Dual-Readout Tyrosinase Activity Assay Facilitated by a Chromo-Fluorogenic Reaction between Catechols and Naphthoresorcin.,Analytical Chemistry

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Dual-Readout Tyrosinase Activity Assay Facilitated by a Chromo-Fluorogenic Reaction between Catechols and Naphthoresorcin.
Analytical Chemistry ( IF 6.7 ) Pub Date : 2019-12-20 , DOI: 10.1021/acs.analchem.9b05204
Jiahui Zhao _{1,

2} , Guoyong Liu _{1,

3} , Jian Sun ₁ , Qifeng Wang ₄ , Zong-Jun Li ₁ , Xiurong Yang _{1,

2,

3}

Affiliation

Analyte-responsive chromo-fluorogenic reactions under accessible conditions are important for designing small-molecule spectroscopic probes. We describe a series of newly constructed motifs based on the chromo-fluorogenic reaction between catechol derivatives (typically hydroxytyrosol, dopamine, and levodopa) and naphthoresorcin (NR) in aqueous solution under ambient conditions. The weakly absorptive and fluorogenic catechols/NR was converted to products having visible absorption and bright fluorescence within several minutes. The chromo-fluorophores produced from this reaction had a maximum absorbance at 458 nm and emission at 480 nm with high fluorescence quantum yields (30-84%). Inspired by the tyrosinase-catalyzed hydroxylation of monophenols to catechols, the tyrosinase-enabled chromo-fluorogenic reaction was verified by using monophenol (typically tyrosol) as the substrate. In this regard, a dual-readout tyrosinase activity assay was developed by virtue of the in situ "turn-on" optical signals. Furthermore, a test of tyrosinase inhibition, by using a common inhibitor kojic acid, demonstrated the potential of the chromo-fluorogenic reaction for developing other tyrosinase related assays and signal transduction.

中文翻译：

邻苯二酚和萘二酚之间的发色荧光反应促进了酪氨酸酶的双重读出。

在可达到的条件下，分析物响应性发色荧光反应对于设计小分子光谱探针很重要。我们根据环境条件下水溶液中邻苯二酚衍生物（通常为羟基酪醇，多巴胺和左旋多巴）和萘酚（NR）之间的发色荧光反应，描述了一系列新构建的基序。弱吸收性和荧光性邻苯二酚/ NR在几分钟内转化为具有可见吸收和明亮荧光的产物。该反应产生的发色团在458 nm处具有最大吸光度，在480 nm处具有较高的荧光量子产率（30-84％）。受酪氨酸酶催化的单酚羟基化为邻苯二酚的启发，通过使用单酚（通常为酪醇）作为底物验证了酪氨酸酶促发色荧光反应。在这方面，借助于原位“开启”光信号开发了双重读出的酪氨酸酶活性测定法。此外，通过使用常见的抑制剂曲酸对酪氨酸酶抑制作用的测试证明了发色荧光反应在开发其他酪氨酸酶相关测定和信号转导方面的潜力。

更新日期：2020-01-04

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