Enhancement of poly(ethylene glycol) mucoadsorption by biomimetic end group functionalization

Catron, Nathaniel D.; Lee, Haeshin; Messersmith, Phillip B.

doi:10.1116/1.2422894

Cited by 60 publications

(45 citation statements)

References 41 publications

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“…Although the exact reaction mechanism is uncertain, likely candidates include Michael addition or Schiff base reactions with primary amines on the surface. Single-molecule studies of Dopa interacting with mucin revealed strong non covalent interactions (85). Although the nature of the interactions was not determined, the single-molecule results were in qualitative agreement with an observed increase in mucoadhesion upon functionalization of Dopa with PEG (85).…”

Section: Mussel-inspired Synthetic Polymersmentioning

confidence: 99%

Mussel-Inspired Adhesives and Coatings

Lee

Messersmith

Israelachvili

et al. 2011

Annu. Rev. Mater. Res.

1,487

1,514

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Mussels attach to solid surfaces in the sea. Their adhesion must be rapid, strong, and tough, or else they will be dislodged and dashed to pieces by the next incoming wave. Given the dearth of synthetic adhesives for wet polar surfaces, much effort has been directed to characterizing and mimicking essential features of the adhesive chemistry practiced by mussels. Studies of these organisms have uncovered important adaptive strategies that help to circumvent the high dielectric and solvation properties of water that typically frustrate adhesion. In a chemical vein, the adhesive proteins of mussels are heavily decorated with Dopa, a catecholic functionality. Various synthetic polymers have been functionalized with catechols to provide diverse adhesive, sealant, coating, and anchoring properties, particularly for critical biomedical applications.

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Section: Mussel-inspired Synthetic Polymersmentioning

confidence: 99%

Mussel-Inspired Adhesives and Coatings

Lee

Messersmith

Israelachvili

et al. 2011

Annu. Rev. Mater. Res.

1,487

1,514

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“…2(A)], which promotes its absorption to mucosal tissues32, 33 and hydroxyapatite surfaces 34, 35. The benzene ring of catechol is capable of interacting with other aromatic rings through π–π electron interaction [Fig.…”

Section: Chemistry Of Adhesion: Mussel Adhesive Proteinsmentioning

confidence: 99%

Recent approaches in designing bioadhesive materials inspired by mussel adhesive protein

Forooshani

Lee

2016

J. Polym. Sci. Part A: Polym. Chem.

523

464

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Marine mussels secret protein‐based adhesives, which enable them to anchor to various surfaces in a saline, intertidal zone. Mussel foot proteins (Mfps) contain a large abundance of a unique, catecholic amino acid, Dopa, in their protein sequences. Catechol offers robust and durable adhesion to various substrate surfaces and contributes to the curing of the adhesive plaques. In this article, we review the unique features and the key functionalities of Mfps, catechol chemistry, and strategies for preparing catechol‐functionalized polymers. Specifically, we reviewed recent findings on the contributions of various features of Mfps on interfacial binding, which include coacervate formation, surface drying properties, control of the oxidation state of catechol, among other features. We also summarized recent developments in designing advanced biomimetic materials including coacervate‐forming adhesives, mechanically improved nano‐ and micro‐composite adhesive hydrogels, as well as smart and self‐healing materials. Finally, we review the applications of catechol‐functionalized materials for the use as biomedical adhesives, therapeutic applications, and antifouling coatings. © 2016 The Authors. Journal of Polymer Science Part A: Polymer Chemistry Published by Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 9–33

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“…This confirms that the improved mucoadhesion is due to intact HCA and not its oxidation products. The increased adhesion measured on HCA/CH hydrogels indicates the presence of catechol groups at the interface between this hydrogel and the mucosa; catechol groups may in fact act as "bridges" between CH and mucin, as previously proposed by Catron et al 27 In order to test the effect of catechol oxidation on mucoadhesion, we measured the adhesion strength of the hydrogels upon oxidation with NaIO 4 . When NaIO 4 was applied on the 2 h-swollen hydrogels, DOPA/CH, HCA/CH, and DA/CH changed color to dark brown, thus confirming the presence of unreleased catechol compounds in them ( Figure 5).…”

Section: ■ Introductionmentioning

confidence: 95%

Mollusk Glue Inspired Mucoadhesives for Biomedical Applications

Soliman

Barralet

et al. 2012

Langmuir

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Chitosan (CH), partially N-deacetylated chitin, is a biodegradable and biocompatible polymer that has shown great potential in drug delivery and tissue engineering applications. Although bioadhesive, CH has limited mucoadhesion in wet conditions due to weak interactions with biological surfaces. DOPA (3,4-dihydroxy-L-phenylalanine), a catechol-containing molecule naturally present in marine mussel foot proteins, has been shown to increase the mucoadhesion of several polymers. We report here a simple and bioinspired approach to enhance CH mucoadhesion in wet conditions by preparing mixed hydrogels including CH and different catechol-containing compounds, namely DOPA, hydrocaffeic acid (HCA), and dopamine (DA). We characterized the hydrogels for their swelling, release kinetics of the catechol compounds, and mucoadhesive strength to rabbit small intestine. The swelling of the hydrogels was pH dependent with maximum swelling at pH 1. The hydrogel swelling was higher in the presence of the DOPA and DA but lower in the presence of HCA. HCA/CH hydrogel also showed the slowest catechol release, most likely due to electrostatic interactions between CH and HCA. Lower hydrogel swelling and slower HCA release resulted in increased mucoadhesion: HCA/CH showed more than 2-fold enhancement of mucoadhesion to rabbit small intestine compared to CH alone. Since it is known that catechol compounds can be oxidized, we analyzed the oxidation of DOPA, HCA, and DA at different pH values and its effect on mucoadhesion. We found that oxidation occurring before contact with the intestinal mucosa did not improve mucoadhesion, while oxidation occurring during the contact further increased the mucoadhesion of HCA/CH hydrogels. These results show that mucoadhesion of CH hydrogels can be increased with a simple bioinspired approach, which has the potential to be applied to other polymers since it does not require any chemical modification.

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Enhancement of poly(ethylene glycol) mucoadsorption by biomimetic end group functionalization

Cited by 60 publications

References 41 publications

Mussel-Inspired Adhesives and Coatings

Mussel-Inspired Adhesives and Coatings

Recent approaches in designing bioadhesive materials inspired by mussel adhesive protein

Mollusk Glue Inspired Mucoadhesives for Biomedical Applications

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