Defining the Catechol–Cation Synergy for Enhanced Wet Adhesion to Mineral Surfaces

Rapp, M.; Maier, Greg P.; Dobbs, Howard A.; Higdon, Nicholas J.; Waite, J. Herbert; Butler, Alison; Israelachvili, Jacob N.

doi:10.1021/jacs.6b03453

Cited by 169 publications

(176 citation statements)

References 38 publications

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“…Furthermore, the catechol surface can potentially be enriched with amines or guanidiniums, which both have been shown to improve catechol mediated adhesion . Another alternative could be a polymeric catechol conjugated to a UPy‐moiety, as polymeric L‐DOPA addition showed positive effects.…”

Section: Methodsmentioning

confidence: 99%

Renal Epithelial Monolayer Formation on Monomeric and Polymeric Catechol Functionalized Supramolecular Biomaterials

Gaal

Fedecostante

Fransen

et al. 2018

Macromolecular Bioscience

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Induction of a functional, tight monolayer of renal epithelial cells on a synthetic membrane to be applied in a bioartificial kidney device requires for bio‐activation of the membrane. The current golden standard in bio‐activation is the combination of a random polymeric catechol (L‐DOPA) coating and collagen type IV (Col IV). Here the possibility of replacing this with defined monomeric catechol functionalization on a biomaterial surface using supramolecular ureido‐pyrimidinone (UPy)‐moieties is investigated. Monomeric catechols modified with a UPy‐unit are successfully incorporated and presented in supramolecular UPy‐polymer films and membranes. Unfortunately, these UPy‐catechols are unable to improve epithelial cell monolayer formation over time, solely or in combination with Col IV. L‐DOPA combined with Col IV is able to induce a tight monolayer capable of transport on electrospun supramolecular UPy‐membranes. This study shows that a random polymeric catechol coating cannot be simply mimicked by defined monomeric catechols as supramolecular additives. There is still a long way to go in order to synthetically mimic simple natural structures.

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Section: Methodsmentioning

confidence: 99%

Renal Epithelial Monolayer Formation on Monomeric and Polymeric Catechol Functionalized Supramolecular Biomaterials

Gaal

Fedecostante

Fransen

et al. 2018

Macromolecular Bioscience

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“…Two additional siderophore analogs were synthesized to probe the role of cations in wet adhesion [47]. Tren-Arg-Cam (TAC, Fig.…”

Section: Fig 7 Catechol-cation Synergy In Siderophore Analogsmentioning

confidence: 99%

“…Both TAC and TLLC perform similarly to TLC in SFA experiments. All three siderophore analogs are able to displace the hydration layer, form a monolayer between the mica surfaces, and produce strong adhesion [47]. However, TAC produces only 50-60% of the maximum TLC adhesion and has a critical adsorption concentration (CAC) approximately 10x higher than TLC.…”

Section: Fig 7 Catechol-cation Synergy In Siderophore Analogsmentioning

confidence: 99%

“…8c). adapted from [47]. both undergo a pH-dependent oxidation with higher pH promoting faster oxidation rates [46].…”

Section: Fig 7 Catechol-cation Synergy In Siderophore Analogsmentioning

confidence: 99%

“…Cationic Lys may also contribute to adhesion through electrostatic interactions with the negatively charged mica surface [47]. between two mica surfaces.…”

mentioning

confidence: 99%

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Siderophores and mussel foot proteins: the role of catechol, cations, and metal coordination in surface adhesion

Maier

Butler

2017

J Biol Inorg Chem

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Metal coordination, hydrogen bonding, redox reactions, and covalent crosslinking are seemingly disparate chemical and physicochemical processes that are all accomplished in natural materials by the catechol functional group. This review focuses on the reactivity of catechols in tris-2,3-dihydroxybenzoyl-containing microbial siderophores and synthetic analogs, as well as Dopa-(3,4-dihydroxyphenylalanine)-containing mussel foot proteins that adhere to surfaces in aqueous conditions.Mussel foot proteins with a high content of Dopa and cationic amino acids, Lys and Arg, adhere strongly to mica, an aluminosilicate mineral, in aqueous conditions. The siderophore cyclic trichrysobactin, tris-(2,3-dihydroxybenzoyl-D-Lys-L-Ser) and related synthetic analogs in which the tri-Ser macrolactone is replaced by Tren, tris-(2-aminoethyl)amine, also adheres strongly to mica. Variation in the nature of the catechol and cationic groups in synthetic analogs reveals a synergism between the cationic amino acid and the catechol, required for strong aqueous adhesion. Autoxidation and iron(III)-catalyzed oxidation of 2,3-dihydroxy and 3,4-dihydroxy catechols is also considered. These siderophore analogs provide a platform to understand catechol interactions and reactivity on surfaces, which may ultimately improve the design of synthetic materials that address diverse challenges in medicine, materials science, as well as other disciplines, in which surface adhesion in aqueous conditions is important.

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A Universal Strategy for Tough Adhesion of Wet Soft Material

Gao

Chen

Han

et al. 2020

Adv Funct Materials

139

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Achieving adhesion between hydrogels and diverse materials in a facile and universal way is challenging. Existing methods rely on special chemical or physical properties of the hydrogel and adherends, which lead to limited applicability and complicated pretreatments. A stitch‐bonding strategy is proposed here by introducing a polymer chain with versatile functional group and triggerable crosslinking property inspired by catechol chemistry. The polymer chain can stitch the hydrogel by forming a network in topological entanglement with the preexisting hydrogel network, and directly bond to the adherend surface by versatile chemical interactions. Through this, the polymer chain solution works as a universal glue for facile adhesion of hydrogels to diverse substrates like metals, glasses, elastomers, plastics, and living tissues, without requiring any chemical design or pretreatment for the hydrogel and adherends. The adhesion energy between polyacrylamide hydrogel and diverse substrates can reach 200–400 J m−2, and it can reach ≈900 J m−2 with a toughened polyacrylic acid polyacrylamide hydrogel. The mechanism of stitch‐bonding strategy is illustrated by studying various influence factors.

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Defining the Catechol–Cation Synergy for Enhanced Wet Adhesion to Mineral Surfaces

Cited by 169 publications

References 38 publications

Renal Epithelial Monolayer Formation on Monomeric and Polymeric Catechol Functionalized Supramolecular Biomaterials

Renal Epithelial Monolayer Formation on Monomeric and Polymeric Catechol Functionalized Supramolecular Biomaterials

Siderophores and mussel foot proteins: the role of catechol, cations, and metal coordination in surface adhesion

A Universal Strategy for Tough Adhesion of Wet Soft Material

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