A Novel Methacryloyl-Masked NIR Fluorescent Probe for Detection of Cysteine and Its Application in Bioimaging.

IF 3.9 2区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - A European Journal Pub Date : 2024-11-19 DOI:10.1002/chem.202402840

Prasad M Sonawane, Neha Jain, JunHyuk Kim, Su Jeong Park, Sandip V Mulay, Satish Balasaheb Nimse, David G Churchill

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Abstract

Cysteine (Cys) detection is recognized as an essential element in this investigation due to the critical function of Cys in several physiological processes in living organisms. A new NIR fluorescent probe SNC-Cys has been synthesized by incorporating a five-membered malononitrile derivatized ring as an electron withdrawing group, and a methacryloyl group detection moiety for cysteine. After adding Cys, SNC-Cys shows an emission of 654 nm and further works as a "Turn-on" probe via ICT photomechanism. SNC-Cys has high sensitivity and selectivity for Cys (LOD = 0.46 µM) and can discriminate it from other closely related amino acids, molecules with structural similarity, and in some cases very close functional group likeness. Thus, these results allow the effective imaging of Cys in living A549 cells which indicates good cell permeability and high applicability in live cell imaging. This study anticipates that SNC-Cys could be an aid in the detection of Cys-relevant diseases.

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用于检测半胱氨酸的新型甲基丙烯酰掩蔽近红外荧光探针及其在生物成像中的应用

由于半胱氨酸（Cys）在生物体内的多个生理过程中起着关键作用，因此半胱氨酸（Cys）的检测被认为是这项研究的重要内容。我们合成了一种新的近红外荧光探针 SNC-Cys，该探针以五元丙二腈衍生环作为取电子基团，并以甲基丙烯酰基作为半胱氨酸的检测分子。加入 Cys 后，SNC-Cys 的发射波长为 654 纳米，并通过 ICT 光机制进一步发挥 "开启 "探针的作用。SNC-Cys 对 Cys 具有很高的灵敏度和选择性（LOD = 0.46 µM），可以将其与其他密切相关的氨基酸、结构相似的分子以及某些功能基团非常相似的分子区分开来。因此，这些结果允许对 A549 活细胞中的 Cys 进行有效成像，这表明活细胞成像具有良好的细胞渗透性和高度适用性。这项研究预计，SNC-Cys 可以帮助检测与 Cys 相关的疾病。

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来源期刊

Chemistry - A European Journal 化学-化学综合

CiteScore

7.90

自引率

4.70%

发文量

1808

审稿时长

1.8 months

期刊介绍： Chemistry—A European Journal is a truly international journal with top quality contributions (2018 ISI Impact Factor: 5.16). It publishes a wide range of outstanding Reviews, Minireviews, Concepts, Full Papers, and Communications from all areas of chemistry and related fields. Based in Europe Chemistry—A European Journal provides an excellent platform for increasing the visibility of European chemistry as well as for featuring the best research from authors from around the world. All manuscripts are peer-reviewed, and electronic processing ensures accurate reproduction of text and data, plus short publication times. The Concepts section provides nonspecialist readers with a useful conceptual guide to unfamiliar areas and experts with new angles on familiar problems. Chemistry—A European Journal is published on behalf of ChemPubSoc Europe, a group of 16 national chemical societies from within Europe, and supported by the Asian Chemical Editorial Societies. The ChemPubSoc Europe family comprises: Angewandte Chemie, Chemistry—A European Journal, European Journal of Organic Chemistry, European Journal of Inorganic Chemistry, ChemPhysChem, ChemBioChem, ChemMedChem, ChemCatChem, ChemSusChem, ChemPlusChem, ChemElectroChem, and ChemistryOpen.