Mussel-Inspired Histidine-Based Transient Network Metal Coordination Hydrogels

Fullenkamp, Dominic E; He, Linghui; Barrett, Devin G.; Burghardt, Wesley R.; Messersmith, Phillip B.

doi:10.1021/ma301791n

Cited by 271 publications

(354 citation statements)

References 54 publications

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“…We notice that the catechol might not be the only group that has coordination ability in our polyoxetane-based adhesive, and the triazole group formed via CuAAC could also form networks by forming triazole-metal complex [26,27], which might also contributes to the enhancement of the cohesive strength and adhesive strength. Also, the triazole group is structurally similar to the imidazole moiety in histidine, another important amino acid moiety in mfps that has the coordination ability [28,29]. Thus we speculated that one possible reason for lower catechol content requirement to achieve excellent bonding strength in our case is the coordination ability of triazole groups towards Fe 3þ .…”

Section: Characterization Of the Adhesive Propertiesmentioning

confidence: 84%

Synthesis and adhesive property study of polyoxetanes grafted with catechols via Cu(I)-catalyzed click chemistry

Jia

et al. 2014

Polymer

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a b s t r a c tMussel-inspired catechol-containing polymers have drawn great attention due to their outstanding adhesive properties. Catechol-containing polyethylene glycol (cPEG) is a well-studied catechol-containing polymer used for tissue repair. Nevertheless, catechols can only be attached to the chain ends of polyethylene glycols thus the bonding strength of the resulting polymers is limited. Aiming at solving the problem, a series of clickable polyoxetane copolymers with grafted catechol moieties were synthesized in an efficient manner. Upon addition of FeCl 3 as the cross-linker, strong bonding strength of the adhesive was achieved. Polymer containing 15.5 molar percent of catechol showed the strongest bonding strength up to 5.59 MPa on sanded stainless steel. It was found that the triazole groups also contributed to the overall adhesive performance. This polyoxetane-based adhesive also displayed strong bonding ability to a variety of other substrates including porcine skin.

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Section: Characterization Of the Adhesive Propertiesmentioning

confidence: 84%

Synthesis and adhesive property study of polyoxetanes grafted with catechols via Cu(I)-catalyzed click chemistry

Jia

et al. 2014

Polymer

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“…23 Additionally, a new generation of biomimetic self-repairing metallopolymers has arisen, which directly draw inspiration from the byssal threads. [24][25][26][27] In spite of these advances, many challenges still persist. Thus, a thorough experimental and theoretical understanding of the molecular processes underlying the SB mechanism is crucial.…”

Section: Introductionmentioning

confidence: 99%

“…It was shown, for example, that the type of coordination bond (i.e. the metal and ligand utilized) affects the stiffness and strength of a polymer 25,27,28 and that the fracture toughness as well as the extensibility of materials based on SBs is strongly dependent on the pulling speed. 29,30 Furthermore, it was shown that the topology of SBs and thermal backbone fluctuations strongly affect the efficacy of SBs 31 and that the spatial distribution of SBs can have a strong effect on mechanics 32 -a random distribution of SBs is necessary to provide the system with shear deformability.…”

Section: Introductionmentioning

confidence: 99%

Influence of sacrificial bonds on the mechanical behaviour of polymer chains

Nabavi

Harrington

Fratzl

et al. 2014

Bioinspired, Biomimetic and Nanobiomaterials

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A growing focus in modern materials science is the attempt to transfer principles found in nature into new technological concepts with the goal of producing novel materials with tailored mechanical properties. One of these principles used in nature is the concept of sacrificial bonding (i.e. non-covalent cross-links that rupture prior to the protein backbone), which is associated with increased toughness in many biological materials. In the present work, the influence of the number and distribution of sacrificial bonds (SBs) on three main mechanical parameters-strength, work to fracture and apparent stiffness-is investigated in a simple model system using computer simulations. The results show that the work to fracture is mainly determined by the number of SBs present in the system, while the apparent stiffness and, to a lesser extent, the strength is altered when the distribution of SBs is changed. IntroductionIn contrast to engineered materials, biological organisms utilize a relatively limited selection of building blocks to synthesize materials (e.g. proteins, sugars, environmentally abundant ions). In spite of this, however, natural materials span an extremely wide range of mechanical properties, which is achieved by hierarchical structuring of the material over multiple length scales and by a combination of materials with opposing mechanical properties. One common and successful strategy to increase the toughness of protein-based biological materials is to use so-called sacrificial bonds (SBs).2 These non-covalent cross-links are weaker than the covalent bonds that comprise the protein backbone, and consequently, upon loading, they rupture before the covalent bonds fail. By doing so, SBs reveal hidden length (i.e. the length increase associated with unfolding of folded proteins) providing an efficient energy dissipation mechanism, while the overall material integrity survives.3 Furthermore, these bonds are reversible and may reform when the load is released, allowing for molecular repair. SBs have been found in a large variety of biologial materials like wood, 4 bone 5-7 and in some softer biological fibres such as silk, 8 whelk egg capsule 9 and mussel byssus threads. 10-13In materials such as silk, SBs are often weak hydrogen bonds combined in large numbers in regular protein conformations in order to collectively produce high stiffness 14 ; however, in the case of the mussel byssus, much stronger interactions between metal ions and proteins are employed. In this regard, the mussel byssus is an especially fascinating material. The mussel secretes the collageneous byssal threads as a means of creating a secure attachment in wave-swept rocky seashore habitats. Among the impressive properties of the mussel byssus are its high extensibility of over 100%, high stiffness and toughness, 10 its hard and wearresistant outer coating [15][16][17][18] and, last but not least, its ability to create strong and long-lasting underwater adhesion to a variety of surfaces.17 A fundamental aspect shaping each of these prope...

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“…11,12 Cu 2+ /carboxyl, 13 Fe 3+ /catechol, 14,15 and Ni 2+ /histidine interactions were also employed. 16,17 Self-healing is a very interesting and useful feature of metal-coordinated gels; broken gel pieces can seal together with a mild mechanical force.…”

mentioning

confidence: 99%

Self-healing metal-coordinated hydrogels using nucleotide ligands

et al. 2015

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A supramolecular gel formed by Zn 2+ coordination with adenosine monophosphate (AMP) is reported. The adenine base, the monophosphate, and Zn 2+ are all important for gel formation. Mechanically disrupted gels can re-form upon centrifugation; applications of this gel for guest molecule entrapment are explored.Supramolecular gels have received considerable attention in recent years both as intriguing examples of self-assembly and as a means of creating smart materials.1-5 These gels are formed by noncovalent interactions to assemble supramolecular networks that trap solvent. 6Among the various types of supramolecular gels, those crosslinked by metal coordination are particular interesting. A few types of ligands have been developed for this purpose. For example, Craig and coworkers reported organopalladium−pyridine coordination. 16,17 Self-healing is a very interesting and useful feature of metal-coordinated gels; broken gel pieces can seal together with a mild mechanical force.Most of previously reported gels have to use specially designed ligands (e.g. incorporating a segment of PEG chain in addition to the metal ligand) to facilitate solvent trapping and gelation. Few reports are based on pure small molecule ligands. We reason that small molecule ligands will allow a higher metal density and thus may display different properties.Adenine, a purine nucleobase, is an important ligand in supramolecular chemistry. Adenine and its derivatives can form many complexes by coordination (with metal ions) and hydrogen bonding (with organic molecules). [18][19][20] With metal ions, it may form metalorganic frameworks, 21 and nanoparticles. [22][23][24][25] Recently, the gelation of adenine with tricarboxylic acid compounds was reported based on hydrogen bonding and π-π stacking. 26,27 We are interested in exploring whether it is possible to achieve gelation by metal coordination with adenine derivatives. Guanine and its derivatives have been mixed with monovalent metal ions to form gels based on quadruplex formation. 28-31 However, little has been done on adenine derivatives. Nanoparticles are the most common products. [22][23][24][25] Compared to nanoparticles, hydrogels are more attractive materials for making stimuli-responsible materials. [32][33][34][35][36][37][38][39] In this work, we communicate such an example, its property in guest molecule encapsulation, and healing.Since most previous work focused on adenine nucleobase and nucleoside as ligands, we started with nucleotide coordination in this work. Zn 2+ was chosen as the metal because it is a good Lewis acid that can be coordinated by a diverse range of ligands. In addition, it is a relatively biocompatible metal with low toxicity. We first studied the reaction between Zn 2+ and three kinds of nucleotides (AMP, GMP and CMP). TMP was not included since thymine has very weak coordination ability at neutral pH. Zn 2+ was respectively titrated into the solutions of AMP, GMP and CMP, and the UV-vis extinction at 550 nm was recorded. Since none of the products are c...

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Mussel-Inspired Histidine-Based Transient Network Metal Coordination Hydrogels

Cited by 271 publications

References 54 publications

Synthesis and adhesive property study of polyoxetanes grafted with catechols via Cu(I)-catalyzed click chemistry

Synthesis and adhesive property study of polyoxetanes grafted with catechols via Cu(I)-catalyzed click chemistry

Influence of sacrificial bonds on the mechanical behaviour of polymer chains

Self-healing metal-coordinated hydrogels using nucleotide ligands

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