Design and synthesis of novel xanthone-triazole derivatives as potential antidiabetic agents: α-Glucosidase inhibition and glucose uptake promotion

Ye, Gao-Jie; Lan, Tian; Huang, Zhixin; Cheng, Xiao‐Ning; Cai, Chao-Yun; Ding, Sen-Miao; Xie, Minli; Wang, Bo

doi:10.1016/j.ejmech.2019.05.045

Cited by 91 publications

(38 citation statements)

References 44 publications

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“…The α-glucosidase inhibitory evaluation of the purchased 52 compounds was performed according to the previously described protocol (Tang et al, 2014;Ye et al, 2019). α-Glucosidase (Sigma, G5003) derived from baker's yeast, and pNPG (Sigma, N1377) and the substrate were both purchased from Sigma-Aldrich.…”

Section: α-Glycosidase Inhibitory Assaymentioning

confidence: 99%

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Discovery of New α-Glucosidase Inhibitors: Structure-Based Virtual Screening and Biological Evaluation

et al. 2021

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α-Glycosidase inhibitors could inhibit the digestion of carbohydrates into glucose and promote glucose conversion, which have been used for the treatment of type 2 diabetes. In the present study, 52 candidates of α-glycosidase inhibitors were selected from commercial Specs compound library based on molecular docking–based virtual screening. Four different scaffold compounds (7, 22, 37, and 44) were identified as α-glycosidase inhibitors with IC50 values ranging from 9.99 to 35.19 μM. All these four compounds exerted better inhibitory activities than the positive control (1-deoxynojirimycin, IC50 = 52.02 μM). The fluorescence quenching study and kinetic analysis revealed that all these compounds directly bind to α-glycosidase and belonged to the noncompetitive α-glycosidase inhibitors. Then, the binding modes of these four compounds were carefully investigated. Significantly, these four compounds showed nontoxicity (IC50 > 100 μM) toward the human normal hepatocyte cell line (LO2), which indicated the potential of developing into novel candidates for type 2 diabetes treatment.

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Section: α-Glycosidase Inhibitory Assaymentioning

confidence: 99%

“…Controlling blood glucose levels is thought to be the main strategy for treating diabetes and reducing diabetes complications (Ye et al, 2019). α-Glucosidase is a key carbohydrate hydrolase that regulates blood glucose by specifically hydrolyzing 1,4-α-glucopyranosidic bond to produce α-glucose (Kazmi et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

Discovery of New α-Glucosidase Inhibitors: Structure-Based Virtual Screening and Biological Evaluation

et al. 2021

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“…Eaton's reagent [188,189] The xanthone α-mangostin (1) ( Figure 6) is considered a reliable agent that can be used in the prevention and treatment of various diseases, especially cancer and inflammatory conditions. The anticancer and cytotoxic properties of this compound have been evidenced in several in vitro and in vivo studies, demonstrating that it can act on all stages of carcinogenesis: initiation, promotion and progression.…”

Section: Derivativesmentioning

confidence: 99%

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

Klein‐Júnior

Campos

Niero

et al. 2020

Chemistry & Biodiversity

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Xanthones are a class of heterocyclic natural products that have been widely studied for their pharmacological potential. In fact, they have been serving as scaffolds for the design of derivatives focusing on drug development. One of the main study targets of xanthones is their anticancer activity. Several compounds belonging to this class have already demonstrated cytotoxic and antitumor effects, making it a promising group for further exploration. This review therefore focuses on recently published studies, emphasizing their natural and synthetic sources and describing the main mechanisms of action responsible for the anticancer effect of promising xanthones.

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“…Except of thiazole and thiazolidinone rings 1,2,4-triazole system attracted scientific interest due to the anti-inflammatory [34,35], antibacterial [36,37], anticancer [38], antiviral [38] and many other activities [39][40][41].…”

Section: Introductionmentioning

confidence: 99%

New Substituted 5-Benzylideno-2-Adamantylthiazol[3,2-b][1,2,4]Triazol-6(5H)ones as Possible Anti-Inflammatory Agents

et al. 2021

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Background: Inflammation is a complex response to noxious stimuli promoted by the release of chemical mediators from the damaged cells. Metabolic products of arachidonic acid, produced by the action of cyclooxygenase and lipoxygenase, play important roles in this process. Several non-steroidal anti-inflammatory drugs act as cyclooxygenase inhibitors. However, almost all of them have undesired side effects. Methods: Prediction of the anti-inflammatory action of the compounds was performed using PASS Program. The anti-inflammatory activity was evaluated by the carrageenan paw edema test. COX and LOX inhibitory actions were tested using ovine COX-1, human recombinant COX-2 and soybean LOX-1, respectively. Docking analysis was performed using Autodock. Results: All designed derivatives had good prediction results according to PASS and were synthesized and experimentally evaluated. The compounds exhibited in vivo anti-inflammatory action with eleven being equal or better than indomethacin. Although, some of them had no or low inhibitory effect on COX-1/2 or LOX, certain compounds exhibited COX-1 inhibition much higher than naproxen and COX-2 inhibition, well explained by Docking analysis. Conclusions: A number of compounds with good anti-inflammatory action were obtained. Although, some exhibited remarkable COX inhibitory action this activity did not follow the anti-inflammatory results, indicating the implication of other mechanisms.

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Design and synthesis of novel xanthone-triazole derivatives as potential antidiabetic agents: α-Glucosidase inhibition and glucose uptake promotion

Cited by 91 publications

References 44 publications

Discovery of New α-Glucosidase Inhibitors: Structure-Based Virtual Screening and Biological Evaluation

Discovery of New α-Glucosidase Inhibitors: Structure-Based Virtual Screening and Biological Evaluation

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

New Substituted 5-Benzylideno-2-Adamantylthiazol[3,2-b][1,2,4]Triazol-6(5H)ones as Possible Anti-Inflammatory Agents

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