A hydro-metallogel of an amphiphilic <scp>l</scp>-histidine with ferric ions: shear-triggered self-healing and shrinkage

Chen, Jie; Wang, Tianyu; Liu, Minghua

doi:10.1039/c6qi00238b

Cited by 35 publications

(27 citation statements)

References 55 publications

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“…Among different amino acids, histidine is well-known for its affinity toward transition metal ions and hence mostly found in the catalytic triad of enzymes having transition metal ions as cofactors . Histidyl residues of metal activated enzymes and metalloproteins are postulated to play an important role in metal binding. , Even though histidine acts as a most versatile amino acid in the biological system, its potential in the development of stimuli responsive biomaterial is not much explored . Histidine-metal interaction has already been known for its catalytic activity as well as generation of higher order structures. , However, to the best of our knowledge, none of the studies have systematically elucidated the effect of differential coordination between transition metal ions and histidine on sol–gel equilibrium.…”

Section: Introductionmentioning

confidence: 99%

“…Histidine-metal interaction has already been known for its catalytic activity as well as generation of higher order structures. , However, to the best of our knowledge, none of the studies have systematically elucidated the effect of differential coordination between transition metal ions and histidine on sol–gel equilibrium. Recently, rational incorporation of l -histidine in the sequence to impart ion sensitivity to the amphiphile has also been tried. ,, Gelation was induced in a nongelator histidine containing tripeptide by utilizing the ion binding ability of the histidine complemented by electrostatic interactions . Gelation ability of only histidine has also been explored, and a multistimuli responsive hydrogel was formed in the presence of zinc ions .…”

Section: Introductionmentioning

confidence: 99%

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Inducing Differential Self-Assembling Behavior in Ultrashort Peptide Hydrogelators Using Simple Metal Salts

2019

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Controlling the self-assembly pathways can be an effective means to create complex multifunctional structures based on a single gelator design. To this direction, an ion mediated approach to control and direct supramolecular structure of the low molecular weight peptide hydrogelator would be an excellent methodology for bottom-up nanofabrication of these advanced functional materials. Our work primarily aims to understand the role of different metal ions as well as anions in modulating the self-assembly of the peptide amphiphiles. Our approach relies on rational incorporation of histidine in the peptide amphiphile, which can impart an ion responsive behavior to the hydrogels. Interestingly, the selfassembly pathway of histidine based dipeptide amphiphile was found to be largely influenced by various metal salts. A gel to sol transition occurred at physiological pH in the presence of Cu 2+ , Ni 2+ and Co 2+ ions, owing to their strong interactions with the histidine, thus shifting the gelation to pH 3.0. However, in the case of Fe 2+ and Mn 2+ , the weak interactions of histidine−metal ion can still hold the gel at physiological pH but gel strength was significantly decreased. Our studies provide a clear insight into this ion-responsive behavior across a wide pH range, which is mainly governed by the stability of a peptide−metal ion complex as per Irving−Williams series. Moreover, anions also influenced the mechanical strength as well as morphology of the nanostructures owing to their differential interaction with water as depicted in the Hofmeister series of anions. This bioinspired approach will provide an elegant strategy for accessing diverse structures, which are "out of equilibrium" and otherwise only accessible through differential molecular design. We envisage that our systematic studies on histidine−metal ion interaction can be an extremely useful methodology, which will pave a way to design and develop the stimuli responsive biomaterials.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Inducing Differential Self-Assembling Behavior in Ultrashort Peptide Hydrogelators Using Simple Metal Salts

2019

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“…However, examples of amino acid or short peptide based metallo-hydrogels are relatively scarce. 34,35 Liu and co-workers have reported a Cu 2+ -selective histidine containing bolaamphiphilic metallo-hydrogel that shows good tolerance toward concentrated acid environment and it exhibits very good selectivity toward Cu 2+ ions. 36 Banerjee and co-workers have reported tyrosine containing metallo-hydrogel with multiple stimuli responsiveness.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Amino acids and peptides are good candidates for chelating metal ions using various functional groups present in their side chains. However, examples of amino acid or short peptide based metallo-hydrogels are relatively scarce. , Liu and co-workers have reported a Cu 2+ -selective histidine containing bola-amphiphilic metallo-hydrogel that shows good tolerance toward concentrated acid environment and it exhibits very good selectivity toward Cu 2+ ions . Banerjee and co-workers have reported tyrosine containing metallo-hydrogel with multiple stimuli responsiveness .…”

Section: Introductionmentioning

confidence: 99%

Amino-Acid-Based Metallo-Hydrogel That Acts Like an Esterase

Gayen

Basu

Bairagi

et al. 2018

ACS Appl. Bio Mater.

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A histidine based amphiphile containing a C14 fatty acyl chain, N-histidyl N-myristry ethyl amine (AM1, 14.7mM) forms hydrogels in the presence of Fe 3+ (within the range 1.47 to 4.41mM) and Hg 2+ (within the range 3.67 to 11.02 mM) ions in aqueous dispersions at pH 6.6 (27C). The imidazole ring of the histidine residue plays a vital role to interact with these metalions. The thermal and mechanical stability of these metallo-hydrogels can be tuned by changing the proportion of amphiphile to metal ion ratio (1:0.1 to 1:0.3 for Fe 3+ containing gel and 1:0.25 to 1:0.75 for Hg 2+ containing gel). The metallo-hydrogels were characterized by different spectroscopic and microscopic techniques, low-and wide-angle powder X-ray diffraction and small-angle X-ray scattering studies. FT-IR and NMR spectroscopic studies indicate the participation of the imidazole ring in metal-ion binding. Low-and wide-angle powder X-ray diffraction and small-angle X-ray scattering data are in favour of a layered structure of the supramolecular assembly of the AM1 in presence of metal-ions. Both, the amphiphiles and the metal ion induced hydrogels reveal catalytic activity of p-nitrophenyl esters hydrolysis for the acetyl, n-butyl and n-octyl esters. Ferric ion containing metallo-hydrogel exhibits higher catalytic activity than the corresponding AM1 aggregate in the absence of metal-ions.

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“…[395][396][397][398][399][400][401] Furthermore, there are examples where the aged gel shows a shrinking behavior. [402][403][404] Recently, Sugiura et al constructed a hydrogel system involving hydrazone-oxime exchange reaction in response to hydroxylamine (Fig. 29).…”

Section: Time Programmable Self-regulating Gel To Gel Transitionsmentioning

confidence: 99%

Stimuli responsive dynamic transformations in supramolecular gels

2021

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A hydro-metallogel of an amphiphilic l-histidine with ferric ions: shear-triggered self-healing and shrinkage

Abstract: An amphiphilic l-histidine derivative was found to form a hydro-metallogel showing dual shrinkage and self-healing properties.

Cited by 35 publications

References 55 publications

Inducing Differential Self-Assembling Behavior in Ultrashort Peptide Hydrogelators Using Simple Metal Salts

Inducing Differential Self-Assembling Behavior in Ultrashort Peptide Hydrogelators Using Simple Metal Salts

Amino-Acid-Based Metallo-Hydrogel That Acts Like an Esterase

Stimuli responsive dynamic transformations in supramolecular gels

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