Stabilizing self-assembled Fmoc–F<sub>5</sub>–Phe hydrogels by co-assembly with PEG-functionalized monomers

Ryan, Derek M.; Doran, Todd M.; Nilsson, Bradley L.

doi:10.1039/c0cc02217a

Cited by 94 publications

(118 citation statements)

References 14 publications

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“…[73][74][75][76] It has already been mentioned that G produces a self supporting tight gel in the presence of KCl but it has poor lifetime stability (15 min at the mgc and see Fig. 1d and Table 1).…”

Section: Co-gelmentioning

confidence: 91%

Self-assembly of guanosine and deoxy-guanosine into hydrogels: monovalent cation guided modulation of gelation, morphology and self-healing properties

2014

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+ on the stimulation of purine nucleosides guanosine (G) and deoxy-guanosine (dG) to self-assemble into hydrogels. The gelation properties in terms of gel crystallization, lifetime stability, thermo-reversibility, minimum gelation concentration, gel melting temperature, thixotropic property and others were thoroughly investigated and compared not only between two nucleosides but also among different metal ions. A few metal ions were found to induce G/dG to form gels with much improved lifetime stability. The results revealed that dG is a much better gelator than G for introduction of a thixotropic property. Interestingly, morphological, fluorescence and rheological (thixotropic) properties of the gels were found to modulate significantly by changing the metal ions. In the presence of K + ions, G produces a self supporting tight gel but it has poor lifetime stability. In contrast, the presence of K + ions stimulates dG to form a very loose gel but with excellent lifetime stability and thixotropic property. In this context, we have successfully engineered a self-supporting stable co-gel using a simple co-gelation method by mixing an equimolar amount of K + induced G and dG gels and this co-gel shows long lifetime stability, self-healing and injectable properties which may allow for a broad range of biological applications.Furthermore, an Ag + induced G gel was exploited for the light triggered in situ fabrication of uniform AgNPs within a gel to make a nano-bio hybrid material.

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Section: Co-gelmentioning

confidence: 91%

Self-assembly of guanosine and deoxy-guanosine into hydrogels: monovalent cation guided modulation of gelation, morphology and self-healing properties

2014

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“…32,33 Fmoc-DOPA is especially interesting due to the multifunctional nature of the catecholic moiety, which is capable to act as an antioxidant, radical trapper, metal chelator, oxidizable reducing agent, etc. 13,31,[47][48][49][50] Here, we demonstrate the ability to obtain hybrid gels which combine chemical properties of one building block and physical properties of the other. 32 In this work, we examined the self-assembly and combined hydrogelation of the structurallyrelated Fmoc-Tyr and Fmoc-DOPA (Fig.…”

Section: Introductionmentioning

confidence: 94%

Synergetic functional properties of two-component single amino acid-based hydrogels

et al. 2015

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The formation of hydrogels by low molecular weight building blocks results in important supramolecular assemblies for technological applications. N-modified amino acids are especially interesting components for the organization of such structures due to the high efficiency of association, inherent biocompatibility, and structural diversity. The fluorenylmethoxycarbonyl (Fmoc)-modified tyrosine (Fmoc-Tyr) has been extensively studied as a notably simple yet highly efficient hydrogelator. Here we present the ability to use a combination of Fmoc-Tyr and the catechol-containing Fmoc-3,4-dihydroxyphenylalanine (Fmoc-DOPA) to form a functional two-component hydrogel which combines the physical characteristics as observed with Fmoc-Tyr hydrogels together with the functionality of the catechol groups. We demonstrate that a combination of the two building blocks results in the rapid formation of three-dimensional selfsupporting gels. Rheological analysis indicated that the observed hybrid gel has very high storage modulus, in the same order of magnitude as that of the Fmoc-Tyr gel. In addition to the envisioned mechanical properties, the combined gel also displayed a clear silver ion reduction activity. Taken together, we illustrate the ability to utilize two-component gels to achieve synergetic properties, combining rigidity and functionality.behavior, as previously reported. 32 TEM imaging of the weak Fmoc-DOPA gel revealed fibrillar assemblies which appeared linear, unbranched and extending to the length of micrometers (Fig. 2b). The width of the fibers ranged from 5 to 10 nm and lateral bundling was observed. The obtained Fmoc-Tyr hydrogels were semi-transparent and presented similar underlying fibers, albeit wider, with an approximated width of 15 nm, as imaged by TEM (Fig 2b). These observations are in line with previous reports concerning the hydrogelation of Fmoc-Tyr by using the solvent-switch method. 30 Next, we examined the hybrid hydrogels. These gels presented similar macroscopic behavior to those of Fmoc-Tyr and similar fibrillar assemblies of 15 nm in width were imaged by TEM (Fig. 2b).absence of silver nitrate, which were higher than their respective loss moduli by an order of magnitude (Fig. S4). This direct comparison of rheological properties shows that the high mechanical rigidity of the Fmoc-Tyr:Fmoc-DOPA hybrid gels is retained in their redox-active state, further demonstrating the functional synergy of the two gelators.

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“…Furthermore, polyethylene glycol (PEG) chains were introduced into Fmoc-F 5 -Phe to increase the solubility of the fibers which could lead to shear-responsiveness. [44] Indeed, co-assembly of Fmoc-F5-Phe and Fmoc-F 5 -Phe-PEG yielded hydrogels with adequate mechanical rigidity and ideal shear-responsiveness. Later, the C-terminal carboxylic acid groups of Fmoc-F5-Phe and Fmoc-3-F-Phe were modified to amide and methyl esters.…”

Section: Amino Acid Based Nanostructuresmentioning

confidence: 99%

Amino Acid Based Self‐assembled Nanostructures: Complex Structures from Remarkably Simple Building Blocks

Chakraborty

Gazit

2018

ChemNanoMat

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Amino acids are the simplest biological building blocks capable of forming discreet nanostructures by supramolecular self-assembly. The understanding of the process of organization of amino acid nanostructures is of fundamental importance for the study of metabolic diseases as well as for materials science applications. Although peptide self-assembled structures have been the topic of many review articles, much less attention has been devoted to the ability of amino acid building blocks, both natural and synthetic, to form ordered assemblies with defined architectures and notable physical properties, by the process of self-association. Herein, we try to shed light on amino acid based nanostructures, their fabrication and implications. We discuss self-assembled nanostructures, including hydrogels with nanoscale order, obtained from both modified and unmodified single amino acids. We also envision some future prospects in this emerging field.

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Stabilizing self-assembled Fmoc–F₅–Phe hydrogels by co-assembly with PEG-functionalized monomers

Abstract: Hydrogels derived from self-assembled Fmoc-F(5)-Phe fibrils are stabilized with respect to shear-response by co-assembly with C-terminal PEG-functionalized Fmoc-F(5)-Phe.

Cited by 94 publications

References 14 publications

Self-assembly of guanosine and deoxy-guanosine into hydrogels: monovalent cation guided modulation of gelation, morphology and self-healing properties

Self-assembly of guanosine and deoxy-guanosine into hydrogels: monovalent cation guided modulation of gelation, morphology and self-healing properties

Synergetic functional properties of two-component single amino acid-based hydrogels

Amino Acid Based Self‐assembled Nanostructures: Complex Structures from Remarkably Simple Building Blocks

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Stabilizing self-assembled Fmoc–F5–Phe hydrogels by co-assembly with PEG-functionalized monomers

Abstract: Hydrogels derived from self-assembled Fmoc-F(5)-Phe fibrils are stabilized with respect to shear-response by co-assembly with C-terminal PEG-functionalized Fmoc-F(5)-Phe.

Cited by 94 publications

References 14 publications

Self-assembly of guanosine and deoxy-guanosine into hydrogels: monovalent cation guided modulation of gelation, morphology and self-healing properties

Self-assembly of guanosine and deoxy-guanosine into hydrogels: monovalent cation guided modulation of gelation, morphology and self-healing properties

Synergetic functional properties of two-component single amino acid-based hydrogels

Amino Acid Based Self‐assembled Nanostructures: Complex Structures from Remarkably Simple Building Blocks

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Stabilizing self-assembled Fmoc–F₅–Phe hydrogels by co-assembly with PEG-functionalized monomers