Synthesis of catechol and zwitterion-bifunctionalized poly(ethylene glycol) for the construction of antifouling surfaces

Author(s): Li Qun Xu ¹ ^, ² ^, ³ ^, ⁴ , Dicky Pranantyo ¹ ^, ² ^, ³ ^, ⁴ , Koon-Gee Neoh ¹ ^, ² ^, ³ ^, ⁴ , En-Tang Kang ¹ ^, ² ^, ³ ^, ⁴ , Serena Lay-Ming Teo ⁵ ^, ² ^, ⁶ ^, ⁴ , Guo Dong Fu ⁷ ^, ⁸ ^, ⁹ ^, ¹⁰

Publication date (Electronic): 2016

Journal: Polymer Chemistry

Publisher: Royal Society of Chemistry (RSC)

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Abstract

Versatile antifouling coatings from catechol and zwitterion-bifunctionalized poly(ethylene glycol).

Abstract

The synthesis of catechol-containing small molecules and macromolecules always requires multiple reaction steps, coupling agents, or enzymes. In this study, a simple and scalable strategy for the preparation of catechol-containing poly(ethylene glycol) (CaPEG) by epoxide–amine polymerization of PEG diglycidyl ether with dopamine is described. The as-formed tertiary amine groups in the backbone of CaPEG can be converted into sulfobetaine structures in an alkylsulfonation step, leading to the formation of catechol and zwitterion-bifunctionalized PEG (SBCaPEG). The resulting catechol-containing CaPEG and SBCaPEG can be anchored on various substrate surfaces, including stainless steel (SS), titanium and silicon wafer, under mild conditions. Since SS is susceptible to fouling by a variety of microorganisms, the antifouling properties of the polymer-coated SS surfaces are studied in detail. The CaPEG- and SBCaPEG-coated SS surfaces effectively reduced the adsorption of protein (albumin–fluorescein isothiocyanate conjugate and bovine plasma fibrinogen), as well as the adhesion of bacteria ( Pseudomonas sp. and Escherichia coli) and microalgae ( Amphora coffeaeformis), as compared to that of the pristine SS surface. In comparison with the CaPEG-coated SS surfaces, the zwitterionic SBCaPEG-coated SS surfaces exhibited even better antifouling efficiencies.

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Antifouling coatings: recent developments in the design of surfaces that prevent fouling by proteins, bacteria, and marine organisms.

Indrani Banerjee, Ravindra Pangule, Ravi Kane (2011)

The major strategies for designing surfaces that prevent fouling due to proteins, bacteria, and marine organisms are reviewed. Biofouling is of great concern in numerous applications ranging from biosensors to biomedical implants and devices, and from food packaging to industrial and marine equipment. The two major approaches to combat surface fouling are based on either preventing biofoulants from attaching or degrading them. One of the key strategies for imparting adhesion resistance involves the functionalization of surfaces with poly(ethylene glycol) (PEG) or oligo(ethylene glycol). Several alternatives to PEG-based coatings have also been designed over the past decade. While protein-resistant coatings may also resist bacterial attachment and subsequent biofilm formation, in order to overcome the fouling-mediated risk of bacterial infection it is highly desirable to design coatings that are bactericidal. Traditional techniques involve the design of coatings that release biocidal agents, including antibiotics, quaternary ammonium salts (QAS), and silver, into the surrounding aqueous environment. However, the emergence of antibiotic- and silver-resistant pathogenic strains has necessitated the development of alternative strategies. Therefore, other techniques based on the use of polycations, enzymes, nanomaterials, and photoactive agents are being investigated. With regard to marine antifouling coatings, restrictions on the use of biocide-releasing coatings have made the generation of nontoxic antifouling surfaces more important. While considerable progress has been made in the design of antifouling coatings, ongoing research in this area should result in the development of even better antifouling materials in the future. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.