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      Catechol-Functionalized Synthetic Polymer as a Dental Adhesive to Contaminated Dentin Surface for a Composite Restoration

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          Abstract

          This study reports a synthetic polymer functionalized with catechol groups as dental adhesives. We hypothesize that a catechol-functionalized polymer functions as a dental adhesive for wet dentin surfaces, potentially eliminating the complications associated with saliva contamination. We prepared a random copolymer containing catechol and methoxyethyl groups in the side chains. The mechanical and adhesive properties of the polymer to dentin surface in the presence of water and salivary components were determined. It was found that the new polymer combined with an Fe 3+ additive improved bond strength of a commercial dental adhesive to artificial saliva contaminated dentin surface as compared to a control sample without the polymer. Histological analysis of the bonding structures showed no leakage pattern, probably due to the formation of Fe–catechol complexes, which reinforce the bonding structures. Cytotoxicity test showed that the polymers did not inhibit human gingival fibroblast cells proliferation. Results from this study suggest a potential to reduce failure of dental restorations due to saliva contamination using catechol-functionalized polymers as dental adhesives.

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          Most cited references50

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          A reversible wet/dry adhesive inspired by mussels and geckos.

          The adhesive strategy of the gecko relies on foot pads composed of specialized keratinous foot-hairs called setae, which are subdivided into terminal spatulae of approximately 200 nm (ref. 1). Contact between the gecko foot and an opposing surface generates adhesive forces that are sufficient to allow the gecko to cling onto vertical and even inverted surfaces. Although strong, the adhesion is temporary, permitting rapid detachment and reattachment of the gecko foot during locomotion. Researchers have attempted to capture these properties of gecko adhesive in synthetic mimics with nanoscale surface features reminiscent of setae; however, maintenance of adhesive performance over many cycles has been elusive, and gecko adhesion is greatly diminished upon full immersion in water. Here we report a hybrid biologically inspired adhesive consisting of an array of nanofabricated polymer pillars coated with a thin layer of a synthetic polymer that mimics the wet adhesive proteins found in mussel holdfasts. Wet adhesion of the nanostructured polymer pillar arrays increased nearly 15-fold when coated with mussel-mimetic polymer. The system maintains its adhesive performance for over a thousand contact cycles in both dry and wet environments. This hybrid adhesive, which combines the salient design elements of both gecko and mussel adhesives, should be useful for reversible attachment to a variety of surfaces in any environment.
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            Dental adhesion review: aging and stability of the bonded interface.

            Most of current dental adhesive systems show favorable immediate results in terms of retention and sealing of bonded interface, thereby counteracting polymerization shrinkage that affects resin-based restorative materials. Despite immediate efficacy, there are major concerns when dentin bonded interfaces are tested after aging even for short time period, i.e. 6 months. This study critically discusses the latest peer-reviewed reports related to formation, aging and stability of resin bonding, focusing on the micro and nano-phenomena related to adhesive interface degradation. Most simplified one-step adhesives were shown to be the least durable, while three-step etch-and-rinse and two-step self-etch adhesives continue to show the highest performances, as reported in the overwhelming majority of studies. In other words, a simplification of clinical application procedures is done to the detriment of bonding efficacy. Among the different aging phenomena occurring at the dentin bonded interfaces, some are considered pivotal in degrading the hybrid layer, particularly if simplified adhesives are used. Insufficient resin impregnation of dentin, high permeability of the bonded interface, sub-optimal polymerization, phase separation and activation of endogenous collagenolytic enzymes are some of the recently reported factors that reduce the longevity of the bonded interface. In order to overcome these problems, recent studies indicated that (1) resin impregnation techniques should be improved, particularly for two-step etch-and-rinse adhesives; (2) the use of conventional multi-step adhesives is recommended, since they involve the use of a hydrophobic coating of nonsolvated resin; (3) extended curing time should be considered to reduce permeability and allow a better polymerization of the adhesive film; (4) proteases inhibitors as additional primer should be used to increase the stability of the collagens fibrils within the hybrid layer inhibiting the intrinsic collagenolytic activity of human dentin.
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              Chemical aspects of self-etching enamel-dentin adhesives: a systematic review.

              The paper gives an overview on the components and the polymer chemical aspects of currently used self-etching enamel-dentin primers/adhesives. In addition, the contribution of new adhesives monomers and cross-linkers exhibiting enhanced hydrolytic stability than methacrylates to improve the performance of single-bottle adhesives is discussed. Information from original scientific papers or reviews about enamel-dentin adhesives, the patent literature concerning dental adhesives and manufacturer information of commercial self-etching adhesives were included in this review. The most efficient self-etching enamel-dentin adhesives are based on strongly acidic adhesive monomers, containing dihydrogenphosphate, phosphonic acids or carboxylic acid groups. Serious problems of single-bottle water-based, strongly acidic self-etching enamel-dentin adhesives arise both from the hydrolytic instability of the methacrylate monomers used and the side reaction of the applied initiator components. The stability of the self-etching enamel-dentin adhesives can be improved by using new acrylic ether phosphonic acids or mono- or difunctional acrylamides, while more stable and compatible components have to be developed in the future.
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                Author and article information

                Journal
                Biomacromolecules
                Biomacromolecules
                bm
                bomaf6
                Biomacromolecules
                American Chemical Society
                1525-7797
                1526-4602
                15 July 2015
                10 August 2015
                : 16
                : 8
                : 2265-2275
                Affiliations
                []Department of Dental Biomaterials and Bioengineering, College of Dentistry, Yonsei University , Seoul, 03722, Republic of Korea
                [2a] Department of Cariology, Restorative Sciences and Endodontics, School of Dentistry, and §Department of Biologic and Materials Sciences, School of Dentistry, University of Michigan , Ann Arbor, Michigan 48109, United States
                Author notes
                Article
                10.1021/acs.biomac.5b00451
                4534835
                26176305
                bef12776-dd4b-4ad6-97d3-eea2f04a44c5
                Copyright © 2015 American Chemical Society

                This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

                History
                : 06 April 2015
                : 25 June 2015
                Categories
                Article
                Custom metadata
                bm5b00451
                bm-2015-00451y

                Biochemistry
                Biochemistry

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