Dithiol Aryl Arsenic Compounds as Potential Diagnostic and Therapeutic Radiopharmaceuticals

Inorg Chem. 2016 Aug 15;55(16):8091-8. doi: 10.1021/acs.inorgchem.6b01175. Epub 2016 Jul 25.

Abstract

Arsenic-72 ((72)As) and (77)As have nuclear properties useful for positron emission tomography (PET) and radiotherapy, respectively. The thiophilic nature of arsenic led to the evaluation of dithioarylarsines for potential use in radiopharmaceuticals. Several dithioarylarsines were synthesized from their arylarsonic acids and dithiols and were fully characterized by NMR, ESI-MS, and X-ray crystallography. This chemistry was translated to the no-carrier-added (nca) (77)As level. Because arsenic was available at the nca nanomolar level only as [(77)As]arsenate, this required addition of an aryl group directly to the As to form the [(77)As]arylarsonic acid. The [(77)As]arsenate was reduced from (77)As (V) to (77)As (III), and a modified Bart reaction was used to incorporate the aryl ring onto the (77)As, which was followed by dithiol addition. Various modifications and optimizations resulted in 95% radiochemical yield of nca [(77)As]p-ethoxyphenyl-1,2-ethanedithiolatoarsine.

MeSH terms

  • Arsenicals / chemical synthesis
  • Arsenicals / chemistry*
  • Chemistry Techniques, Synthetic
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Radiopharmaceuticals / chemical synthesis
  • Radiopharmaceuticals / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Toluene / analogs & derivatives
  • Toluene / chemistry

Substances

  • Arsenicals
  • Radiopharmaceuticals
  • Toluene
  • dithiol