A double bond-conjugated dimethylnitrobenzene-type photolabile nitric oxide donor with improved two-photon cross section

A double bond-conjugated dimethylnitrobenzene-type photolabile nitric oxide donor with improved two-photon cross section
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具有改进的双光子截面的双键共轭二甲基硝基苯型光不稳定一氧化氮供体

DOI:
10.1016/j.bmcl.2015.05.095
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发表时间:
2015
期刊:
Bioorg. Med. Chem. Lett.
影响因子:
--
通讯作者:
H. Nakagawa
H. Nakagawa
中科院分区:
--
文献类型:
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作者:
1.N. Ieda;K. Hishikawa;K. Eto;K. Kitamura;M. Kawaguchi;T. Suzuki;K. Fukuhara;N. Miyata;T. Furuta;J. Nabekura;H. Nakagawa

文献摘要

相似文献

光控NO供体能够在生理条件下精确时空释放NO。我们设计并合成了一种新型的二甲基硝基苯型NO供体Flu-DNB-DB,它含有一个碳碳双键取代了先前报道的Flu-DNB的酰胺键。Flu-DNB-DB响应于蓝色波长区域中的单光子激活而释放NO,并且在720 nm处显示出大大增加的双光子截面(δu)(Flu-DNB:0.12 GM,Flu-DNB-DB:0.98 GM)。我们表明,Flu-DNB-DB能够精确控制细胞内释放的NO在响应于950 nm脉冲激光照射短至1秒。这种近红外光可控的NO光源为研究NO的生物学作用提供了一个有价值的工具。
Photocontrollable NO donors enable precise spatiotemporal release of NO under physiological conditions. We designed and synthesized a novel dimethylnitrobenzene-type NO donor, Flu-DNB-DB, which contains a carbon–carbon double bond in place of the amide bond of previously reported Flu-DNB. Flu-DNB-DB releases NO in response to one-photon activation in the blue wavelength region, and shows a greatly increased two-photon cross-section (δu) at 720 nm (Flu-DNB: 0.12 GM, Flu-DNB-DB: 0.98 GM). We show that Flu-DNB-DB enables precisely controlled intracellular release of NO in response to 950 nm pulse laser irradiation for as little as 1 s. This near-infrared-light-controllable NO source should be a valuable tool for studies on the biological roles of NO.