Radiosynthesis and in vivo tumor uptake of 2-deoxy-2-[18F] fluoro-myo-inositol

Laurence Carroll; Meg Perumal; Neil Vasdev; Edward Robins; Eric O. Aboagye

doi:10.1016/j.bmcl.2012.08.022

Radiosynthesis and in vivo tumor uptake of 2-deoxy-2-[¹⁸F] fluoro-myo-inositol

Laurence Carroll, Meg Perumal, Neil Vasdev, Edward Robins, Eric O. Aboagye

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

5 Scopus citations

Abstract

Inositols play an important role in membrane lipid metabolism and mitogenic signaling of most cancer cells. There is paucity of data on the distribution of radiolabelled inositols. Based on work previously carried out on 1-deoxy-1-[¹⁸F]fluoro-scyllo-inositol ([¹⁸F]2), we began a program of work to label myo-inositol (2-deoxy-2-[¹⁸F]fluoro-myo- inositol, [¹⁸F]1), the most abundant inositol in cells. Fluorination of a triflate precursor 4 afforded the desired [¹⁸F]1 following deprotection with a radiochemical yield of 8% n.d.c. [¹⁸F]1 showed higher uptake in vivo in a human breast cancer xenograft model, MDA-MB-231, compared to [¹⁸F]2. Thus, we have developed a new inositol radiotracer that could have utility for studying inositol uptake in tumors.

Original language	English (US)
Pages (from-to)	6148-6150
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	19
DOIs	https://doi.org/10.1016/j.bmcl.2012.08.022
State	Published - Oct 1 2012
Externally published	Yes

Keywords

Cancer
Fluorine-18
Inositol
PET Imaging

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1016/j.bmcl.2012.08.022

Cite this

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title = "Radiosynthesis and in vivo tumor uptake of 2-deoxy-2-[18F] fluoro-myo-inositol",

abstract = "Inositols play an important role in membrane lipid metabolism and mitogenic signaling of most cancer cells. There is paucity of data on the distribution of radiolabelled inositols. Based on work previously carried out on 1-deoxy-1-[18F]fluoro-scyllo-inositol ([18F]2), we began a program of work to label myo-inositol (2-deoxy-2-[18F]fluoro-myo- inositol, [18F]1), the most abundant inositol in cells. Fluorination of a triflate precursor 4 afforded the desired [18F]1 following deprotection with a radiochemical yield of 8% n.d.c. [18F]1 showed higher uptake in vivo in a human breast cancer xenograft model, MDA-MB-231, compared to [18F]2. Thus, we have developed a new inositol radiotracer that could have utility for studying inositol uptake in tumors.",

keywords = "Cancer, Fluorine-18, Inositol, PET Imaging",

author = "Laurence Carroll and Meg Perumal and Neil Vasdev and Edward Robins and Aboagye, {Eric O.}",

note = "Funding Information: Funding provided by CR-UK&EPSRC Cancer Imaging Centre at Imperial College London, in association with the MRC and Department of Health (England) Grant C2536/A10337 and UK Medical Research Council core funding grant U.1200.02.005.00001.01. We would also like to thank Dr. Mark Nitz for providing a sample of compound 3 . ",

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AU - Carroll, Laurence

AU - Perumal, Meg

AU - Vasdev, Neil

AU - Robins, Edward

AU - Aboagye, Eric O.

N1 - Funding Information: Funding provided by CR-UK&EPSRC Cancer Imaging Centre at Imperial College London, in association with the MRC and Department of Health (England) Grant C2536/A10337 and UK Medical Research Council core funding grant U.1200.02.005.00001.01. We would also like to thank Dr. Mark Nitz for providing a sample of compound 3 .

PY - 2012/10/1

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N2 - Inositols play an important role in membrane lipid metabolism and mitogenic signaling of most cancer cells. There is paucity of data on the distribution of radiolabelled inositols. Based on work previously carried out on 1-deoxy-1-[18F]fluoro-scyllo-inositol ([18F]2), we began a program of work to label myo-inositol (2-deoxy-2-[18F]fluoro-myo- inositol, [18F]1), the most abundant inositol in cells. Fluorination of a triflate precursor 4 afforded the desired [18F]1 following deprotection with a radiochemical yield of 8% n.d.c. [18F]1 showed higher uptake in vivo in a human breast cancer xenograft model, MDA-MB-231, compared to [18F]2. Thus, we have developed a new inositol radiotracer that could have utility for studying inositol uptake in tumors.

AB - Inositols play an important role in membrane lipid metabolism and mitogenic signaling of most cancer cells. There is paucity of data on the distribution of radiolabelled inositols. Based on work previously carried out on 1-deoxy-1-[18F]fluoro-scyllo-inositol ([18F]2), we began a program of work to label myo-inositol (2-deoxy-2-[18F]fluoro-myo- inositol, [18F]1), the most abundant inositol in cells. Fluorination of a triflate precursor 4 afforded the desired [18F]1 following deprotection with a radiochemical yield of 8% n.d.c. [18F]1 showed higher uptake in vivo in a human breast cancer xenograft model, MDA-MB-231, compared to [18F]2. Thus, we have developed a new inositol radiotracer that could have utility for studying inositol uptake in tumors.

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