Fluorescent 6-amino-6-deoxyglycoconjugates for glucose transporter mediated bioimaging
- Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, Collaborative Innovation Center of Chemical Science and Engineering, School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin, 300072 (China)
- School of Life Science, Tianjin University, 92 Weijin Road, Nankai District, Tianjin, 300072 (China)
- Department of Biochemistry, Gudui BioPharma Technology Inc., 5 Lanyuan Road, Huayuan Industrial Park, Tianjin, 300384 (China)
Two novel fluorescent bioprobes, namely, 6N-Gly-Cy3 and 6N-Gly-Cy5, were designed and synthesized for real-time glucose transport imaging as well as potentially useful tracer for galactokinase metabolism. The structure of the bioprobes was fully characterized by {sup 1}H NMR, {sup 13}C NMR, IR, and HRMS. The fluorescence properties, glucose transporter (GLUT) specificity, and the quenching and safety profiles were studied. The cellular uptake of both bioprobes was competitively diminished by D-glucose, 2-deoxy-D-glucose and GLUT specific inhibitor in a dose-dependent manner in human colon cancer cells (HT29). Comparison study results revealed that the 6N-derived bioprobes are more useful for real-time imaging of cell-based glucose uptake than the structurally similar fluorescent tracer 6-NBDG which was not applicable under physiological conditions. The up to 96 h long-lasting quenching property of 6N-Gly-Cy5 in HT29 suggested the potential applcability of the probe for cell labeling in xenograft transplantation as well as in vivo animal imaging studies. - Highlights: • Cy-3 and Cy-5 derived fluorescent 6-amino-6-deoxyglycoconjugates were prepared for glucose transporter mediated bioimaging. • The cellular uptake of the probes was inhibited by natural GLUT substrates and inhibitor. • The probes are useful for real-time imaging of cell-based glucose uptake under physiological conditions. • The probes showed up to 96 h long-lasting quenching profile in labeled cancer cells.
- OSTI ID:
- 22696693
- Journal Information:
- Biochemical and Biophysical Research Communications, Journal Name: Biochemical and Biophysical Research Communications Journal Issue: 3 Vol. 480; ISSN 0006-291X; ISSN BBRCA9
- Country of Publication:
- United States
- Language:
- English
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