1397682-63-1Relevant academic research and scientific papers
NIR fluorescent DCPO glucose analogues and their application in cancer cell imaging
Chen, Shiguang,Fang, Yanfen,Zhu, Qiwen,Zhang, Wanli,Zhang, Xiongwen,Lu, Wei
, p. 81894 - 81901 (2016/09/09)
Given the increased glucose uptake in cancer cells than normal cells, near-infrared (NIR) fluorescent glucose analogues have been previously synthesized and applied in cancer cell imaging. However, most NIR dyes usually have one or more charge in their structures, which may cause low cell membrane permeability and hamper their application in cell imaging. Here we report the synthesis and characterization of a series of DCPO-conjugated glucose analogues (N0-N4), which have no charge in their structures and have different lengths of the spacer arm. Experiments in different cancer cell lines showed the uptake of N0-N4 was dependent on the protein levels of GLUT-1. The distance between the dyes and glucose was adjusted by the length of PEG. Of these five glucose analogues, the length of the linker in N2 which contains a diethylene glycol was the most appropriate spacer arm, a longer or shorter linker exhibited reduced cellular uptake efficiency. Moreover, the uptake of DCPO-conjugated glucose analogues could be inhibited by phloretin, a GLUT-1 inhibitor or competitively inhibited by unlabeled d-glucose. Therefore, our study has reported a novel type of NIR-conjugated glucose analogues, whose cell permeability ensured the potential application for cancer cell bioimaging in the NIR region. We also demonstrated, for the first time, that the length of the linker between the dyes and glucose was also an important factor that will affect the delivery efficiency of the glucose analogues to cells.
Mimicking biological membranes with programmable glycan ligands self-assembled from amphiphilic Janus glycodendrimers
Zhang, Shaodong,Moussodia, Ralph-Olivier,Sun, Hao-Jan,Leowanawat, Pawaret,Muncan, Adam,Nusbaum, Christopher D.,Chelling, Kathleen M.,Heiney, Paul A.,Klein, Michael L.,André, Sabine,Roy, René,Gabius, Hans-J.,Percec, Virgil
supporting information, p. 10899 - 10903 (2015/03/30)
An accelerated modular synthesis produced 18 amphiphilic Janus glycodendrimers with three different topologies formed from either two or one carbohydrate head groups or a mixed constellation with a noncarbohydrate hydrophilic arm. By simple injection of their THF solutions into water or buffer, all of the Janus compounds self-assembled into uniform, stable, and soft unilamellar vesicles, denoted glycodendrimersomes. The mixed constellation topology glycodendrimersomes were demonstrated to be most efficient in binding plant, bacterial, and human lectins. This evidence with biomedically relevant receptors offers a promising perspective for the application of such glycodendrimersomes in targeted drug delivery, vaccines, and other areas of nanomedicine.
