A Reductant-Resistant and Metal-Free Fluorescent Probe for Nitroxyl Applicable to Living Cells,Journal of the American Chemical Society

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A Reductant-Resistant and Metal-Free Fluorescent Probe for Nitroxyl Applicable to Living Cells
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2013-08-20 , DOI: 10.1021/ja404757s
Kodai Kawai ₁ , Naoya Ieda ₁ , Kazuyuki Aizawa ₁ , Takayoshi Suzuki ₁ , Naoki Miyata ₁ , Hidehiko Nakagawa _{1,

2}

Affiliation

Nitroxyl (HNO) is a one-electron reduced and protonated derivative of nitric oxide (NO) and has characteristic biological and pharmacological effects distinct from those of NO. However, studies of its biosynthesis and activities are restricted by the lack of versatile HNO detection methods applicable to living cells. Here, we report the first metal-free and reductant-resistant HNO imaging probe available for use in living cells, P-Rhod. It consists of a rhodol derivative moiety as the fluorophore, linked via an ester moiety to a diphenylphosphinobenzoyl group, which forms an aza-ylide upon reaction with HNO. Intramolecular attack of the aza-ylide on the ester carbonyl group releases a fluorescent rhodol derivative. P-Rhod showed high selectivity for HNO in the presence of various biologically relevant reductants, such as glutathione and ascorbate, in comparison with previous HNO probes. We show that P-Rhod can detect not only HNO enzymatically generated in the horseradish peroxidase-hydroxylamine system in vitro but also intracellular HNO release from Angeli's salt in living cells. These results suggest that P-Rhod is suitable for detection of HNO in living cells.

中文翻译：

适用于活细胞的耐还原剂和无金属硝基荧光探针

Nitroxyl (HNO) 是一氧化氮 (NO) 的单电子还原质子化衍生物，具有不同于 NO 的特征性生物学和药理作用。然而，由于缺乏适用于活细胞的多功能 HNO 检测方法，对其生物合成和活性的研究受到限制。在这里，我们报告了第一个可用于活细胞的无金属和抗还原剂 HNO 成像探针 P-Rhod。它由作为荧光团的酚醛衍生物部分组成，通过酯部分连接到二苯基膦基苯甲酰基，后者在与 HNO 反应时形成氮杂-叶立德。氮杂-叶立德对酯羰基的分子内攻击会释放出荧光硫醇衍生物。P-Rhod 在各种生物相关还原剂（如谷胱甘肽和抗坏血酸盐）存在下对 HNO 显示出高选择性，与以前的 HNO 探针相比。我们表明，P-Rhod 不仅可以检测体外辣根过氧化物酶-羟胺系统中酶促生成的 HNO，还可以检测活细胞中安吉利盐的细胞内 HNO 释放。这些结果表明 P-Rhod 适用于检测活细胞中的 HNO。

更新日期：2013-08-20

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