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Dithiol Aryl Arsenic Compounds as Potential Diagnostic and Therapeutic Radiopharmaceuticals.

Publication ,  Journal Article
DeGraffenreid, AJ; Feng, Y; Wycoff, DE; Morrow, R; Phipps, MD; Cutler, CS; Ketring, AR; Barnes, CL; Jurisson, SS
Published in: Inorg Chem
August 15, 2016

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.

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Published In

Inorg Chem

DOI

EISSN

1520-510X

Publication Date

August 15, 2016

Volume

55

Issue

16

Start / End Page

8091 / 8098

Location

United States

Related Subject Headings

  • Toluene
  • Spectrometry, Mass, Electrospray Ionization
  • Radiopharmaceuticals
  • Molecular Structure
  • Magnetic Resonance Spectroscopy
  • Inorganic & Nuclear Chemistry
  • Crystallography, X-Ray
  • Chemistry Techniques, Synthetic
  • Arsenicals
  • 0399 Other Chemical Sciences
 

Citation

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DeGraffenreid, A. J., Feng, Y., Wycoff, D. E., Morrow, R., Phipps, M. D., Cutler, C. S., … Jurisson, S. S. (2016). Dithiol Aryl Arsenic Compounds as Potential Diagnostic and Therapeutic Radiopharmaceuticals. Inorg Chem, 55(16), 8091–8098. https://doi.org/10.1021/acs.inorgchem.6b01175
DeGraffenreid, Anthony J., Yutian Feng, Donald E. Wycoff, Ryan Morrow, Michael D. Phipps, Cathy S. Cutler, Alan R. Ketring, Charles L. Barnes, and Silvia S. Jurisson. “Dithiol Aryl Arsenic Compounds as Potential Diagnostic and Therapeutic Radiopharmaceuticals.Inorg Chem 55, no. 16 (August 15, 2016): 8091–98. https://doi.org/10.1021/acs.inorgchem.6b01175.
DeGraffenreid AJ, Feng Y, Wycoff DE, Morrow R, Phipps MD, Cutler CS, et al. Dithiol Aryl Arsenic Compounds as Potential Diagnostic and Therapeutic Radiopharmaceuticals. Inorg Chem. 2016 Aug 15;55(16):8091–8.
DeGraffenreid, Anthony J., et al. “Dithiol Aryl Arsenic Compounds as Potential Diagnostic and Therapeutic Radiopharmaceuticals.Inorg Chem, vol. 55, no. 16, Aug. 2016, pp. 8091–98. Pubmed, doi:10.1021/acs.inorgchem.6b01175.
DeGraffenreid AJ, Feng Y, Wycoff DE, Morrow R, Phipps MD, Cutler CS, Ketring AR, Barnes CL, Jurisson SS. Dithiol Aryl Arsenic Compounds as Potential Diagnostic and Therapeutic Radiopharmaceuticals. Inorg Chem. 2016 Aug 15;55(16):8091–8098.
Journal cover image

Published In

Inorg Chem

DOI

EISSN

1520-510X

Publication Date

August 15, 2016

Volume

55

Issue

16

Start / End Page

8091 / 8098

Location

United States

Related Subject Headings

  • Toluene
  • Spectrometry, Mass, Electrospray Ionization
  • Radiopharmaceuticals
  • Molecular Structure
  • Magnetic Resonance Spectroscopy
  • Inorganic & Nuclear Chemistry
  • Crystallography, X-Ray
  • Chemistry Techniques, Synthetic
  • Arsenicals
  • 0399 Other Chemical Sciences