title: Fluorescent 6-amino-6-deoxyglycoconjugates for glucose transporter mediated bioimaging.
abstract: 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 by1H NMR,13C 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.
authors.affiliation: 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, PR China.
authors.forename: Xiangyin
authors.initials: X
authors.lastname: Liu
authors.affiliation: School of Life Science, Tianjin University, 92 Weijin Road, Nankai District, Tianjin, 300072, PR China.
authors.forename: Shengnan
authors.initials: S
authors.lastname: Liu
authors.affiliation: 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, PR China.
authors.forename: Xinyu
authors.initials: X
authors.lastname: Liu
authors.affiliation: 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, PR China.
authors.forename: Yunli
authors.initials: Y
authors.lastname: Shi
authors.affiliation: Department of Biochemistry, Gudui BioPharma Technology Inc., 5 Lanyuan Road, Huayuan Industrial Park, Tianjin, 300384, PR China.
authors.forename: Jinna
authors.initials: J
authors.lastname: Yang
authors.affiliation: 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, PR China.
authors.forename: Zhenhua
authors.initials: Z
authors.lastname: Huang
authors.affiliation: 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, PR China.
authors.forename: Hongxia
authors.initials: H
authors.lastname: Zhao
authors.affiliation: 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, PR China. Electronic address: qingzhi@tju.edu.cn.
authors.forename: Qingzhi
authors.initials: Q
authors.lastname: Gao
mesh_terms: D002232:Carbocyanines / Q000138:chemical synthesis / Q000493:pharmacokinetics*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000493:pharmacokinetics; D051246:Glucose Transport Proteins, Facilitative / Q000378:metabolism*; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000493:pharmacokinetics; D019073:HT29 Cells; D006801:Humans; D008856:Microscopy, Fluorescence / Q000379:methods*; D057054:Molecular Imaging / Q000379:methods*; D013050:Spectrometry, Fluorescence / Q000379:methods
chemical_list: D002232:Carbocyanines; D005456:Fluorescent Dyes; D051246:Glucose Transport Proteins, Facilitative; D006001:Glycoconjugates; C089187:cyanine dye 3; C085321:cyanine dye 5
keywords: Cyanine; Fluorescent bioprobe; Fluorometric competition; Glucose transporter; Glycoconjugate