Synthesis and Evaluation of Fluorine-18-Labeled L-Rhamnose Derivatives

Xiang Zhang; Falguni Basuli; Zhen-Dan Shi; Swati Shah; Jianfeng Shi; Amelia Mitchell; Jianhao Lai; Zeping Wang; Dima A. Hammoud; Rolf E. Swenson

doi:10.3390/molecules28093773

Molecules (Apr 2023)

Synthesis and Evaluation of Fluorine-18-Labeled L-Rhamnose Derivatives

Xiang Zhang,
Falguni Basuli,
Zhen-Dan Shi,
Swati Shah,
Jianfeng Shi,
Amelia Mitchell,
Jianhao Lai,
Zeping Wang,
Dima A. Hammoud,
Rolf E. Swenson

Affiliations

Xiang Zhang: Chemistry and Synthesis Center, National Heart, Lung, and Blood Institute, National Institutes of Health, Rockville, MD 20850, USA
Falguni Basuli: Chemistry and Synthesis Center, National Heart, Lung, and Blood Institute, National Institutes of Health, Rockville, MD 20850, USA
Zhen-Dan Shi: Chemistry and Synthesis Center, National Heart, Lung, and Blood Institute, National Institutes of Health, Rockville, MD 20850, USA
Swati Shah: Center for Infectious Disease Imaging, Radiology and Imaging Sciences, Clinical Center, National Institutes of Health, Bethesda, MD 20892, USA
Jianfeng Shi: Chemistry and Synthesis Center, National Heart, Lung, and Blood Institute, National Institutes of Health, Rockville, MD 20850, USA
Amelia Mitchell: Center for Infectious Disease Imaging, Radiology and Imaging Sciences, Clinical Center, National Institutes of Health, Bethesda, MD 20892, USA
Jianhao Lai: Center for Infectious Disease Imaging, Radiology and Imaging Sciences, Clinical Center, National Institutes of Health, Bethesda, MD 20892, USA
Zeping Wang: Center for Infectious Disease Imaging, Radiology and Imaging Sciences, Clinical Center, National Institutes of Health, Bethesda, MD 20892, USA
Dima A. Hammoud: Center for Infectious Disease Imaging, Radiology and Imaging Sciences, Clinical Center, National Institutes of Health, Bethesda, MD 20892, USA
Rolf E. Swenson: Chemistry and Synthesis Center, National Heart, Lung, and Blood Institute, National Institutes of Health, Rockville, MD 20850, USA

DOI: https://doi.org/10.3390/molecules28093773
Journal volume & issue: Vol. 28, no. 9
p. 3773

Abstract

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The use of radiolabeled glucose for PET imaging resulted in the most commonly used tracer in the clinic, 2-deoxy-2-[18F]fluoroglucose (FDG). More recently, other radiolabeled sugars have been reported for various applications, including imaging tumors and infections. Therefore, in this study, we developed a series of fluorine-18-labeled L-rhamnose derivatives as potential PET tracers of various fungal and bacterial strains. Acetyl-protected triflate precursors of rhamnose were prepared and radiolabeled with fluorine-18 followed by hydrolysis to produce L-deoxy [18F]fluororhamnose. The overall radiochemical yield was 7–27% in a 90 min synthesis time with a radiochemical purity of 95%. In vivo biodistribution of the ligands using PET imaging showed that 2-deoxy-2-[18F]fluoro-L-rhamnose is stable for at least up to 60 min in mice and eliminated via renal clearance. The tracer also exhibited minimal tissue or skeletal uptake in healthy mice resulting in a low background signal.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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