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

Priyanka Tiwari, Arindam Gupta, Vaibhav Shivhare, Rishabh Ahuja, Avinash Singh Mandloi, Ankit Mishra, Anindya Basu, Anita Dutt Konar
Author Information
  1. Priyanka Tiwari: Department of Applied Chemistry, Rajiv Gandhi Technological University, Bhopal, Madhya Pradesh 462033, India.
  2. Arindam Gupta: Department of Chemistry, IISER, Bhopal 462066, India. ORCID
  3. Vaibhav Shivhare: Department of Applied Chemistry, Rajiv Gandhi Technological University, Bhopal, Madhya Pradesh 462033, India.
  4. Rishabh Ahuja: Department of Applied Chemistry, Rajiv Gandhi Technological University, Bhopal, Madhya Pradesh 462033, India.
  5. Avinash Singh Mandloi: Faculty of Pharmacy, VNS Group of Institutions, Bhopal, Madhya Pradesh 462044, India.
  6. Ankit Mishra: Faculty of Pharmacy, VNS Group of Institutions, Bhopal, Madhya Pradesh 462044, India.
  7. Anindya Basu: School of Pharmaceutical Sciences, Rajiv Gandhi Technological University, Bhopal 462036, India.
  8. Anita Dutt Konar: Department of Applied Chemistry, Rajiv Gandhi Technological University, Bhopal, Madhya Pradesh 462033, India. ORCID

Abstract

The wound recovery phenomenon remains as one of the long challenging concerns worldwide. In search of user-friendly 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 -) such that a potential scaffold could be fished out from the design. Our investigations revealed that all the hydrogelators displayed not only excellent self-healing 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 (, , , ), four Gram-negative bacteria (, , , spp.), and two fungal strains ( and ). 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 was seived out from a pool of seven, and we proceeded toward its 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 and analysis certifies hydrogelator as an ideal dressing material that might hold immense promise for future wound care management.

Keywords

MeSH Term

Rats
Animals
Rats, Wistar
Anti-Bacterial Agents
Anti-Infective Agents
Staphylococcus aureus
Antioxidants
Mammals

Chemicals

Anti-Bacterial Agents
Anti-Infective Agents
Antioxidants

Word Cloud

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