Self-healing hydrogels triggered by amino acids

Zanna, Nicola; Merlettini, Andrea; Tomasini, Claudia

doi:10.1039/c6qo00476h

Cited by 20 publications

(20 citation statements)

References 52 publications

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“…Thixotropy [47,48,49,50] is a gel property related to the sol/gel equilibrium and describes the system ability to recover the gel status after a strong stress that induces transformation into sol. Moreover, self-healing property [18,48,51,52,53] may be defined as the ability to autonomously reconstruct the bonding interactions after damage.…”

Section: Resultsmentioning

confidence: 99%

“…The rest of the material is constituted by liquid phase, usually a solvent that can partially dissolve the gelator. The transformation process of the solution containing the gelator in a gel is due to the addition of an external stimulus (a trigger), such as temperature variation [9,10], ultrasound sonication, pH change [11,12,13,14] or the addition of a chemical species [15,16,17,18] which enables the alignment of the fibers.…”

Section: Introductionmentioning

confidence: 99%

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Low Molecular Weight Gelators Based on Functionalized l-Dopa Promote Organogels Formation

Giuri

Zanna

Tomasini

2019

Gels

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We prepared the small pseudopeptide Lau-l-Dopa(OBn)2-d-Oxd-OBn (Lau = lauric acid; l-Dopa = l-3,4-dihydroxyphenylalanine; d-Oxd = (4R,5S)-4-methyl-5-carboxyl-oxazolidin-2-one; Bn = benzyl) through a number of coupling reactions between lauric acid, protected l-Dopa and d-Oxd with an excellent overall yield. The ability of the product to form supramolecular organogels has been tested with different organic solvents of increasing polarity and compared with the results obtained with the small pseudopeptide Fmoc-l-Dopa(OBn)2-d-Oxd-OBn. The mechanical and rheological properties of the organogels demonstrated solvent-dependent properties, with a storage modulus of 82 kPa for the ethanol organogel. Finally, to have a preliminary test of the organogels’ ability to adsorb pollutants, we treated a sample of the ethanol organogel with an aqueous solution of Rhodamine B (RhB) for 24 h. The water solution slowly lost its pink color, which became trapped in the organogel.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Low Molecular Weight Gelators Based on Functionalized l-Dopa Promote Organogels Formation

Giuri

Zanna

Tomasini

2019

Gels

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“…Our group recently reported the formation of thermoreversible and/or thixotrophic hydrogels induced by the self-assembly of bolamphiphilic or Fmoc-protected pseudopeptides [54]. Several agents have been tested as self-assembly triggers and pH regulators: pH variation due to the slow hydrolysis of glucono-δ-lactone (GdL) [55,56], or the addition of an amino acid [57] or metal cation [58]. The resulting gels have been characterized by the measurement of the melting points (T gel ), transparency, gelation time, and viscoelastic properties, together with ECD analysis.…”

Section: Thixotropic Hydrogels Prepared Using Biocompatible Low Momentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Peptide-Based Physical Gels Endowed with Thixotropic Behaviour

Zanna

Tomasini

2017

Gels

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Thixotropy is one of the oldest documented rheological phenomenon in colloid science and may be defined as an increase of viscosity in a state of rest and a decrease of viscosity when submitted to a constant shearing stress. This behavior has been exploited in recent years to prepare injectable hydrogels for application in drug delivery systems. Thixotropic hydrogels may be profitably used in the field of regenerative medicine, which promotes tissue healing after injuries and diseases, as the molten hydrogel may be injected by syringe and then self-adapts in the space inside the injection site and recovers the solid form. We will focus our attention on the preparation, properties, and some applications of biocompatible thixotropic hydrogels.

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“…We recently reported several pseudopeptides that freeze water in low concentration and form hydrogels that possess high mechanical strength and transparency [47,48,49]. All these molecules showed a good propensity to self-assemble in water, due to the presence of the d -Oxd or d -pGlu moiety [Oxd = (4 R ,5 S )-4-methyl-5-carboxyl-oxazolidin-2-one, pGlu = pyroglutamic acid] in their skeleton [50,51] that imposes a constraint to the chain, together with the presence of aromatic rings contained in aromatic amino acids, such as Phe or Tyr (Phe: phenylalanine; Tyr: tyrosine).…”

Section: Introductionmentioning

confidence: 99%

Tuning Mechanical Properties of Pseudopeptide Supramolecular Hydrogels by Graphene Doping

et al. 2019

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Supramolecular hydrogels, obtained from small organic molecules, may be advantageous over polymeric ones for several applications, because these materials have some peculiar properties that differentiate them from the traditional polymeric hydrogels, such as elasticity, thixotropy, self-healing propensity, and biocompatibility. We report here the preparation of strong supramolecular pseudopeptide-based hydrogels that owe their strength to the introduction of graphene in the gelling mixture. These materials proved to be strong, stable, thermoreversible and elastic. The concentration of the gelator, the degree of graphene doping, and the nature of the trigger are crucial to get hydrogels with the desired properties, where a high storage modulus coexists with a good thixotropic behavior. Finally, NIH-3T3 cells were used to evaluate the cell response to the presence of the most promising hydrogels. The hydrogels biocompatibility remains good, if a small degree of graphene doping is introduced.

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Self-healing hydrogels triggered by amino acids

Cited by 20 publications

References 52 publications

Low Molecular Weight Gelators Based on Functionalized l-Dopa Promote Organogels Formation

Low Molecular Weight Gelators Based on Functionalized l-Dopa Promote Organogels Formation

Peptide-Based Physical Gels Endowed with Thixotropic Behaviour

Tuning Mechanical Properties of Pseudopeptide Supramolecular Hydrogels by Graphene Doping

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