Synthesis of MMP inhibitor radiotracers [11C]methyl-CGS 27023A and its analogs, new potential PET breast cancer imaging agents

Xiangshu Fei, Qi-Huang Zheng, Gary Hutchins, Xuan Liu, K. Lee Stone, Kathy A. Carlson, Bruce H. Mock, Wendy L. Winkle, Barbara E. Glick-Wilson, Kathy Miller, Rose Fife, George W. Sledge, Hui Bin Sun, Raymond E. Carr

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

[11C]Methyl-CGS 27023A (1a) and its analogs [11C]methyl-2-picolyl-CGS 27023A (1b), [11C]methyl-benzyl-CGS 27023A (1c), [11C]methyl-2-nitro-CGS 27023A (1d), [11C]methyl-3-nitro-CGS 27023A (1e), and [11C]methyl-4-nitro-CGS 27023A (1f), novel radiolabeled matrix metalloproteinase (MMP) inhibitors, have been synthesized for evaluation as new potential positron emission tomography (PET) breast cancer imaging agents. The appropriate precursors for radiolabeling were obtained in four to five steps from starting material amino acid D-valine with moderate to excellent chemical yields. Precursors were labeled by [11C]methyl triflate through 11C-O-methylation method at the aminohydroxyl position under basic conditions and isolated by solid-phase extraction (SPE) purification to produce pure target compounds in 40-60% radiochemical yields (decay corrected to end of bombardment), in 20-25 min synthesis time.

Original languageEnglish
Pages (from-to)449-470
Number of pages22
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume45
Issue number6
DOIs
StatePublished - 2002

Fingerprint

Positron emission tomography
Matrix Metalloproteinase Inhibitors
Positron-Emission Tomography
Breast Neoplasms
Imaging techniques
Methylation
Solid Phase Extraction
Valine
Purification
CGS 27023A
Amino Acids

Keywords

  • [C]methyl-CGS 27023A
  • Breast cancer
  • Carbon-11
  • Matrix metalloproteinase inhibitor
  • Positron emission tomography
  • Radiotracer

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Clinical Biochemistry
  • Molecular Medicine
  • Pharmacology

Cite this

Synthesis of MMP inhibitor radiotracers [11C]methyl-CGS 27023A and its analogs, new potential PET breast cancer imaging agents. / Fei, Xiangshu; Zheng, Qi-Huang; Hutchins, Gary; Liu, Xuan; Stone, K. Lee; Carlson, Kathy A.; Mock, Bruce H.; Winkle, Wendy L.; Glick-Wilson, Barbara E.; Miller, Kathy; Fife, Rose; Sledge, George W.; Sun, Hui Bin; Carr, Raymond E.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 45, No. 6, 2002, p. 449-470.

Research output: Contribution to journalArticle

Fei, Xiangshu ; Zheng, Qi-Huang ; Hutchins, Gary ; Liu, Xuan ; Stone, K. Lee ; Carlson, Kathy A. ; Mock, Bruce H. ; Winkle, Wendy L. ; Glick-Wilson, Barbara E. ; Miller, Kathy ; Fife, Rose ; Sledge, George W. ; Sun, Hui Bin ; Carr, Raymond E. / Synthesis of MMP inhibitor radiotracers [11C]methyl-CGS 27023A and its analogs, new potential PET breast cancer imaging agents. In: Journal of Labelled Compounds and Radiopharmaceuticals. 2002 ; Vol. 45, No. 6. pp. 449-470.
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