Chromone-based benzohydrazide derivatives as potential α-glucosidase inhibitor: Synthesis, biological evaluation and molecular docking study

Fan, Meiyan; Yang, Wei; Peng, Zhiyuan; He, Yan; Wang, Guangcheng

doi:10.1016/j.bioorg.2022.106276

Cited by 30 publications

(9 citation statements)

References 48 publications

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“…The K I values of 6c , 9b , and 10c are 21.5, 1.25, and 139.0 µM, respectively. The K I values for these compounds are less than K m , indicating that they have a higher affinity for the enzyme than the substrate used in the assay [ 48 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Molecular Docking Studies of Alkoxy- and Imidazole-Substituted Xanthones as α-Amylase and α-Glucosidase Inhibitors

Aguila-Muñoz,

Vázquez-Lira,

Sarmiento-Tlale

et al. 2023

Molecules

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Current antidiabetic drugs have severe side effects, which may be minimized by new selective molecules that strongly inhibit α-glucosidase and weakly inhibit α-amylase. We have synthesized novel alkoxy-substituted xanthones and imidazole-substituted xanthones and have evaluated them for their in silico and in vitro α-glucosidase and α-amylase inhibition activity. Compounds 6c, 6e, and 9b promoted higher α-glucosidase inhibition (IC50 = 16.0, 12.8, and 4.0 µM, respectively) and lower α-amylase inhibition (IC50 = 76.7, 68.1, and >200 µM, respectively) compared to acarbose (IC50 = 306.7 µM for α-glucosidase and 20.0 µM for α-amylase). Contrarily, derivatives 10c and 10f showed higher α-amylase inhibition (IC50 = 5.4 and 8.7 µM, respectively) and lower α-glucosidase inhibition (IC50 = 232.7 and 145.2 µM, respectively). According to the structure–activity relationship, attaching 4-bromobutoxy or 4′-chlorophenylacetophenone moieties to the 2-hydroxy group of xanthone provides higher α-glucosidase inhibition and lower α-amylase inhibition. In silico studies suggest that these scaffolds are key in the activity and interaction of xanthone derivatives. Enzymatic kinetics studies showed that 6c, 9b, and10c are mainly mixed inhibitors on α-glucosidase and α-amylase. In addition, drug prediction and ADMET studies support that compounds 6c, 9b, and 10c are candidates with antidiabetic potential.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Molecular Docking Studies of Alkoxy- and Imidazole-Substituted Xanthones as α-Amylase and α-Glucosidase Inhibitors

Aguila-Muñoz,

Vázquez-Lira,

Sarmiento-Tlale

et al. 2023

Molecules

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“…The reported IC 50 values for triazine‐triazole, chromone‐based benzohydrazide and chromone hydrazone derivatives against α‐glucosidase were observed in the range from 11.63 ± 0.15 to 37.44 ± 0.35, 4.51 ± 0.09 to 27.21 ± 0.83, and 20.1 ± 0.19 μM to 45.7 ± 0.23 μM, respectively. [ 103–105 ] In the study of Tripath et al in 2014, [ 8 ] α‐glucosidase inhibition values for [Co (en) 3 ]·SO 4 and [Co (en) 3 ]·2Cl complexes were reported as 927.89 and 784.12 μM. In 2017, [ 4 ] the IC 50 value of α − glucosidase inhibition for the Zn complex containing N 2 O 2 was found to be 0.23 mM.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, DFT calculations, α‐glucosidase inhibitor activity, and docking studies on Schiff base metal complexes containing isothiocyanate

Özge

Avcı

Sönmez

et al. 2023

Applied Organom Chemis

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Diabetes is one of the fastest growing global health crises of the 21st century.One of the current therapeutic approaches used in the treatment of diabetes involves the suppression of carbohydrate hydrolyzing enzymes such as α-glucosidase. In this context, α-glucosidase inhibitors are important in the treatment and prevention of diabetes. For this reason, new Schiff base complexes 4), [Hg(L 1 ) 2 (NCS)Cl], (5); L 1 : N-(pyridin-2-ylmethylene)methanamine} were synthesized to investigate α-glucosidase inhibitor potentials. The IC 50 values of complexes 1-5 were found at 0.2376 ± 0.82 and 251.403 ± 2.54-μM range. Among these complexes, complex 5 has the highest α-glucosidase inhibitor property. The spectral investigations for the complexes 1/2-5 characterized by XRD/LC-HRMS were performed by UV-Vis and FT-IR spectra. Furthermore, the TD-DFT/DFT calculations were fulfilled by using CAM-B3LYP and ωB97XD/6-311+G(d,p)//LanL2DZ levels to obtain optimum complex structures, spectral, linear and nonlinear optical properties for 1-5. According to obtained theoretical nonlinear optical results, complex 3 is a strong indicator in terms of microscopic nonlinear optical (NLO) properties. The docking studies of these complexes were examined to display the target protein interactions with these complexes.

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“…CD spectroscopy of PTP1B and its mixture with compound MY17 was conducted at 200–250 nm based on a previous report. , The concentrations of PTP1B and MY17 were both 7.15 μM. The secondary-structure contents of PTP1B were obtained using the SELCON3 algorithm.…”

Section: Methodsmentioning

confidence: 99%

Identification of 1,3,4-Thiadiazolyl-Containing Thiazolidine-2,4-dione Derivatives as Novel PTP1B Inhibitors with Antidiabetic Activity

Li,

Min

et al. 2024

J. Med. Chem.

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Forty-one 1,3,4-thiadiazolyl-containing thiazolidine-2,4dione derivatives (MY1−41) were designed and synthesized as protein tyrosine phosphatase 1B (PTP1B) inhibitors with activity against diabetes mellitus (DM). All synthesized compounds (MY1−41) presented potential PTP1B inhibitory activities, with half-maximal inhibitory concentration (IC 50 ) values ranging from 0.41 ± 0.05 to 4.68 ± 0.61 μM, compared with that of the positive control lithocholic acid (IC 50 = 9.62 ± 0.14 μM). The most potent compound, MY17 (IC 50 = 0.41 ± 0.05 μM), was a reversible, noncompetitive inhibitor of PTP1B. Circular dichroism spectroscopy and molecular docking were employed to analyze the binding interaction between MY17 and PTP1B. In HepG2 cells, MY17 treatment could alleviate palmitic acid (PA)-induced insulin resistance by upregulating the expression of phosphorylated insulin receptor substrate and protein kinase B. In vivo, oral administration of MY17 could reduce the fasting blood glucose level and improve glucose tolerance and dyslipidemia in mice suffering from DM.

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Chromone-based benzohydrazide derivatives as potential α-glucosidase inhibitor: Synthesis, biological evaluation and molecular docking study

Cited by 30 publications

References 48 publications

Synthesis and Molecular Docking Studies of Alkoxy- and Imidazole-Substituted Xanthones as α-Amylase and α-Glucosidase Inhibitors

Synthesis and Molecular Docking Studies of Alkoxy- and Imidazole-Substituted Xanthones as α-Amylase and α-Glucosidase Inhibitors

Synthesis, DFT calculations, α‐glucosidase inhibitor activity, and docking studies on Schiff base metal complexes containing isothiocyanate

Identification of 1,3,4-Thiadiazolyl-Containing Thiazolidine-2,4-dione Derivatives as Novel PTP1B Inhibitors with Antidiabetic Activity

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