Mohamad, Norhadi and Phua, Yoong Hui and Abu Bakar, Mohamad Hafizi and Omar, Mohammad Tasyriq Che and Wahab, Habibah A. and Supratman, Unang and Awang, Khalijah and Azmi, Mohamad Nurul (2021) Synthesis, biological evaluation of ortho-carboxamidostilbenes as potential inhibitors of hyperglycemic enzymes, and molecular docking study. Journal of Molecular Structure, 1245. ISSN 0022-2860, DOI https://doi.org/10.1016/j.molstruc.2021.131007.
Full text not available from this repository.Abstract
A new series of ortho-carboxamidostilbenes derivatives were synthesized via Heck Coupling and screened for their alpha-amylase and alpha-glucosidase inhibitory potential. The results indicated that all the synthesized compounds showed a substantial alpha-glucosidase inhibitory potential (IC50 between 3-78 mu g/mL) compared to acarbose (IC50 = 16.14 +/- 1.05 mu g/mL) as the standard. In addition, the IC50 values against alpha-amylase varying from 3-300 mu g/mL when compared to a standard drug acarbose (IC50 = 21.12 +/- 0.29 mu g/mL). In silico studies were carried out to understand the binding interaction between active compounds and enzymes. The results indicated that the binding energy displayed by compound 5a-5e ranging from -7.9 to -9.0 and -7.2 to -8.5 kcal/mol for the C-terminal subunit of human maltase glucoamylase, ctMGAM (alpha-glucosidase) and alpha-amylase, respectively. The interaction modes of 5d (IC50 = 2.90 +/- 0.58 mu g/mL) in ctMGAM, showed that alkyl and methoxy group interacted with TRP1369 via hydrogen bond and hydrophobic interaction, respectively. Meanwhile, the interaction modes of 5e with (IC50 = 2.94 +/- 0.69 mu g/mL) in alpha-amylase showed that the methoxy group interacted with TYR151 via conventional hydrogen bond. These compounds may be considered promising candidates for the development of new anti-diabetic agents. (C) 2021 Elsevier B.V. All rights reserved.
| Item Type: | Article |
|---|---|
| Funders: | Universiti Sains Malaysia[1001.PKIMIA.8012310], MyPair PHC Hibiscus[203.PKIMIA. 6782002] |
| Uncontrolled Keywords: | Ortho-carboxamidostilbenes;Heck coupling;Alpha-amylase; Alpha-glucosidase;Molecular docking |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science |
| Depositing User: | Ms Zaharah Ramly |
| Date Deposited: | 15 Jul 2022 08:12 |
| Last Modified: | 15 Jul 2022 08:12 |
| URI: | http://eprints.um.edu.my/id/eprint/34109 |
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