A biocatalytic and thermoreversible hydrogel from a histidine-containing tripeptide

García, Ana María; Kurbasic, Marina; Kralj, Slavko; Melchionna, Michele; Marchesan, Silvia

doi:10.1039/c7cc03371k

Cited by 74 publications

(66 citation statements)

References 30 publications

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“…There are a few reportson the histidine containing short peptide based hydrogelatorswith esterase activity [54][55][56][57][58] . Korendovychand coworkers have reported a Zn 2+ ion stabilized amyloid fibril with esterase acivity, whose catalytic activity drops several times in absence of the metal ion 59 .Therefore, it is of great interest to make amino acid/peptide based molecules with a ligating group that can bind with a suitable metal ion like Fe 3+ , Hg 2+ , Cu 2+ , Zn 2+ and any of these metal complexes can eventually self-associate by using various non-covalent interactions to form either gels or soluble aggregates.…”

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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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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“…To strengthen the thermoreversibility data, we performed a DSC analysis . The DSC thermogram indicated a wide endotherm for the gel to sol transition at 10–15 °C for both the Hydrogelators I and II (Figure B, C)..…”

Section: Resultsmentioning

confidence: 99%

Rationally Designed Bioinspiredδ‐Amino Valeric Acid Based Hydrogel: One Shot Solution for Drug Delivery and Effluent Management

et al. 2019

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Tailoring peptide hydrogelators with tunable mechanical properties and diversified applicabilities is an eternal pursuit today. Here, we report the rational design approach of a short, simple enantiomeric segment, Boc‐δ‐Ava‐L‐Phe‐OH (Hydrogelator I) Boc‐δ‐Ava‐D‐Phe‐OH (Hydrogelator II) that manifests β‐sheet conformation and nanofibrous morphology at supramolecular level. Our hydrogelators have excellent biocompatibility, proteolytic stability, thermoreversibility and self‐healing properties. Remarkably, these Hydrogelators not only demonstrate an unprecedented ability to release the anticancer drugs 5‐Fluoro uracil/curcumin/Doxorubicin at physiological pH and room temperature but also modulates an effective route in successful removal of harmful organic effluents from waste water, with the aptitude to reuse the hydrogelator few times. Interestingly it has been investigated that subtle changes in molecular structure of the gelator, turns the gelator into a nongelator molecule (Boc‐Gaba‐L‐Phe‐OH ;Compound III) and (Boc‐Acp‐L‐Phe‐OH ;Compound IV) supported by MD simulation studies. Overall this study establishes innovative design principles towards the development of advanced functional materials for future drug delivery applications and waste water management.

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“…These supramolecular systems feature amphipathic assemblies, whereby the different stereoconfiguration allows displaying hydrophobic side chains on the same side of the peptide backbone [19,20]. This design was also successfully applied to His-D Phe-D Phe, which displayed biocatalytic activity only in the self-assembled form, although it formed hydrogels at the very high concentration of 50 mM, thus limiting its practical use [21].…”

Section: Introductionmentioning

confidence: 99%

Biocatalysis of d,l-Peptide Nanofibrillar Hydrogel

Carlomagno¹,

Cringoli²,

Kralj³

et al. 2020

Molecules

Self Cite

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Self-assembling peptides are attracting wide interest as biodegradable building blocks to achieve functional nanomaterials that do not persist in the environment. Amongst the many applications, biocatalysis is gaining momentum, although a clear structure-to-activity relationship is still lacking. This work applied emerging design rules to the heterochiral octapeptide sequence His–Leu–DLeu–Ile–His–Leu–DLeu–Ile for self-assembly into nanofibrils that, at higher concentration, give rise to a supramolecular hydrogel for the mimicry of esterase-like activity. The peptide was synthesized by solid-phase and purified by HPLC, while its identity was confirmed by 1H-NMR and electrospray ionization (ESI)-MS. The hydrogel formed by this peptide was studied with oscillatory rheometry, and the supramolecular behavior of the peptide was investigated with transmission electron microscopy (TEM) analysis, circular dichroism (CD) spectroscopy, thioflavin T amyloid fluorescence assay, and attenuated total reflectance (ATR) Fourier-transform infrared (FT-IR) spectroscopy. The biocatalytic activity was studied by monitoring the hydrolysis of p-nitrophenyl acetate (pNPA) at neutral pH, and the reaction kinetics followed an apparent Michaelis–Menten model, for which a Lineweaver–Burk plot was produced to determine its enzymatic parameters for a comparison with the literature. Finally, LC–MS analysis was conducted on a series of experiments to evaluate the extent of, if any, undesired peptide acetylation at the N-terminus. In conclusion, we provide new insights that allow gaining a clearer picture of self-assembling peptide design rules for biocatalysis.

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A biocatalytic and thermoreversible hydrogel from a histidine-containing tripeptide

Abstract: We report the first histidine-containing self-assembling tripeptide devoid of capping groups that forms a thermoreversible hydrogel under physiological conditions and catalyses hydrolysis of an ester, providing a minimalist building block for functional soft materials.

Cited by 74 publications

References 30 publications

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

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

Rationally Designed Bioinspiredδ‐Amino Valeric Acid Based Hydrogel: One Shot Solution for Drug Delivery and Effluent Management

Biocatalysis of d,l-Peptide Nanofibrillar Hydrogel

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