Cyclic Hydroxamic Acid Analogues of Bacterial Siderophores as Iron-Complexing Agents prepared through the Castagnoli-Cushman Reaction of Unprotected Oximes

Chemistry. 2017 Dec 14;23(70):17667-17673. doi: 10.1002/chem.201704389. Epub 2017 Nov 29.

Abstract

The first application of multicomponent chemistry (the Castagnoli-Cushman reaction) toward the convenient one-step preparation of cyclic hydroxamic acids is described. Cyclic hydroxamic acids are close analogues of bacterial siderophores (iron-binding compounds) and form stable complexes with Fe3+ ions as confirmed by spectrophotometric measurements. These compounds are potential components for the design of chelating agents for iron overload disease therapy, as well as siderophore-based carrier systems for antibiotic delivery across the bacterial cell wall.

Keywords: Castagnoli-Cushman reaction; cyclic hydroxamic acids; homophthalic anhydride; iron chelation; multicomponent chemistry.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / metabolism
  • Cell Wall / drug effects
  • Cell Wall / metabolism
  • Ferric Compounds / chemistry*
  • Hydroxamic Acids / chemistry*
  • Iron Chelating Agents / chemistry
  • Iron Chelating Agents / metabolism
  • Iron Chelating Agents / pharmacology
  • Isomerism
  • Molecular Conformation
  • Oximes / chemistry*
  • Siderophores / chemistry*
  • Spectrophotometry
  • Streptomyces / metabolism

Substances

  • Anti-Bacterial Agents
  • Ferric Compounds
  • Hydroxamic Acids
  • Iron Chelating Agents
  • Oximes
  • Siderophores