In Vitro Antibacterial Activity of Rhodanine Derivatives against Pathogenic Clinical Isolates

AbdelKhalek, Ahmed; Ashby, Charles R.; Patel, Bhargav A.; Talele, Tanaji T.; Seleem, Mohamed N.

doi:10.1371/journal.pone.0164227

Cited by 19 publications

(14 citation statements)

References 19 publications

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“…The time-dependent killing for S. aureus ATCC 29213 and MRSA 43300 with IBG, VAN at 10 × MIC was investigated previously ( AbdelKhalek et al, 2016 ). The OD 600nm was measured to determine bacterial lysis when S. aureus (OD 600nm ∼0.4) treated with 10 × MIC of IBG, VAN, and BAC (positive control) for 4 h ( Kim et al, 2018 ).…”

Section: Methodsmentioning

confidence: 99%

Isopropoxy Benzene Guanidine Kills Staphylococcus aureus Without Detectable Resistance

et al. 2021

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Serious infections caused by multidrug-resistant Staphylococcus aureus clearly urge the development of new antimicrobial agents. Drug repositioning has emerged as an alternative approach that enables us to rapidly identify effective drugs. We first reported a guanidine compound, isopropoxy benzene guanidine, had potent antibacterial activity against S. aureus. Unlike conventional antibiotics, repeated use of isopropoxy benzene guanidine had a lower probability of resistance section. We found that isopropoxy benzene guanidine triggered membrane damage by disrupting the cell membrane potential and cytoplasmic membrane integrity. Furthermore, we demonstrated that isopropoxy benzene guanidine is capable of treating invasive MRSA infections in vivo studies. These findings provided strong evidence that isopropoxy benzene guanidine represents a new chemical lead for novel antibacterial agent against multidrug-resistant S. aureus infections.

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Section: Methodsmentioning

confidence: 99%

Isopropoxy Benzene Guanidine Kills Staphylococcus aureus Without Detectable Resistance

et al. 2021

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“…Several reports suggest that heterocyclic compounds with rhodanine scaffold are known to inhibit several pharmaceutical targets from demonstrating enhanced antimicrobial activity (20). 3, 5-disubstituted rhodanine derivatives inhibited the S. aureus supercoiling activity by targeting the GyrB ATPase function (21) and other rhodanine derivatives such as 5-(2-hydroxybenzylidene) has shown moderate antibacterial activity, reported as GyrB inhibitor (22) , phenylalaninederived (z)-5-arylmethylidene rhodamine (23) ,2-(5-(3,4-Dichlorobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid and 2-(5-(3-Phenoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid (24) have shown significant anti MRSA activity, can be used for treatment of gram-positive MRSA (25). Rhodanines which have a privileged scaffold in drug discovery, wide spectrum of pharmacological activity (26) and structural modification enable potent, selective drugs to be developed.…”

Section: Introductionmentioning

confidence: 99%

Design of a novel DNA Gyrase B inhibitor with a rhodanine scaffold:in silicoandin vitroapproaches

Pudipeddi

Vasudevan

Shanmugam

et al. 2021

Preprint

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Methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin intermediate-resistant Staphylococcus aureus (VRSA) is one among the WHO high priority pathogens. Among these two, MRSA is the most globally documented pathogen that necessitates the pressing demand for new classes of anti-MRSA drugs. Bacterial gyrase targeted therapeutics are unique strategies to overcome cross-resistance as they are present only in bacteria and absent in higher eukaryotes. The GyrB subunit is essential for the catalytic functions of the bacterial enzyme DNA Gyrase, thereby constituting a promising druggable target. The current study performed a structure-based virtual screening to designing GyrB target-specific candidate molecules. The de novo ligand design of novel hit molecules was performed using a rhodanine scaffold. Through a systematic in silico screening process, the hit molecules were screened for their synthetic accessibility, drug likeliness and pharmacokinetics properties in addition to its target specific interactions. Of the total 374 hit molecules obtained through de novo ligand design, qsl-304 emerged as the most promising ligand. qsl-304 was synthesized through a one-step chemical synthesis procedure, and the in vitro activity was proven, with an IC50 of 31.23 μg/mL against the novobiocin resistant clinical isolate of Staphylococcus aureus sa-P2003. Further studies on time-kill kinetics showed the bacteriostatic nature with the diminished recurrence of resistance.

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“…The compounds revealing antifungal activity are also presented among 2-thioxo-4-thiazolidinones. A derivative of 2-(rhodanine-3-yl)-3-phenylpropanoic acid showed the micromolar ran ges of MIC towards the isolates of Gram (+) and Gram (-) bacteria including the vancomycin resistant strains as well as Candida albicans and was not toxic to mouse murine macrophages and human keratinocytes [24]. Taking into account the literature data on antibacterial, antifungal and antiparasitic properties of thiazolidinone derivatives, the feasibility of their synthesis and further chemical optimization, the aim of presented research was the design of potentially active antimicrobials on the base of rhodanine-3-carboxylic acids.…”

Section: Introductionmentioning

confidence: 99%

5-Ene-rhodanine-3-carboxylic acids as potential antimicrobial and antiparasitic agents

Kryshchyshyn‐Dylevych

2020

Biopolym. Cell

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Design, synthesis and study of antibacterial, antifungal and trypanocidal activity of a series of novel 2-thioxo-4-thiazolidinone-3-carboxylic acids with different arylidene substituents in C5 position. Methods. Organic wet synthesis, analytical and spectral methods, pharmacological screening, SAR analysis. Results. A series of 5-(aminomethylene)-4-oxo-2-thioxothiazolidin-3-ylcarboxylic acids and their analogs IIIa-IIIj were synthesized in the reactions of 5-(ethoxymethylene)-4-oxo-2-thioxothiazolidin-3-ylcarboxylic acids IIa,b or ethyl 5-(ethoxymethylene)-4-oxo-2-thioxothiazolidin-3-ylpropanoate IIc with various amines and ammonium hydrogen carbonate. Five of the synthesized compounds IIIb, IIIf and IIIh-j were tested towards a series of Gram (+) and Gram (-) bacteria and four yeasts strains at a dose of 1mM. In general, the tested compounds are promising building scaffolds for the development of antifungal agents as all of them inhibited growth of clinical strain of Candida albicans. Moreover, pyridine containing 3-[5-(aminomethylene)-rhodanine-3-yl]carboxylates showed good trypanocidal activity and low cytotoxicity towards normal fibroblasts. Conclusions. A series of novel 3-[5-(aminomethylene)-4-oxo-2-thioxothiazolidin-3-yl]carboxylic acids derivatives were synthesized. Study of their antibacterial and antifungal action allowed identifying a hit-compound ethyl 3-[5-[(4-(fluoroanilino)methylene]-4-oxo-2-thioxothiazolidin-3-yl] propanoate IIIf, which is active against clinical strains of Staphylococcus lentus and Candida ssp. In general, most of the studied compounds showed good antifungal properties.

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In Vitro Antibacterial Activity of Rhodanine Derivatives against Pathogenic Clinical Isolates

Cited by 19 publications

References 19 publications

Isopropoxy Benzene Guanidine Kills Staphylococcus aureus Without Detectable Resistance

Isopropoxy Benzene Guanidine Kills Staphylococcus aureus Without Detectable Resistance

Design of a novel DNA Gyrase B inhibitor with a rhodanine scaffold:in silicoandin vitroapproaches

5-Ene-rhodanine-3-carboxylic acids as potential antimicrobial and antiparasitic agents

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