In this study, we developed zwitterionic surface coatings of carboxybetaine by mimicking natural melanogenesis. We synthesized an unnatural tyrosine-conjugated carboxybetaine (Tyr-CB) that undergoes melanin-like oxidation upon treatment with tyrosinase under various aqueous conditions. The thickness of the resulting poly(Tyr-CB) film was tuned by adjusting the pH during the coating process. The poly(Tyr-CB)-coated surfaces demonstrated excellent antifouling performance against proteins and cells and imparted (super)hydrophilicity to various substrates. Additionally, post-functionalization with external biotin-PEG-thiol was achieved by targeting the oxidized quinone groups within the poly(Tyr-CB) film network. This enabled biospecific binding to streptavidin, while non-specific interactions were suppressed due to the antifouling background. As our one-step antifouling coating method is simple, involves aqueous conditions, and could be generically used to coat various substrates, it can be a versatile and valuable tool for biosensing, high-throughput screening, and cell-surface engineering.
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http://dx.doi.org/10.1021/acs.langmuir.4c04852 | DOI Listing |
Langmuir
January 2025
Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 46241, Republic of Korea.
In this study, we developed zwitterionic surface coatings of carboxybetaine by mimicking natural melanogenesis. We synthesized an unnatural tyrosine-conjugated carboxybetaine (Tyr-CB) that undergoes melanin-like oxidation upon treatment with tyrosinase under various aqueous conditions. The thickness of the resulting poly(Tyr-CB) film was tuned by adjusting the pH during the coating process.
View Article and Find Full Text PDFLangmuir
June 2023
Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 46241, Korea.
In this study, we developed a substrate-independent initiator film that can undergo surface-initiated polymerization to form an antifouling brush. Inspired by the melanogenesis found in nature, we synthesized a tyrosine-conjugated bromide initiator (Tyr-Br) that contains phenolic amine groups as the dormant coating precursor and α-bromoisobutyryl groups as the initiator. The resultant Tyr-Br was stable under ambient air conditions and underwent melanin-like oxidation only in the presence of tyrosinase to form an initiator film on various substrates.
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