Synthesis and preliminary evaluation of a novel glutamine derivative: (2S, 4S)4-[18F]FEBGln. Issue 9 (1st May 2019)

• Record Type: Journal Article
• Authors: Huang, Yong; Liu, Song; Wu, Renbo; Zhang, Lifang; Zhang, Yan; Hong, Haiyan; Zhang, Aili; Xiao, Hao; Liu, Yajing; Wu, Zehui; Zhu, Lin; Kung, Hank F.
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 29:Issue 9(2019)
• Page Start: 1047
• Page End: 1050
• Publication Date: 2019-05-01
• Subjects: Glutamine -- Synthesis -- Transporter -- Radiosynthesis -- Amino acid; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2019.03.012
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Highlights: A novel glutamine derivative was prepared. The labeled phase transfer catalyst 18-C-6 and potassium bicarbonate. (2S, 4S)4-[ 18 F]FEBGln main transporter is system L and ASC2. 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-[ 18 F]FEBGln ([ 18 F]4), through efficient organic and radiosyntheses. In vitro assays of [ 18 F]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. [ 18 F]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.