Synthesis, spectroscopic characterizations, enzyme inhibition, molecular docking study and DFT calculations of new Schiff bases of sulfa drugs

Alyar, Saliha; Sen, Tulin; Özmen, Ümmühan Özdemir; Alyar, Hamit; Adem, Şevki; Şen, Cihan

doi:10.1016/j.molstruc.2019.03.002

Cited by 67 publications

(49 citation statements)

References 47 publications

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“…The functional groups, namely hydroxyl, carbonyl, and amino moieties, of this compound actively participated in the interactions with the active site residues of the enzyme, and may have contributed to the inhibition activities. The findings are in line with the previous study, where it had been reported that the oxygen and nitrogen atoms played an important role in exerting the inhibition activities by forming hydrogen bonds with the residues of the enzyme [72,73]. On the other hand, the lower binding affinity exhibited by the compound 11-AG docked complex may be due to the absence of hydrophobic interactions that may also play a crucial role in ligand binding towards the AG enzyme.…”

Section: In-silico Studysupporting

confidence: 92%

GC-MS- and NMR-Based Metabolomics and Molecular Docking Reveal the Potential Alpha-Glucosidase Inhibitors from Psychotria malayana Jack Leaves

et al. 2021

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Psychotria malayana Jack leaf, known in Indonesia as “daun salung”, is traditionally used for the treatment of diabetes and other diseases. Despite its potential, the phytochemical study related to its anti-diabetic activity is still lacking. Thus, this study aimed to identify putative inhibitors of α-glucosidase, a prominent enzyme contributing to diabetes type 2 in P. malayana leaf extract using gas chromatography-mass spectrometry (GC-MS)- and nuclear magnetic resonance (NMR)-based metabolomics, and to investigate the molecular interaction between those inhibitors and the enzyme through in silico approach. Twenty samples were extracted with different solvent ratios of methanol–water (0, 25, 50, 75, and 100% v/v). All extracts were tested on the alpha-glucosidase inhibition (AGI) assay and analyzed using GC-MS and NMR. Multivariate data analysis through a partial least square (PLS) and orthogonal partial square (OPLS) models were developed in order to correlate the metabolite profile and the bioactivity leading to the annotation of the putative bioactive compounds in the plant extracts. A total of ten putative bioactive compounds were identified and some of them reported in this plant for the first time, namely 1,3,5-benzenetriol (1); palmitic acid (2); cholesta-7,9(11)-diene-3-ol (3); 1-monopalmitin (4); β-tocopherol (5); α-tocopherol (6); 24-epicampesterol (7); stigmast-5-ene (8); 4-hydroxyphenylpyruvic acid (10); and glutamine (11). For the evaluation of the potential binding modes between the inhibitors and protein, the in silico study via molecular docking was performed where the crystal structure of Saccharomyces cerevisiae isomaltase (PDB code: 3A4A) was used. Ten amino acid residues, namely ASP352, HIE351, GLN182, ARG442, ASH215, SER311, ARG213, GLH277, GLN279, and PRO312 established hydrogen bond in the docked complex, as well as hydrophobic interaction of other amino acid residues with the putative compounds. The α-glucosidase inhibitors showed moderate to high binding affinities (−5.5 to −9.4 kcal/mol) towards the active site of the enzymatic protein, where compounds 3, 5, and 8 showed higher binding affinity compared to both quercetin and control ligand.

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Section: In-silico Studysupporting

confidence: 92%

GC-MS- and NMR-Based Metabolomics and Molecular Docking Reveal the Potential Alpha-Glucosidase Inhibitors from Psychotria malayana Jack Leaves

et al. 2021

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“…The theoretical calculations were performed for the optimization of structure of the compound using DFT method in gas phase. [ 10 ] The Gaussian 09 bundle was used for the visualization of theoretical results. [ 11 ] From the optimized geometries, the chemical shift (δ) values were calculated through gauge independent atomic orbital (GIAO) using B3LYP and LANL2DZ basis set.…”

Section: Methodsmentioning

confidence: 99%

Triorganotin (IV) carboxylates as potential anticancer agents: Their synthesis, physiochemical characterization, and cytotoxic activity against HeLa and MCF‐7 cancer cells

Uddin

Rashid

Haider

et al. 2021

Applied Organom Chemis

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Three triorganotin (IV) cyclopentane carboxylates were synthesized and structurally characterized by in solid state by Fourier‐transform infrared spectroscopy and single crystal diffraction, and in solution by NMR (1H, 13C, and 119Sn) spectroscopy. The complexes were tested for their anticancer activity against MCF‐7 and HeLa cells along with normal BHK‐21 cells. As revealed by MTT assay, complex 2 was identified as the most potent derivative with an IC50 value of 2.59 and 0.051 μM against HeLa and MCF‐7 cells, respectively. The results were compared with cisplatin as reference drug. Fluorescent microscopic studies using 4′,6‐diamidino‐2‐phenylindole (DAPI) and propidium iodide (PI) staining confirmed the occurrence of apoptosis in HeLa cells treated with the most active complex 2. The complex 2 also triggered the release of lactate dehydrogenase (LDH) in treated HeLa and MCF‐7 cells whereas a luminescence assay displayed a remarkable increase in the activity of caspase‐9 and ‐3. Moreover, flow cytometric results revealed that complex 2 caused G0/G1 arrest in the treated HeLa cells. The complexes were further screened for DNA binding studies through UV‐vis spectroscopy and cyclic voltammetry. The high activity of complex 2 was attributed to its higher Lewis acidity as indicated by natural bond orbital (NBO) analysis. Theoretical modelling and molecular docking studies were also conducted to study the reactivity of complexes against VEGFR 2 Kinase.

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“…The computational calculations were accomplished by DFT approach to optimize the structures in the gas phase [2]. 66 The Gaussian 09 package was used to visualize all the theoretical results. 67 The chemical shi (d) values were calculated from the optimized geometries by employing Gauge Independent Atomic Orbital (GIAO) with B3LYP functional and LANL2DZ basis set.…”

Section: Computational Detailsmentioning

confidence: 99%

“…Fig.9Absorption spectra of 200 mM of compound C2 in absence (0 mM) and presence(66, 132, 198, 264, 330, 396 mM) of DNA. The arrow direction shows increasing concentration of DNA.…”

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confidence: 99%

New triorganotin(iv) compounds with aromatic carboxylate ligands: synthesis and evaluation of the pro-apoptotic mechanism

et al. 2021

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Synthesis, spectroscopic characterizations, enzyme inhibition, molecular docking study and DFT calculations of new Schiff bases of sulfa drugs

Cited by 67 publications

References 47 publications

GC-MS- and NMR-Based Metabolomics and Molecular Docking Reveal the Potential Alpha-Glucosidase Inhibitors from Psychotria malayana Jack Leaves

GC-MS- and NMR-Based Metabolomics and Molecular Docking Reveal the Potential Alpha-Glucosidase Inhibitors from Psychotria malayana Jack Leaves

Triorganotin (IV) carboxylates as potential anticancer agents: Their synthesis, physiochemical characterization, and cytotoxic activity against HeLa and MCF‐7 cancer cells

New triorganotin(iv) compounds with aromatic carboxylate ligands: synthesis and evaluation of the pro-apoptotic mechanism

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