A rhodanine derivative as a potential antibacterial and anticancer agent: Crystal structure, spectral characterization, DFT calculations, Hirshfeld surface analysis, in silico molecular docking and ADMET studies

Guerraoui, Amal; Goudjil, Meriem; Direm, Amani; Guerraoui, Abdenour; Şengün, İlkin Yücel; Parlak, Cemal; Djedouani, Amel; Chelazzi, L.; Monti, Fiorella; Lunedei, E.; Boumaza, A.

doi:10.1016/j.molstruc.2023.135025

Cited by 16 publications

(6 citation statements)

References 87 publications

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“…In our case, the HOMO energy was found in the range of −5.01 to −5.93 eV while LUMO in the range of −1.55 to −1.87 eV, leading to a HOMO–LUMO gap (Δ E ) value between 3.14 and 4.21 eV. This value is similar to that of the structurally close thiazolidinone derivatives reported earlier …”

Section: Resultssupporting

confidence: 87%

Synthesis, Characterization, Antiglycation Evaluation, Molecular Docking, and ADMET Studies of 4-Thiazolidinone Derivatives

Haque,

Khan,

Alenezi

et al. 2023

ACS Omega

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The design and development of new small-molecule glycation inhibitors are essential for preventing various chronic diseases, including diabetes mellitus, immunoinflammation, cardiovascular, and neurodegenerative diseases. 4-Thiazolidinone or thiazolidine-4-one is a well-known heterocyclic compound with the potential to inhibit the formation of advanced glycation end products. In the present work, we report the synthesis and characterization of four new 5-arylidene 3-cyclopropyl-2-(phenylimino)thiazolidin-4-one (1−4) compounds and their human serum albumin glycation inhibitory activity. One of the compounds 5-(2H-1,3-benzodioxol-5-ylmethylidene)-3-cyclopropyl-2-(phenylimino)-1,3-thiazolidin-4-one (3) showed potent inhibition in the synthesis of initial, intermediary, and final products of glycation reactions. Besides, conformational changes in the α-helix and β-sheet (due to hyperglycemia) were also found to be reversed upon the addition of (3). Experimental findings were complemented by computational [molecular docking, ADME/Tox, and density functional theory (DFT)] studies. The docking scores of the compounds were in order 1 > 3 > 2 > 4, indicating the importance of the polar group at the 5-arylidene moiety. The results of ADME/Tox and DFT calculations revealed the safe nature of the compounds with high drug-likeness and stability. Overall, we speculate that the results of this study could provide valuable insights into the biological activity of 4thiazolidinones.

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Section: Resultssupporting

confidence: 87%

Synthesis, Characterization, Antiglycation Evaluation, Molecular Docking, and ADMET Studies of 4-Thiazolidinone Derivatives

Haque,

Khan,

Alenezi

et al. 2023

ACS Omega

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“…After crystallization, the structures of pure Z isomers of compounds 5 , 6 , 7 , and 11 could be obtained by single-crystal X-ray diffraction (Figure b), evidencing the expected constitutions. The crystal structures of Z isomeric 5 , 6 , and 11 have also been published before. Pure E isomers of derivatives 1 , 5 , and 8 were isolated after high-performance liquid chromatography separation.…”

Section: Resultsmentioning

confidence: 99%

Rhodanine-Based Chromophores: Fast Access to Capable Photoswitches and Application in Light-Induced Apoptosis

Köttner,

Wolff,

Mayer

et al. 2024

J. Am. Chem. Soc.

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Molecular photoswitches are highly desirable in all chemistry-related areas of research. They provide effective outside control over geometric and electronic changes at the nanoscale using an easy to apply, waste-free stimulus. However, simple and effective access to such molecular tools is typically not granted, and elaborate syntheses and substitution schemes are needed in order to obtain efficient photoswitching properties. Here we present a series of rhodanine-based photoswitches that can be prepared in one simple synthetic step without requiring elaborate purification. Photoswitching is induced by UV and visible light in both switching directions, and thermal stabilities of the metastable states as well as quantum yields are very high. An additional benefit is the hydrogen-bonding capacity of the rhodanine fragment, which enables applications in supramolecular or medicinal chemistry. We further show that the known rhodanine-based inhibitor SMI-16a is a photoswitchable apoptosis inducer. The biological activity of SMI-16a can effectively be switched ON or OFF by reversible photoisomerization between the inactive E and the active Z isomer. Rhodanine-based photoswitches therefore represent an easy to access and highly valuable molecular toolbox for implementing light responsiveness to the breadth of functional molecular systems.

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“…Additionally, their toxicity was calculated using the online server admetSAR 1.0 ( ), 57 which forecasts the values of the studied molecule’s carcinogenicity, the acute oral toxicity, Ames toxicity, and inhibition of the human Ether-a-go-go-related gene.…”

Section: Methodsmentioning

confidence: 99%

New Thiophenyl-pyrazolyl-thiazole Hybrids as DHFR Inhibitors: Design, Synthesis, Antimicrobial Evaluation, Molecular Modeling, and Biodistribution Studies

Dawood,

Sayed,

Tohamy

et al. 2023

ACS Omega

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The antibiotic resistance problems constitute a considerable threat to human health worldwide; thus, the discovery of new antimicrobial candidates to conquer this issue is an imperative requirement. From this view, new thiophenyl-pyrazolyl-thiazole hybrids 3–10 were synthesized and screened for their antibacterial efficiency versus Gram – and Gram + bacterial strains compared to the reference drug amoxicillin. It was noticed that the new hybrids displayed significant antibacterial efficacy versus Gram – bacteria, especially against Pseudomonas aeruginosa. Also, all the screened candidates demonstrated a noticeable antifungal effect against Candida albicans (MICs = 3.9–125 μg/mL) relative to fluconazole (MIC = 250 μg/mL). Moreover, the new hybrids were investigated for their antituberculosis potency against Mycobacterium tuberculosis (RCMB 010126). Derivatives 4c, 6b, 8b, 9b, and 10b demonstrated prominent antituberculosis efficiency (MICs = 0.12–1.95 μg/mL) compared with the reference drug isoniazid (MIC = 0.12 μg/mL). The latter derivatives were further assessed for their inhibitory potency versus M. tuberculosis DHFR enzyme. The compounds 4c, 6b and 10b presented a remarkable suppression effect with IC50 values of 4.21, 5.70, and 10.59 μM, respectively, compared to that of trimethoprim (IC50 = 6.23 μM). Furthermore, biodistribution profile using radiolabeling way revealed a perceived uptake of 131I-compound 6b into infection induced models. The docking study for the new hybrids 4c, 6b, 8b, 9b and 10b was performed to illustrate the various binding modes with Mtb DHFR enzyme. In silico ADMET studies for the most potent inhibitors 4c, 6b and 10b were also accomplished to predict their pharmacokinetic and physicochemical features.

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A rhodanine derivative as a potential antibacterial and anticancer agent: Crystal structure, spectral characterization, DFT calculations, Hirshfeld surface analysis, in silico molecular docking and ADMET studies

Cited by 16 publications

References 87 publications

Synthesis, Characterization, Antiglycation Evaluation, Molecular Docking, and ADMET Studies of 4-Thiazolidinone Derivatives

Synthesis, Characterization, Antiglycation Evaluation, Molecular Docking, and ADMET Studies of 4-Thiazolidinone Derivatives

Rhodanine-Based Chromophores: Fast Access to Capable Photoswitches and Application in Light-Induced Apoptosis

New Thiophenyl-pyrazolyl-thiazole Hybrids as DHFR Inhibitors: Design, Synthesis, Antimicrobial Evaluation, Molecular Modeling, and Biodistribution Studies

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