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 D. Hutchins; Xuan Liu; K. Lee Stone; Kathy A. Carlson; Bruce H. Mock; Wendy L. Winkle; Barbara E. Glick-Wilson; Kathy D. Miller; Rose S. Fife; George W. Sledge; Hui Bin Sun; Raymond E. Carr

doi:10.1002/jlcr.570

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

Orthopaedic Surgery

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

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 language	English (US)
Pages (from-to)	449-470
Number of pages	22
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	45
Issue number	6
DOIs	https://doi.org/10.1002/jlcr.570
State	Published - 2002

Keywords

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

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Radiology Nuclear Medicine and imaging
Drug Discovery
Spectroscopy
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1002/jlcr.570

Cite this

Fei, X., Zheng, Q. H., Hutchins, G. D., Liu, X., Stone, K. L., Carlson, K. A., Mock, B. H., Winkle, W. L., Glick-Wilson, B. E., Miller, K. D., Fife, R. S., Sledge, G. W., Sun, H. B., & Carr, R. E. (2002). Synthesis of MMP inhibitor radiotracers [¹¹C]methyl-CGS 27023A and its analogs, new potential PET breast cancer imaging agents. Journal of Labelled Compounds and Radiopharmaceuticals, 45(6), 449-470. https://doi.org/10.1002/jlcr.570

Fei, X, Zheng, QH, Hutchins, GD, Liu, X, Stone, KL, Carlson, KA, Mock, BH, Winkle, WL, Glick-Wilson, BE, Miller, KD, Fife, RS, Sledge, GW, Sun, HB & Carr, RE 2002, 'Synthesis of MMP inhibitor radiotracers [¹¹C]methyl-CGS 27023A and its analogs, new potential PET breast cancer imaging agents', Journal of Labelled Compounds and Radiopharmaceuticals, vol. 45, no. 6, pp. 449-470. https://doi.org/10.1002/jlcr.570

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

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.",

keywords = "Breast cancer, Carbon-11, Matrix metalloproteinase inhibitor, Positron emission tomography, Radiotracer, [C]methyl-CGS 27023A",

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

year = "2002",

doi = "10.1002/jlcr.570",

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AU - Fei, Xiangshu

AU - Zheng, Qi Huang

AU - Hutchins, Gary D.

AU - Liu, Xuan

AU - Stone, K. Lee

AU - Carlson, Kathy A.

AU - Mock, Bruce H.

AU - Winkle, Wendy L.

AU - Glick-Wilson, Barbara E.

AU - Miller, Kathy D.

AU - Fife, Rose S.

AU - Sledge, George W.

AU - Sun, Hui Bin

AU - Carr, Raymond E.

PY - 2002

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KW - Breast cancer

KW - Carbon-11

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KW - Positron emission tomography

KW - Radiotracer

KW - [C]methyl-CGS 27023A

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