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Bioorg Med Chem Lett. 2019 May 1;29(9):1047-1050. doi: 10.1016/j.bmcl.2019.03.012. Epub 2019 Mar 11.

Synthesis and preliminary evaluation of a novel glutamine derivative: (2S,4S)4-[18F]FEBGln.

Author information

1
Beijing Institute of Brain Disorders, Capital Medical University, Beijing 100069, China.
2
College of Chemistry, Beijing Normal University, Beijing 100875, China.
3
Beijing Institute of Brain Disorders, Capital Medical University, Beijing 100069, China. Electronic address: wzhhuey2012@ccmu.edu.cn.
4
Beijing Institute of Brain Disorders, Capital Medical University, Beijing 100069, China; Department of Radiology, University of Pennsylvania, Philadelphia 19104, United States. Electronic address: kunghf@sunmac.spect.upenn.edu.

Abstract

We report the preparation of a novel glutamine derivative, (2S,4S)-2,5-diamino-4-(4-(2-fluoroethoxy)benzyl)-5-oxopentanoic acid, (2S, 4S)4-[18F]FEBGln ([18F]4), through efficient organic and radiosyntheses. In vitro assays of [18F]4 using MCF-7 cells showed that it entered cells via multiple amino acid transporter systems including system L and ASC2 transporters but not through the system A transporter. [18F]4 showed promising properties for tumor imaging and may serve as a lead compound for further optimizing and targeting the system L transporter associated with enhanced glutamine metabolism in cancer cells.

KEYWORDS:

Amino acid; Glutamine; Radiosynthesis; Synthesis; Transporter

PMID:
30871772
DOI:
10.1016/j.bmcl.2019.03.012

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