: Polymersomes, composed of amphiphilic polystyrene-block-poly(acrylic acid) (PS-b-PAA), with the periphery being covered with azide groups, were used for further functionalization using "click" chemistry.

Cited by 198 publications

References 30 publications

Functionalization of Block Copolymer Vesicle Surfaces

Functionalization of Block Copolymer Vesicle Surfaces

Well‐defined poly(oxazoline)‐b‐poly(acrylate) amphiphilic copolymers: From synthesis by polymer–polymer coupling to self‐organization in water

Synthesis and characterization of functional six-membered ring carbonates for the preparation of orthogonal couplers

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