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Novel C-2 Symmetric Molecules as -Glucosidase and -Amylase Inhibitors: Design, Synthesis, Kinetic Evaluation, Molecular Docking and Pharmacokinetics
Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.
Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.ORCID iD: 0000-0002-7112-9296
Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.ORCID iD: 0000-0002-8491-5229
Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.
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2019 (English)In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 24, no 8, article id 1511Article in journal (Refereed) Published
Abstract [en]

A series of symmetrical salicylaldehyde-bishydrazine azo molecules, 5a-5h, have been synthesized, characterized by H-1-NMR and C-13-NMR, and evaluated for their in vitro -glucosidase and -amylase inhibitory activities. All the synthesized compounds efficiently inhibited both enzymes. Compound 5g was the most potent derivative in the series, and powerfully inhibited both -glucosidase and -amylase. The IC50 of 5g against -glucosidase was 0.35917 +/- 0.0189 mu M (standard acarbose IC50 = 6.109 +/- 0.329 mu M), and the IC50 value of 5g against -amylase was 0.4379 +/- 0.0423 mu M (standard acarbose IC50 = 33.178 +/- 2.392 mu M). The Lineweaver-Burk plot indicated that compound 5g is a competitive inhibitor of -glucosidase. The binding interactions of the most active analogues were confirmed through molecular docking studies. Docking studies showed that 5g interacts with the residues Trp690, Asp548, Arg425, and Glu426, which form hydrogen bonds to 5g with distances of 2.05, 2.20, 2.10 and 2.18 angstrom, respectively. All compounds showed high mutagenic and tumorigenic behaviors, and only 5e showed irritant properties. In addition, all the derivatives showed good antioxidant activities. The pharmacokinetic evaluation also revealed promising results

Place, publisher, year, edition, pages
MDPI , 2019. Vol. 24, no 8, article id 1511
Keywords [en]
bis-azo Schiff bases, dual inhibitor, -glucosidase inhibitor, -amylase, antioxidant, SAR, chemo-informatics, kinetic mechanism, molecular docking
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-387217DOI: 10.3390/molecules24081511ISI: 000467765700066PubMedID: 30999646OAI: oai:DiVA.org:uu-387217DiVA, id: diva2:1329920
Available from: 2019-06-25 Created: 2019-06-25 Last updated: 2019-06-25Bibliographically approved

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