Quinoline Based Monocarbonyl Curcumin Analogs as Potential Antifungal and Antioxidant Agents: Synthesis, Bioevaluation and Molecular Docking Study

Chem Biodivers. 2020 Feb;17(2):e1900624. doi: 10.1002/cbdv.201900624. Epub 2020 Jan 22.

Abstract

In search for new fungicidal and free radical scavenging agents, we synthesized a focused library of 2-chloroquinoline based monocarbonyl analogs of curcumin (MACs). The synthesized MACs were evaluated for in vitro antifungal and antioxidant activity. The antifungal activity was evaluated against five different fungal strains such as Candida albicans, Fusarium oxysporum, Aspergillus flavus, Aspergillus niger, and Cryptococcus neoformans, respectively. Most of the synthesized MACs displayed promising antifungal activity compared to the standard drug Miconazole. Furthermore, molecular docking study on a crucial fungal enzyme sterol 14α-demethylase (CYP51) could provide insight into the plausible mechanism of antifungal activity. MACs were also screened for in vitro radical scavenging activity using butylated hydroxytoluene (BHT) as a standard. Almost all MACs exhibited better antioxidant activity compared to BHT.

Keywords: antifungal activity; antioxidant activity; molecular docking study; monocarbonyl analogs of curcumin; synthesis.

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / metabolism
  • Antifungal Agents / pharmacology
  • Antioxidants / chemistry*
  • Aspergillus / drug effects
  • Binding Sites
  • Candida albicans / drug effects
  • Catalytic Domain
  • Cryptococcus neoformans / drug effects
  • Curcumin / analogs & derivatives*
  • Curcumin / metabolism
  • Curcumin / pharmacology
  • Fungal Proteins / chemistry
  • Fungal Proteins / metabolism*
  • Microbial Sensitivity Tests
  • Molecular Docking Simulation*
  • Quinolines / chemistry*
  • Sterol 14-Demethylase / chemistry
  • Sterol 14-Demethylase / metabolism

Substances

  • Antifungal Agents
  • Antioxidants
  • Fungal Proteins
  • Quinolines
  • Sterol 14-Demethylase
  • Curcumin