Low-dimensional compounds containing bioactive ligands. Part XVII: Synthesis, structural, spectral and biological properties of hybrid organic-inorganic complexes based on [PdCl4]2- with derivatives of 8-hydroxyquinolinium

J Inorg Biochem. 2022 Mar:228:111697. doi: 10.1016/j.jinorgbio.2021.111697. Epub 2021 Dec 30.

Abstract

In this study, four hybrid organic-inorganic compounds (8-H2Q)2[PdCl4] (1), (H2ClQ)2[PdCl4] (2), (H2NQ)2[PdCl4] (3) and (H2MeQ)2[PdCl4]·2H2O (4) (where 8-H2Q = 8-hydroxyquinolinium, H2ClQ = 5-chloro-8-hydroxyquinolinium, H2NQ = 5-nitro-8-hydroxyquinolinium and H2MeQ = 2-methyl-8-hydroxyquinolinium) were synthesized through organic cation modulation. Single-crystal X-ray structure analysis of compounds 1 and 3 indicates that their structures are planar and consist of [PdCl4]2- anions and 8-H2Q or H2NQ cations, respectively. Both ionic components are held together through ionic interactions and hydrogen bonds forming infinite chains linked through π-π interactions to form 2D structures. Furthermore, NMR spectroscopy, UV-Vis spectroscopy, elemental analysis, and FT-IR spectroscopy were used to explore the synthesized compounds. The DNA interaction, antimicrobial activity, antiproliferative activity, and radical scavenging effect of the compounds were evaluated. The hybrid compounds and their free ligands can interact with the calf thymus DNA via an intercalation mode involving the insertion of the aromatic chromophore between the base pairs of DNA; compound 1 has the highest binding affinity. Moreover, they have high antimicrobial efficacy against the tested 14 strains of microorganisms with minimum inhibitory concentration values ranging from <1.95 to 250 μg/mL. The antiproliferative activity of the compounds was investigated against three different cancer cell lines, and their selectivity was verified on mesenchymal stem cells. Compounds 1 and 2 displayed selective and high cytotoxicity against human lung and breast cancer cells and showed moderate cytotoxicity against colon cancer cells. Accordingly, they might be auspicious candidates for future pharmacological investigations in lung and breast cancer research.

Keywords: 2D structures; 8-hydroxyquinoline, hybrid compounds; Antimicrobial activity; Cytotoxicity; Palladium(II).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • A549 Cells
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Antineoplastic Agents / pharmacology
  • Chelating Agents / chemistry
  • Coordination Complexes / chemistry*
  • Crystallography, X-Ray / methods
  • DNA / chemistry
  • Free Radical Scavengers / chemistry
  • HCT116 Cells
  • Humans
  • Hydroxyquinolines / chemical synthesis
  • Hydroxyquinolines / chemistry*
  • Ligands
  • Magnetic Resonance Spectroscopy / methods
  • Microbial Sensitivity Tests / methods
  • Molecular Structure
  • Palladium / chemistry*
  • Quinolinium Compounds / chemical synthesis
  • Quinolinium Compounds / chemistry*
  • Reactive Oxygen Species / metabolism

Substances

  • Anti-Infective Agents
  • Antineoplastic Agents
  • Chelating Agents
  • Coordination Complexes
  • Free Radical Scavengers
  • Hydroxyquinolines
  • Ligands
  • Quinolinium Compounds
  • Reactive Oxygen Species
  • tetrachloropalladium
  • Palladium
  • DNA
  • calf thymus DNA