1-Alkylamino-3H-naphtho[1,2,3-de]quinoline-2,7-diones. Visualization of lipid droplets in living cells

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2024-11-13 DOI:10.1016/j.dyepig.2024.112541

Sergei A. Chernenko , Anton L. Shatsauskas , Yuri V. Shatalin , Victoria S. Shubina , Margarita I. Kobyakova , Tatyana Yu Zheleznova , Anastasia S. Kostyuchenko , Alexander S. Fisyuk

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Abstract

A series of previously unknown 1-alkylamino-3H-naphtho[1,2,3-de]quinoline-2,7-diones, 1-alkylamino-6-nitro-3H-naphtho[1,2,3-de]quinoline-2,7-diones, and 1-alkylamino-6-amino-3H-naphtho[1,2,3-de]quinoline-2,7-diones was obtained by nucleophilic substitution of the tosyl group of 1-tosyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione with aliphatic amines. Among the synthesized compounds, fluorophores emitting light from the blue-green to orange-red region of the visible spectrum with fluorescence quantum yields up to 0.39 were found. Some of the synthesized compounds showed phototoxic effects on human breast carcinoma cell line BT474. It was shown that 3-butyl-1-(butylamino)-6-nitronaphthoquinolinedione stains exclusively lipid droplets, has a large Stokes shift and can be used for visualization of these organelles.

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1-烷基氨基-3H-萘并[1,2,3-de]喹啉-2,7-二酮。活细胞中脂滴的可视化

1-对甲基苯磺酰-3H-萘并[1,2,3-de]喹啉-2,7-二酮的对甲苯基团与脂肪族胺发生亲核取代反应，得到了 1-烷基氨基-6-氨基-3H-萘并[1,2,3-de]喹啉-2,7-二酮。在合成的化合物中，发现了发出可见光谱蓝绿至橙红区域光的荧光团，荧光量子产率高达 0.39。一些合成化合物对人类乳腺癌细胞系 BT474 具有光毒性作用。研究表明，3-丁基-1-(丁氨基)-6-硝基萘醌二酮只对脂滴染色，具有较大的斯托克斯偏移，可用于这些细胞器的可视化。

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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.