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 Bin Sun, Bruce H. Mock, K. Lee Stone, Tanya D. Martinez, Kathy Miller, George W. Sledge, Gary Hutchins

Research output: Contribution to journal › Article

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
Pages (from-to)761-770
Number of pages10
JournalNuclear Medicine and Biology
Volume29
Issue number7
DOIs
StatePublished - Oct 2002

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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; Bin Sun, Hui; Mock, Bruce H.; Lee Stone, K.; Martinez, Tanya D.; Miller, Kathy; Sledge, George W.; Hutchins, Gary.

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

Research output: Contribution to journal › Article

Zheng, Q-H, Fei, X, Liu, X, Wang, JQ, Bin Sun, H, Mock, BH, Lee Stone, K, Martinez, TD, Miller, K, Sledge, GW & Hutchins, G 2002, 'Synthesis and preliminary biological evaluation of MMP inhibitor radiotracers [11C]methyl-halo-CGS 27023A analogs, new potential PET breast cancer imaging agents', Nuclear Medicine and Biology, vol. 29, no. 7, pp. 761-770. https://doi.org/10.1016/S0969-8051(02)00338-4
Zheng Q-H, Fei X, Liu X, Wang JQ, Bin Sun H, Mock BH et al. Synthesis and preliminary biological evaluation of MMP inhibitor radiotracers [11C]methyl-halo-CGS 27023A analogs, new potential PET breast cancer imaging agents. Nuclear Medicine and Biology. 2002 Oct;29(7):761-770. https://doi.org/10.1016/S0969-8051(02)00338-4
Zheng, Qi-Huang ; Fei, Xiangshu ; Liu, Xuan ; Wang, Ji Quan ; Bin Sun, Hui ; Mock, Bruce H. ; Lee Stone, K. ; Martinez, Tanya D. ; Miller, Kathy ; Sledge, George W. ; Hutchins, Gary. / 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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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.",
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