Facile Method To Prepare Microcapsules Inspired by Polyphenol Chemistry for Efficient Enzyme Immobilization

Zhang, Shaohua; Jiang, Zhongyi; Wang, Xiaoli; Yang, Chen; Shi, Jiafu

doi:10.1021/acsami.5b03823

Cited by 66 publications

(52 citation statements)

References 45 publications

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“…1,2 It consists of a center glucose molecule with all five hydroxyl moieties esterified with two gallic acid (3,4,5-trihydroxybenzoic acid) molecules. The trihydroxylphenyl groups play an important role in binding a variety of substrates through chemical and physical interactions, [3][4][5][6][7][8][9][10][11][12][13] which are similar to the adhesion mechanism of 3,4-dihydroxyphenylalanine (DOPA)-enriched adhesive proteins of blue mussels. 14 TA can be deposited onto various organic and inorganic substrates because of its inherent affinity towards surfaces.…”

Section: Introductionmentioning

confidence: 99%

Thiol Reactive Maleimido-Containing Tannic Acid for the Bioinspired Surface Anchoring and Post-Functionalization of Antifouling Coatings

Pranantyo

Neoh

et al. 2016

ACS Sustainable Chem. Eng.

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Inspired by tea stains, a new surface anchor, maleimido-containing tannic acid (TAMA), was developed to introduce the maleimido functionality onto the stainless steel (SS) surfaces. The feasibility of maleimido groups to serve as anchoring sites for surface functionalization via Michael addition was explored in a model experiment using thiol-containing 1H,1H,2H,2H-perfluorodecanethiol. The surface conjugation efficiency of TAMA with the thiol-containing compounds via Michael addition was also compared to that of the surface with tannic acid (TA) only. Water-soluble thiolated carboxymethyl chitosan (CMCSSH) was then grafted on the SS surface pre-anchored with TAMA via solution immersion and spin coating.The deposition of CMCSSH was characterized by contact angle measurement, surface zeta potential, and X-ray photoelectron spectroscopy (XPS). The antifouling efficacy of the CMCSSH coatings was evaluated by protein adsorption and bacterial adhesion. The cytotoxic effect of the CMCSSH coatings on mammalian cells was evaluated using the standard 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay with 3T3 fibroblasts.

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Section: Introductionmentioning

confidence: 99%

Thiol Reactive Maleimido-Containing Tannic Acid for the Bioinspired Surface Anchoring and Post-Functionalization of Antifouling Coatings

Pranantyo

Neoh

et al. 2016

ACS Sustainable Chem. Eng.

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“…[4] Furthermore,t he total charge depends on the ionogenic groups at different pH values,w here it can change from À1t o+ 1( Supporting Information, Figure S3 and Table S1). Thec alculated pKav alues for the functional groups are 9.4 AE 0.8 and 3.2 AE 0.8 for the acid (aromatic N, À NHÀ)a nd base (ÀOH), respectively.F urthermore,t he maximum buffer capacity is in the pH range from 1.1 to 11.9.…”

mentioning

confidence: 99%

“…Among various types of inorganic building blocks in MOFs,t he copper paddlewheel cluster,[ Cu 2 (O 2 C À ) 4 ], has been ubiquitously applied to construct porous MOFs with high accessible surface areas and ahigh concentration of open metal sites (OMSs). [5] Therefore,w er eacted the buffer molecule H 4 BDPO with copper nitrate (for details,s ee the Supporting Information) under suitable conditions to form the copper paddlewheel cluster that led to am icroporous MOF,[Cu 24 (BDPO) 12 (H 2 O) 12 ]·30 DMF·14 H 2 O(namely JUC-1000, DMF = N,N'-dimethylformamide).…”

mentioning

confidence: 99%

“…Thel igand can undergo changes in its total charge at high or low pH values due to the presence of À O À / À OH, À NH À / À NH + À ,and À N = / À NH + = pairs (the so-called buffering effect). [4] Furthermore,t he total charge depends on the ionogenic groups at different pH values,w here it can change from À1t o+ 1( Supporting Information, Figure S3 and Table S1). As such, this ligand, within aMOF,can serve as ab uffer guard to prevent assault from acidic and alkaline media.…”

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confidence: 99%

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A Stable Metal–Organic Framework Featuring a Local Buffer Environment for Carbon Dioxide Fixation

et al. 2018

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A majority of metal-organic frameworks (MOFs) fail to preserve their physical and chemical properties after exposure to acidic, neutral, or alkaline aqueous solutions, therefore limiting their practical applications in many areas. The strategy demonstrated herein is the design and synthesis of an organic ligand that behaves as a buffer to drastically boost the aqueous stability of a porous MOF (JUC-1000), which maintains its structural integrity at low and high pH values. The local buffer environment resulting from the weak acid-base pairs of the custom-designed organic ligand also greatly facilitates the performance of JUC-1000 in the chemical fixation of carbon dioxide under ambient conditions, outperforming a series of benchmark catalysts.

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“…Based on catechol adhesiveness as well as cross‐linking reactions and interactions between catechol groups, many polyphenol and catechol‐based compounds without amine groups can form functional coatings . In particular, tannic acid has been used to fabricate useful coating materials, often based on its formation of coordination complexes with ferric ions . However, the durability of these films for many applications is problematic as the coordination complexes can be broken down in the presence of chelating agents and under acidic conditions .…”

Section: Catecholamine Polymers: Chemistry and Structurementioning

confidence: 99%

Versatile Surface Modification Using Polydopamine and Related Polycatecholamines: Chemistry, Structure, and Applications

Barclay

Hegab

Clarke

et al. 2017

Adv Materials Inter

277

221

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Almost ten years ago, Lee et al. [13] formulated a universal adhesive coating based on observation of the strong attachment by mussels through their byssal threads to virtually all types of inorganic and organic surfaces. The amino acid compositions of the mussel foot proteins that generate the attachment are rich in catechol and amine groups. [13][14][15] These groups associate under marine conditions, forming strong covalent and noncovalent interactions with substrates. [13] This led to the idea that both catechol and amine groups were crucial in forming robust, wide spectrum adhesive nanolayers [16,17] and consequently dopamine was conceived as a powerful building block for spontaneous deposition of thin polymer films. The dopamine monomer is deposited onto unadulterated surfaces through self-assembly and oxidative cross-linking from mild pH aqueous solution in a rapid reaction. This results in a durable, nanoscale, conformal, and hydrophilic coating that can be readily modified to introduce specific surface chemistries for a particular application. [18][19][20][21][22] These bioinspired, polydopamine materials are chemically and structurally indistinguishable from eumelanins found in the human body, [23,24] providing excellent biocompatibility. Additionally, polydopamine has broad electromagnetic absorption and excellent photothermal energy conversion [25] as well as having ionic-electronic hybrid conductivity. [26] Along with the excellent coating performance, these properties provide a vast array of potential applications for polydopamine materials.In this article, we explain what is known about polydopamine and related catecholamine coatings; their formation, the adhesion mechanism, and their physicochemical properties and we also review the applications of these materials (Figure 1). Since 2011, there have been a number of reviews on this subject matter, including general reviews on the physicochemical properties of polydopamine coatings [11,20,[27][28][29] and their applications. [20,27,30] There are also a number of more specific reviews on the chemical synthesis and modulation of polycatecholamine coatings, [31] the biomedical applications of these coatings, [8,[32][33][34] their electronic properties, [26,35] the use of polydopamine to make films at fluid interfaces, [36] in hierarchically constructed particles, [33] and capsules, [30] exploitation of polycatecholamine coatings in membrane filtration, [37] polydopamine-derived carbon materials, [38] and the use of coordination chemistry in catechol-based materials. [39] Nonetheless, this area of research is growing so rapidly [25,27] that many recent Polydopamine and related polycatecholamines can be easily deposited onto almost any surface from mild, aqueous solution. This results in durable, nanoscale coatings that exhibit high biocompatibility and have useful chemical and electronic properties. Additionally, these materials can be readily chemically and physically modified, and consequently, they are used extensively for surface modification. This ...

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Facile Method To Prepare Microcapsules Inspired by Polyphenol Chemistry for Efficient Enzyme Immobilization

Cited by 66 publications

References 45 publications

Thiol Reactive Maleimido-Containing Tannic Acid for the Bioinspired Surface Anchoring and Post-Functionalization of Antifouling Coatings

Thiol Reactive Maleimido-Containing Tannic Acid for the Bioinspired Surface Anchoring and Post-Functionalization of Antifouling Coatings

A Stable Metal–Organic Framework Featuring a Local Buffer Environment for Carbon Dioxide Fixation

Versatile Surface Modification Using Polydopamine and Related Polycatecholamines: Chemistry, Structure, and Applications

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