Biological effects of bis-hydrazone compounds bearing isovanillin moiety on the aldose reductase

Yapar, Gönül; Duran, Hatice Esra; Lolak, Nabih; Akocak, Süleyman; Türkeş, Cüneyt; Durgun, Mustafa; Işık, Mesut; Beydemır, Şükrü

doi:10.1016/j.bioorg.2021.105473

Cited by 56 publications

(49 citation statements)

References 91 publications

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“…The Maestro ver. 13.1, 41 Protein Preparation Wizard, 42 SiteMap, 43 Receptor Grid Generation, 44 LigPrep, 45 Glide Ligand Docking, 46 and Prime MM‐GBSA 47 tools from the Small‐Molecule Drug Discovery Suite 2022‐1 for Mac (Schrödinger, LLC, NY, USA) were used to perform molecular docking calculations. Fluorophenylthioureas were sketched in the 2D‐sdf format using ChemDraw ver.…”

Section: Methodsmentioning

confidence: 99%

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Screening of in vitro and in silico effect of Fluorophenylthiourea compounds on glucose 6‐phosphate dehydrogenase and 6‐phosphogluconate dehydrogenase enzymes

Yıldız

Demir

Küfrevioğlu

2022

J of Molecular Recognition

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Inhibition studies of enzymes in the pentose phosphate pathway (PPP) have recently emerged as a promising technique for pharmacological intervention in several illnesses. Glucose 6-phosphate dehydrogenase (G6PD) and 6-phosphogluconate dehydrogenase (6PGD) are the most important enzymes of the PPP. For this purpose, in the current study, we examined the effect of some fluorophenylthiourea on G6PD and 6PGD enzyme activity. These compounds exhibited moderate inhibitory activity against G6PD and 6PGD with K I values ranging from 21.60 ± 8.42 to 39.70 ± 11.26 μM, and 15.82 ± 1.54 to 29.97 ± 5.72 μM, respectively.2,6-difluorophenylthiourea displayed the most potent inhibitory effect for G6PD, and 2-fluorophenylthiourea demonstrated the most substantial inhibitory effect for 6PGD. Furthermore, the molecular docking analyses of the fluorophenylthioureas, competitive inhibitors, were performed to understand the binding interactions at the enzymes' binding site.6-phosphogluconate dehydrogenase, fluorophenylthiourea, glucose 6-phosphate dehydrogenase, molecular docking | INTRODUCTIONOne of the main intracellular reducing agents, nicotinamide adenine dinucleotide phosphate (NADPH), is mainly produced by the pentose phosphate pathway (PPP) and is crucial for the thioredoxin and glutathione systems. 1-4 PPP is the main pathway for glucose catabolism and the biosynthesis of aromatic amino acids, nucleic acids, glucose 6-phosphate dehydrogenase (G6PD), and 6-phosphogluconate dehydrogenase (6PGD) enzymes. These enzymes are the most important enzymes of the PPP play an essential role in the formation of NADPH. [5][6][7][8] On the other hand, an activated PPP affects tumor metabolism, such as angiogenesis, favoring tumor metastasis, promoting malignant transformation, protecting cells from apoptosis, and increasing tumor progression. [9][10][11][12] In recent years, overexpression of PPP enzymes in many types of cancer has been the focus of interest for researchers. The mechanism of PPP enzymes associated with cancer progression is still under investigation. The research found that 6PGD was regulated in many types of cancer, such as colon, leukemia, breast, ovarian, liver, and thyroid. [13][14][15] Thiourea structures have several biological activities, like anticancer and antibacterial activities, and especially on the central nervous system of rodents, they have a high impact. [16][17][18] The thiourea skeleton has an essential role in pharmaceutical chemistry. Studies have shown solid cytotoxic activity against cancer cells. [19][20][21] The desired inhibitory activity of these drugs against various inhibitors is crucial in the death of cancer cells. Recently, evaluation of novel derivatives of thiourea as anti-angiogenic and antitumor agents has been published. [22][23][24]

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Section: Methodsmentioning

confidence: 99%

“…The Maestro ver. 13.1, 41 Protein Preparation Wizard, 42 SiteMap, 43 Receptor Grid Generation, 44 LigPrep, 45 Glide Ligand Docking, 46 and Prime MM-GBSA 47 F I G U R E 1 (A) SDS-PAGE analysis of purified Glucose 6-phosphate dehydrogenase (G6PD) and 6-phosphogluconate dehydrogenase (6PGD).…”

Section: In Silico Studiesmentioning

confidence: 99%

Screening of in vitro and in silico effect of Fluorophenylthiourea compounds on glucose 6‐phosphate dehydrogenase and 6‐phosphogluconate dehydrogenase enzymes

Yıldız

Demir

Küfrevioğlu

2022

J of Molecular Recognition

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“…[84][85][86] For 3SRG-ligand complexes, the ability of MM-GBSA [87][88][89] to predict relative binding affinity in the VSGB energy model and OPLS4 force field was also tested. Furthermore, the QikProp module [90][91][92] was used to predict the ADME-Tox characteristics of the methyl benzoate derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17).…”

Section: Computational Studiesmentioning

confidence: 99%

Methyl benzoate derivatives: in vitro Paraoxonase 1 inhibition and in silico studies

Korkmaz

Türkeş

Demir

et al. 2022

J Biochem & Molecular Tox

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Paraoxonase 1 (PON1) can metabolize some compounds such as aromatic carboxylic acid and unsaturated aliphatic esters, arylesters, cyclic carbonate, plucuronide drugs, some carbamate insecticide classes, nerve gases, and lactone compounds. Methyl benzoate has recently been shown to display potent toxicity against several insect species. In the current study, we aimed to investigate the effect of the methyl benzoate compounds (1–17) on PON1 activity. Methyl benzoate compounds inhibited PON1 with KI values ranging from 25.10 ± 4.73 to 502.10 ± 64.72 μM. Compound 10 (methyl 4‐amino‐2‐bromo benzoate) showed the best inhibition (KI = 25.10 ± 4.73 μM). Furthermore, using the ADME‐Tox, Glide XP, and MM‐GBSA tools of the Schrödinger Suite 2021‐4, a complete ligand–receptor interaction prediction was performed to characterize the methyl benzoates (1–17), probable binding modalities versus the PON1.

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“…Furthermore, due to their diverse pharmacological activities, hydrazone derivatives have recently attracted the attention of medicinal chemists. Many studies have found that these compounds have a wide range of biological activities, such as anticancer [14] , antidiabetic [15] , antioxidant [16] , antimicrobial [ 17 , 18 ], antituberculosis [19] , anticholinesterase [20] , antifungal [21] and antiviral [ 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

New bis hydrazone: Synthesis, X-ray crystal structure, DFT computations, conformational study and in silico study of the inhibition activity of SARS-CoV-2

Tabbiche

Bouchama

Chafai

et al. 2022

Journal of Molecular Structure

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Biological effects of bis-hydrazone compounds bearing isovanillin moiety on the aldose reductase

Cited by 56 publications

References 91 publications

Screening of in vitro and in silico effect of Fluorophenylthiourea compounds on glucose 6‐phosphate dehydrogenase and 6‐phosphogluconate dehydrogenase enzymes

Screening of in vitro and in silico effect of Fluorophenylthiourea compounds on glucose 6‐phosphate dehydrogenase and 6‐phosphogluconate dehydrogenase enzymes

Methyl benzoate derivatives: in vitro Paraoxonase 1 inhibition and in silico studies

New bis hydrazone: Synthesis, X-ray crystal structure, DFT computations, conformational study and in silico study of the inhibition activity of SARS-CoV-2

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