Well-defined single-chain polymer nanoparticles via thiol-Michael addition

Kröger, A. Pia P.; Boonen, Roy J.E.A.

doi:10.1016/j.polymer.2017.05.040

Cited by 25 publications

(35 citation statements)

References 71 publications

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“…P O was cross-linked via thiol-Michael addition under continuous addition of the deprotected polymer to a cross-linker solution containing a phosphine initiator as described previously. 14 The residual thiol moieties were passivated by excess methyl acrylate, and product nanoparticles ( NP O ) were isolated via precipitation. Separate signals corresponding to the methyl group of methyl acrylate at 3.71 ppm and to the butyl ester moiety of butanediol diacrylate at 1.75 ppm are identified in the 1 H NMR spectrum ( Figure S1 ).…”

Section: Resultsmentioning

confidence: 99%

“…The nanoparticle formation in an organic solvent was performed as described earlier. 14 In brief, 1,4-butanediol diacrylate (11.9 μL, 0.25 mmol, 1.00 equiv) and tri( n -butyl)phosphine (11.0 μL, 0.05 mmol, 0.2 equiv) were added to 100 mL of nitrogen-purged dichloromethane. The solution of deprotected P O (500 mg, 0.25 mmol equiv thiol monomer) in THF (10 mL) was dropwise added to the continuously stirred cross-linker solution over 30 min.…”

Section: Methodsmentioning

confidence: 99%

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Biocompatible Single-Chain Polymer Nanoparticles for Drug Delivery—A Dual Approach

Kröger

Hamelmann

Juan

et al. 2018

ACS Appl. Mater. Interfaces

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Single-chain polymer nanoparticles (SCNPs) are protein-inspired materials based on intramolecularly cross-linked polymer chains. We report here the development of SCNPs as uniquely sized nanocarriers that are capable of drug encapsulation independent of the polarity of the employed medium. Synthetic routes are presented for SCNP preparation in both organic and aqueous environments. Importantly, the SCNPs in organic media were successfully rendered water soluble, resulting in two complementary pathways toward water-soluble SCNPs with comparable resultant physicochemical characteristics. The solvatochromic dye Nile red was successfully encapsulated inside the SCNPs following both pathways, enabling probing of the SCNP interior. Moreover, the antibiotic rifampicin was encapsulated in organic medium, the loaded nanocarriers were rendered water soluble, and a controlled release of rifampicin was evidenced. The absence of discernible cytotoxic effects and promising cellular uptake behavior bode well for the application of SCNPs in controlled therapeutics delivery.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Biocompatible Single-Chain Polymer Nanoparticles for Drug Delivery—A Dual Approach

Kröger

Hamelmann

Juan

et al. 2018

ACS Appl. Mater. Interfaces

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“…Thiol–ene Michael addition can be further used for the preparation of single‐chain nanoparticles. Paulusse and co‐workers reported well‐defined nanoparticles via intramolecular thiol‐Michael addition between thiol bearing styrene‐, acrylate, and methacrylate‐based polymers and bifunctional acrylates …”

Section: Click Chemistry For Functionalization Of Reactive Particlesmentioning

confidence: 99%

Reactive Precursor Particles as Synthetic Platform for the Generation of Functional Nanoparticles, Nanogels, and Microgels

Gruber

Navarro

Klinger

2019

Adv Materials Inter

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Precise control of the chemical functionality of polymer nanoparticles is a key requirement in tailoring their (dynamic) colloidal properties toward advanced applications. However, current synthetic techniques are still limited in the versatility of chemical design and preparation of such functional colloidal nanomaterials. Two major challenges remain: First, various particle preparation methods are restricted in their functional group tolerance, thus hindering certain combinations of polymer backbones with specific functional groups. Second, the preparation of particles with different functionalities requires the synthesis of different particle batches. But this often results in a simultaneous variation of colloidal features. As a result, the accurate determination of important structure–property relations is still hindered. To address these restrictions, postmodification of preformed reactive particles is gaining more attention. This technique has evolved from polymer synthesis, where postpolymerization functionalization enables the introduction of a plethora of functional groups without changing the degree of polymerization and the molecular weight distribution. Similarly, modifying precursor particles enables the introduction of functional groups into particles while reducing variations in colloidal features, e.g., particle size and size distribution. This powerful synthetic method complements established procedures for functionalization of particle surfaces, thereby enabling the facile preparation of (multi‐)functional particle libraries, which will allow precise investigations of structure–property relations.

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“…Recently, a variety of reactive fluorophore molecules (dansylhydrazine [ 47 ], fluorescein [ 50 ], naphthalene [ 51 ]) have been successfully conjugated to different (polystyrene [ 47 ], polydimethylamino ethyl methacrylate [ 50 ], polymethyl methacrylate [ 51 ]) nanoparticles by post-functionalization ( Figure 7 c). This illustrates the versatility of the SCNP post-functionalization technique to endow SCNPs with florescent properties.…”

Section: Fluorescent Single-chain Nanoparticles: Synthesis Routesmentioning

confidence: 99%

Advances in Fluorescent Single-Chain Nanoparticles

2017

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Fluorophore molecules can be monitored by fluorescence spectroscopy and microscopy, which are highly useful and widely used techniques in cell biology, biochemistry, and medicine (e.g., biomarker analysis, immunoassays, cancer diagnosis). Several fluorescent micro- and nanoparticle systems based on block copolymer micelles and cross-linked polymer networks, quantum dots, π-conjugated polymers, and dendrimers have been evaluated as optical imaging systems. In this review, we highlight recent advances in the construction of fluorescent single-chain nanoparticles (SCNPs), which are valuable artificial soft nano-objects with a small tunable size (as small as 3 nm). In particular, the main methods currently available to endow SCNPs with fluorescent properties are discussed in detail, showing illustrative examples.

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Well-defined single-chain polymer nanoparticles via thiol-Michael addition

Cited by 25 publications

References 71 publications

Biocompatible Single-Chain Polymer Nanoparticles for Drug Delivery—A Dual Approach

Biocompatible Single-Chain Polymer Nanoparticles for Drug Delivery—A Dual Approach

Reactive Precursor Particles as Synthetic Platform for the Generation of Functional Nanoparticles, Nanogels, and Microgels

Advances in Fluorescent Single-Chain Nanoparticles

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