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Structural elucidation, molecular docking, ?-amylase and ?-glucosidase inhibition studies of 5-amino-nicotinic acid derivatives.

ABSTRACT: In this study, 5-amino-nicotinic acid derivatives (1-13) have been designed and synthesized to evaluate their inhibitory potential against ?-amylase and ?-glucosidase enzymes. The synthesized compounds (1-13) exhibited promising ?-amylase and ?-glucosidase activities. IC50 values for ?-amylase activity ranged between 12.17?±?0.14 to 37.33?±?0.02 µg/mL?±?SEM while for ?-glucosidase activity the IC50 values were ranged between 12.01?±?0.09 to 38.01?±?0.12 µg/mL?±?SEM. In particular, compounds 2 and 4-8 demonstrated significant inhibitory activities against ?-amylase and ?-glucosidase and the inhibitory potential of these compounds was comparable to the standard acarbose (10.98?±?0.03 and 10.79?±?0.17 µg/mL?±?SEM, respectively). In addition, the impact of substituent on the inhibitory potential of these compounds was assessed to establish structure activity relationships. Studies in molecular simulations were conducted to better comprehend the binding properties of the compounds. All the synthesized compounds were extensively characterized with modern spectroscopic methods including 1H-NMR, 13C-NMR, FTIR, HR-MS and elemental analysis.

SUBMITTER: Nawaz M

PROVIDER: S-EPMC7362424 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Structural elucidation, molecular docking, α-amylase and α-glucosidase inhibition studies of 5-amino-nicotinic acid derivatives.

Nawaz Muhammad M Taha Muhammad M Qureshi Faiza F Ullah Nisar N Selvaraj Manikandan M Shahzad Sumaira S Chigurupati Sridevi S Waheed Abdul A Almutairi Fadiah Ammar FA

BMC chemistry 20200714 1

In this study, 5-amino-nicotinic acid derivatives (1-13) have been designed and synthesized to evaluate their inhibitory potential against α-amylase and α-glucosidase enzymes. The synthesized compounds (1-13) exhibited promising α-amylase and α-glucosidase activities. IC50 values for α-amylase activity ranged between 12.17 ± 0.14 to 37.33 ± 0.02 µg/mL ± SEM while for α-glucosidase activity the IC50 values were ranged between 12.01 ± 0.09 to 38.01 ...[more]

PMID: 32685927

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Project description:IntroductionThe current study was designed to synthesize derivatives of succinimide and compare their biological potency in anticholinesterase, alpha-glucosidase inhibition, and antioxidant assays.MethodsIn this research, two succinimide derivatives including (S)-1-(2,5-dioxo-1-phenylpyrrolidin-3-yl) cyclohexanecarbaldehyde (Compound 1) and (R)-2-((S)-2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-phenylpropanal (Compound 2) were synthesized using Michael addition. Both the compounds, ie, 1 and 2 were evaluated for in-vitro acetylcholinesterase (AChE), butyrylctcholinesterase (BChE), antioxidant, and α-glucosidase inhibitory potentials. Furthermore, molecular docking was performed using Molecular Operating Environment (MOE) to explore the binding mode of both the compounds against different enzymes. Lineweaver-Burk plots of enzyme inhibitions representing the reciprocal of initial enzyme velocity versus the reciprocal of substrate concentration in the presence of synthesized compounds and standard drugs were constructed using Michaelis-Menten kinetics.ResultsIn AChE inhibitory assay, compounds 1 and 2 exhibited IC50 of 343.45 and 422.98 µM, respectively, against AChE enzyme. Similarly, both the compounds showed IC50 of 276.86 and 357.91 µM, respectively, against BChE enzyme. Compounds 1 and 2 displayed IC50 of 157.71 and 471.79 µM against α-glucosidase enzyme, respectively. In a similar pattern, compound 1 exhibited to be more potent as compared to compound 2 in all the three antioxidant assays. Compound 1 exhibited IC50 values of 297.98, 332.94, and 825.92 µM against DPPH, ABTS, and H2O2 free radicals, respectively. Molecular docking showed a triple fold in the AChE and BChE activity for compound 1 compared with compound 2. The compound 1 revealed good interaction against both the AChE and BChE enzymes which revealed the high potency of this compound compared to compound 2.ConclusionBoth succinimide derivatives exhibited considerable inhibitory activities against cholinesterases and α-glucosidase enzymes. Of these two, compound 1 revealed to be more potent against all the in-vitro targets which was supported by molecular docking with the lowest binding energies. Moreover, compound 1 also proved to have antiradical properties.

Dataset Information

Structural elucidation, molecular docking, ?-amylase and ?-glucosidase inhibition studies of 5-amino-nicotinic acid derivatives.

Publications

Structural elucidation, molecular docking, α-amylase and α-glucosidase inhibition studies of 5-amino-nicotinic acid derivatives.

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