Boron Dipyrromethene As a Fluorescent Caging Group for Single-Photon Uncaging with Long-Wavelength Visible Light
Boron Dipyrromethene As a Fluorescent Caging Group for Single-Photon Uncaging with Long-Wavelength Visible Light
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DOI：
10.1021/cb500525p
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发表时间：
2014-10-01
影响因子：
4
通讯作者：
Urano, Yasuteru
中科院分区：
文献类型：
--
作者：
Umeda, Nobuhiro;Takahashi, Hironori;Urano, Yasuteru
笼化化合物是精确时空调节细胞功能的有用工具，但在大多数情况下，释放笼化化合物需要紫外线（UV）光，这是细胞毒性的，并且对组织的渗透有限。因此，需要能够被较长波长的光激活的笼状化合物。本文描述了一种新的4-芳氧基二吡咯甲基硼（BODIPY）衍生物的光消除反应，并表明BODIPY可以作为苯酚基团的笼化基团。我们开发了一种新的bodipy笼型组胺化合物，该化合物在蓝绿色可见光下可光激活，以一种时空可控的方式刺激培养的HeLa细胞。这种笼化策略有望广泛应用于开发探测各种细胞功能的工具。
Caged compounds are useful tools for precise spatiotemporal modulation of cell functions, but in most cases uncaging requires ultraviolet (UV) light, which is cytotoxic and has limited tissue penetration. Therefore, caged compounds that can be activated by longer-wavelength light are required. Here we describe a novel photoelimination reaction of 4-aryloxy boron dipyrromethene (BODIPY) derivatives and show that BODIPY can function as a caging group for phenol groups. We developed a novel BODIPY-caged histamine compound, which is photoactivatable with blue-green visible light to stimulate cultured HeLa cells in a spatiotemporally well-controlled manner. This caging strategy is expected to be widely applicable to develop tools for probing various cellular functions.