Can the stereogenicity in aromatic/non-aromatic residues influence the mechanical integrity, antimicrobial and anti-inflammatory preferences of auxin derivatized hydrogels?

Khan, Nasreen; Gupta, Arindam; shivhare, vaibhav; Ahuja, Rishabh; Basu, Anindya; Konar, Anita Dutt

doi:10.1039/d2nj04559a

Cited by 6 publications

(28 citation statements)

References 49 publications

(103 reference statements)

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“…Also, a peak at 1690 cm _1 belonging to H-bonded urethane CO appears to be prominent for the homochiral hydrogelators. These data collectively give the impression of the presence of β-sheet like assemblies in the hydrogelators. ,, …”

Section: Resultsmentioning

confidence: 89%

“…It does not come as a surprise that the introduction of D-residues at the appropriate position in a sequence leads to the enhancement of gelation strength. ,, However, at times, it fails to do so.…”

Section: Resultsmentioning

confidence: 99%

“…Before starting the experiments, fresh inocula of the organisms were prepared from their respective culture obtained from NCCS Pune as lyophilized powder. The in vitro antimicrobial activity of all the hydrogelators against the reported microorganisms was analyzed by optical density methods as described ,, (Table , Tables S3 and S4 , Figures S21–S34).…”

Section: Methodsmentioning

confidence: 99%

“…The propensity of the scaffolds to undergo gel-to-sol-to-gel transition on the application/removal of mechanical stress demonstrates unprecedented advantages in medical applications due to the exceptional tunability and reversible nature of supramolecular interactions. However, these mechanoresponsive hydrogels often occupy the backseat due to the weak mechanical integrity that impedes their suitability as preferential candidates for biomedical research. − …”

Section: Introductionmentioning

confidence: 99%

“…Along this drift, the chiral orchestration of amino acids depicts a promising strategy to improve the mechanical performance and scope of materials. Simple replacement of a single stereogenic center with its isomer in a peptide magnificently alters the self-assembled architectures and, consequently, the hydrogelation properties. ,− Using this concept in one of our previous reports, we have fished out the most potent hydrogelator ( I ) from a set of four and investigated its wound-healing efficacy. Although the hydrogelator showed good anti-inflammatory and antimicrobial activities, it indicated a moderate recovery behavior, which might be due to the proteolytic instability and insufficient antimicrobial potency, inevitable for a good wound dressing material …”

Section: Introductionmentioning

confidence: 99%

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Stereogenic Harmony Fabricated Mechanoresponsive Homochiral Triphenylalanine Analogues with Synergistic Antibacterial Performances: A Potential Weapon for Dermal Wound Management

Tiwari,

Gupta,

Shivhare

et al. 2023

ACS Appl. Bio Mater.

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The wound recovery phenomenon remains as one of the long challenging concerns worldwide. In search of userfriendly dressing materials, in this report, we fabricated a rational combinatorial strategy utilizing stereogenic harmony in a triphenylalanine fragment and appending it to δ-amino valeric acid at the N-terminus (hydrogelators I−VII) such that a potential scaffold could be fished out from the design. Our investigations revealed that all the hydrogelators displayed not only excellent selfhealing performance as well as high mechanical strength at physiological pH but also mechanical stress-triggered gel−sol−gel transition properties. The structural and morphological investigation confirmed the presence of β-sheet-like assemblies stabilized by intermolecular H-bonding and π−π interactions. Moreover, these scaffolds showed substantial antibacterial as well as antifungal efficacy against common wound pathogens, i.e, four Gram-positive bacteria (Staphylococcus aureus, Streptococcus mutans, B. subtilis, E. fecalis), four Gram-negative bacteria (Escherichia coli, Klebsiella pneumonia, P. aerugonosa, Proteus spp.), and two fungal strains (C. albicans and A. niger). The manifestation of consistent antioxidant properties might be due to the enhancement of amphiphilicity in hydrogelators, which has led to the generation of reactive oxygen species (ROS) in a facile manner, a probable mechanism to damage the microbial membrane, the driving force behind the antimicrobial efficacy. Also, the constructs exhibited proteolytic resistance and remarkable biocompatibility toward mammalian cells. Thus, based on the above benchmarks, the homochiral hydrogelator IV was seived out from a pool of seven, and we proceeded toward its in vivo evaluation using full-thickness excisional wounds in Wister rats. The scaffolds also accentuated the re-epithelialization as well in comparison to the negative control, thereby facilitating the wound closure process in a very short span of time (10 days). Overall, our in vitro and in vivo analysis certifies hydrogelator IV as an ideal dressing material that might hold immense promise for future wound care management.

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Section: Resultsmentioning

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Stereogenic Harmony Fabricated Mechanoresponsive Homochiral Triphenylalanine Analogues with Synergistic Antibacterial Performances: A Potential Weapon for Dermal Wound Management

Tiwari,

Gupta,

Shivhare

et al. 2023

ACS Appl. Bio Mater.

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A Homochiral Diphenylalanine Analog Based Mechanoresponsive Hydrogel: An Insight Towards Its Wound Healing Efficacy

Tiwari,

Shivhare,

Ahuja

et al. 2023

Chemistry & Biodiversity

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Deciphering the most promising strategy for the evolution of potential wound‐healing therapeutics is one of the greatest challenging affairs to date. The development of peptide‐based smart scaffolds with innate antimicrobial, anti‐inflammatory, and antioxidant properties is an appealing way out. Aligned to the goal a set of Hydrogelators I – IV were developed utilizing the concept of chiral orchestration in diphenylalanine fragment, such that the most potent construct with all the bench marks namely mechanoresponsiveness, biocompatibility, consistent antimicrobial and antioxidant properties, could be fished out from the design. Interestingly, our invitro Antifungal and Lipid peroxidation analysis identified the homochiral isomer (Hydrogelator I), as an ideal candidate for the wound healing experiment. So we proceeded for the invivo measurements in Wister rats. Indeed the wound images demonstrated that with increased recovery time, hydrogelator I displayed a significant reduction in the lesion diameter compared to the marketed drug, and negative control. Even the histopathological measurements using H & E staining demonstrated diminished tissue destruction, neutrophil infiltration necrosis, and lymphatic proliferation in the hydrogelators, incomparison to others, backed by invivo lipid peroxidation data. Overall our investigation certifies hydrogelator I as an effective therapeutic for managing the wound healing complication.

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Effect of Amino Acid Types on the Mechanical and Antimicrobial Properties of Amino Acid‐Based Polyionic Liquid Hydrogels

Fan,

He,

Zhou

et al. 2024

Macromol. Rapid Commun.

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Polyionic liquid hydrogels have attracted increasing attention due to their unique properties and potential applications. However, research on amino acid‐based polyionic liquid hydrogels is still in their infancy stage. Moreover, the effect of amino acid types on the properties of hydrogels has rarely been studied. In this work, amino acid‐based polyionic liquid hydrogels (D/L‐PCAA hydrogels) were synthesized by copolymerizing vinyl choline‐amino acid ionic liquids and acrylic acids using Al3+ as a crosslinking agent and bacterial cellulose (BC) as a reinforcing agent. The effects of amino acid types on mechanical and antimicrobial properties were systematically investigated. D‐arginine‐based hydrogel (D‐PCArg) showed the highest tensile strength (220.7 KPa), D‐phenylalanine‐based hydrogel (D‐PCPhe) exhibited the highest elongation at break (1346%), and L‐aspartic acid‐based hydrogel (L‐PCAsp) had the highest elastic modulus (206.9 KPa) and toughness (1.74 MJ m−3). D/L‐PCAsp hydrogels demonstrated stronger antibacterial capacity against E. coli and S. aureus and D/L‐PCPhe hydrogels possessed higher antifungal activity against C. neoformans. Moreover, the resultant hydrogels exhibited prominent hemocompatibility and low toxicity, as well as excellent self‐healing capabilities (86%) and conductivity (2.8 S m−1). These results indicated that D/L‐PCAA hydrogel provided a promise for applications in wound dressings.This article is protected by copyright. All rights reserved

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Can the stereogenicity in aromatic/non-aromatic residues influence the mechanical integrity, antimicrobial and anti-inflammatory preferences of auxin derivatized hydrogels?

Abstract: A Heterochiral Diphenylalanine Auxin Derivative exhibited remarkable mechanical strength and antimicrobial propensities at room temperature (N. Khan, A. Gupta, V. Shivhare, R. Ahuja, M. Varshney, A. Basu, and A. Dutt...

Cited by 6 publications

References 49 publications

Stereogenic Harmony Fabricated Mechanoresponsive Homochiral Triphenylalanine Analogues with Synergistic Antibacterial Performances: A Potential Weapon for Dermal Wound Management

Stereogenic Harmony Fabricated Mechanoresponsive Homochiral Triphenylalanine Analogues with Synergistic Antibacterial Performances: A Potential Weapon for Dermal Wound Management

A Homochiral Diphenylalanine Analog Based Mechanoresponsive Hydrogel: An Insight Towards Its Wound Healing Efficacy

Effect of Amino Acid Types on the Mechanical and Antimicrobial Properties of Amino Acid‐Based Polyionic Liquid Hydrogels

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