New thiadiazole modified chitosan derivative to control the growth of human pathogenic microbes and cancer cell lines

Abstract

The emergence of multidrug-resistant microbes and the propagation of cancer cells are global health issues. The unique properties of chitosan and its derivatives make it an important candidate for therapeutic applications. Herein, a new thiadiazole derivative, 4-((5-(butylthio)-1,3,4-thiadiazol-2-yl) amino)-4-oxo butanoic acid (BuTD-COOH) was synthesized and used to modify the chitosan through amide linkages, forming a new thiadiazole chitosan derivative (BuTD-CH). The formation of thiadiazole and the chitosan derivative was confirmed by FT-IR, 1H/13C-NMR, GC–MS, TGA, Elemental analysis, and XPS. The BuTD-CH showed a high antimicrobial effect against human pathogens Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus, and Candida albicans with low MIC values of 25–50 μg ml−1 compared to unmodified chitosan. The in-vitro cytotoxicity of BuTD-CH was evaluated against two cancer cell lines (MCF-7 and HepG2) and one normal cell (HFB4) using the MTT method. The newly synthesized derivatives showed high efficacy against cancerous cells and targeted them at low concentrations (IC50 was 178.9 ± 9.1 and 147.8 ± 10.5 μg ml−1 for MCF-7 and HepG2, respectively) compared with normal HFB4 cells (IC50 was 335.7 ± 11.4 μg ml−1). Thus, low concentrations of newly synthesized BuTD-CH could be safely used as an antimicrobial and pharmacological agent for inhibiting the growth of human pathogenic microbes and hepatocellular and adenocarcinoma therapy.

Myco-synthesized copper oxide nanoparticles using harnessing metabolites of endophytic fungal strain Aspergillus terreus: an insight into antibacterial, anti-Candida, biocompatibility, anticancer, and antioxidant activities

“…One of the biggest threats to global health that has not yet been addressed is cancer development infection. Recently, several active substances including NPs demonstrated strong activity against a variety of cancer cells, allowing them to be included in cancer therapy or employed as carriers or delivery systems for medications used to treat cancer [ 3 , 93 ]. The nanomaterial-based cancer treatment, especially those fabricated by green approaches, are widely investigated because of their biocompatibility, permeability, easy scale-up, biodegradability, safe to normal cells at specific concentrations [ 14 , 94 ].…”

Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched Polymers

“…IR spectra were recorded on an Alpha Bruker FT-IR spectrometer; solid samples were prepared in the form of KBr tablets; the IR spectra of solutions were recorded in dismountable CaF 2 cuvettes. The NMR spectra were recorded on a superconducting pulsed broadband two-channel NMR spectrometer AVANCE III 500 MHz Bruker BioSpin for liquid-phase samples at 500 MHz ( 1 H spectra) and 126 MHz ( 13 C spectra) for samples in DMSO-d 6 and CDCl 3 with 1% tetramethylsilane (TMS). Elemental analysis was performed on a CHNS/O elemental analyzer "Vario Micro cube" Elementar GmbH.…”

“…Nowadays, the search for new compounds for medico-biological applicants is an urgent task. Along with small molecules, polymer compounds are being actively studied as potential bioactive compounds [1][2][3][4][5][6].…”

Exploration of newly synthesized azo-thiohydantoins as the potential alkaline phosphatase inhibitors via advanced biochemical characterization and molecular modeling approaches

“…The results of previous studies have generated interest in aromatic heterocycles with two nitrogen atoms in their rings. These compounds have been found to exhibit a diverse range of biological activities, including anticancer, analgesic, anti-inflammatory, antimicrobial, antiviral, anticonvulsant, antihistaminic, and anti-HIV properties [ 12 – 14 ]. The significance of hydantoins inhibitor in medicinal chemistry has been emphasized by its recent success [ 15 ].…”