Core-crosslinked worm-like micelles from polyether-based diblock terpolymers

Elter, Johanna K.; Biehl, Philip; Gottschaldt, Michael; Schacher, Felix H.

doi:10.1039/c9py01054h

Cited by 7 publications

(9 citation statements)

References 57 publications

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“…In a second polymerization step, we added a hydrophobic block consisting of EHGE and FGE via AROP (Scheme ). The diblock terpolymer was purified as described in our previous work and its composition is given in Table …”

Section: Resultsmentioning

confidence: 99%

“…The initiator can also carry a functional group to enable the attachment of small molecules for active cell targeting to the surface of the nanoparticle, often realized via click chemistry . To generate the hydrophobic block, several glycidyl ethers can be used . Therefore, it is possible to introduce quite a range of functionalities or side chain motifs.…”

Section: Introductionmentioning

confidence: 99%

“…However, this technique can only be used for at least moderately hydrophilic structures. Also, dissolution times can vary depending on the molecular weight of the block copolymer . A special case of direct dissolution is the (re)hydration of a thin polymer film.…”

Section: Introductionmentioning

confidence: 99%

“…36 To generate the hydrophobic block, several glycidyl ethers can be used. 37 Therefore, it is possible to introduce quite a range of functionalities or side chain motifs. Varying sterical demand or different intermolecular interactions can influence micellar morphologies, 38 while stimuli-responsive moieties like amines can help to realize a triggered drug release mechanism.…”

Section: Introductionmentioning

confidence: 99%

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Core-Crosslinked Fluorescent Worm-Like Micelles for Glucose-Mediated Drug Delivery

et al. 2021

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We herein report the fabrication of core-crosslinked, fluorescent, and surface-functionalized worm-like block copolymer micelles as drug delivery vehicles. The polyether-based diblock terpolymer [allyl-poly(ethylene oxide)-block-poly(2-ethylhexyl glycidyl ether-co-furfuryl glycidyl ether)] was synthesized via anionic ring opening polymerization, and self-assembly in water as a selective solvent led to the formation of long filomicelles. Subsequent cross-linking was realized using hydrophobic bismaleimides as well as a designed fluorescent cross-linker for thermally induced Diels−Alder reactions with the furfuryl units incorporated in the hydrophobic block of the diblock terpolymer. As a fluorescent cross-linker, we synthesized and incorporated a cyanine 5-based bismaleimide in the cross-linking process, which can be used for fluorescence tracking of the particles. Furthermore, we covalently attached glucose to the allyl end groups present on the surface of the micelles to investigate active glucose-mediated transport into suitable cell lines. First studies in 2D as well as 3D cell culture models suggest a glucose-dependent uptake of the particles into cells despite their unusually large size compared to other nanoparticle systems used in drug delivery.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Core-Crosslinked Fluorescent Worm-Like Micelles for Glucose-Mediated Drug Delivery

et al. 2021

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“…Pre-ordering of the diblock terpolymers in the thin polymer film may influence the resulting solution structure. [22,61] Crosslinking procedures for the micelles are described within the results and discussion section.…”

Section: Methodsmentioning

confidence: 99%

Polyether‐Based Diblock Terpolymer Micelles with Pendant Anthracene Units—Light‐Induced Crosslinking and Limitations Regarding Reversibility

Elter

Eichhorn

Schacher

2021

Macromol. Rapid Commun.

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The synthesis of 9-methylanthracenyl glycidyl ether (AnthGE) as a crosslinkable monomer that can be applied in anionic ring opening polymerization is reported. Diblock terpolymers of the composition methoxy-poly(ethylene oxide)-block-poly(2-ethylhexyl glycidyl ether-co-9-methylanthracenyl glycidyl ether) (mPEO-b-P(EHGE-co-AnthGE) with 10 to 24 wt% of AnthGE are synthesized and characterized. Their micellization behavior, as well as their light-induced core-crosslinking via irradiation with UV light (𝝀 = 365 nm) is studied. The results are compared with studies on the dimerization, and the dimer cleavage via irradiation with UV-C light (𝝀 = 254 nm), of the same diblock terpolymer in organic solution, and the small-molecule model compound 9-methoxymethylanthracene. Differences in 1 H NMR spectra of the crosslinked or dimerized compounds and reaction kinetics of the dimerization reactions under different conditions suggest possible side reactions for the case of the core-crosslinking of micelles in aqueous solution. These side reactions limit the reversibility of the anthracene dimerization reaction in aqueous solutions, even if the anthracene molecule is encapsulated within the hydrophobic core of a polymeric micelle.

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Inside Block Copolymer Micelles—Tracing Interfacial Influences on Crosslinking Efficiency in Nanoscale Confined Spaces

Höppener

Elter

Schacher

et al. 2023

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Recently, several studies have demonstrated the excellent capabilities of tip‐enhanced Raman spectroscopyfor in‐depth investigations of structural properties of matter with unprecedented resolution and chemical specificity. These capabilities are utilized here to study the internal structure of core‐crosslinked micelles, which are formed by self‐assembly of the diblock terpolymer poly(ethylene oxide)‐block‐poly(furfuryl glycidylether‐co‐tert‐butylglycidyl ether). Supplementing force–volume atomic force microscopy experiments address additionally the nanomechanical properties. Particularly, TERS enables investigating the underlying principles influencing the homogeneity and efficiency of the Diels–Alder core‐crosslinking process in the confined hydrophobic core. While the central core region is homogenously crosslinked, a breakdown of the crosslinking reaction is observed in the core–corona interfacial region. The results corroborate that a strong crosslinking efficiency is directly correlated to the formation of a mixed zone of the glycidyl ether and PEO corona blocks reaching ≈5 nm into the core region. Concomitantly a strong exclusion of the encapsulated bismaleimide crosslinker from the interfacial region is observed. It is conceivable that a changed structure, chemical composition and altered nanomechanical properties of this interfacial region may also influence the crosslinking efficiency across the entire core region by a modification of the solubility of the crosslinker in the interfacial core‐corona region.

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Core-crosslinked worm-like micelles from polyether-based diblock terpolymers

Abstract: We herein report on the synthesis of polyether-based diblock terpolymers and their self-assembly into complex solution structures (e.g. filomicelles). The aggregates were core-crosslinked and their structure was influenced via ultrasonication.

Cited by 7 publications

References 57 publications

Core-Crosslinked Fluorescent Worm-Like Micelles for Glucose-Mediated Drug Delivery

Core-Crosslinked Fluorescent Worm-Like Micelles for Glucose-Mediated Drug Delivery

Polyether‐Based Diblock Terpolymer Micelles with Pendant Anthracene Units—Light‐Induced Crosslinking and Limitations Regarding Reversibility

Inside Block Copolymer Micelles—Tracing Interfacial Influences on Crosslinking Efficiency in Nanoscale Confined Spaces

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