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Synthesis of (2-[{sup 11}C]Methoxy)rotenone, a marker of mitochondrial complex I activity

Abstract

Recent studies suggest that defects in the function of the complexes of the electron transport chain might be involved in the pathology of neurological diseases such as mitochondrial encephalopathies, Parkinson's Huntington's and Alzheimer's disease. Rotenone is a potent reversible competitive inhibitor of complex I (NADH-CoQ reductase). To study the possible involvement of complex I in such diseases, we synthesized (2-[{sup 11}C]methoxy)rotenone by [{sup 11}C]alkylation of 2-O-desmethyl rotenone methyl enol ether followed by hydrolysis of the enol ether to the ketone using aqueous trifluoroacetic acid. (2-[{sup 11}C]Methoxy)rotenone was purified by high pressure liquid chromatography (silica gel) and was obtained in 7-10% yields decay corrected to end of bombardment in synthesis times typically shorter than 48 min. Radiochemical purities were over 95% and specific activities averaged 1000 Ci/mmol at end of synthesis.
Publication Date:
Jan 01, 1995
Product Type:
Journal Article
Resource Relation:
Journal Name: Nuclear Medicine and Biology; Journal Volume: 22; Journal Issue: 1; Other Information: Copyright (c) 1995 Elsevier Science B.V., Amsterdam, The Netherlands, All rights reserved; Country of input: International Atomic Energy Agency (IAEA); PBD: Jan 1995
Subject:
62 RADIOLOGY AND NUCLEAR MEDICINE; BIOCHEMISTRY; CARBON 11; DOSIMETRY; MITOCHONDRIA; RADIONUCLIDE KINETICS; RADIOPHARMACEUTICALS; SYNTHESIS; UPTAKE
OSTI ID:
20348382
Country of Origin:
United Kingdom
Language:
English
Other Identifying Numbers:
Journal ID: ISSN 0969-8051; NMBIEO; TRN: GB03R0923033140
Submitting Site:
GBN
Size:
page(s) 65-69
Announcement Date:

Citation Formats

Charalambous, A, Mangner, T J, and Kilbourn, M R. Synthesis of (2-[{sup 11}C]Methoxy)rotenone, a marker of mitochondrial complex I activity. United Kingdom: N. p., 1995. Web. doi:10.1016/0969-8051(94)00075-U.
Charalambous, A, Mangner, T J, & Kilbourn, M R. Synthesis of (2-[{sup 11}C]Methoxy)rotenone, a marker of mitochondrial complex I activity. United Kingdom. doi:10.1016/0969-8051(94)00075-U.
Charalambous, A, Mangner, T J, and Kilbourn, M R. 1995. "Synthesis of (2-[{sup 11}C]Methoxy)rotenone, a marker of mitochondrial complex I activity." United Kingdom. doi:10.1016/0969-8051(94)00075-U. https://www.osti.gov/servlets/purl/10.1016/0969-8051(94)00075-U.
@misc{etde_20348382,
title = {Synthesis of (2-[{sup 11}C]Methoxy)rotenone, a marker of mitochondrial complex I activity}
author = {Charalambous, A, Mangner, T J, and Kilbourn, M R}
abstractNote = {Recent studies suggest that defects in the function of the complexes of the electron transport chain might be involved in the pathology of neurological diseases such as mitochondrial encephalopathies, Parkinson's Huntington's and Alzheimer's disease. Rotenone is a potent reversible competitive inhibitor of complex I (NADH-CoQ reductase). To study the possible involvement of complex I in such diseases, we synthesized (2-[{sup 11}C]methoxy)rotenone by [{sup 11}C]alkylation of 2-O-desmethyl rotenone methyl enol ether followed by hydrolysis of the enol ether to the ketone using aqueous trifluoroacetic acid. (2-[{sup 11}C]Methoxy)rotenone was purified by high pressure liquid chromatography (silica gel) and was obtained in 7-10% yields decay corrected to end of bombardment in synthesis times typically shorter than 48 min. Radiochemical purities were over 95% and specific activities averaged 1000 Ci/mmol at end of synthesis.}
doi = {10.1016/0969-8051(94)00075-U}
journal = {Nuclear Medicine and Biology}
issue = {1}
volume = {22}
journal type = {AC}
place = {United Kingdom}
year = {1995}
month = {Jan}
}