Catechols as versatile platforms in polymer chemistry

Faure, Emilie; Falentin‐Daudre, Céline; Jérôme, Christine; Lyskawa, Joël; Fournier, David; Woisel, Patrice; Detrembleur, Christophe

doi:10.1016/j.progpolymsci.2012.06.004

Cited by 537 publications

(452 citation statements)

References 282 publications

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“…Early studies showed that the presence of 3,4-dihydroxy-L-phenylalanine (DOPA) and lysine-rich proteins were responsible for the extremely robust adhesion of mussels 3,[5][6][7][8] . In 2007, Lee et al reported the first publication using dopamine (DA), with a similar molecular structure of DOPA, to obtain an adhesive pDA film 5,7,9 .…”

Section: Introductionmentioning

confidence: 99%

“…In 2007, Lee et al reported the first publication using dopamine (DA), with a similar molecular structure of DOPA, to obtain an adhesive pDA film 5,7,9 . Later on new pDA properties as well as interesting applications in biosensors, sensors, remediation, biomineralization, drug delivery and hyperthermia have been reported 3,[6][7][8][9][10][11][12][13][14][15] . The very reactive residual quinone groups in pDA allow further derivatizations with nitrogen and thiol residues through Schiff base formation or Michael-type addition respectively 3,6,7,16,17 .…”

Section: Introductionmentioning

confidence: 99%

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Amperometric magnetobiosensors using poly(dopamine)-modified Fe₃O₄ magnetic nanoparticles for the detection of phenolic compounds

et al. 2015

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aThe synthesis of poly(dopamine)-modified magnetic nanoparticles (MNPs) and their application to prepare electrochemical enzyme biosensor useful to detect phenolic compounds is reported in this work. MNPs of about 16 nm were synthetized by co-precipitation method and conveniently modified with poly(dopamine). Non-modified and modified MNPs were characterized using X-ray photoelectron spectroscopy (XPS), Raman and infrared spectroscopy, X-ray diffraction (XRD) and atomic force microscopy (AFM). Horseradish peroxidase (HRP) was covalently immobilized onto the surface of the poly(dopamine)-modified MNPs via Michael addition and/or Schiff base formation and used to construct a biosensor for phenolic compounds by capturing the HRP-modified-nanoparticles onto the surface of a magnetic-modified glassy carbon electrode (GCE). Cyclic voltammetry and amperometry were used to study the electrochemical and analytical properties of the biosensor using hydroquinone (HQ) as redox probe. Among different phenolic compounds studied the biosensor exhibited higher sensitivity for HQ, 1.38 A M −1 cm −2, with limits of detection and quantification of 0.3 and 1.86 µM, respectively. The analytical biosensor performance for HQ and 2-aminophenol compared advantageously with previous phenolic biosensors reported in the literature.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Amperometric magnetobiosensors using poly(dopamine)-modified Fe₃O₄ magnetic nanoparticles for the detection of phenolic compounds

et al. 2015

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“…1−5 However, other constitutional features of mfps, e.g., cationic residues (lysine, K), anionic residues (aspartic acid, D), nonionic polar residues (asparagine, N), and nonpolar residues (alanine, A), have not typically been included in mussel-inspired synthetic wet-adhesion systems. 1,2 Here, we studied the microphase behavior and wet-adhesion of copolyampholytes with fixed catechol content and varied other key functionalities. Potential effects of aromatic moieties (Tyr, Trp) besides Dopa in mfp-3s have not been specifically tested in the present structural design of the model copolyampholytes.…”

mentioning

confidence: 99%

Microphase Behavior and Enhanced Wet-Cohesion of Synthetic Copolyampholytes Inspired by a Mussel Foot Protein

Seo¹,

Das²,

Zalicki³

et al. 2015

J. Am. Chem. Soc.

133

144

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Numerous attempts have been made to translate mussel adhesion to diverse synthetic platforms. However, the translation remains largely limited to the Dopa (3,4-dihydroxyphenylalanine) or catechol functionality, which continues to raise concerns about Dopa's inherent susceptibility to oxidation. Mussels have evolved adaptations to stabilize Dopa against oxidation. For example, in mussel foot protein 3 slow (mfp-3s, one of two electrophoretically distinct interfacial adhesive proteins in mussel plaques), the high proportion of hydrophobic amino acid residues in the flanking sequence around Dopa increases Dopa's oxidation potential. In this study, copolyampholytes, which combine the catechol functionality with amphiphilic and ionic features of mfp-3s, were synthesized and formulated as coacervates for adhesive deposition on surfaces. The ratio of hydrophilic/hydrophobic as well as cationic/anionic units was varied in order to enhance coacervate formation and wet adhesion properties. Aqueous solutions of two of the four mfp-3s-inspired copolymers showed coacervate-like spherical microdroplets (ϕ ≈ 1−5 μm at pH ∼4 (salt concentration ∼15 mM). The mfp-3s-mimetic copolymer was stable to oxidation, formed coacervates that spread evenly over mica, and strongly bonded to mica surfaces (pull-off strength: ∼17.0 mJ/m 2 ). Increasing pH to 7 after coacervate deposition at pH 4 doubled the bonding strength to ∼32.9 mJ/m 2 without oxidative cross-linking and is about 9 times higher than native mfp-3s cohesion. This study expands the scope of translating mussel adhesion from simple Dopa-functionalization to mimicking the context of the local environment around Dopa. M arine mussels (Figure 1a) attach to hard surfaces, e.g., mineral and metal, in the intertidal zone where waves with and without suspended sand often exceed 25 m/sec velocities. 3,4-Dihydroxyphenylalanine (Dopa), a main constituent in mussel foot proteins (mfps) and substantially contributing to wet adhesion, has been incorporated in synthetic polymers to mimic the bio wet-adhesion. 1−5 However, other constitutional features of mfps, e.g., cationic residues (lysine, K), anionic residues (aspartic acid, D), nonionic polar residues (asparagine, N), and nonpolar residues (alanine, A), have not typically been included in mussel-inspired synthetic wet-adhesion systems. 1,2Here, we studied the microphase behavior and wet-adhesion of copolyampholytes with fixed catechol content and varied other key functionalities. Potential effects of aromatic moieties (Tyr, Trp) besides Dopa in mfp-3s have not been specifically tested in the present structural design of the model copolyampholytes. Conditions for the experiments were adjusted according to the microenvironmental conditions of adhesive protein deposition under the mussel's foot including acidic to neutral pH and ionic strength of ≤100 mM. 3,4 In mussel adhesion, polyelectrolyte adhesive proteins or mfps are presented to target surfaces after being condensed as a dense fluid by complex coacervation, a critical ste...

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“…Meanwhile, its polymerization state, polydopamine, shows similar structure and strong adhesion as those of the mussel protein. [12][13][14] In alkaline conditions, polydopamine film can be easily formed by the polymerization of dopamine after its deposition on the surface of substrate. As an intermediate, functional molecule can be adhered onto the solid surface by bonding interactions with the polydopamine film.…”

Section: Underwater Adhesion Of Catechol Groups or Their Derivativesmentioning

confidence: 99%

Recent Progress of Mussel‐Inspired Underwater Adhesives

Zhang

Song

et al. 2017

Chin. J. Chem.

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Underwater adhesion is greatly desired in tissue transplantation, medical treatment, ocean transportation, and so on. However, common commercial polymeric adhesives are rather weakened and easily destroyed in water environment. In nature, some marine organisms, such as mussels, barnacles, or tube worms, exhibiting excellent underwater adhesion up to robust bonding on the rock of sea floor, can give exciting solutions to address the problem. Among these marine organisms, mussels exhibit unique underwater adhesion via the foot proteins of byssus. It has been verified that the catechol groups from the side chain of the mussel foot proteins is the main contribution to the unique underwater adhesion. Hence, inspired by the mussels' underwater adhesion, many mussel-mimetic polymers with catechol as end chains or side chains have been developed in the past decades. Here, we review recent progress of mussel-inspired underwater adhesives polymers from their catechol-functional design to their potential applications in intermediates, anti-biofouling, self-healing of hydrogels, biological adhesives, and drug delivery. The review may provide basis and help for the development of the commercial underwater adhesives.

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Catechols as versatile platforms in polymer chemistry

Cited by 537 publications

References 282 publications

Amperometric magnetobiosensors using poly(dopamine)-modified Fe₃O₄ magnetic nanoparticles for the detection of phenolic compounds

Amperometric magnetobiosensors using poly(dopamine)-modified Fe₃O₄ magnetic nanoparticles for the detection of phenolic compounds

Microphase Behavior and Enhanced Wet-Cohesion of Synthetic Copolyampholytes Inspired by a Mussel Foot Protein

Recent Progress of Mussel‐Inspired Underwater Adhesives

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Catechols as versatile platforms in polymer chemistry

Cited by 537 publications

References 282 publications

Amperometric magnetobiosensors using poly(dopamine)-modified Fe3O4 magnetic nanoparticles for the detection of phenolic compounds

Amperometric magnetobiosensors using poly(dopamine)-modified Fe3O4 magnetic nanoparticles for the detection of phenolic compounds

Microphase Behavior and Enhanced Wet-Cohesion of Synthetic Copolyampholytes Inspired by a Mussel Foot Protein

Recent Progress of Mussel‐Inspired Underwater Adhesives

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Amperometric magnetobiosensors using poly(dopamine)-modified Fe₃O₄ magnetic nanoparticles for the detection of phenolic compounds

Amperometric magnetobiosensors using poly(dopamine)-modified Fe₃O₄ magnetic nanoparticles for the detection of phenolic compounds