Synthesis of new hypoxia markers EF1 and [18F]-EF1

Alexander V. Kachur; William R. Dolbier; Sydney M. Evans; Chyng Yann Shiue; Grace G. Shiue; Kirsten A. Skov; Ian R. Baird; Brian R. James; An Rong Li; Alex Roche; Cameron J. Koch

doi:10.1016/S0969-8043(99)00096-2

Synthesis of new hypoxia markers EF1 and [¹⁸F]-EF1

Alexander V. Kachur, William R. Dolbier, Sydney M. Evans, Chyng Yann Shiue, Grace G. Shiue, Kirsten A. Skov, Ian R. Baird, Brian R. James, An Rong Li, Alex Roche, Cameron J. Koch

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

35 Scopus citations

Abstract

We report on the preparation of a hypoxia marker 2-(2-nitroimidazol-1[H]-yl)-N-(3-fluoropropyl)acetamide (EF1) and its ¹⁸F analog, 2-(2-nitroimidazol-1[H]-yl)-N-(3-[¹⁸F]fluoropropyl)acetamide ([¹⁸F]-EF1). Two methods for the preparation of 3-fluoropropylamine, the EF1 side chain, are described. [¹⁸F]-EF1 was prepared with a radiochemical yield of 2% by nucleophilic substitution of bromine in 2-(2-nitroimidazol-1[H]-yl)-N-(3-bromopropyl)acetamide (EBr1) by carrier-added ¹⁸F in DMSO at 120°C.Our results demonstrate the preparation of clinically relevant amounts of [¹⁸F]-EF1 for use as a non-invasive hypoxia marker with detection using positron emission tomography (PET). Copyright (C) 1999 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	643-650
Number of pages	8
Journal	Applied Radiation and Isotopes
Volume	51
Issue number	6
DOIs	https://doi.org/10.1016/S0969-8043(99)00096-2
State	Published - Dec 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Radiation

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10.1016/S0969-8043(99)00096-2

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@article{911a281680c14384abe12e8b792a9e71,

title = "Synthesis of new hypoxia markers EF1 and [18F]-EF1",

abstract = "We report on the preparation of a hypoxia marker 2-(2-nitroimidazol-1[H]-yl)-N-(3-fluoropropyl)acetamide (EF1) and its 18F analog, 2-(2-nitroimidazol-1[H]-yl)-N-(3-[18F]fluoropropyl)acetamide ([18F]-EF1). Two methods for the preparation of 3-fluoropropylamine, the EF1 side chain, are described. [18F]-EF1 was prepared with a radiochemical yield of 2% by nucleophilic substitution of bromine in 2-(2-nitroimidazol-1[H]-yl)-N-(3-bromopropyl)acetamide (EBr1) by carrier-added 18F in DMSO at 120°C.Our results demonstrate the preparation of clinically relevant amounts of [18F]-EF1 for use as a non-invasive hypoxia marker with detection using positron emission tomography (PET). Copyright (C) 1999 Elsevier Science Ltd.",

author = "Kachur, {Alexander V.} and Dolbier, {William R.} and Evans, {Sydney M.} and Shiue, {Chyng Yann} and Shiue, {Grace G.} and Skov, {Kirsten A.} and Baird, {Ian R.} and James, {Brian R.} and Li, {An Rong} and Alex Roche and Koch, {Cameron J.}",

note = "Funding Information: This work was supported by the Departments of Radiation Oncology and Radiology, School of Medicine, University of Pennsylvania and by NSERC of Canada.",

year = "1999",

month = dec,

doi = "10.1016/S0969-8043(99)00096-2",

language = "English (US)",

volume = "51",

pages = "643--650",

journal = "Applied Radiation and Isotopes",

issn = "0969-8043",

publisher = "Elsevier Limited",

number = "6",

}

Synthesis of new hypoxia markers EF1 and [¹⁸F]-EF1. / Kachur, Alexander V.; Dolbier, William R.; Evans, Sydney M.; Shiue, Chyng Yann; Shiue, Grace G.; Skov, Kirsten A.; Baird, Ian R.; James, Brian R.; Li, An Rong; Roche, Alex; Koch, Cameron J.

In: Applied Radiation and Isotopes, Vol. 51, No. 6, 12.1999, p. 643-650.

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

TY - JOUR

T1 - Synthesis of new hypoxia markers EF1 and [18F]-EF1

AU - Kachur, Alexander V.

AU - Dolbier, William R.

AU - Evans, Sydney M.

AU - Shiue, Chyng Yann

AU - Shiue, Grace G.

AU - Skov, Kirsten A.

AU - Baird, Ian R.

AU - James, Brian R.

AU - Li, An Rong

AU - Roche, Alex

AU - Koch, Cameron J.

N1 - Funding Information: This work was supported by the Departments of Radiation Oncology and Radiology, School of Medicine, University of Pennsylvania and by NSERC of Canada.

PY - 1999/12

Y1 - 1999/12

N2 - We report on the preparation of a hypoxia marker 2-(2-nitroimidazol-1[H]-yl)-N-(3-fluoropropyl)acetamide (EF1) and its 18F analog, 2-(2-nitroimidazol-1[H]-yl)-N-(3-[18F]fluoropropyl)acetamide ([18F]-EF1). Two methods for the preparation of 3-fluoropropylamine, the EF1 side chain, are described. [18F]-EF1 was prepared with a radiochemical yield of 2% by nucleophilic substitution of bromine in 2-(2-nitroimidazol-1[H]-yl)-N-(3-bromopropyl)acetamide (EBr1) by carrier-added 18F in DMSO at 120°C.Our results demonstrate the preparation of clinically relevant amounts of [18F]-EF1 for use as a non-invasive hypoxia marker with detection using positron emission tomography (PET). Copyright (C) 1999 Elsevier Science Ltd.

AB - We report on the preparation of a hypoxia marker 2-(2-nitroimidazol-1[H]-yl)-N-(3-fluoropropyl)acetamide (EF1) and its 18F analog, 2-(2-nitroimidazol-1[H]-yl)-N-(3-[18F]fluoropropyl)acetamide ([18F]-EF1). Two methods for the preparation of 3-fluoropropylamine, the EF1 side chain, are described. [18F]-EF1 was prepared with a radiochemical yield of 2% by nucleophilic substitution of bromine in 2-(2-nitroimidazol-1[H]-yl)-N-(3-bromopropyl)acetamide (EBr1) by carrier-added 18F in DMSO at 120°C.Our results demonstrate the preparation of clinically relevant amounts of [18F]-EF1 for use as a non-invasive hypoxia marker with detection using positron emission tomography (PET). Copyright (C) 1999 Elsevier Science Ltd.

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SN - 0969-8043

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ER -

Synthesis of new hypoxia markers EF1 and [¹⁸F]-EF1

Abstract

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