Synthesis, in-vitro evaluation, molecular docking, and kinetic studies of pyridazine-triazole hybrid system as novel α-glucosidase inhibitors

Moghimi, Setareh; Salarinejad, Somayeh; Toolabi, Mahsa; Firoozpour, Loghman; Ebrahimi, Seyed Esmaeil Sadat; Safari, Fatemeh; Madani-Qamsari, Fatemeh; Mojtabavi, Somayeh; Faramarzi, Mohammad Ali; Karima, Saeed; Pakrad, Roya; Foroumadi, Alireza

doi:10.1016/j.bioorg.2021.104670

Cited by 31 publications

(12 citation statements)

References 50 publications

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“…The aim of type 2 diabetes (also known as diabetes mellitus) treatment is to lower blood glucose levels and manages any complications that may arise. Many reports suggest that triazole derivatives have greater pharmacological activity against type 2 diabetes mellitus [68–69] . Inflammation is a multifarious, self‐protective method, where the body gets the gathering of leukocytes and local fluid.…”

Section: Resultsmentioning

confidence: 99%

Design, Vibrational and Fluorescence Spectroscopic Properties, and Molecular Docking Studies of 3‐(5‐Bromobenzofuran‐3‐ylmethyl)‐5‐(4‐methoxyphenyl)‐4H‐[1,2,4]‐triazole by Experimental and Density Functional Theory Methods

Khemalapure¹,

Hiremath²,

Basanagouda³

et al. 2023

ChemistrySelect

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In this work, we have reported the spectral and several other properties of 3‐(5‐bromobenzofuran‐3‐ylmethyl)‐5‐(4‐methoxy‐phenyl)‐4H‐[1,2,4]triazole (BBT) molecule. Primarily, the experimental and computational analyses have been conducted for this molecule and compared the results. The computational studies have been conducted by Gaussian software with the help of DFT/B3LYP/6‐311++G (d, p) basis set. First, we have optimised BBT molecule to conduct the overall computational studies. The detailed computational and experimental vibrational analyses of BBT have been carried out. The electronic absorption and emission spectra of BBT have been observed in a variety of solvents with different solvent parameters like refractive index n, and dielectric constant ϵ. In solvatochromic studies, bathochromic (red) shift have observed in the absorption and emission spectra as an outcome of solute‐solvent interaction due to π → π* ${{\pi }^{{^\ast}}}$ transition. The solvent correlation methods experimentally investigated for the ground and excited‐state dipole moments. Along with these studies, we have also conducted Frontier Molecular Orbital (FMO) and Molecular Electrostatic Potential (MEP) analyses. Further, Molecular docking and drug likeness studies have also been performed to determine the pharmacological properties of the title molecule.

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Section: Resultsmentioning

confidence: 99%

Design, Vibrational and Fluorescence Spectroscopic Properties, and Molecular Docking Studies of 3‐(5‐Bromobenzofuran‐3‐ylmethyl)‐5‐(4‐methoxyphenyl)‐4H‐[1,2,4]‐triazole by Experimental and Density Functional Theory Methods

Khemalapure¹,

Hiremath²,

Basanagouda³

et al. 2023

ChemistrySelect

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“…Therefore, they play an important role in the absorption of sugars in the digestive tract, as erythrocytes can only absorb monosaccharides. The inhibitors of these enzymes are used in the treatment of type 2 diabetes patients [ 41 ]. In the literature, it has been reported that CS inhibits the alpha amylase [ 1 ].…”

Section: Resultsmentioning

confidence: 99%

Chondroitin Sulfate-Based Cryogels for Biomedical Applications

Demirci

Şahiner

Ari

et al. 2021

Gels

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Cryogels attained from natural materials offer exceptional properties in applications such as tissue engineering. Moreover, Halloysite Nanotubes (HNT) at 1:0.5 weight ratio were embedded into CS cryogels to render additional biomedical properties. The hemolysis index of CS cryogel and CS:HNT cryogels was calculated as 0.77 ± 0.41 and 0.81 ± 0.24 and defined as non-hemolytic materials. However, the blood coagulation indices of CS cryogel and CS:HNT cryogels were determined as 76 ± 2% and 68 ± 3%, suggesting a mild blood clotting capability. The maximum% swelling capacity of CS cryogel was measured as 3587 ± 186%, 4014 ± 184%, and 3984 ± 113%, at pH 1.0, pH 7.4 and pH 9.0, respectively, which were reduced to 1961 ± 288%, 2816 ± 192, 2405 ± 73%, respectively, for CS:HNT cryogel. It was found that CS cryogels can hydrolytically be degraded 41 ± 1% (by wt) in 16-day incubation, whereas the CS:HNT cryogels degraded by 30 ± 1 wt %. There is no chelation for HNT and 67.5 ± 1% Cu(II) chelation for linear CS was measured. On the other hand, the CS cryogel and CS:HNT cryogel revealed Cu(II) chelating capabilities of 60.1 ± 12.5%, and 43.2 ± 17.5%, respectively, from 0.1 mg/mL Cu(II) ion stock solution. Additionally, at 0.5 mg/mL CS, CS:HNT, and HNT, the Fe(II) chelation capacity of 99.7 ± 0.6, 86.2 ± 4.7% and only 11.9 ± 4.5% were measured, respectively, while no Fe(II) was chelated by linear CS chelated Fe(II). As the adjustable and controllable swelling properties of cryogels are important parameters in biomedical applications, the swelling properties of CS cryogels, at different solution pHs, e.g., at the solution pHs of 1.0, 7.4 and 9.0, were measured as 3587 ± 186%, 4014 ± 184%, and 3984 ± 113%, respectively, and the maximum selling% values of CS:HNT cryogels were determined as 1961 ± 288%, 2816 ± 192, 2405 ± 73%, respectively, at the same conditions. Alpha glucosidase enzyme interactions were investigated and found that CS-based cryogels can stimulate this enzyme at any CS formulation.

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“…Inhibition type and inhibition mode of ASOPC on α -glucosidase were determined as previously described by Moghimi et al) 43 , with minor modifications. Briefly, inhibition type (reversible or irreversible) was determined by performing the above-mentioned assay using four different enzyme concentrations (0.0375, 0.075, 0.15, 0.3 Unit/mL) without or with ASOPC at different concentrations (0.0625, 0.25, 0.5 µg/mL), while substrate concentration was kept constant.…”

Section: Methodsmentioning

confidence: 99%

Oligomeric Proanthocyanidin Complex from Avocado Seed as A Promising α-glucosidase Inhibitor: Characteristics and Mechanisms

et al. 2022

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Although considered as an abundant source of agricultural by-products, avocado (Persea americana Mill.) seed, with several biological activities and bioactive components, might become a promising resource for phytopharmaceutical development. In this study, through bioassay-guided isolation of the main α-glucosidase inhibitors in avocado seed, we discovered the major α-glucosidase inhibitor to be avocado seed oligomeric proanthocyanidin complex (ASOPC). Thiolysis and UPLC-DAD-HRESIMS showed the presence of A- and B-type procyanidins, and B-type propelargonidin with (epi)afzelechin as extension unit. Mean degree of polymerization (mDP) of ASOPC was calculated as 7.3±1. Furthermore, ASOPC appeared to be a strong, reversible, competitive inhibitor of α-glucosidase, with IC50 value of 0.1 µg/mL, which was significantly lower than Acarbose (IC50 = 75.6 µg/mL), indicated that ASOPC is a potential natural α-glucosidase inhibitor. These findings would contribute to the direction of utilizing avocado seed bioactive components with the possibility to be used as natural anti-diabetic agents.

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Synthesis, in-vitro evaluation, molecular docking, and kinetic studies of pyridazine-triazole hybrid system as novel α-glucosidase inhibitors

Cited by 31 publications

References 50 publications

Design, Vibrational and Fluorescence Spectroscopic Properties, and Molecular Docking Studies of 3‐(5‐Bromobenzofuran‐3‐ylmethyl)‐5‐(4‐methoxyphenyl)‐4H‐[1,2,4]‐triazole by Experimental and Density Functional Theory Methods

Design, Vibrational and Fluorescence Spectroscopic Properties, and Molecular Docking Studies of 3‐(5‐Bromobenzofuran‐3‐ylmethyl)‐5‐(4‐methoxyphenyl)‐4H‐[1,2,4]‐triazole by Experimental and Density Functional Theory Methods

Chondroitin Sulfate-Based Cryogels for Biomedical Applications

Oligomeric Proanthocyanidin Complex from Avocado Seed as A Promising α-glucosidase Inhibitor: Characteristics and Mechanisms

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