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Semi-Telechelic Polymers from Mechanochemical C─C Bond Activation.

ABSTRACT: Unstrained C─C bond activation is attained in homopolymers through mechanochemical bond scission followed by functionalization to yield mostly semi-telechelic polymer chains. Ball milling poly(ethylene oxide) (PEO) in the presence of 1-(bromoacetyl)pyrene (BAPy) yields the pyrene terminated PEO. Similarly, milling with 2,4'-dibromoacetophenone followed by Suzuki coupling allows the introduction of various aryl end groups. PEOs with a molecular weight below 20 kDa show no functionalization, supporting a mechanochemical mechanism. The protocol is also tested with doxorubicin, yielding the drug-polymer conjugate. PEO halogenation is also demonstrated by milling PEO with iodine, N-bromosuccinimide, or N-iodosuccinimide, which can then be reacted with an amine substituted anthracene. Grinding additional carbon polymers with BAPy indicates that this functionalization method is general for different polymer chemistries.

SUBMITTER: Schwarz R

PROVIDER: S-EPMC10700232 | biostudies-literature | 2023 Dec

REPOSITORIES: biostudies-literature

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Semi-Telechelic Polymers from Mechanochemical C─C Bond Activation.

Schwarz Rony R Diesendruck Charles E CE

Advanced science (Weinheim, Baden-Wurttemberg, Germany) 20231023 34

Unstrained C─C bond activation is attained in homopolymers through mechanochemical bond scission followed by functionalization to yield mostly semi-telechelic polymer chains. Ball milling poly(ethylene oxide) (PEO) in the presence of 1-(bromoacetyl)pyrene (BAPy) yields the pyrene terminated PEO. Similarly, milling with 2,4'-dibromoacetophenone followed by Suzuki coupling allows the introduction of various aryl end groups. PEOs with a molecular weight below 20 kDa show no functionalization, suppo ...[more]

PMID: 37870199

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Project description:Design, synthesis, and application of cyclodextrin (CD) containing thermoresponsive hydrogels fabricated from thiol-reactive telechelic polymers are reported. Hydrophilic polymers containing 2-hydroxyethyl methacrylate and/or di(ethylene glycol)methylether methacrylate monomers as side chains and thiol-reactive groups at chain ends were synthesized. A series of hydrogels was fabricated using thiol-ene conjugation of these thiol-reactive polymers with multivalent thiol-containing CDs as crosslinkers. Clear and transparent hydrogels were obtained with good conversion (79-89%) by utilizing the "nucleophilic" and "radical" thiol-ene "click" reactions. Analysis of the amount of residual thiol groups in these hydrogels using Ellman's reagent suggested that gels with a moderately well-defined network structure were obtained. Hydrogels fabricated using different telechelic polymers were examined for their properties such as morphology, equilibrium water uptake, and rheological characteristics. Cytocompatibility of these hydrogels was ascertained by a cell viability assay that demonstrated low toxicity toward fibroblast cells. Thereafter, the CD-containing hydrogels were evaluated for the loading and controlled release of puerarin, an antiglaucoma drug. Utilization of thermoresponsive polymers as the matrix for these hydrogels allows use of temperature as a stimulus to modulate the drug release. A slower and more sustained drug release was observed at physiological temperatures compared to ambient conditions. The effect of temperature on the elasticity of the hydrogel was investigated rheologically to demonstrate that the collapse of the network structure occurs near physiological temperatures. The increased hydrophobicity and compactness of the gel matrix at higher temperatures results in a slower drug release. The strategy employed here demonstrates that tuning the matrix composition of hydrogels with well-defined network structures through appropriate choice of responsive copolymers allows design of materials with control of their physical properties and drug-release behavior.

Dataset Information

Semi-Telechelic Polymers from Mechanochemical C─C Bond Activation.

Publications

Semi-Telechelic Polymers from Mechanochemical C─C Bond Activation.

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