Tricarbonyl (99m)Tc(i) and Re(i)-thiosemicarbazone complexes: synthesis, characterization and biological evaluation for targeting bacterial infection

Dalton Trans. 2015 Sep 28;44(36):16136-48. doi: 10.1039/c5dt02264a.

Abstract

Methyl, ethyl and phenyl nitrofuryl thiosemicarbazone ligands (, and respectively) were radiolabeled with freshly prepared aqueous solution of a fac[(99m)Tc(CO)3(H2O)3](+) precursor. The radiochemical yield was around 98% as determined by thin layer chromatography and HPLC. The complexes exhibited substantial stability. The corresponding Re(i) complexes were prepared from a Re(CO)5Br precursor to understand the coordination behavior of the ligands against a tricarbonyl rhenium(i) precursor. The rhenium(i) complexes were characterized by means of IR, NMR and mass spectroscopic studies as well as by X-ray crystallography, and correlated with the technetium complexes by means of HPLC studies. Electrochemical reduction of monomeric Re(CO)3-complexes of nitrofuryl ethyl thiosemicarbazone was also studied using cyclic voltammetry. Biodistribution studies of (99m)Tc(CO)3-labeled thiosemicarbazones in rats intramuscularly infected with S. aureus exhibited substantial in vivo stability of the complex and moderate accumulation at the site of focal infection.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Dose-Response Relationship, Drug
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology*
  • Radiopharmaceuticals / chemical synthesis
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / pharmacology*
  • Rats
  • Rats, Inbred Strains
  • Rhenium / chemistry
  • Rhenium / pharmacology*
  • Staphylococcal Infections / drug therapy*
  • Staphylococcus aureus / drug effects
  • Structure-Activity Relationship
  • Technetium Compounds / chemistry
  • Technetium Compounds / pharmacology*
  • Thiosemicarbazones / chemistry
  • Thiosemicarbazones / pharmacology*

Substances

  • Organometallic Compounds
  • Radiopharmaceuticals
  • Technetium Compounds
  • Thiosemicarbazones
  • Rhenium