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

Qi Huang Zheng, Xiangshu Fei, Xuan Liu, Ji Quan Wang, Hui (Herb) Sun, Bruce H. Mock, K. Lee Stone, Tanya D. Martinez, Kathy D. Miller, George W. Sledge, Gary D. Hutchins

Research output: Contribution to journalArticle

77 Citations (Scopus)

Abstract

A series of [11C]methyl-halo-CGS 27023A analogs (2-F, 1a; 4-F, 1b; 2-Cl, 1c; 3-Cl, 1d; 4-Cl, 1e; 2-Br, 1f; 3-Br, 1g; 4-Br, 1h; 4-I, 1i), novel radiolabeled matrix metalloproteinase (MMP) inhibitors, have been synthesized for evaluation as new potential positron emission tomography (PET) breast cancer imaging agents. The precursors halo-CGS 27023A analogs (2-F, 6a; 4-F, 6b; 2-Cl, 6c; 3-Cl, 6d; 4-Cl, 6e; 2-Br, 6f; 3-Br, 6g; 4-Br, 6h; 4-I, 6i) for radiolabeling were obtained in four 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 (US)
Pages (from-to)761-770
Number of pages10
JournalNuclear Medicine and Biology
Volume29
Issue number7
DOIs
StatePublished - Oct 2002
Externally publishedYes

Fingerprint

Matrix Metalloproteinase Inhibitors
Positron-Emission Tomography
Breast Neoplasms
Solid Phase Extraction
Valine
Methylation
Amino Acids
CGS 27023A
methyl triflate

Keywords

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

ASJC Scopus subject areas

  • Cancer Research
  • Molecular Medicine
  • Radiology Nuclear Medicine and imaging

Cite this

Synthesis and preliminary biological evaluation of MMP inhibitor radiotracers [11C]methyl-halo-CGS 27023A analogs, new potential PET breast cancer imaging agents. / Zheng, Qi Huang; Fei, Xiangshu; Liu, Xuan; Wang, Ji Quan; Sun, Hui (Herb); Mock, Bruce H.; Lee Stone, K.; Martinez, Tanya D.; Miller, Kathy D.; Sledge, George W.; Hutchins, Gary D.

In: Nuclear Medicine and Biology, Vol. 29, No. 7, 10.2002, p. 761-770.

Research output: Contribution to journalArticle

Zheng, Qi Huang ; Fei, Xiangshu ; Liu, Xuan ; Wang, Ji Quan ; Sun, Hui (Herb) ; Mock, Bruce H. ; Lee Stone, K. ; Martinez, Tanya D. ; Miller, Kathy D. ; Sledge, George W. ; Hutchins, Gary D. / Synthesis and preliminary biological evaluation of MMP inhibitor radiotracers [11C]methyl-halo-CGS 27023A analogs, new potential PET breast cancer imaging agents. In: Nuclear Medicine and Biology. 2002 ; Vol. 29, No. 7. pp. 761-770.
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AU - Wang, Ji Quan

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AU - Mock, Bruce H.

AU - Lee Stone, K.

AU - Martinez, Tanya D.

AU - Miller, Kathy D.

AU - Sledge, George W.

AU - Hutchins, Gary D.

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