One–Pot Phosphate-Mediated Synthesis of Novel 1,3,5-Trisubstituted Pyridinium Salts: A New Family of S. aureus Inhibitors

Pesnot, Thomas; Gershater, Markus; Edwards, Martin; Ward, John M.; Hailes, Helen C.

doi:10.3390/molecules22040626

Cited by 6 publications

(4 citation statements)

References 28 publications

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“…Related synthetic counterparts previously showed strong antibiotic activity against S. aureus . Yet, no activity against bacterial or fungal strains was observed for dispyridine ( 3 ).…”

Section: Results and Discussionmentioning

confidence: 99%

“…22 Related synthetic counterparts previously showed strong antibiotic activity against S. aureus. 23 Yet, no activity against bacterial or fungal strains was observed for dispyridine (3). For the dispyrrolopyridines (4 and 5), a series of pyrrolo [2,3-b]pyrimidine derivatives has been synthesized and showed promising inhibitory effects against fluoroquinolone-resistant MRSA and other bacteria.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

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Discovery and Biosynthesis of Antimicrobial Phenethylamine Alkaloids from the Marine Flavobacterium Tenacibaculum discolor sv11

et al. 2022

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The bacterial genus Tenacibaculum has been associated with various ecological roles in marine environments. Members of this genus can act, for example, as pathogens, predators, or episymbionts. However, natural products produced by these bacteria are still unknown. In the present work, we investigated a Tenacibaculum strain for the production of antimicrobial metabolites. Six new phenethylamine (PEA)-containing alkaloids, discolins A and B (1 and 2), dispyridine (3), dispyrrolopyridine A and B (4 and 5), and dispyrrole (6), were isolated from media produced by the predatory bacterium Tenacibaculum discolor sv11. Chemical structures were elucidated by analysis of spectroscopic data. Alkaloids 4 and 5 exhibited strong activity against Gram-positive Bacillus subtilis DSM10, Mycobacterium smegmatis ATCC607, Listeria monocytogenes DSM20600, and Staphylococcus aureus ATCC25923, with minimum inhibitory concentration (MIC) values ranging from 0.5 to 4 μg/mL, and moderate activity against Candida albicans FH2173 and Aspergillus flavus ATCC9170. Compound 6 displayed moderate antibacterial activities against Grampositive bacteria. Dispyrrolopyridine A (4) was active against efflux pump deficient Escherichia coli ATCC25922 ΔtolC, with an MIC value of 8 μg/mL, as well as against Caenorhabditis elegans N2 with an MIC value of 32 μg/mL. Other compounds were inactive against these microorganisms. The biosynthetic route toward discolins A and B (1 and 2) was investigated using in vivo and in vitro experiments. It comprises an enzymatic decarboxylation of phenylalanine to PEA catalyzed by DisA, followed by a nonenzymatic condensation to form the central imidazolium ring. This spontaneous formation of the imidazolium core was verified by means of a synthetic one-pot reaction using the respective building blocks. Six additional strains belonging to three Tenacibaculum species were able to produce discolins, and several DisA analogues were identified in various marine flavobacterial genera, suggesting the widespread presence of PEA-derived compounds in marine ecosystems.

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“…Related synthetic counterparts previously showed strong antibiotic activity against S. aureus . Yet, no activity against bacterial or fungal strains was observed for dispyridine ( 3 ).…”

Section: Results and Discussionmentioning

confidence: 99%

Section: Journal Of Natural Productsmentioning

confidence: 99%

Discovery and Biosynthesis of Antimicrobial Phenethylamine Alkaloids from the Marine Flavobacterium Tenacibaculum discolor sv11

et al. 2022

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“…Penicillin and streptomycin are commonly used as auxiliary reagents in culture media to prevent contamination of cells with fungi and bacteria. Excessive intake of antibiotics might lead to the development of drug resistance in pathogenic bacteria and thus jeopardize human health . As the results show in Figure A, the penicillin content in CCM was 2.16 ng/g, which was lower than the 50 ng/g specified in the Chinese national standard.…”

Section: Resultsmentioning

confidence: 77%

“…Excessive intake of antibiotics might lead to the development of drug resistance in pathogenic bacteria and thus jeopardize human health. 52 As the results show in Figure 5A, the penicillin content in CCM was 2.16 ng/ g, which was lower than the 50 ng/g specified in the Chinese national standard. The streptomycin residue in CCM was 90.72 ng/g, which was lower than the 1000 ng/g specified in the Chinese national standard.…”

Section: In Vitro Simulated Dilution Of Cell-cultured Fish Meatmentioning

confidence: 71%

Cell-Cultured Fish Meat via Scale-Up Expansion of Carassius auratus Skeletal Muscle Cells Using Edible Porous Microcarriers and Quality Evaluation

Yin,

Wang,

Hur

et al. 2024

J. Agric. Food Chem.

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Emerging technologies for cell-cultured fish meat as an environmentally friendly protein source for humans still have many obstacles, including large-scale production of high-quality cells, differentiation and bioassembly of cellular material, and improvement of the quality of meat products. Here, we used edible porous microcarriers as scaffolds to support scalable skeletal muscle cell expansion to prepare centimeter-scale cell-cultured fish (CCM) of Carassius auratus for the first time. The quality of CCM was assessed by analyzing the texture, nutrition, flavor, and safety. The results indicated that CCM demonstrated a softer texture than natural fish due to a high moisture content. CCM contained higher protein and lower fat contents, with no significant difference in energy from natural golden crucian carp meat (NGM). CCM had better digestible properties, and 17 volatile components were identified in CCM, ten cocontained compared to NGM. ELISA quantified penicillin, streptomycin, vitamin D, and insulin residues as risk factors in CCM. In conclusion, we utilized edible porous microcarriers to scale-up the expansion of Carassius auratus skeletal muscle cells and bioassembled high-quality CCM of Carassius auratus for the first time, which represents a state-ofthe-art protocol applicable to different fish species and even to other economic animals and provides a theoretical basis for scaling up cell-cultured meat production.

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Electrochemical Characteristics of a Novel Pyridinium Salt as a Candidate Drug Molecule and Its Interaction with DNA

et al. 2020

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In this article, for the first time, the electrochemical properties of a novel pyridine derivative, 4‐(2‐(2‐hydroxybenzylidene) hydrazinyl)‐1‐(3‐phenylpropyl) pyridinium bromide (abbreviated as 4‐Pyri), and its interaction with double stranded DNA (dsDNA) was investigated. The interaction between candidate drug molecule (4‐Pyri) and dsDNA was analyzed by examining 4‐Pyri (+0.6 V and +0.8 V) and guanine (+1.0 V) oxidation signal changes with Differential Pulse Voltammetry (DPV) and Cyclic Voltammetry (CV). Electrochemical Impedance Spectroscopy (EIS) was used to show the resistance changes before and after the interaction between 4‐Pyri and dsDNA. We showed that after the interaction with 4‐Pyri, the oxidation currents of guanine decreased dramatically, whereas the intrinsic oxidation currents of 4‐Pyri dramatically increased. 4‐Pyri oxidation current differences before and after the interaction with dsDNA enabled us to determine such interaction separately from guanine oxidation signals. In addition, resistance differences were observed at before and after the interaction with each other that confirmed the possible interaction. In addition, toxicity effect (S%) value, which is an important parameter for electrochemical studies indicated 4‐Pyri's toxicity to dsDNA. Our results demonstrated that 4‐Pyri interacts with dsDNA, and could be used as a potential candidate drug molecule due to its remarkable impact on dsDNA.

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One–Pot Phosphate-Mediated Synthesis of Novel 1,3,5-Trisubstituted Pyridinium Salts: A New Family of S. aureus Inhibitors

Cited by 6 publications

References 28 publications

Discovery and Biosynthesis of Antimicrobial Phenethylamine Alkaloids from the Marine Flavobacterium Tenacibaculum discolor sv11

Discovery and Biosynthesis of Antimicrobial Phenethylamine Alkaloids from the Marine Flavobacterium Tenacibaculum discolor sv11

Cell-Cultured Fish Meat via Scale-Up Expansion of Carassius auratus Skeletal Muscle Cells Using Edible Porous Microcarriers and Quality Evaluation

Electrochemical Characteristics of a Novel Pyridinium Salt as a Candidate Drug Molecule and Its Interaction with DNA

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