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Synthesis and Biological Evaluation of an (18)Fluorine-Labeled COX Inhibitor—[(18)F]Fluorooctyl Fenbufen Amide—For Imaging of Brain Tumors

Molecular imaging of brain tumors remains a great challenge, despite the advances made in imaging technology. An anti-inflammatory compound may be a useful tool for this purpose because there is evidence of inflammatory processes in brain tumor micro-environments. Fluorooctylfenbufen amide (FOFA) wa...

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Autores principales: Huang, Ying-Cheng, Chang, Yu-Chia, Yeh, Chun-Nan, Yu, Chung-Shan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273898/
https://www.ncbi.nlm.nih.gov/pubmed/27007363
http://dx.doi.org/10.3390/molecules21030387
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author Huang, Ying-Cheng
Chang, Yu-Chia
Yeh, Chun-Nan
Yu, Chung-Shan
author_facet Huang, Ying-Cheng
Chang, Yu-Chia
Yeh, Chun-Nan
Yu, Chung-Shan
author_sort Huang, Ying-Cheng
collection PubMed
description Molecular imaging of brain tumors remains a great challenge, despite the advances made in imaging technology. An anti-inflammatory compound may be a useful tool for this purpose because there is evidence of inflammatory processes in brain tumor micro-environments. Fluorooctylfenbufen amide (FOFA) was prepared from 8-chlorooctanol via treatment with potassium phthalimide, tosylation with Ts(2)O, fluorination with KF under phase transfer catalyzed conditions, deprotection using aqueous hydrazine, and coupling with fenbufen. The corresponding radiofluoro product [(18)F]FOFA, had a final radiochemical yield of 2.81 mCi and was prepared from activated [(18)F]F(−) (212 mCi) via HPLC purification and concentration. The radiochemical purity was determined to be 99%, and the specific activity was shown to exceed 22 GBq/μmol (EOS) based on decay-corrected calculations. Ex-vivo analysis of [(18)F]FOFA in plasma using HPLC showed that the agent had a half-life of 15 min. PET scanning showed significant accumulation of [(18)F]FOFA over tumor loci with reasonable contrast in C6-glioma bearing rats. These results suggest that this molecule is a promising agent for the visualization of brain tumors. Further investigations should focus on tumor micro-environments.
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spelling pubmed-62738982018-12-28 Synthesis and Biological Evaluation of an (18)Fluorine-Labeled COX Inhibitor—[(18)F]Fluorooctyl Fenbufen Amide—For Imaging of Brain Tumors Huang, Ying-Cheng Chang, Yu-Chia Yeh, Chun-Nan Yu, Chung-Shan Molecules Article Molecular imaging of brain tumors remains a great challenge, despite the advances made in imaging technology. An anti-inflammatory compound may be a useful tool for this purpose because there is evidence of inflammatory processes in brain tumor micro-environments. Fluorooctylfenbufen amide (FOFA) was prepared from 8-chlorooctanol via treatment with potassium phthalimide, tosylation with Ts(2)O, fluorination with KF under phase transfer catalyzed conditions, deprotection using aqueous hydrazine, and coupling with fenbufen. The corresponding radiofluoro product [(18)F]FOFA, had a final radiochemical yield of 2.81 mCi and was prepared from activated [(18)F]F(−) (212 mCi) via HPLC purification and concentration. The radiochemical purity was determined to be 99%, and the specific activity was shown to exceed 22 GBq/μmol (EOS) based on decay-corrected calculations. Ex-vivo analysis of [(18)F]FOFA in plasma using HPLC showed that the agent had a half-life of 15 min. PET scanning showed significant accumulation of [(18)F]FOFA over tumor loci with reasonable contrast in C6-glioma bearing rats. These results suggest that this molecule is a promising agent for the visualization of brain tumors. Further investigations should focus on tumor micro-environments. MDPI 2016-03-21 /pmc/articles/PMC6273898/ /pubmed/27007363 http://dx.doi.org/10.3390/molecules21030387 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Huang, Ying-Cheng
Chang, Yu-Chia
Yeh, Chun-Nan
Yu, Chung-Shan
Synthesis and Biological Evaluation of an (18)Fluorine-Labeled COX Inhibitor—[(18)F]Fluorooctyl Fenbufen Amide—For Imaging of Brain Tumors
title Synthesis and Biological Evaluation of an (18)Fluorine-Labeled COX Inhibitor—[(18)F]Fluorooctyl Fenbufen Amide—For Imaging of Brain Tumors
title_full Synthesis and Biological Evaluation of an (18)Fluorine-Labeled COX Inhibitor—[(18)F]Fluorooctyl Fenbufen Amide—For Imaging of Brain Tumors
title_fullStr Synthesis and Biological Evaluation of an (18)Fluorine-Labeled COX Inhibitor—[(18)F]Fluorooctyl Fenbufen Amide—For Imaging of Brain Tumors
title_full_unstemmed Synthesis and Biological Evaluation of an (18)Fluorine-Labeled COX Inhibitor—[(18)F]Fluorooctyl Fenbufen Amide—For Imaging of Brain Tumors
title_short Synthesis and Biological Evaluation of an (18)Fluorine-Labeled COX Inhibitor—[(18)F]Fluorooctyl Fenbufen Amide—For Imaging of Brain Tumors
title_sort synthesis and biological evaluation of an (18)fluorine-labeled cox inhibitor—[(18)f]fluorooctyl fenbufen amide—for imaging of brain tumors
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273898/
https://www.ncbi.nlm.nih.gov/pubmed/27007363
http://dx.doi.org/10.3390/molecules21030387
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