Bioorthogonal Phosphorogenic Rhenium(I) Polypyridine Sydnone Complexes for Specific Lysosome Labeling.,ChemPlusChem

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Bioorthogonal Phosphorogenic Rhenium(I) Polypyridine Sydnone Complexes for Specific Lysosome Labeling.
ChemPlusChem ( IF 3.0 ) Pub Date : 2020-03-05 , DOI: 10.1002/cplu.202000029
Justin Shum ₁ , Pei-Zhi Zhang ₁ , Lawrence Cho-Cheung Lee ₁ , Kenneth Kam-Wing Lo _{1,

2,

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Affiliation

Many novel bioorthogonal reactions have been developed for labeling, such as the strain‐promoted sydnone‐alkyne cycloaddition (SPSAC), but sydnone‐based probes with phosphorogenicity (i. e., phosphorescence turn‐on upon reaction) have not been investigated to date. Herein, we report the synthesis, characterization, and photophysical properties of rhenium(I) polypyridine complexes containing a sydnone moiety as bioorthogonal phosphorogenic probes. Their reactions with strained alkyne derivatives and the associated photophysical changes were examined. Upon SPSAC with bicyclo[6.1.0]non‐4‐yn‐9‐ylmethanol (BCN‐OH), the complexes exhibited emission enhancement in the range of 8.8 to 17.3. Importantly, conjugation of the complexes with BCN‐modified bovine serum albumin (BCN‐BSA) led to the increase in emission enhancement to as high as 38.9 and extended lifetimes in the range of 1.80 to 4.71 μs. Additionally, the bioorthogonal ligation of one of the complexes with a morpholine derivative was shown to induce specific lysosomal labeling in live cells; colocalization studies with LysoTracker Deep Red indicated a Pearson's coefficient of 0.83.

中文翻译：

用于特定溶酶体标记的生物正交发磷R（I）聚吡啶酮复合物。

已经开发出许多用于标记的新型生物正交反应，例如应变促进的sydnone-炔烃环加成（SPSAC），但是迄今为止尚未研究具有磷光性（即反应后开启磷光）的基于sydnone的探针。在这里，我们报告的合成，表征和photo（I）聚吡啶络合物含有sydnone部分作为生物正交磷光探针的光物理性质。他们的反应与应变炔烃衍生物和相关的光物理变化。SPSAC与双环[6.1.0] non-4-yn-9基甲醇（BCN-OH）配合使用时，该配合物显示出8.8至17.3的发射增强。重要的是，复合物与BCN修饰的牛血清白蛋白（BCN-BSA）的缀合导致发射增强增加至38。9和延长的寿命在1.80至4.71μs的范围内。此外，其中一种复合物与吗啉衍生物的生物正交连接显示可在活细胞中诱导特异性溶酶体标记。LysoTracker深红色的共定位研究表明皮尔逊系数为0.83。

更新日期：2020-03-05

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