Antioxidant and Antimicrobial Activities of Some Novel 2-Thiohydantoin Derivatives

Mutlaq, Dakhil Zughayir; Al-Shawi, Ali A. A.; AbdulJabar, Layla Adnan

doi:10.21608/ejchem.2020.47419.2963

Cited by 4 publications

(7 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On the other hand, compound 7a showed a considerable free radical scavenging activity with IC 50 of 65.5 µg/mL. These results are in agreement with previous reported studies which demonstrated that 2-thiohydantoins possess a potential antioxidant activity [32,41,75,76] The authors showed that this class of compounds possesses DPPH inhibition ranging from 2.77 to 47.98% at 100 µg/mL [39]. Our findings revealed that compounds 5a and 7a (1,3,5-trisubstitued-2-thiohydantoin) exhibited substantial antioxidant capability compared to that of the well-known antioxidant drug Torloxo.…”

Section: Evaluation Of Free Radical Scavenging Activitysupporting

confidence: 92%

“…On the other hand, compound 7a showed a considerable free radical scavenging activity with IC50 of 65.5 µg/mL. These results are in agreement with previous reported studies which demonstrated that 2-thiohydantoins possess a potential antioxidant activity [32,41,75,76]. Recently, Camargo et al reported the antioxidant activity of a set of C5-substitued-2-thiohydantoins and showed that this class of compounds possesses IC50 values of 40-200 µM toward DPPH-based scavenging activity [41].…”

Section: Evaluation Of Free Radical Scavenging Activitysupporting

confidence: 89%

“…Therefore, this class of compounds could be applied to preserve the cells from oxidative stress while employing their antidiabetic effect [85]. It should be noticed that previous studies mainly investigated the antioxidant activity of 3N or C5-substituted-2-thionhydantoins [32,39,41,75,76]. To the best of our knowledge, this is the first report to explore the antioxidant activity of 1,3,5-trisubstituted-2-thiohydantoins.…”

Section: Evaluation Of Reactive Oxygen Species Productionmentioning

confidence: 96%

“…This class of five-membered heterocycles is characterized by the presence of a reactive cyclic thiourea core and possesses several positions for substitution (N1, N3, and C5) [29]. A simple substitution on the 2-thiohydantoin scaffold can result in a variety of biological effects, such as anticancer, anti-inflammatory, antimicrobial, antidiabetic, antiviral, and antioxidant activity [30][31][32]. To date, the antidiabetic potential of 2-thiohydantoin scaffold has not been fully explored; however, several studies have demonstrated the antidiabetic activity of 2-thiohydantoin.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Antidiabetic Potential of Novel 1,3,5-Trisubstituted-2-Thioxoimidazloidin-4-One Analogues: Insights into α-Glucosidase, α-Amylase, and Antioxidant Activities

et al. 2022

View full text Add to dashboard Cite

As the ninth leading cause of death globally, diabetes mellitus (DM) is considered to be the worst chronic metabolic disease requiring an enormous need for healthcare with over 578 million expected cases by 2023. Several recent findings have demonstrated that mediating the activity of carbohydrate-hydrolyzing enzymes, including α-amylase and α-glucosidase, could be a potential strategy for managing the development of DM. In the presented study, a novel set of 1,3,5-trisubstituted-2-thioxoimidazolidin-4-ones was designed, synthesized, and characterized. The antidiabetic activity of the synthesized compounds was explored by assessing their inhibitory activity toward α-amylase and α-glucosidase enzymes. The results demonstrated that this class of compounds exhibits considerable inhibitory activity toward both α-amylase and α-glucosidase enzymes. Among the synthesized compounds, compound 5a demonstrated the most inhibitory activity with IC50 of 5.08 and µg/mL and 0.21 µg/mL toward α-glucosidase and α-amylase activities, respectively, as compared to the drug Acarbose (IC50 =5.76 µg/mL and 0.39 µg/mL, respectively). To gain insights into the antidiabetic potential of compound 5a, we assessed the cytotoxic and antioxidant activities. Our findings indicated that compound 5a displays considerable cytotoxicity toward WI-38 cells with an IC50 of 88.54 µg/mL, as compared to the drug Celecoxib (IC50 =93.05 µg/mL). Further, compound 5a exhibited a high scavenging activity toward 2,2-Diphenyl1-picrylhydrazyl (DPPH) free radicals (IC50 = 51.75 µg/mL) and showed a low potential to produce ROS as indicated by the monitoring of the generated H2O2 (132.4 pg/mL), as compared to Trolox (IC50 =58.09 µg/mL) and Celecoxib (171.6 pg/mL). Finally, we performed extensive molecular modeling studies to affirm the binding affinity of this class of compounds to the binding pocket of α-amylase and α-glucosidase enzymes. Collectively, our findings indicate that this class of compounds, particularly compound 5a, could be utilized as a lead structure for the development of novel compounds with potential antidiabetic and antioxidant activities.

show abstract

Section: Evaluation Of Free Radical Scavenging Activitysupporting

confidence: 92%

“…On the other hand, compound 7a showed a considerable free radical scavenging activity with IC50 of 65.5 µg/mL. These results are in agreement with previous reported studies which demonstrated that 2-thiohydantoins possess a potential antioxidant activity [32,41,75,76]. Recently, Camargo et al reported the antioxidant activity of a set of C5-substitued-2-thiohydantoins and showed that this class of compounds possesses IC50 values of 40-200 µM toward DPPH-based scavenging activity [41].…”

Section: Evaluation Of Free Radical Scavenging Activitysupporting

confidence: 89%

Section: Evaluation Of Reactive Oxygen Species Productionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Antidiabetic Potential of Novel 1,3,5-Trisubstituted-2-Thioxoimidazloidin-4-One Analogues: Insights into α-Glucosidase, α-Amylase, and Antioxidant Activities

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Among already applied drugs, quinolones and thiohydantoin derivatives are used as chemotherapeutics and antibiotics. Compounds containing 2-thiohydantoin core reveal antibacterial [ 1 , 2 , 3 ], antifungal [ 4 ], antitumor [ 5 ], antiparasitic [ 6 ], and antiviral activity [ 7 ]. Compounds with 2-quinolone core are also known for their broad range of biological effects [ 8 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

Preliminary Studies of Antimicrobial Activity of New Synthesized Hybrids of 2-Thiohydantoin and 2-Quinolone Derivatives Activated with Blue Light

et al. 2022

View full text Add to dashboard Cite

Thiohydantoin and quinolone derivatives have attracted researchers’ attention because of a broad spectrum of their medical applications. The aim of our research was to synthesize and analyze the antimicrobial properties of novel 2-thiohydantoin and 2-quinolone derivatives. For this purpose, two series of hybrid compounds were synthesized. Both series consisted of 2-thiohydantoin core and 2-quinolone derivative ring, however one of them was enriched with an acetic acid group at N3 atom in 2-thiohydantoin core. Antibacterial properties of these compounds were examined against bacteria: Staphylococcus aureus, Bacillus subtilis, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae. The antimicrobial assay was carried out using a serial dilution method to obtain the MIC. The influence of blue light irradiation on the tested compounds was investigated. The relative yield of singlet oxygen (1O2*, 1Δg) generation upon excitation with 420 nm was determined by a comparative method, employing perinaphthenone (PN) as a standard. Antimicrobial properties were also investigated after blue light irradiation of the suspensions of the hybrids and bacteria placed in microtitrate plates. Preliminary results confirmed that some of the hybrid compounds showed bacteriostatic activity to the reference Gram-positive bacterial strains and a few of them were bacteriostatic towards Gram-negative bacteria, as well. Blue light activation enhanced bacteriostatic effect of the tested compounds.

show abstract

Study of the Anticancer and Antimicrobial Biological Activity of a New Series of Thiohydantoin Derivatives

Hays,

Mutlaq

2023

Baghdad Sci.J

View full text Add to dashboard Cite

Recently, some prostate cancer patients have acquired resistance to the second -generation drugs (anzalutamide and apalutamide) prescribed for the treatment of this disease due to the emergence of the F876L mutation, which represents a challenge to modern medicine. In this study, a new series of 2-thiohydantoin derivatives were prepared through the reaction of different derivatives of maleimide (1c-4c) with isothiocyanate derivatives. The prepared compounds were diagnosed using FT-IR,1H-NMR ,13C-NMR, Mass spectra. The prepared series compounds has been studied against prostate cancer cells. The MTT assay was used to determine the activity of the prepared compounds against prostate cancer cells. The data indicated, depending on the IC50 values, that some of the prepared compounds have anti-prostate cancer activity. The results indicate that compounds 1d and 2d have good anti-prostate cancer activity compared to the rest of the compounds. The prepared series of compounds were also studied against selected types of bacteria and fungi, as the results showed that some of the compounds in the series had anti-bacterial and anti-fungal activity.

show abstract

Antioxidant and Antimicrobial Activities of Some Novel 2-Thiohydantoin Derivatives

Cited by 4 publications

References 20 publications

Antidiabetic Potential of Novel 1,3,5-Trisubstituted-2-Thioxoimidazloidin-4-One Analogues: Insights into α-Glucosidase, α-Amylase, and Antioxidant Activities

Antidiabetic Potential of Novel 1,3,5-Trisubstituted-2-Thioxoimidazloidin-4-One Analogues: Insights into α-Glucosidase, α-Amylase, and Antioxidant Activities

Preliminary Studies of Antimicrobial Activity of New Synthesized Hybrids of 2-Thiohydantoin and 2-Quinolone Derivatives Activated with Blue Light

Study of the Anticancer and Antimicrobial Biological Activity of a New Series of Thiohydantoin Derivatives

Contact Info

Product

Resources

About