title: Dithiol Aryl Arsenic Compounds as Potential Diagnostic and Therapeutic Radiopharmaceuticals.
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.
authors.affiliation: Department of Chemistry and ‡Research Reactor Center (MURR), University of Missouri , Columbia, Missouri 65211, United States.
authors.forename: Anthony J
authors.initials: AJ
authors.lastname: DeGraffenreid
authors.affiliation: Department of Chemistry and ‡Research Reactor Center (MURR), University of Missouri , Columbia, Missouri 65211, United States.
authors.forename: Yutian
authors.initials: Y
authors.lastname: Feng
authors.affiliation: Department of Chemistry and ‡Research Reactor Center (MURR), University of Missouri , Columbia, Missouri 65211, United States.
authors.forename: Donald E
authors.initials: DE
authors.lastname: Wycoff
authors.affiliation: Department of Chemistry and ‡Research Reactor Center (MURR), University of Missouri , Columbia, Missouri 65211, United States.
authors.forename: Ryan
authors.initials: R
authors.lastname: Morrow
authors.affiliation: Department of Chemistry and ‡Research Reactor Center (MURR), University of Missouri , Columbia, Missouri 65211, United States.
authors.forename: Michael D
authors.initials: MD
authors.lastname: Phipps
authors.affiliation: Department of Chemistry and ‡Research Reactor Center (MURR), University of Missouri , Columbia, Missouri 65211, United States.
authors.forename: Cathy S
authors.initials: CS
authors.lastname: Cutler
authors.affiliation: Department of Chemistry and ‡Research Reactor Center (MURR), University of Missouri , Columbia, Missouri 65211, United States.
authors.forename: Alan R
authors.initials: AR
authors.lastname: Ketring
authors.affiliation: Department of Chemistry and ‡Research Reactor Center (MURR), University of Missouri , Columbia, Missouri 65211, United States.
authors.forename: Charles L
authors.initials: CL
authors.lastname: Barnes
authors.affiliation: Department of Chemistry and ‡Research Reactor Center (MURR), University of Missouri , Columbia, Missouri 65211, United States.
authors.forename: Silvia S
authors.initials: SS
authors.lastname: Jurisson
mesh_terms: D001152:Arsenicals / Q000138:chemical synthesis / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D019275:Radiopharmaceuticals / Q000138:chemical synthesis / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D014050:Toluene / Q000031:analogs & derivatives / Q000737:chemistry
chemical_list: D001152:Arsenicals; D019275:Radiopharmaceuticals; D014050:Toluene; C004848:dithiol