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Factors affecting the uncaging efficiency of 500 nm light-activatable BODIPY caging group
Bioorganic & Medicinal Chemistry Letters ( IF 2.5 ) Pub Date : 2017-11-16 , DOI: 10.1016/j.bmcl.2017.11.030
Minoru Kawatani , Mako Kamiya , Hironori Takahashi , Yasuteru Urano

Photoremovable protective groups, or caging groups, enable us to regulate the activities of bioactive molecules in living cells upon photoirradiation. Nevertheless, requirement of UV light for activating caging group is a significant limitation due to its cell toxicity and its poor tissue penetration. Our group previously reported a 500 nm light-activatable caging group based on BODIPY scaffold, however, its uncaging efficiency was lower than those of conventional caging groups. Here we show that the uncaging quantum yield (QY) of BODIPY caging group depends upon the driving force of photo-induced electron transfer (PeT). We also found that the uncaging QY increased in less polar solvents. We applied these findings to develop BODIPY-caged capsaicin, which is well localized to low-polarity intracellular compartments, as a tool to stimulate TRPV1 in live cells in response to blue-green light.



中文翻译:

影响500 nm光激活BODIPY笼型组解笼效率的因素

可光去除的保护基团或笼蔽基团使我们能够在光照射后调节活细胞中生物活性分子的活性。然而,由于其细胞毒性和较差的组织渗透性,需要紫外线来激活笼养基团是一个很大的限制。我们的研究小组先前报道了一个基于BODIPY支架的500 nm光激活笼养组,但是其解笼效率低于常规笼养组。在这里,我们显示BODIPY笼蔽基团的开笼量子产率(QY)取决于光致电子转移(PeT)的驱动力。我们还发现,开极性QY在极性较小的溶剂中增加。我们利用这些发现开发了BODIPY笼养的辣椒素,该辣椒素很好地定位于低极性的细胞内区室,

更新日期:2017-11-16
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