Search Results (113)

The functionalization of nitrogen-doped graphene with β-Cyclodextrin (designated β/N-rGO) was employed to enhance the dispersibility of graphene materials and to establish an adsorption-catalytic oxidation system using peroxymonosulfate (PMS) for the removal of trace antibiotics from water. The experimental results indicated that β-Cyclodextrin was effectively dispersed on the support structure of nitrogen-doped graphene, which enhanced the specific surface area and dispersibility of the material. The adsorption-catalytic oxidation system comprising β/N-rGO and PMS degraded 92.35% of sulfamethoxazole within 12 min and exhibited significant removal efficiency for sulfonamides, quinolones, macrolides, tetracyclines, β-lactams, and chloramphenicol antibiotics across a pH range of 3–12. The reaction time was reduced by over 10% compared to the unmodified material, with a more pronounced improvement in treatment efficiency, particularly under low-pH conditions. The activation energy of β/N-rGO was estimated to be approximately 4.5 kJ/mol, and elevated temperatures accelerated the reaction, with the removal rate remaining above 85% after five regeneration cycles. Quenching experiments and EPR spectra confirmed that the primary pathway for PMS activation by β/N-rGO was a non-radical process dominated by singlet oxygen. These findings broaden the research and application scope of cyclodextrin–graphene interactions and provide a feasible approach for the removal of trace antibiotics from water. Full article

In the search for new selective inhibitors of human carbonic anhydrase (hCA), particularly the cancer-associated isoforms hCA IX and hCA XII, a series of 4-substituted pyridine-3-sulfonamides was synthesized using the “click” CuAAC reaction, proven by X-ray crystallography, and evaluated for their inhibitory activity against hCA I, hCA II, hCA IX, and hCA XII. Additional molecular docking studies and cytostatic activity assays on three cancer cell lines were conducted. The compounds exhibited a broad range of inhibitory activity, with K_I reaching 271 nM for hCA II, 137 nM for hCA IX, and 91 nM for hCA XII. Notably, compound 4 demonstrated up to 5.9-fold selectivity toward the cancer-associated hCA IX over the ubiquitous hCA II, while compound 6 exhibited a remarkable 23.3-fold selectivity between transmembrane isoforms hCA IX and hCA XII. Molecular docking studies have shown the possibility of selective interaction with the hydrophilic or lipophilic half of the active site, what results from the adjacent (3,4) position of the “tail” in relation to the sulfonamide group. Full article

Salmonella Heidelberg is frequently found in poultry and poultry products and is associated with antimicrobial resistance strains and infections and mortality in humans. Whole-genome sequencing is used to monitor and understand epidemiological factors related to antimicrobial resistance. This study aimed to characterize the phenotypic resistance and sequence the whole genome of Salmonella Heidelberg strains isolated from poultry products in Brazil. Fourteen Salmonella Heidelberg strains isolated from whole broiler chicken carcasses and portions in Brazil between 2013 and 2019 were used in this study. Genus confirmation was performed by polymerase chain reaction. The disk diffusion test was conducted to assess the phenotypical antimicrobial susceptibility of the strains. Whole-genome sequencing was carried out to investigate the presence of antimicrobial resistance genes, plasmids, multilocus sequence typing, and virulence-associated genes. A high frequency of phenotypic resistance to cephalosporins, tetracyclines, and sulfonamides was detected. All strains had mutations in gyrA and parC and contained the genes tet(A), fosA7, and sul. The presence of genes originating from Yersinia pathogenicity islands was also detected. This study identified a high frequency of antimicrobial resistance in Salmonella Heidelberg strains from broilers slaughtered in different regions of Brazil, all belonging to the same sequence type (ST15) and associated with multiple resistance and virulence genes. The presence of the Yersinia high-pathogenicity island was detected, indicating potential virulence. These findings highlight the importance of continuously monitoring antimicrobial resistance to control and prevent foodborne infections and maintain the efficacy of treatments for human salmonellosis. Full article

The degradation of organic matter using TiO₂ nanotube photocatalytic technology is limited by the short lifetime and diffusion radius of the generated hydroxyl radicals, decreasing the removal efficiency. This study developed a chlorine radical-coupled photoelectrocatalytic system, significantly enhancing the performance of TiO₂ nanotube arrays in removing sulfonamide antibiotics (SAs) from cold-water aquaculture systems. The highest degradation rates were observed at 5 mM NaCl and 15 mM NaNO₃. When SA concentrations were 0.1–10 mg/L, degradation efficiency decreased with higher initial concentrations. The best degradation was achieved at an initial pH of 3 for SA. Humic acid and sodium acetate, natural organic matter in the water column, served as low-concentration promoters and high-concentration inhibitors. In our study, three degradation intermediates were identified, and hydrolysis and nitration reactions are proposed as the primary pathways for SA degradation. We confirmed that oxygen radicals play a major role in this system. Furthermore, toxicology experiments revealed the weakening of the toxicity of the degraded products. This study provides an efficient method for treating organic matter in cold-water fish culture water in chloride-containing saline and alkaline waters. Full article

This review investigates the levels of antibiotic residues in animal products, types of antibiotics, and their possible impact on human health in Africa. The literature search involved the use of a systematic survey using data that were published from Africa from 2015 to 2024. The search terms used the Boolean operators with keywords such as antibiotics, antibiotic residues, antibiotics in animal products in Africa, and impact on human health. Only research conducted in Africa was used in the present study. The findings showed that the most prevalent groups of antibiotic residues were aminoglycoside, macrolides, β-lactams, fluoroquinolones, tetracyclines sulfonamides, and phenicols. Tetracycline showed the most prevalent antibiotic residue with 43% mostly from East Africa, followed by sulfonamides at 19%, and β-lactams at 16%; most of the antibiotic residue levels were higher than the World Health Organization permissible limit. Noncompliance with withdrawal periods and maximum residue limits for antibiotics used in food-producing animals may lead to negative outcomes such as allergic reactions, teratogenicity, carcinogenicity, microbiome alterations, and, most notably, antibiotic resistance. As a result, there is a need for constant monitoring of antibiotic residues in animal products in addition to the consideration of alternatives to antibiotics in order to avoid their health implications. Full article

Developing efficient and novel methodologies to construct a C–C bond is highly important in both synthetic chemistry and pharmaceutical sciences. In recent years, the visible light-mediated desulfonylative transformation of sulfonyl compounds has emerged as a powerful tool for the synthesis of diverse C–C bond. To emphasize their practical utility, many methodologies have been successfully applied in the modification of a variety of biologically active compounds which possess unprotected amide or hydroxy groups. In this review, we would like to summarize recent advances in C–C bond formation via the visible light-mediated desulfonylation of sulfonyl chlorides, sulfinates, sulfonamides, sulfones, and sulfonylhydrazones. The reaction design, mechanism research, and the application of these protocols in the modification of biologically active compounds are presented. The challenges and future developments in this area are also discussed. Full article

Our aim in this study was to explain the biological activity of the latest azafluoranthene. The natural product sarumine (12) and its derivatives (13–17) were synthesized and evaluated for their antibacterial and antitumor activities. The synthesis involved a simplified reaction pathway based on biaryl-sulfonamide-protected cyclization, and the compounds were characterized and studied using spectroscopic methods (¹HNMR and ¹³CNMR). Most of the compounds demonstrated improved antibacterial activity. Notably, sarumine demonstrated potent activity against S. aureus and B. subtilis, with an MIC of 8 μg/mL, showing comparable inhibitory effects to the positive control. Furthermore, molecular simulation studies indicated that sarumine exhibited significant binding affinity to FabH. The inhibitory effect of Cl was superior to the others on the structure, and the antitumor activity result also suggested that the inhibitory ability in PC-3 displayed by the R₁ derivatives of F and Cl substitutions was better than that of MDA-MB-231. These findings suggest that sarumine and its derivatives may represent new and promising candidates for further study. Full article

In recent years, microwave heating has become a widely used technique in organic synthesis. The reactions take place within a very short time, under mild conditions with high yields, and produce pure and selective compounds with fewer side reactions. In this context and under green chemistry conditions, we synthesized an organic compound containing two pharmacophore groups, oxazolidinone and sulfonamide, with a good yield. Full article

A series of new unique acetylene derivatives of 8-hydroxy- and 8-methoxyquinoline- 5-sulfonamide 3a–f and 6a–f were prepared by reactions of 8-hydroxy- and 8-methoxyquinoline- 5-sulfonyl chlorides with acetylene derivatives of amine. A series of new hybrid systems containing quinoline and 1,2,3-triazole systems 7a–h were obtained by reactions of acetylene derivatives of quinoline-5-sulfonamide 6a–d with organic azides. The structures of the obtained compounds were confirmed by ¹H and ¹³C NMR spectroscopy and HR-MS spectrometry. The obtained quinoline derivatives 3a–f and 6a–f and 1,2,3-triazole derivatives 7a–h were tested for their anticancer and antimicrobial activity. Human amelanotic melanoma cells (C-32), human breast adenocarcinoma cells (MDA-MB-231), and human lung adenocarcinoma cells (A549) were selected as tested cancer lines, while cytotoxicity was investigated on normal human dermal fibroblasts (HFF-1). All the compounds were also tested against reference strains Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 and representatives of multidrug-resistant clinical isolates of methicillin-resistant S. aureus (MRSA) and vancomycin-resistant E. faecalis. Only the acetylene derivatives of 8-hydroxyquinoline-5-sulfonamide 3a–f were shown to be biologically active, and 8-hydroxy-N-methyl-N-(prop-2-yn-1-yl)quinoline-5-sulfonamide (3c) showed the highest activity against all three cancer lines and MRSA isolates. Its efficacies were comparable to those of cisplatin/doxorubicin and oxacillin/ciprofloxacin. In the non-cancer HFF-1 line, the compound showed no toxicity up to an IC₅₀ of 100 µM. In additional tests, compound 3c decreased the expression of H3, increased the transcriptional activity of cell cycle regulators (P53 and P21 proteins), and altered the expression of BCL-2 and BAX genes in all cancer lines. The unsubstituted phenolic group at position 8 of the quinoline is the key structural fragment necessary for biological activity. Full article

Indazoles are a very important group of nitrogen-containing heterocycles with a wide range of biological and medicinal applications. These properties make them highly attractive for drug development, particularly when combined with sulfonamides to enhance their medicinal potential. In this work, we synthesized an indazole-based sulfonamide, namely the 1-((2-chloro-5-methoxyphenyl)sulfonyl)-5-nitro-1H-indazole (3). The reduction of the nitro group of 5-nitroindazole (1) to its corresponding amine was also performed to yield compound (4). Both compounds’ structures were elucidated using various spectroscopic techniques such as ¹H NMR, ¹³C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS). Our molecular docking studies suggest that compounds (3) and (4) have a strong affinity for MAPK1, indicating their potential as cancer treatments. Full article

Inhibitors of monoamine oxidases (MAOs) are of interest for the treatment of neurodegenerative disorders and other human pathologies. In this frame, the present work describes different synthetic strategies to obtain MAO inhibitors via the coupling of the aminocoumarin core with arylsulfonyl chlorides followed by copper azide-alkyne cycloaddition, leading to coumarin–sulfonamide–nitroindazolyl–triazole hybrids. The nitration position on the coumarin moiety was confirmed through nuclear magnetic resonance spectroscopy and molecular electron density theory in order to elucidate the molecular mechanism and selectivity of the electrophilic aromatic substitution reaction. The coumarin derivatives were evaluated for their inhibitory potency against monoamine oxidases and cholinesterases. Molecular docking calculations provided a rational binding mode of the best compounds in the series with MAO A and B. The work identified hybrids 14a–c as novel MAO inhibitors, with a selective action against isoform B, of potential interest to combat neurological diseases. Full article

Sulfonamides can be effectively removed from wastewater through a photocatalytic process. However, the mineralization achieved by this method is a long-term and expensive process. The effect of shortening the photocatalytic process is the partial degradation and formation of intermediates. The purpose of this study was to evaluate the sensitivity and transformation of photocatalytic reaction intermediates in aerobic biological processes. Sulfadiazine and sulfamethoxazole solutions were used in the study, which were irradiated in the presence of a TiO₂-P25 catalyst. The resulting solutions were then aerated after the addition of river water or activated sludge suspension from a commercial wastewater treatment plant. The reaction kinetics were determined and fifteen products of photocatalytic degradation of sulfonamides were identified. Most of these products were further transformed in the presence of activated sludge suspension or in water taken from the river. They may have been decomposed into other organic and inorganic compounds. The formation of biologically inactive acyl derivatives was observed in the biological process. However, compounds that are more toxic to aquatic organisms than the initial drugs can also be formed. After 28 days, the sulfamethoxazole concentration in the presence of activated sludge was reduced by 66 ± 7%. Sulfadiazine was practically non-biodegradable under the conditions used. The presented results confirm the advisability of using photocatalysis as a process preceding biodegradation. Full article

The UV treatment of 6:2 FTAB involves the mitigation of this persistent chemical by the impact of ultraviolet radiation, which is known for its resistance to environmental breakdown. UV treatment of PFOA and/or 6:2 FTAB, and the role of responsible species and their mechanism have been presented. Our investigation focused on the degradation of perfluorooctanoic acid (PFOA) and 6:2 fluorotelomer sulfonamide alkyl betaine (6:2 FTAB, Capstone B), using UV photolysis under various pH conditions. Initially, we used PFOA as a reference, finding a 90% decomposition after 360 min at the original (unadjusted) pH 5.6, with a decomposition rate constant of (1.08 ± 0.30) × 10⁻⁴ sec⁻¹ and a half-life of 107 ± 2 min. At pH 4 and 7, degradation averaged 85% and 80%, respectively, while at pH 10, it reduced to 57%. For 6:2 FTAB at its natural pH 6.5, almost complete decomposition occurred. The primary UV transformation product was identified as 6:2 fluorotelomer sulfonic acid (6:2 FTSA), occasionally accompanied by shorter-chain perfluoroalkyl acids (PFAAs) including PFHpA, PFHxA, and PFPeA. Interestingly, the overall decomposition percentages were unaffected by pH for 6:2 FTAB, though pH influenced rate constants and half-lives. In PFOA degradation, direct photolysis and reaction with hydrated electrons were presumed mechanisms, excluding the involvement of hydroxyl radicals. The role of superoxide radicals remains uncertain. For 6:2 FTAB, both direct and indirect photolysis were observed, with potential involvement of hydroxyl, superoxide radicals, and/or other reactive oxygen species (ROS). Clarification is needed regarding the role of $e_{aq}^{-}$ in the degradation of 6:2 FTAB. Full article

4-(2-Methyloxazol-4-yl)benzenesulfonamide was synthesized by the reaction of 4-(2-bromoacetyl)benzenesulfonamide with an excess of acetamide. The compound was evaluated as a potential inhibitor of human monoamine oxidase (MAO) A and B and was found to inhibit these enzymes with IC₅₀ values of 43.3 and 3.47 μM, respectively. The potential binding orientation and interactions of the inhibitor with MAO-B were examined by molecular docking, and it was found that the sulfonamide group binds and interacts with residues of the substrate cavity. 4-(2-Methyloxazol-4-yl)benzenesulfonamide showed no cytotoxic effect against human stromal bone cell line (HS-5) in the concentration range of 1–100 µmol. Thus, the new selective MAO-B inhibitor was identified, which may be used as the lead compound for the development of antiparkinsonian agents. Full article