Synthesis and antimicrobial activity of a phenanthroline-isoniazid hybrid ligand and its Ag+ and Mn2+ complexes

Biometals. 2019 Aug;32(4):671-682. doi: 10.1007/s10534-019-00204-5. Epub 2019 Jun 22.

Abstract

Hydrazide ligand, (Z)-N'-(6-oxo-1,10-phenanthrolin-5(6H)-ylidene)isonicotinohydrazide, 1 forms from a 1:1 Schiff base condensation reaction between isoniazid (INH) and 1,10-phenanthroline-5,6-dione (phendione). Ag+ and Mn2+ complexes with 1:2 metal:ligand stoichiometry are prepared: [Ag(1)2]NO3, [Ag(1)2]BF4 and [Mn(1)2](NO3)2. Polymeric {[Ag(1)(NO3)]}n has 1:1 stoichiometry and forms upon infusion of CH2Cl2 into a DMSO solution of [Ag(1)2]NO3. {[Ag(1)(NO3)]}n was structurally characterized using X-ray crystallography. Metal-free 1 and its 1:2 complexes exhibit very good, broad-spectrum antimicrobial activity and are not excessively toxic to mammalian cells (A549 lineage).

Keywords: 1,10-Phenanthroline; Anti-tuberculosis activity; Antibacterial activity; Antibiotic resistance; Metal complexes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • A549 Cells
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology
  • Cell Survival / drug effects
  • Coordination Complexes / chemistry*
  • Humans
  • Isoniazid / chemistry*
  • Manganese / chemistry*
  • Microbial Sensitivity Tests
  • Phenanthrolines / chemistry*
  • Silver / chemistry*

Substances

  • Anti-Infective Agents
  • Coordination Complexes
  • Phenanthrolines
  • Silver
  • Manganese
  • Isoniazid