Development of a chitosan derivative bearing the thiadiazole moiety and evaluation of its antifungal and larvicidal efficacy

Abstract

A new chitosan derivative bearing a new thiadiazole compound was developed, and its antifungal and larvicidal activities were investigated. The chitosan derivative (coded here as PTDz-Cs) was synthesized by the reaction between the carboxylic derivative of the thiadiazole moiety and chitosan. Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (1H/13C-NMR), gas chromatography–mass spectrometry (GC–MS), elemental analysis, X-Ray diffraction (XRD), thermogravimetric analysis (TGA), and X-ray photoelectron spectroscopy (XPS) were used to characterize the developed derivatives. Compared to chitosan, the PTDz-Cs derivative has a less crystalline structure and less thermal stability. The antifungal results revealed that PTDz-Cs exhibited potential activity against Rhizopus microspores, Mucor racemosus, Lichtheimia corymbifera, and Syncephalastrum racemosum where inhibition zones were 17.76, 20.1, 38.2, and 18.3 mm, respectively. The larvicidal efficacy of the PTDz-Cs derivative against A. stephensi larvae was tested, and the results exposed that the LC50 and LC90 values (first instar) were 5.432 and 10.398 ppm, respectively, indicating the high susceptibility of early instar mosquito larvae to PTDz-Cs. These results emphasize that this study provided a new chitosan derivative that could be potentially used in the biomedical fields.

Recent Advances of Chitosan-Based Hydrogels for Skin-Wound Dressings

“…Mohamed et al developed a novel 1,3,4-thiadiazole-modified chitosan, which exhibited excellent antibacterial activity against Escherichia coli , Staphylococcus aureus , Bacillus subtilis , Pseudomonas aeruginosa , and Candida albicans [ 67 ]. Another study found that thiadiazole-modified chitosan possessed higher fungal inhibitory activity and the ability to kill early larvae compared to chitosan [ 68 ]. Chitosan can be chemically modified by clicking chemistry.…”

Strategies for the Preparation of Chitosan Derivatives for Antimicrobial, Drug Delivery, and Agricultural Applications: A Review

“…The acylation reaction has the potential to disrupt both the intramolecular and intermolecular H-bonding within the CS, leading to a reduction in its crystallinity and enhancing water solubility [68]. In recent studies, researchers have explored the reaction of CS with pre-prepared acyl chlorides or acetic acid containing diverse heterocycles like benzothiazole, thiadiazole, thymine, or pyrazoles to produce the acylated CS bearing the heterocycles (2d, 2e) [69][70][71][72][73][74][75][76]. Similarly, Zhang's group developed CS-bearing quinolinyl urea derivatives (2f).…”

New N-Methylimidazole-Functionalized Chitosan Derivatives: Hemocompatibility and Antibacterial Properties

“…Introduction of heterocyclic compounds into the structure of quaternized chitosan can increase the antimicrobial activity of the compound. Previous chemical modifications of chitosan with heterocycles have shown promising biological activities [ 10 , 11 , 12 , 13 ]. In a number of works, the use of chitosan derivatives, including imidazole derivatives, has been shown in the development of hemocompatible delivery systems for medicinal products or to achieve the thromboresistance of surfaces of medical devices/materials (nanoparticles, frameworks, hydrogels and membranes) in contact with blood [ 14 , 15 , 16 , 17 , 18 ].…”