A mitochondria-targeted near-infrared fluorescent probe for pH monitoring in living cells based on the rhodamine-hemicyanine hybrid structure

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2024-09-19 DOI:10.1016/j.dyepig.2024.112465

Xin Ji, Qi Jin, Yongqin Shi, Xiao-Feng Yang

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Abstract

Mitochondrial pH plays a crucial role in cellular metabolism and pathological conditions. Thus, tracking changes in mitochondrial pH is essential for understanding its impact on cellular processes. In this work, we report a mitochondria-targetable near-infrared pH-sensitive fluorescent probe, Rh-NorCy, based on the rhodamine-hemicyanine hybrid structure. Rh-NorCy contains a non-alkylated indolenine moiety as recognition site of pH and a triphenylphosphonium moiety as the mitochondria-targeting group. As the solution pH decreases from 9.1 to 5.8, the indolium N atom in the Rh-NorCy structure undergoes protonation, leading to a red shift of its maximum absorption wavelength from 568 nm to 709 nm and a significant fluorescence enhancement at 748 nm simultaneously. Importantly, Rh-NorCy exhibits a suitable pK_a (7.27) to map the pH variation in the mitochondria. Rh-NorCy demonstrates excellent photostability, minimal cytotoxicity, and strong mitochondria-targeting capability. It has been used to observe mitochondrial pH fluctuations during starvation and carbonylcyanide m-chlorophenylhydrazone (CCCP)-induced mitophagy.

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基于罗丹明-水杨酸杂交结构的用于监测活细胞 pH 值的线粒体靶向近红外荧光探针

线粒体 pH 值在细胞代谢和病理状态中起着至关重要的作用。因此，跟踪线粒体 pH 值的变化对于了解其对细胞过程的影响至关重要。在这项工作中，我们报告了一种基于罗丹明-血丙氨酸杂交结构的线粒体靶向近红外 pH 敏感荧光探针 Rh-NorCy。Rh-NorCy 含有一个非烷基化的吲哚啉分子作为 pH 值识别位点，一个三苯基膦分子作为线粒体靶向基团。当溶液 pH 值从 9.1 降到 5.8 时，Rh-NorCy 结构中的吲哚鎓 N 原子发生质子化，导致其最大吸收波长从 568 纳米红移到 709 纳米，同时在 748 纳米处的荧光显著增强。重要的是，Rh-NorCy 的 pKa 值（7.27）适合绘制线粒体中的 pH 值变化图。Rh-NorCy 具有出色的光稳定性、最小的细胞毒性和强大的线粒体靶向能力。它已被用于观察线粒体在饥饿和羰基氰化间氯苯腙（CCCP）诱导的有丝分裂过程中的 pH 波动。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.