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Synthesis of 2-R1-2-(4-(2-fluoroethoxy)benzamido)acetate as potential PET imaging agents

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Abstract

Radiolabeled acetates have potential use in tumor imaging. Moreover, aryl fatty acid displays antitumor effect with phenylacetate currently in clinical trial. A series of 2-R1-2-(4-(2-fluoroethoxy)benzamido)acetate were synthesized in the present investigation. 2-(4-(2-[18F]fluoroethoxy)benzamido)acetate ([18F]FEBA) was evaluated in tumor-bearing mice. It was compared with 2-[18F]fluoro-2-deoxy-d-glucose ([18F]FDG), showing satisfied stability. Excitingly, the radiochemical purity of [18F]FEBA was more than 99% and the radiochemical yield was up to 25%. Although 2-R1-2-(4-(2-fluoroethoxy)benzamido)acetate deserved further evaluations, the results might provide many experimental foundations and principles for the future study of the novel fluorine-18-labeled pharmaceuticals.

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Abbreviations

[18F]FDG:

2-[18F]fluoro-2-deoxy-d-glucose

[18F]FEBA:

2-(4-(2-[18F]fluoroethoxy)benzamido)acetate

FAS:

Fatty acid synthase

P.I.:

Post injection

PET:

Positron emission tomography

TEA:

Triethylamine

DCC:

N,N-dicyclohexylcarbodiimide

HOBt:

N-hydroxybenzotriazole

DMAP:

N,N-dimethyl-4-pyridinamine

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Acknowledgments

We acknowledged with thanks for financial supports from the National Natural Science Foundation of China (No. 20371009, No. 20671014, and No. 21071022), Key Laboratory of Radioactive Medicine of Ministry Education and Beijing Municipal Commission of Education.

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Authors and Affiliations

  1. Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, Beijing, 100875, China

    Yong He, Jingli Xu, Hang Liu, Man Feng, Xiao Wang, Rui Ding, Chuanmin Qi, Yurong Chen & Ming Wang

  2. Department of Nuclear Medicine, PUMC Hospital, CAMS and PUMC, Beijing, 100730, China

    Fang Li, Zhao-Hui Zhu & Yong-Hong Dang

  3. Institute of Medicine, Peking University, Beijing, 100191, China

    Ying Xie

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  1. Yong He
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  2. Jingli Xu
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  3. Hang Liu
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  4. Man Feng
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  5. Xiao Wang
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  7. Chuanmin Qi
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  9. Fang Li
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  11. Yong-Hong Dang
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Correspondence to Chuanmin Qi.

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He, Y., Xu, J., Liu, H. et al. Synthesis of 2-R1-2-(4-(2-fluoroethoxy)benzamido)acetate as potential PET imaging agents. Med Chem Res 21, 944–951 (2012). https://doi.org/10.1007/s00044-011-9577-5

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  • DOI: https://doi.org/10.1007/s00044-011-9577-5

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