Benzenesulfonamide derivatives as potent acetylcholinesterase, α-glycosidase, and glutathione S-transferase inhibitors: biological evaluation and molecular docking studies.

Taslimi P., Işık M., Türkan F., Durgun M., Türkeş C., Gülçin İ., ...Daha Fazla

Journal of biomolecular structure & dynamics, ss.1-12, 2020 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1080/07391102.2020.1790422
  • Dergi Adı: Journal of biomolecular structure & dynamics
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, BIOSIS, Chemical Abstracts Core, EMBASE, MEDLINE
  • Sayfa Sayıları: ss.1-12
  • Anahtar Kelimeler: alpha-Glycosidase, acetylcholinesterase, glutathione S-transferase, molecular docking, sulfonamide derivatives, ANHYDRASE ISOFORMS I, CARBONIC-ANHYDRASE, ANTIOXIDANT SYSTEM, LIPID-PEROXIDATION, CRYSTAL-STRUCTURE, GLUCOSIDASE, VITRO, BUTYRYLCHOLINESTERASE, ACID, SULFONAMIDES
  • Atatürk Üniversitesi Adresli: Evet

Özet

Sulfonamide derivatives exhibit a wide biological activity and can function as potential medical molecules in the development of a drug. Studies have reported that the compounds have an effect on many enzymes. In this study, the derivatives of amine sulfonamide (1i-11i) were prepared with reduced imine compounds (1-11) with NaBH4 in methanol. The synthesized compounds were fully characterized by spectral data and analytical. The effect of the synthesized derivatives on acetylcholinesterase (AChE), glutathione S-transferase (GST) and a-glycosidase (alpha-GLY) enzymes were determined. For the AChE and alpha-GLY, the most powerful inhibition was observed on 10 and 10i series with K-I value in the range 2.26 +/- 0.45-3.57 +/- 0.97 and 95.73 +/- 13.67-102.45 +/- 11.72 mu M, respectively. K-I values of the series for GST were found in the range of 22.76 +/- 1.23-49.29 +/- 4.49. Finally, the compounds have a stronger inhibitor in lower concentrations by the attachment of functional electronegative groups such as two halogens (-Br and -CI), -OH to the benzene ring and -SO2NH2. The crystal structures of AChE, alpha-GLY, and GST in complex with selected derivatives 4 and 10 show the importance of the functional moieties in the binding modes within the receptors.