Supramolecular gels of gluconamides derived from renewable resources: Antibacterial and anti‐biofilm applications

Carbohydrates are versatile materials widely used for several applications including food, pharmaceuticals, cosmetics, and drug delivery systems due to their inherent properties such as non‐toxicity, biodegradability, and bio‐compatibility. Specifically, the urge on carbohydrate research is due to its significance in the biological system, for example, a glycoprotein found in the extracellular matrix, involved in signaling pathways, cell–cell interaction and cell–matrix interaction. Because of the increase in demand of glycolipids for biological applications, in this report, a set of three structurally related gluconamide‐based amphiphiles were synthesized from renewable resources, δ‐gluconolactone and cashew nut shell liquid. The molecular structure of the synthesized glycolipids was characterized by NMR and mass spectral techniques. Molecular self‐assembly of gluconamide‐based amphiphiles was investigated relative to the molecular structure and nature of the solvent used. Interestingly, the nature of the hydrophobic tail present in the glycolipids influences the self‐assembly pattern, which results in a hydrogel, organogel and highly insoluble nanorods. Gelation studies clearly revealed that the involvement of different magnitude of non‐covalent interactions such as hydrogen bonding, π–π stacking and van der Waals interaction. Morphology of self‐assembled architecture was investigated by optical microscopy, FESEM and FETEM analysis. The mechanism involved in the molecular self‐assembly has been deduced by small angle XRD analysis. Thermo reversibility and the thixotropic nature of the derived gels were identified by rheological measurements. Further, antimicrobial and biofilm inhibitory activity of gluconamide‐based amphiphiles were studied against various pathogenic bacterial strains Staphylococcus aureus, Listeria monocytogenes, Salmonella typhimurium, and Pseudomonas aeruginosa, and found effective in inhibition of biofilm and possesses the antibacterial property. Altogether, gluconamide‐based amphiphiles reported in this paper could be potentially used for some of the human problems caused by bacterial biofilms such as infections in the intravascular catheter, burn‐wounds, chronic sinusitis and implanted medical devices. Molecular self‐assembly of gluconamide‐based amphiphiles furnished supramolecular gels, which could be potentially used for some of the human problems caused by bacterial biofilms