Synthesis of benzoylthiourea derivatives and analysis of their antibacterial performance against planktonic
            <i>Staphylococcus aureus</i>
            and its biofilms

Pinheiro, Luiz C. S.; Hoelz, Lucas Villas Bôas; Ferreira, Maria Lurdes; Oliveira, Luiz Gustavo de; Pereira, Renata Freire Alves; Valle, AC; André, Lialyz Soares Pereira; Scaffo, J.; Pinheiro, Felipe Ramos; Ribeiro, Tainara Aparecida Nunes; Sachs, Daniela; Pascoal, Aislan Cristina Rheder Fagundes; Boechat, Núbia; Aguiar-Alves, Fábio

doi:10.1111/lam.13359

Cited by 7 publications

(3 citation statements)

References 17 publications

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“…Similarly, the S-3,4-dichlorobenzyl isothiourea hydrochloride inhibited the biofilm formation of multi-drug resistant Pseudomonas aeruginosa on polystyrene and polyethylene surfaces ( Bonez et al, 2017 ). The 1,2,4-triazolyl-benzoylthiourea exhibited bacteriostatic activity against planktonic cells of Staphylococcus aureus , and could inhibit biofilm formation as well as eradicate the 6-h biofilm on polystyrene surface ( Pinheiro et al, 2020 ). Finally, the combination of N -[2-(4-ethylphenoxy)methyl]- N -(arylcarbamothioyl)benzamides with Fe 3 O 4 and polyvinylpyrrolidone for coating the silicon and glass catheter surfaces inhibited the adhesion and biofilm formation of S. aureus ATCC 25923 and P. aeruginosa ATCC 27853 on these medical devices ( Limban et al, 2014 ).…”

Section: Resultsmentioning

confidence: 99%

Synergistic antifungal interaction of N-(butylcarbamothioyl) benzamide and amphotericin B against Cryptococcus neoformans

Andriani

Spoladori²,

Fábris³

et al. 2023

Front. Microbiol.

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IntroductionCryptococcus neoformans is one of the leading causes of invasive fungal infections worldwide. Cryptococcal meningoencephalitis is the main challenge of antifungal therapy due to high morbidity and mortality rates, especially in low- and middle-income countries. This can be partly attributed to the lack of specific diagnosis difficulty accessing treatment, antifungal resistance and antifungal toxicity.MethodsIn the present study, the effect of the synthetic thiourea derivative N-(butylcarbamothioyl) benzamide (BTU-01), alone and combined with amphotericin B (AmB), was evaluated in planktonic and sessile (biofilm) cells of C. neoformans.ResultsBTU-01 alone exhibited a fungistatic activity with minimal inhibitory concentrations (MICs) ranging from 31.25 to 62.5 μg/mL for planktonic cells; and sessile MICs ranging from 125.0 to 1000.0 μg/mL. BTU-01 caused a concentration-dependent inhibitory activity on cryptococcal urease and did not interfere with plasma membrane fluidity. Molecular docking was performed on Canavalia ensiformis urease, and BTU-01 showed relevant interactions with the enzyme. The combination of BTU-01 and AmB exhibited synergistic fungicidal activity against planktonic and sessile cells of C. neoformans. Microscopic analysis of C. neoformans treated with BTU-01, alone or combined with AmB, revealed a reduction in cell and capsule sizes, changes in the morphology of planktonic cells; a significant decrease in the number of cells within the biofilm; and absence of exopolymeric matrix surrounding the sessile cells. Neither hemolytic activity nor cytotoxicity to mammalian cells was detected for BTU-01, alone or combined with AmB, at concentrations that exhibited antifungal activity. BTU-01 also displayed drug-likeness properties.ConclusionThese results indicate the potential of BTU-01, for the development of new strategies for controlling C. neoformans infections.

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Section: Resultsmentioning

confidence: 99%

Synergistic antifungal interaction of N-(butylcarbamothioyl) benzamide and amphotericin B against Cryptococcus neoformans

Andriani

Spoladori²,

Fábris³

et al. 2023

Front. Microbiol.

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“…1I–V). 11–15 Even these moieties are found in various commercially available drugs and bioactive molecules known for their therapeutic properties including β-lactams (Fig. 1VI–VIII).…”

Section: Introductionmentioning

confidence: 99%

Aroyl-isothiocyanates/isoselenocyanates as precursors to obtain novel cis-3-aroyl-thiourea/urea-β-lactams: design, synthesis, docking and biological evaluation

Kumar,

Kaur,

Kumari

et al. 2024

New J. Chem.

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“…In this context, thiourea is a relevant class of sulfur-bearing substances with notable synthetic and biological versatility. Thiourea derivatives have shown promising pharmaceutical potential due to their diverse pharmacological activities, including antitumoral [ 11 ], antioxidant [ 12 ], antidiabetic [ 13 ], and antimicrobial [ 14 , 15 , 16 , 17 , 18 , 19 , 20 ] properties. Notably, the thiourea moiety has been identified in several compounds with potential for the development of new therapeutic compounds to treat diseases caused by trypanosomatid species [ 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Antiprotozoal Activity of Benzoylthiourea Derivatives against Trypanosoma cruzi: Insights into Mechanism of Action

et al. 2023

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For decades, only two nitroheterocyclic drugs have been used as therapeutic agents for Chagas disease. However, these drugs present limited effectiveness during the chronic phase, possess unfavorable pharmacokinetic properties, and induce severe adverse effects, resulting in low treatment adherence. A previous study reported that N-(cyclohexylcarbamothioyl) benzamide (BTU-1), N-(tert-butylcarbamothioyl) benzamide (BTU-2), and (4-bromo-N-(3-nitrophenyl) carbamothioyl benzamide (BTU-3) present selective antiprotozoal activity against all developmental forms of Trypanosoma cruzi Y strain. In this study, we investigated the mechanism of action of these compounds through microscopy and biochemical analyses. Transmission electron microscopy analysis showed nuclear disorganization, changes in the plasma membrane with the appearance of blebs and extracellular arrangements, intense vacuolization, mitochondrial swelling, and formation of myelin-like structures. Biochemical results showed changes in the mitochondrial membrane potential, reactive oxygen species content, lipid peroxidation, and plasma membrane fluidity. In addition, the formation of autophagic vacuoles was observed. These findings indicate that BTU-1, BTU-2, and BTU-3 induced profound morphological, ultrastructural, and biochemical alterations in epimastigote forms, triggering an autophagic-dependent cell death pathway.

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Synthesis of benzoylthiourea derivatives and analysis of their antibacterial performance against planktonic Staphylococcus aureus and its biofilms

Cited by 7 publications

References 17 publications

Synergistic antifungal interaction of N-(butylcarbamothioyl) benzamide and amphotericin B against Cryptococcus neoformans

Synergistic antifungal interaction of N-(butylcarbamothioyl) benzamide and amphotericin B against Cryptococcus neoformans

Aroyl-isothiocyanates/isoselenocyanates as precursors to obtain novel cis-3-aroyl-thiourea/urea-β-lactams: design, synthesis, docking and biological evaluation

Antiprotozoal Activity of Benzoylthiourea Derivatives against Trypanosoma cruzi: Insights into Mechanism of Action

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