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NIR fluorescent DCPO glucose analogues and their application in cancer cell imaging

机译：NIR荧光DCPO葡萄糖类似物及其在癌细胞成像中的应用

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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.
机译：鉴于癌细胞中增加的葡萄糖摄取量比正常细胞，近红外（NIR）荧光葡萄糖类似物已经先前已经合成并应用于癌细胞成像。然而，大多数NIR染料通常在其结构中具有一个或多个电荷，这可能导致低细胞膜渗透性并阻碍其在细胞成像中的应用。在这里，我们报告了一系列DCPO缀合的葡萄糖类似物（N0-N4）的合成和表征，其在其结构中没有充电并且具有不同的间隔臂的长度。不同癌细胞系中的实验表明N0-N4的摄取依赖于蛋白质水平的蛋白质水平-1。染料与葡萄糖之间的距离通过PEG的长度调节。在这五种葡萄糖类似物中，含有二甘醇的N 2中的接头的长度是最合适的间隔臂，更长或更短的接头表现出降低的细胞吸收效率。此外，可以通过韧皮素，凝胶-1抑制剂抑制DCPO缀合的葡萄糖类似物的摄取，或者通过未标记的D葡萄糖竞争性抑制。因此，我们的研究报道了一种新型类型的NIR-共轭葡萄糖类似物，其细胞渗透能力确保了NIR区域中的癌细胞生物成像潜在应用。我们还首次证明了染料和葡萄糖之间的接头长度也是将影响葡萄糖类似物对细胞的输送效率的重要因素。

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