Silver(I) pyridinyl complexes with benzothiazole, thiophene, and furan moieties: DNA/protein-binding, antibacterial, antioxidant, and anticancer studies

Arch Pharm (Weinheim). 2023 Jan;356(1):e2200308. doi: 10.1002/ardp.202200308. Epub 2022 Oct 17.

Abstract

We have synthesized and characterized nine Ag(I) complexes of Schiff bases containing thiophene, furan, and pyridine moieties for in vitro antibacterial, antioxidant, anticancer activities, and DNA/bovine serum albumin (BSA) binding studies. Based on the analytical and spectral analyses, a linear geometry was proposed for all the Ag(I) complexes, except for one (with the furan moiety), which formed a distorted T-shaped geometry. UV-vis absorption studies on the interactions of calf thymus-DNA (CT-DNA) with the nine Ag(I) complexes pointed to an intercalative binding mode. With a binding constant Kb of 3.75 × 105 M-1 , the complex bearing a benzothiazole moiety (1) interacted stronger with CT-DNA than the rest of the complexes. Fluorescence spectroscopic data revealed that the complexes had a modest binding affinity for BSA through static quenching. The complexes displayed good antioxidant properties, especially those with a benzothiazole moiety. Notable antibacterial activities against methicillin-resistant Staphylococcus aureus, Staphylococcus aureus, Salmonella typhimurium, Pseudomonas aeruginosa, Escherichia coli, and Klebsiella pneumoniae were observed for complexes with the furan and thiophene moieties. The in vitro anticancer studies of selected complexes against three cancer cell lines showed that the complexes were more effective against the inhibition of the growth of cervical cancer cells relative to cisplatin.

Keywords: anticervical cancer; benzothiazole; furan; heterocycles; thiophene.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Antioxidants* / chemistry
  • Antioxidants* / pharmacology
  • Benzothiazoles / pharmacology
  • DNA / chemistry
  • Methicillin-Resistant Staphylococcus aureus*
  • Schiff Bases / chemistry
  • Serum Albumin, Bovine / chemistry
  • Silver
  • Structure-Activity Relationship
  • Thiophenes / chemistry
  • Thiophenes / pharmacology

Substances

  • Antioxidants
  • Silver
  • Thiophenes
  • Anti-Bacterial Agents
  • DNA
  • Serum Albumin, Bovine
  • Benzothiazoles
  • Schiff Bases