A novel bis(pyrazolyl)methane compound as a potential agent against Gram-positive bacteria

Abstract

This study was designed to propose alternative therapeutic compounds to fight against bacterial pathogens. Thus, a library of nitrogen-based compounds bis(triazolyl)methane (1T–7T) and bis(pyrazolyl)methane (1P–11P) was synthesised following previously reported methodologies and their antibacterial activity was tested using the collection strains of Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa. Moreover, the novel compound 2P was fully characterized by IR, UV–Vis and NMR spectroscopy. To evaluate antibacterial activity, minimal inhibitory concentrations (MICs), minimal bactericidal concentrations (MBCs), minimum biofilm inhibitory concentrations (MBICs), and minimum biofilm eradication concentrations (MBECs) assays were carried out at different concentrations (2–2000 µg/mL). The MTT assay and Resazurin viability assays were performed in both human liver carcinoma HepG2 and human colorectal adenocarcinoma Caco-2 cell lines at 48 h. Of all the synthesised compounds, 2P had an inhibitory effect on Gram-positive strains, especially against S. aureus. The MIC and MBC of 2P were 62.5 and 2000 µg/mL against S. aureus, and 250 and 2000 µg/mL against E. faecalis, respectively. However, these values were > 2000 µg/mL against E. coli and P. aeruginosa. In addition, the MBICs and MBECs of 2P against S. aureus were 125 and > 2000 µg/mL, respectively, whereas these values were > 2000 µg/mL against E. faecalis, E. coli, and P. aeruginosa. On the other hand, concentrations up to 250 µg/mL of 2P were non-toxic doses for eukaryotic cell cultures. Thus, according to the obtained results, the 2P nitrogen-based compound showed a promising anti-Gram-positive effect (especially against S. aureus) both on planktonic state and biofilm, at non-toxic concentrations.

Methacrylate Cationic Nanoparticles Activity against Different Gram-Positive Bacteria

“…The susceptibility of the four clinical strains to different NPs was performed by the previously described microdilution technique on a sterile round-bottomed 96-wells plate [ 30 ]. Different concentrations of the NP under study (from 0.5 to 256 μg/mL) were incubated in each well together with 50 μL of the inoculum of the corresponding bacterial strain.…”

A New Benzimidazolium Ion‐Based “Turn Off” Fluorescent Compound for Detection of Fe3+ Ion and Its Application towards Antimicrobial, Antibiofilm and Cell Imaging Study

“…Although, the effect of compound 4 on OCR of bacteria should be studied in more depth in near future. The organic compounds are proved to be less toxic in mammalian cells because mammalian cell has the ability to degrade the chemical compounds by lysosomal fusions and free radical mediated damage [30,31] …”

“…The peptidoglycan layer of the membranes of Grampositive bacteria (about 20-80 nm) is usually thicker than that of Gram-negative bacteria (about 7-8 nm). [30] This thick cell wall can prevent or hinder the penetration of most of the large organic chemical compounds through the gram negative cell wall. [31] This could be the most probable explanation of high MBC value, lower membrane leakage and low basal OCR of E.coli than S. aureus.…”

“…The organic compounds are proved to be less toxic in mammalian cells because mammalian cell has the ability to degrade the chemical compounds by lysosomal fusions and free radical mediated damage. [30,31] To examine the effect of the corresponding half-MIC (0.5 × MIC or 1 = 2 MIC) doses of 4 on the growth of different bacterial species, we incubated the bacteria with different half -MIC doses of 4 (30 μg/mL, 37.5 μg/mL, 50 μg/mL, 35 μg/mL, 65 μg/ mL, 62.5 μg/mL for Staphylococcus aureus,Enterobacter cloacae, Enterococcus faecalis, Escherichia coli, Vibrio cholerae and Streptococcus pneumoniae respectively) and compared the growth profile of the bacteria with the control where the organism was grown in absence of the compound 4. The results showed that there was no major difference in the growth pattern of the V. cholerae and S. pnuemoniae between their treated and untreated conditions while a noticeable difference was observed in the growth pattern of S. aureus and 11).…”

Hercynite silica sulfuric acid: a novel inorganic sulfurous solid acid catalyst for one-pot cascade organic transformations

“…17,[41][42][43] The functionalized bis(pyrazolyl)methane scaffolds are of great interest due to their various chemical and biological activities. 44 The attractive applications of the functionalized bis(pyrazolyl)methanes have encouraged organic chemists to design numerous synthetic protocols for the synthesis of these pyrazole core-based organic molecules. 45,46 Among them, the one-pot pseudo-ve-component and pseudo-three-component reactions have been widely explored and converted to the standard methodologies to evaluate the efficiency of catalytic species.…”