Low molecular weight hydrogels derived from urea based-bolaamphiphiles as new injectable biomaterials

Ramin, M.; Latxague, Laurent; Sindhu, Kotagudda Ranganath; Chassande, Olivier; Barthélémy, Philippe

doi:10.1016/j.biomaterials.2017.08.034

Cited by 60 publications

(76 citation statements)

References 36 publications

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“…Indeed, a related congruent report has shown that urea‐based nonpeptidic gelators self‐associate through NH/O hydrogen bonds to form stable six‐membered rings based on two donors and one carbonyl acceptor, thereby resulting in stronger urea–urea α‐tape hydrogen bonding interactions . Moreover, the presence of a urea moiety could impart self‐assembled nanostructures with novel functional properties or increased mechanical strength and metabolic stability, as compared to their unmodified counterparts . For these reasons, we selected the urea group as a backbone modification for Fmoc‐FF.…”

supporting

confidence: 83%

Expanding the Functional Scope of the Fmoc‐Diphenylalanine Hydrogelator by Introducing a Rigidifying and Chemically Active Urea Backbone Modification

et al. 2019

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Peptidomimetic low‐molecular‐weight hydrogelators, a class of peptide‐like molecules with various backbone amide modifications, typically give rise to hydrogels of diverse properties and increased stability compared to peptide hydrogelators. Here, a new peptidomimetic low‐molecular‐weight hydrogelator is designed based on the well‐studied N ‐fluorenylmethoxycarbonyl diphenylalanine (Fmoc‐FF) peptide by replacing the amide bond with a frequently employed amide bond surrogate, the urea moiety, aiming to increase hydrogen bonding capabilities. This designed ureidopeptide, termed Fmoc—Phe—NHCONH—Phe—OH (Fmoc‐FuF), forms hydrogels with improved mechanical properties, as compared to those formed by the unmodified Fmoc‐FF. A combination of experimental and computational structural methods shows that hydrogen bonding and aromatic interactions facilitate Fmoc‐FuF gel formation. The Fmoc‐FuF hydrogel possesses properties favorable for biomedical applications, including shear thinning, self‐healing, and in vitro cellular biocompatibility. Additionally, the Fmoc‐FuF, but not Fmoc‐FF, hydrogel presents a range of functionalities useful for other applications, including antifouling, slow release of urea encapsulated in the gel at a high concentration, selective mechanical response to fluoride anions, and reduction of metal ions into catalytic nanoparticles. This study demonstrates how a simple backbone modification can enhance the mechanical properties and functional scope of a peptide hydrogel.

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supporting

confidence: 83%

Expanding the Functional Scope of the Fmoc‐Diphenylalanine Hydrogelator by Introducing a Rigidifying and Chemically Active Urea Backbone Modification

et al. 2019

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“…Among various physical stimuli, temperature‐responsive supramolecular hydrogels are the most widely studied systems, where the hydrogelators undergo sol–gel or gel–sol transitions in response to subtle changes in their surrounding temperature . Akin to thermoreversible hydrogels, the temperature‐dependent phase transitions of supramolecular hydrogels are largely driven by hydrophilic and hydrophobic interactions . One of the first temperature‐responsive supramolecular hydrogels was based on glycosylated amino acid derivatives, for example, N ‐acetyl‐galactosamine‐appended amino acid (GalNAc‐aa), which self‐assembles into a hydrogel above its critical gelation concentration (CGC) ( Figure 2 A) .…”

Section: Physical Stimuli‐responsive Hydrogelsmentioning

confidence: 99%

“…[74][75][76][77][78][79][80] Akin to thermoreversible hydrogels, the temperature-dependent phase transitions of supramolecular hydrogels are largely driven by hydrophilic and hydrophobic interactions. [81][82][83][84][85][86] One of the first temperature-responsive supramolecular hydrogels was based on glycosylated amino acid derivatives, for example, N-acetyl-galactosamine-appended amino acid (GalNAc-aa), which self-assembles into a hydrogel above its critical gelation concentration (CGC) (Figure 2A). [87] CGC is the minimum concentration of the hydrogelator at which gelation occurs.…”

Section: Temperature As a Stimulusmentioning

confidence: 99%

Stimuli‐Responsive Supramolecular Hydrogels and Their Applications in Regenerative Medicine

Hoque

Sangaj

Varghese

2018

Macromolecular Bioscience

144

108

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Supramolecular hydrogels are a class of self-assembled network structures formed via non-covalent interactions of the hydrogelators. These hydrogels capable of responding to external stimuli are considered to be smart materials due to their ability to undergo sol–gel and/or gel–sol transition upon subtle changes in their surroundings. Such stimuli-responsive hydrogels are intriguing biomaterials with applications in tissue engineering, delivery of cells and drugs, modulating tissue environment to promote innate tissue repair, and imaging for medical diagnostics among others. This review summarizes the recent developments in stimuli-responsive supramolecular hydrogels and their potential applications in regenerative medicine. Specifically, various structural aspects of supramolecular hydrogelators involved in self-assembly, the role of external stimuli in tuning/controlling their phase transitions, and how these functions could be harnessed to advance applications in regenerative medicine are focused on. Finally, the key challenges and future prospects for these versatile materials are briefly described.

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“…Notably when reviewing the literature for studies focused on developing injectable biomaterials, many do not directly measure injectability. Focus is instead placed on rheology to identify gelation time, study post‐shear recovery, and measure viscoelastic properties . For studies which directly measure injectability, typically a mechanical tester is used to compress the plunger of a syringe at a set rate (Figure 2A), and measure the force required to extrude the biomaterial, over distance or time (Figure 2B,C).…”

Section: Introductionmentioning

confidence: 99%

“…Focus is instead placed on rheology to identify gelation time, study post-shear recovery, and measure viscoelastic properties. [26][27][28] For studies which directly measure injectability, typically a mechanical tester is used to compress the plunger of a syringe at a set rate (Figure 2A), and measure the force required to extrude the biomaterial, over distance or time ( Figure 2B,C). This set up has been used to assess the injectability of cements, [29][30][31] hydrogels, [32,33] and composites.…”

Section: Introductionmentioning

confidence: 99%

Filling the Gap: A Correlation between Objective and Subjective Measures of Injectability

Robinson

Hughes

Bose

et al. 2020

Adv Healthcare Materials

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Various injectable biomaterials are developed for the minimally invasive delivery of therapeutics. Typically, a mechanical tester is used to ascertain the force required to inject these biomaterials through a given syringe‐needle system. However, currently there is no method to correlate the force measured in the laboratory to the perceived effort required to perform that injection by the end user. In this article, the injection force (F) for a variety of biomaterials, displaying a range of rheological properties, is compared with the effort scores from a 50 person panel study. The maximum injection force measured at crosshead speed 1 mm s−1 is a good proxy for injection effort, with an R2 of 0.89. This correlation leads to the following conclusions: participants can easily inject 5 mL of substance for F < 12 N; considerable effort is required to inject 5 mL for 12 N < F < 38 N; great effort is required and <5 mL can be injected for 38 N < F < 64 N; and materials are entirely non‐injectable for F > 64 N. These values may be used by developers of injectable biomaterials to make decisions about formulations and needle sizes early in the translational process.

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Low molecular weight hydrogels derived from urea based-bolaamphiphiles as new injectable biomaterials

Cited by 60 publications

References 36 publications

Expanding the Functional Scope of the Fmoc‐Diphenylalanine Hydrogelator by Introducing a Rigidifying and Chemically Active Urea Backbone Modification

Expanding the Functional Scope of the Fmoc‐Diphenylalanine Hydrogelator by Introducing a Rigidifying and Chemically Active Urea Backbone Modification

Stimuli‐Responsive Supramolecular Hydrogels and Their Applications in Regenerative Medicine

Filling the Gap: A Correlation between Objective and Subjective Measures of Injectability

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