Dehydroepiandrosterone derived imidazolium salts and their antimicrobial efficacy

Bioorg Chem. 2021 Mar:108:104550. doi: 10.1016/j.bioorg.2020.104550. Epub 2020 Dec 10.

Abstract

Hybrid molecules consisting of steroid-imidazolium salts reveal interesting biological properties, especially regarding antimicrobial activities. Novel dehydroepiandrosterone derived imidazolium salts (11 salts) with side chains of different lengths were obtained in an efficient and straightforward synthetic route. Antimicrobial properties of new salts were examined by determining their minimum inhibitory concentrations (MICs). They were studied against several strains of bacteria, including clinical isolates of MRSA, and fungi. New compounds showed high activity against Gram-positive bacteria and Candida albicans as well as good compatibility with the representatives of the host cells when applied at concentrations corresponding to MIC value. The studies indicated high antimicrobial efficacy of imidazolium salts against the above-mentioned microorganisms with low hemolytic activity at a concentration that restricts the growth of the microorganisms. The interference of salts with the immune defense system, the influence on the biological activity of monocytes/macrophages measured by their viability and metabolic activity was also studied. The new compounds have shown immunoprotective properties.

Keywords: Antibacterial activity; Antibiotic resistance; Antifungal activity; Imidazolium salt; Steroid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Dehydroepiandrosterone / chemical synthesis
  • Dehydroepiandrosterone / chemistry
  • Dehydroepiandrosterone / pharmacology*
  • Dose-Response Relationship, Drug
  • Fungi / drug effects
  • Gram-Positive Bacteria / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Salts / chemical synthesis
  • Salts / chemistry
  • Salts / pharmacology
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Salts
  • Dehydroepiandrosterone