4-Oxycoumarinyl linked acetohydrazide Schiff bases as potent urease inhibitors

Naz, Fouzia; Kanwal,; Latif, Mehreen; Salar, Uzma; Khan, Khalid Mohammed; al‐Rashida, Mariya; Ali, Irfan; Ali, Bakhat; Taha, Muhammad; Perveen, Shahnaz

doi:10.1016/j.bioorg.2020.104365

Cited by 15 publications

(7 citation statements)

References 39 publications

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“…Urease activity was calculated with the rate of production of ammonia, and alteration in absorbance was examined at 630 nm with an ELISA plate reader (Spectra Max M2, Molecular Devices, CA, USA). Thiourea was used as a standard control …”

Section: Methodsmentioning

confidence: 99%

“…Thiourea was used as a standard control. 6 Molecular Docking Study. The Molecular Operating Environment (MOE) software package was used to perform molecular docking study in order to explore the binding mode of the synthesized compounds within the active site of urease enzyme.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…Urea is the chief nitrogenous left-over of biological systems, which is quickly metabolized by the action of microorganisms. − Urease enzyme (EC 3.5.1.5) is present in bacteria, fungi, and plants. It plays a pivotal role in the nitrogen cycle, as it supplies nitrogen for the growth of microorganisms by catalyzing the hydrolysis of urea into ammonia and carbon dioxide at the rate approximately 10 14 faster than a noncatalyzed reaction. − Urease is important for hydrolysis of urea; nevertheless, its over expression leads to various problems in living organisms and causes environmental and economic damages . In humans and other animals, urease hyperactivity leads to various pathological problems, such as kidney stones, peptic ulcers, infection-induced reactive arthritis, and pyelonephritis .…”

Section: Introductionmentioning

confidence: 99%

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N-Aryl-3,4-dihydroisoquinoline Carbothioamide Analogues as Potential Urease Inhibitors

et al. 2021

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N-Aryl-3,4-dihydroisoquinoline carbothioamide analogues 1−22 were synthesized by a simple one-step reaction protocol and subjected to in vitro urease inhibition studies for the first time. All compounds 1−22 were found active and showed significant to moderate urease inhibitory potential. Specifically, analogues 1, 2, 4, and 7 were identified to be more potent (IC 50 = 11.2 ± 0.81−20.4 ± 0.22 μM) than the standard thiourea (IC 50 = 21.7 ± 0.34 μM). The structure−activity relationship showed that compounds bearing electron-donating groups showed superior activity. Molecular docking study on the most active derivatives revealed a good protein−ligand interaction profile against the corresponding target with key interactions, including hydrogen bonding, hydrophobic, and π-anion interactions.

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Section: Methodsmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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N-Aryl-3,4-dihydroisoquinoline Carbothioamide Analogues as Potential Urease Inhibitors

et al. 2021

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“…Biologically induced mineralization occurs when urease-producing bacteria produce calcium carbonate (CaCO 3 ), resulting in the gradual coating of bacterial cells as the number of CaCO 3 crystals increases. This coating makes it difficult for the cells to transport and utilize nutrients required for metabolic activities, leading to their eventual death in solution (Kappaun et al, 2018;Naz et al, 2020). The type, size, and morphology of the mineralization products vary depending on the specific bacterial strains used under the same culture conditions.…”

Section: Introductionmentioning

confidence: 99%

Characterization and genome analysis of Neobacillus mesonae NS-6, a ureolysis-driven strain inducing calcium carbonate precipitation

Xu,

Zhang,

et al. 2023

Front. Microbiol.

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In this study, a highly promising bacterium was isolated from sandstone oil in the Ordos Basin, named strain NS-6 which exhibited exceptional urease production ability and demonstrated superior efficiency in inducing the deposition of calcium carbonate (CaCO3). Through morphological and physiochemical characteristics analysis, as well as 16S rRNA sequencing, strain NS-6 was identified as Neobacillus mesonae. The activity of urease and the formation of CaCO3 increased over time, reaching a maximum of 7.9 mmol/L/min and 184 mg (4.60 mg/mL) respectively at 32 h of incubation. Scanning Electron Microscopy (SEM) revealed CaCO3 crystals ranging in size from 5 to 6 μm, and Energy Dispersive X-ray (EDX) analysis verified the presence of calcium, carbon, and oxygen within the crystals. X-ray Diffraction (XRD) analysis further confirmed the composition of these CaCO3 crystals as calcite and vaterite. Furthermore, the maximum deposition of CaCO3 by strain NS-6 was achieved using response surface methodology (RSM), amounting to 193.8 mg (4.845 mg/mL) when the concentration of calcium ions was 0.5 mmol/L supplemented with 0.9 mmol/L of urea at pH 8.0. Genome-wide analysis revealed that strain NS-6 possesses a chromosome of 5,736,360 base pairs, containing 5,442 predicted genes, including 3,966 predicted functional genes and 1,476 functionally unknown genes. Genes like ureA, ureB, and ureC related to urea catabolism were identified by gene annotation, indicating that strain NS-6 is a typical urease-producing bacterium and possesses a serial of genes involved in metabolic pathways that mediated the deposition of CaCO3 at genetic level.

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“…In addition, among potential pharmacological properties, these molecules are known to exhibit inhibitory effect on urease. Therefore, these pharmacologically important scaffolds are combined into single hybrid molecules to evaluate their potential as urease inhibitors [1a,b] …”

Section: Introductionmentioning

confidence: 99%

Methimazole Analogs as Urease Inhibitors: Synthesis, In Silico and In Vitro Evaluation

Çapan

2022

ChemistrySelect

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Urease plays a key role in urinary tract and gastrointestinal infections for which inhibition of it could prove to be substantial as a potential therapeutic option. Here, synthesized thirty novel compounds in four different series based on methimazole skeleton, also known as thiamazole, a drug that is used for the treatment of hyperthyroidism. Characterization of novel compounds consisting oxadiazoles, hydrazine-1-carbothioamides and N'-arylidenebenzohydrazides were performed by 1 H-, 13 C-NMR and high resolution mass spectrometry (HRMS).The synthesized molecules were examined for structure-activity relationship in urease inhibition and found to exhibit inhibitory potency in a range of IC50 = 3.56-14.08 μM compared to urea and acetohydroxamic acid used as standard. Moreover, molecular docking was performed to understand ligand binding interactions in the active site of the enzyme (Jack bean urease, Protein Data Bank ID 3LA4). The promise of addressing urinary tract and gastrointestinal disorders through urease inhibition is discussed.

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4-Oxycoumarinyl linked acetohydrazide Schiff bases as potent urease inhibitors

Cited by 15 publications

References 39 publications

N-Aryl-3,4-dihydroisoquinoline Carbothioamide Analogues as Potential Urease Inhibitors

N-Aryl-3,4-dihydroisoquinoline Carbothioamide Analogues as Potential Urease Inhibitors

Characterization and genome analysis of Neobacillus mesonae NS-6, a ureolysis-driven strain inducing calcium carbonate precipitation

Methimazole Analogs as Urease Inhibitors: Synthesis, In Silico and In Vitro Evaluation

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