Enzymatic Synthesis of KDN-Containing Sialylated Lactuloses and their Bacteriostatic Activities on Staphylococcus aureus

2019 ◽  
Vol 41 (6) ◽  
pp. 1115-1115
Author(s):  
Jie Zeng Jie Zeng ◽  
Ruiyao Zhang Ruiyao Zhang ◽  
Saddam Muthana Saddam Muthana ◽  
Haiyan Gao Haiyan Gao ◽  
Mengdi Song Mengdi Song ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Nucleic Acids ◽  
Fluorescence Analysis ◽  
Antibacterial Activities ◽  
Biological Tissues ◽  
Synthetic Approach ◽  
One Pot ◽  
Morphological Alterations ◽  
Maximum Inhibition ◽  
Electron Scanning Microscope

Sialic acids are found in various biological tissues and are known to play important roles in many biological processes. However, many sialylated oligosaccharides are not adequately available to study their biological functions and potential uses. Herein, we reported an efficient synthetic approach to obtain sialylated lactulose containing deaminoneuraminc acid (KDN). Both KDNα2,3lactulose and KDNα2,6lactulose were synthesized via one-pot multienzyme sialylation system. The bacteriostatic activities of these two sialylated lactuloses against Staphylococcus aureus (S. aureus) were analyzed by using approach of optical density OD600 measurements. In addition, integrity of cell membrane of S. aureus was examined by fluorescence analysis, protein leakage quantification and electron scanning microscope (SEM). The results showed that the maximum inhibition ratios of KDNα2,3lactulose and KDNα2,6lactulose within the first 10 h was up to 34.33% and 32.18%, respectively. KDNα2,3lactulose displayed slightly better inhibition against the growth of S. aureus than that of KDNα2,6lactulose. The addition of KDNα2,3lactulose and KDNα2,6lactulose caused a significant decrease (pandlt;0.05) in fluorescence intensity compared with control to 47.05and#177;3.06% and 51.16and#177;2.40, respectively, indicated that those two sialylated lactuloses had some extent interference with nucleic acids synthesis or caused decomposition of nucleic acids in S. aureus cells. Fluorescence microscopy results showed that S. aureus of KDNα2,3lactulose and KDNα2,6lactulose group present obvious loss of viability. The leakage amount of proteins in S. aureus treated with KDNα2,3lactulose and KDNα2,6lactulose increased by 223 μg/mL and 205.4 μg/mL, respectively. The morphological alterations on the cells observed by SEM confirmed that KDN-containing sialylated lactuloses possessed antibacterial activities. In a word, KDN-containing sialylated lactuloses have certain effects on inhibiting the growth of S. aureus.

scholarly journals Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds

Molecules ◽  
2020 ◽  
Vol 25 (12) ◽  
pp. 2863 ◽  
Author(s):  
Viktor A. Zapol’skii ◽  
Ursula Bilitewski ◽  
Sören R. Kupiec ◽  
Isabell Ramming ◽  
Dieter E. Kaufmann
Keyword(s):  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Heterocyclic Compounds ◽  
Nitrogen Heterocycles ◽  
Building Blocks ◽  
Antibacterial Activities ◽  
Synthetic Approach ◽  
Selective Synthesis ◽  
Ic50 Values ◽  
Thiophene Derivatives

Substituted nitrogen heterocycles are structural key units in many important pharmaceuticals. A new synthetic approach towards heterocyclic compounds displaying antibacterial activity against Staphylococcus aureus or cytotoxic activity has been developed. The selective synthesis of a series of 64 new N-heterocycles from the three nitrobutadienes 2-nitroperchloro-1,3-butadiene, 4-bromotetrachloro-2-nitro-1,3-butadiene and (Z)-1,1,4-trichloro-2,4-dinitrobuta-1,3-diene proved feasible. Their reactions with N-, O- and S-nucleophiles provide rapid access to push-pull substituted benzoxazolines, benzimidazolines, imidazolidines, thiazolidinones, pyrazoles, pyrimidines, pyridopyrimidines, benzoquinolines, isothiazoles, dihydroisoxazoles, and thiophenes with unique substitution patterns. Antibacterial activities of 64 synthesized compounds were examined. Additionally, seven compounds (thiazolidinone, nitropyrimidine, indole, pyridopyrimidine, and thiophene derivatives) exhibited a significant cytotoxicity with IC50-values from 1.05 to 20.1 µM. In conclusion, it was demonstrated that polyhalonitrobutadienes have an interesting potential as structural backbones for a variety of highly functionalized, pharmaceutically active heterocycles.

scholarly journals Formulation and Antibacterial Activity Evaluation of Quaternized Aminochitosan Membrane for Wound Dressing Applications

Polymers ◽  
2021 ◽  
Vol 13 (15) ◽  
pp. 2428
Author(s):  
Ahmed M. Omer ◽  
Tamer M. Tamer ◽  
Randa E. Khalifa ◽  
Abdelazeem S. Eltaweil ◽  
Mona M. Agwa ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Surface Roughness ◽  
Antibacterial Activity ◽  
Wound Dressing ◽  
Antibacterial Activities ◽  
Sample Concentration ◽  
Inhibition Concentration ◽  
Maximum Inhibition ◽  
Chitosan Biopolymer

Much attention has been paid to chitosan biopolymer for advanced wound dressing owing to its exceptional biological characteristics comprising biodegradability, biocompatibility and respectable antibacterial activity. This study intended to develop a new antibacterial membrane based on quaternized aminochitosan (QAMCS) derivative. Herein, aminochitosan (AMCS) derivative was quaternized by N-(2-Chloroethyl) dimethylamine hydrochloride with different ratios. The pre-fabricated membranes were characterized by several analysis tools. The results indicate that maximum surface potential of +42.2 mV was attained by QAMCS3 membrane compared with +33.6 mV for native AMCS membrane. Moreover, membranes displayed higher surface roughness (1.27 ± 0.24 μm) and higher water uptake value (237 ± 8%) for QAMCS3 compared with 0.81 ± 0.08 μm and 165 ± 6% for neat AMCS membranes. Furthermore, the antibacterial activities were evaluated against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus cereus. Superior antibacterial activities with maximum inhibition values of 80–98% were accomplished by QAMCS3 membranes compared with 57–72% for AMCS membrane. Minimum inhibition concentration (MIC) results denote that the antibacterial activities were significantly boosted with increasing of polymeric sample concentration from 25 to 250 µg/mL. Additionally, all membranes unveiled better biocompatibility and respectable biodegradability, suggesting their possible application for advanced wound dressing.

Synthesis, Biological Screening and Docking Study of Some Novel Pyrazolopyrano[2,3-B]quinolin Derivatives as Potent Antibacterial Agents

2022 ◽  
Vol 18 ◽  
Author(s):  
Hamideh. Emtiazi ◽  
Ali Salari Sharif ◽  
Mina Ardestani
Keyword(s):  
Staphylococcus Aureus ◽  
Molecular Docking ◽  
Hydrophobic Interactions ◽  
Biological Activities ◽  
Aromatic Aldehydes ◽  
Dna Gyrase ◽  
Docking Study ◽  
Antibacterial Activities ◽  
Synthetic Methods ◽  
One Pot

Background: Pyranopyrazoles have a variety of biological activities and can be obtained by various starting materials and synthetic methods. Also, pyrazolopyrano[2,3-b]quinolins that contain pyranopyrazole moiety, have some biological activities such as anti acetylcholinesterase, anti butyrylcholinesterase activity. In this research, our objective is to prepare pyranopyrazole compounds and pyrazolopyrano[2,3-b]quinolins in a simple way and then evaluate their antibacterial effect. Methods: In this study, pyrano[2,3-c]pyrazole derivatives have been synthesized by condensing malononitrile, aromatic aldehydes, and 3-methyl-1-phenyl-2-pyrazolin-5-one in the presence of magnesium perchlorate as a catalyst. Then we prepared pyrazolopyrano[2,3-b]quinolins via subsequent Friedlander reaction between cyclohexanone and the obtained pyrano[2,3-c]pyrazoles. Also, the antimicrobial activity of the synthesized pyrazolopyrano[2,3-b]quinolins against Staphylococcus aureus, Methicillin-resistant Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli were measured. Then we studied molecular docking of them to find the predicted compounds' interactions and binding energy with DNA-gyrase with the AutoDock 4.2 software. Results: Pyrazolopyrano[2,3-b]quinolins were synthesized in optimized conditions. Evaluation of their antibacterial activities showed that these compounds have moderate to good antibacterial activities against four bacteria species. Also molecular docking tests of docked compounds showed a strong bonding interaction with DNA-Gyrase and had been docked into the intercalation place of DNA of DNA-gyrase complex. The molecule bounded to the DNA stabilized by the H bonds, hydrophobic interactions, and π-π interaction. Conclusion: We have developed an efficient and one-pot ecofriendly protocol for the synthesis of some novel pyrano[2,3-c]pyrazol derivatives and pyrazolopyrano[2,3-b]quinolins under simple conditions and then tested them for their antibacterial activities. Also, we studied molecular docking of them. These compounds showed moderate to good inhibitory action.

One-pot Synthesis of Pyrazolone Sulfones by Iodine-catalyzed Sulfenylation of Pyrazolones with Aryl Sulfonyl Hydrazides Followed by Oxidation in Water

2018 ◽  
Vol 15 (3) ◽  
pp. 380-387
Author(s):  
Xia Zhao ◽  
Xiaoyu Lu ◽  
Lipeng Zhang ◽  
Tianjiao Li ◽  
Kui Lu
Keyword(s):  
Double Bond ◽  
Efficient Method ◽  
Room Temperature ◽  
Sulfonyl Chloride ◽  
Antibacterial Activities ◽  
Oxidation Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Amide Form

Aim and Objective: Pyrazolone sulfones have been reported to exhibit herbicidal and antibacterial activities. In spite of their good bioactivities, only a few methods have been developed to prepare pyrazolone sulfones. However, the substrate scope of these methods is limited. Moreover, the direct sulfonylation of pyrazolone by aryl sulfonyl chloride failed to give pyrazolone sulfones. Thus, developing a more efficient method to synthesize pyrazolone sulfones is very important. Materials and Method: Pyrazolone, aryl sulphonyl hydrazide, iodine, p-toluenesulphonic acid and water were mixed in a sealed tube, which was heated to 100°C for 12 hours. The mixture was cooled to 0°C and m-CPBA was added in batches. The mixture was allowed to stir for 30 min at room temperature. The crude product was purified by silica gel column chromatography to afford sulfuryl pyrazolone. Results: In all cases, the sulfenylation products were formed smoothly under the optimized reaction conditions, and were then oxidized to the corresponding sulfones in good yields by 3-chloroperoxybenzoic acid (m-CPBA) in water. Single crystal X-ray analysis of pyrazolone sulfone 4aa showed that the major tautomer of pyrazolone sulfones was the amide form instead of the enol form observed for pyrazolone thioethers. Moreover, the C=N double bond isomerized to form an α,β-unsaturated C=C double bond. Conclusion: An efficient method to synthesize pyrazolone thioethers by iodine-catalyzed sulfenylation of pyrazolones with aryl sulfonyl hydrazides in water was developed. Moreover, this method was employed to synthesize pyrazolone sulfones in one-pot by subsequent sulfenylation and oxidation reactions.

scholarly journals Antimicrobial Efficacy and Spectrum of Phosphorous-Fluorine Co-Doped TiO2 Nanoparticles on the Foodborne Pathogenic Bacteria Campylobacter jejuni, Salmonella Typhimurium, Enterohaemorrhagic E. coli, Yersinia enterocolitica, Shewanella putrefaciens, Listeria monocytogenes and Staphylococcus aureus

Foods ◽  
2021 ◽  
Vol 10 (8) ◽  
pp. 1786
Author(s):  
György Schneider ◽  
Bettina Schweitzer ◽  
Anita Steinbach ◽  
Botond Zsombor Pertics ◽  
Alysia Cox ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Campylobacter Jejuni ◽  
Food Industry ◽  
Pathogenic Bacteria ◽  
Antibacterial Activities ◽  
Tio2 Nps ◽  
E Coli ◽  
Foodborne Pathogenic Bacteria ◽  
And Staphylococcus Aureus ◽  
Co Doped

Contamination of meats and meat products with foodborne pathogenic bacteria raises serious safety issues in the food industry. The antibacterial activities of phosphorous-fluorine co-doped TiO2 nanoparticles (PF-TiO2) were investigated against seven foodborne pathogenic bacteria: Campylobacter jejuni, Salmonella Typhimurium, Enterohaemorrhagic E. coli, Yersinia enterocolitica, Shewanella putrefaciens, Listeria monocytogenes and Staphylococcus aureus. PF-TiO2 NPs were synthesized hydrothermally at 250 °C for 1, 3, 6 or 12 h, and then tested at three different concentrations (500 μg/mL, 100 μg/mL, 20 μg/mL) for the inactivation of foodborne bacteria under UVA irradiation, daylight exposure or dark conditions. The antibacterial efficacies were compared after 30 min of exposure to light. Distinct differences in the antibacterial activities of the PF-TiO2 NPs, and the susceptibilities of tested foodborne pathogenic bacterium species were found. PF-TiO2/3 h and PF-TiO2/6 h showed the highest antibacterial activity by decreasing the living bacterial cell number from ~106 by ~5 log (L. monocytogenes), ~4 log (EHEC), ~3 log (Y. enterolcolitca, S. putrefaciens) and ~2.5 log (S. aureus), along with complete eradication of C. jejuni and S. Typhimurium. Efficacy of PF-TiO2/1 h and PF-TiO2/12 h NPs was lower, typically causing a ~2–4 log decrease in colony forming units depending on the tested bacterium while the effect of PF-TiO2/0 h was comparable to P25 TiO2, a commercial TiO2 with high photocatalytic activity. Our results show that PF-co-doping of TiO2 NPs enhanced the antibacterial action against foodborne pathogenic bacteria and are potential candidates for use in the food industry as active surface components, potentially contributing to the production of meats that are safe for consumption.

scholarly journals In VitroActivities of Daptomycin-, Vancomycin-, and Teicoplanin-Loaded Polymethylmethacrylate against Methicillin-Susceptible, Methicillin-Resistant, and Vancomycin-Intermediate Strains of Staphylococcus aureus

2011 ◽  
Vol 55 (12) ◽  
pp. 5480-5484 ◽  
Author(s):  
Yuhan Chang ◽  
Wen-Chien Chen ◽  
Pang-Hsin Hsieh ◽  
Dave W. Chen ◽  
Mel S. Lee ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
High Performance ◽  
Low Dose ◽  
Antibacterial Activities ◽  
High Dose ◽  
Bone Cements ◽  
Antibacterial Effects ◽  
Methicillin Resistant ◽  
Content Type

ABSTRACTThe objective of this study was to evaluate the antibacterial effects of polymethylmethacrylate (PMMA) bone cements loaded with daptomycin, vancomycin, and teicoplanin against methicillin-susceptibleStaphylococcus aureus(MSSA), methicillin-resistantStaphylococcus aureus(MRSA), and vancomycin-intermediateStaphylococcus aureus(VISA) strains. Standardized cement specimens made from 40 g PMMA loaded with 1 g (low-dose), 4 g (middle-dose) or 8 g (high-dose) antibiotics were tested for elution characteristics and antibacterial activities. The patterns of release of antibiotics from the cement specimens were evaluated usingin vitrobroth elution assay with high-performance liquid chromatography. The activities of broth elution fluid against differentStaphylococcus aureusstrains (MSSA, MRSA, and VISA) were then determined. The antibacterial activities of all the tested antibiotics were maintained after being mixed with PMMA. The cements loaded with higher dosages of antibiotics showed longer elution periods. Regardless of the antibiotic loading dose, the teicoplanin-loaded cements showed better elution efficacy and provided longer inhibitory periods against MSSA, MRSA, and VISA than cements loaded with the same dose of vancomycin or daptomycin. Regarding the choice of antibiotics for cement loading in the treatment ofStaphylococcus aureusinfection, teicoplanin was superior in terms of antibacterial effects.

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