A new hydroxynaphthalimide-based merocyanine dye for imaging a mitochondrial viscosity in living cells

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-08-30 DOI:10.1016/j.dyepig.2025.113180

M.A. Pavlova , A.V. Efremenko , P.A. Panchenko , S.S. Golubtsova , A.V. Feofanov , O.A. Fedorova

引用次数: 0

Abstract

A new derivative of 3-styryl-4-hydroxynaphthalimide NI-Qu has been synthesized. It absorbs in the red region and exhibits long wavelength fluorescence, sensitive to the viscosity and polarity of the medium. The protonated and deprotonated forms of the dye were characterized by optical spectroscopy and NMR. It is shown that the deprotonated form of NI-Qu exhibits pronounced negative solvatochromism in organic solvents. NI-Qu demonstrates a 107-fold increase in fluorescence intensity at 695 nm during changing viscosity of glycerol-water mixtures from 0.89 cP to 906 cP with a linear dependence of the fluorescence quantum yield on viscosity over the entire viscosity range studied. Experiments in vitro showed low cytotoxicity of NI-Qu and its applicability as a selective fluorescent probe for viscosity in mitochondria in living cells.

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一种用于成像活细胞线粒体黏度的新型羟萘酰亚胺基merocyanine染料

合成了一种新的3-苯基-4-羟基萘酰亚胺NI-Qu衍生物。它在红色区域吸收，并表现出长波长荧光，对介质的粘度和极性敏感。通过光谱学和核磁共振对染料的质子化和去质子化形式进行了表征。结果表明，NI-Qu的去质子化形式在有机溶剂中表现出明显的负溶剂变色。NI-Qu显示，当甘油-水混合物的粘度从0.89 cP变化到906 cP时，695 nm处的荧光强度增加了107倍，在整个粘度范围内，荧光量子产率与粘度呈线性关系。体外实验表明，NI-Qu具有较低的细胞毒性，可作为活细胞线粒体粘度的选择性荧光探针。

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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.