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Succinimidyl Carbonate-Based Amine-Reactive Polymer Brushes: Facile Fabrication of Functional Interfaces AITranslate

Bogazici University; Bogazici University; Bogazici University;Institut des Materiaux and Institut des Sciences et Ingenierie Chimiques, Laboratoire des Polymeres; Bogazici University
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Publisher: ACS
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Abstract AITranslate

Polymeric coatings that can undergo effective functionalization with ligands and (bio)molecules necessary for intended applications are widely employed to engineer functional interfaces. Herein, amine-reactive polymer brushes are fabricated using a succinimidyl group-activated carbonate monomer, and their facile post-polymerization functionalization is demonstrated through ligand-mediated protein immobilization and detection. Copolymer brushes containing varying amounts of the reactive monomer and an ethylene glycol-based methacrylate comonomer were obtained using surface-mediated reversible addition fragmentation chain transfer polymerization. Post-polymerization functionalization of the thus-obtained copolymer brushes with a fluorine-containing amine, namely, 4-(trifluoromethyl)benzylamine, demonstrated highly efficient functionalization at ambient temperature. To demonstrate possible applications, polymer brushes functionalized with a bioactive ligand, namely, biotin, were used to detect the target protein, streptavidin. The biotin–streptavidin interaction on brushes could also be employed to conjugate protein-coated quantum dots. Importantly, comparison of the attachment of 4-(trifluoromethyl)benzylamine on activated carbonate group-containing brushes with reaction of the same molecule on traditional active ester-based brushes demonstrated higher extent of conjugation to carbonate brushes. Finally, orthogonal functionalization of the copolymer brushes with an amino-functionalized molecule and a maleimide-containing fluorescent dye in spatial control using microcontact printing was demonstrated. One can envision that the facile fabrication and efficient functionalization of succinimidyl carbonate-based amine-reactive brushes afford an attractive platform for applications using functional interfaces for diagnostic purposes.

KeyWords AITranslate

polymeric coatings biofunctionalization polymer brushes succinimidyl carbonate carbamate formation amine conjugation
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Basic Information:

DOI:https://doi.org/10.1021/acsapm.1c00107

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Citation Information:

Polymeric coatings that can undergo effective functionalization with ligands and (bio)molecules necessary for intended applications are widely employed to engineer functional interfaces. Herein, amine-reactive polymer brushes are fabricated using a succinimidyl group-activated carbonate monomer, and their facile post-polymerization functionalization is demonstrated through ligand-mediated protein immobilization and detection. Copolymer brushes containing varying amounts of the reactive monomer and an ethylene glycol-based methacrylate comonomer were obtained using surface-mediated reversible addition fragmentation chain transfer polymerization. Post-polymerization functionalization of the thus-obtained copolymer brushes with a fluorine-containing amine, namely, 4-(trifluoromethyl)benzylamine, demonstrated highly efficient functionalization at ambient temperature. To demonstrate possible applications, polymer brushes functionalized with a bioactive ligand, namely, biotin, were used to detect the target protein, streptavidin. The biotin–streptavidin interaction on brushes could also be employed to conjugate protein-coated quantum dots. Importantly, comparison of the attachment of 4-(trifluoromethyl)benzylamine on activated carbonate group-containing brushes with reaction of the same molecule on traditional active ester-based brushes demonstrated higher extent of conjugation to carbonate brushes. Finally, orthogonal functionalization of the copolymer brushes with an amino-functionalized molecule and a maleimide-containing fluorescent dye in spatial control using microcontact printing was demonstrated. One can envision that the facile fabrication and efficient functionalization of succinimidyl carbonate-based amine-reactive brushes afford an attractive platform for applications using functional interfaces for diagnostic purposes.

quote

GB/T 7714-2015 [1] Tugce Nihal Gevrek, Aysun Degirmenci, Rana Sanyal, et al. ACS Applied Polymer Materials, 2021(3). DOI:10.1021/acsapm.1c00107.
MLA [1] Tugce Nihal Gevrek, et al., ACS Applied Polymer Materials, no. 3, 2021, https://doi.org/10.1021/acsapm.1c00107.
APA [1] Tugce Nihal Gevrek, Aysun Degirmenci, Rana Sanyal, HarmAnton Klok, & Amitav Sanyal. (2021). ACS Applied Polymer Materials(3). https://doi.org/10.1021/acsapm.1c00107
IEEE [1] Tugce Nihal Gevrek, Aysun Degirmenci, Rana Sanyal, HarmAnton Klok, and Amitav Sanyal, ACS Applied Polymer Materials, no. 3, 2021, doi: 10.1021/acsapm.1c00107. keywords: {polymeric coatings;biofunctionalization;polymer brushes;succinimidyl carbonate;carbamate formation;amine conjugation}