A study of structure-activity relationship and anion-controlled quinolinyl Ag(I) complexes as antimicrobial and antioxidant agents as well as their interaction with macromolecules

Biometals. 2022 Apr;35(2):363-394. doi: 10.1007/s10534-022-00377-6. Epub 2022 Mar 11.

Abstract

In this communication, we feature the synthesis and in-depth characterization of a series of silver(I) complexes obtained from the complexation of quinolin-4-yl Schiff base ligands ((E)-2-((quinolin-4-ylmethylene)amino)phenol La, 2-(quinolin-4-yl)benzo[d]thiazole Lb, (E)-N-(2-fluorophenyl)-1-(quinolin-4-yl)methanimine Lc, (E)-N-(4-chlorophenyl)-1-(quinolin-4-yl)methanimine Ld, (E)-1-(quinolin-4-yl)-N-(p-tolyl)methanimine Le, (E)-1-(quinolin-4-yl)-N-(thiophen-2-ylmethyl)methanimine Lf) and three different silver(I) anions (nitrate, perchlorate and triflate). Structurally, the complexes adopted different coordination geometries, which included distorted linear or distorted tetrahedral geometry. The complexes were evaluated in vitro for their potential antibacterial and antioxidant activities. In addition, their interactions with calf thymus-DNA (CT-DNA) and bovine serum albumin (BSA) were evaluated. All the complexes had a wide spectrum of effective antibacterial activity against gram-positive and gram-negative bacterial and good antioxidant properties. The interactions of the complexes with CT-DNA and BSA were observed to occur either through intercalation or through a minor groove binder, while the interaction of the complexes with BSA reveals that some of the complexes can strongly quench the fluorescence of BSA through the static mechanism. The molecular docking studies of the complexes were also done to further elucidate the modes of interaction with CT-DNA and BSA.

Keywords: 4-Quinolinyl derivatives; Groove binding; In vitro biological studies; Intercalation; Silver(I) anion variation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Anti-Infective Agents*
  • Antineoplastic Agents* / chemistry
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Coordination Complexes* / chemistry
  • Coordination Complexes* / pharmacology
  • Molecular Docking Simulation
  • Serum Albumin, Bovine / chemistry
  • Structure-Activity Relationship

Substances

  • Anions
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antineoplastic Agents
  • Antioxidants
  • Coordination Complexes
  • Serum Albumin, Bovine