{"title":"Benzylidenemalononitrile bridged long-wavelength emission luminogens with “washing-free” properties for monitoring the dynamics of LDs","authors":"","doi":"10.1016/j.dyepig.2024.112459","DOIUrl":null,"url":null,"abstract":"<div><p>Understanding the physiological functions and monitoring the dynamics of lipid droplets (LDs) in living cells are crucial, because they play important roles in energy reservoir and as sources of lipid molecules, and can be potentially used as biomarkers in cancer diagnose. Organic small-molecule based luminogens with long-wavelength emission are advantageous imaging tools for visualizing the dynamics of LDs, as the long wavelength fluorescence has lower scattering and absorption by biomolecules, deeper penetration ability into tissues, and reduced interference effect. In this work, we report the design, synthesis and LDs imaging properties of two long-wavelength emitting organic luminogens (OLs) <strong>APBM</strong> and <strong>PyBM</strong>. The two materials have typical donor-acceptor-donor (D-A-D) structure with a benzylidenemalononitrile moiety as the acceptor, bridging different electron donors, i.e., <em>N</em>,<em>N</em>-dimethylamino phenyl for <strong>APBM</strong>, and pyrene for <strong>PyBM</strong>, respectively. The strong electron-withdrawing benzylidenemalononitrile moiety inducing intense intramolecular charge transfer effect, which endows the emissions of <strong>APBM</strong> and <strong>PyBM</strong> as far as 668 nm and 605 nm in the solid state, and on the other hand, creates their twisted molecular conformation. As a result, the OLs exhibit aggregation-induced-emission behaviors, due to the restriction of intramolecular motions, evolving the “washing-free” properties of the materials in bioimaging. <strong>APBM</strong> and <strong>PyBM</strong> both have low cytotoxicity and good photostability, and are able to light up HepG2 cells efficiently. In addition, <strong>APBM</strong> shows excellent LDs targeting ability, and it is successfully used to discriminate normal cells and cancer cells, and monitor the dynamics of LDs under different nutritional conditions, and the interactions with mitochondria.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":null,"pages":null},"PeriodicalIF":4.1000,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Dyes and Pigments","FirstCategoryId":"88","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0143720824005254","RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
Understanding the physiological functions and monitoring the dynamics of lipid droplets (LDs) in living cells are crucial, because they play important roles in energy reservoir and as sources of lipid molecules, and can be potentially used as biomarkers in cancer diagnose. Organic small-molecule based luminogens with long-wavelength emission are advantageous imaging tools for visualizing the dynamics of LDs, as the long wavelength fluorescence has lower scattering and absorption by biomolecules, deeper penetration ability into tissues, and reduced interference effect. In this work, we report the design, synthesis and LDs imaging properties of two long-wavelength emitting organic luminogens (OLs) APBM and PyBM. The two materials have typical donor-acceptor-donor (D-A-D) structure with a benzylidenemalononitrile moiety as the acceptor, bridging different electron donors, i.e., N,N-dimethylamino phenyl for APBM, and pyrene for PyBM, respectively. The strong electron-withdrawing benzylidenemalononitrile moiety inducing intense intramolecular charge transfer effect, which endows the emissions of APBM and PyBM as far as 668 nm and 605 nm in the solid state, and on the other hand, creates their twisted molecular conformation. As a result, the OLs exhibit aggregation-induced-emission behaviors, due to the restriction of intramolecular motions, evolving the “washing-free” properties of the materials in bioimaging. APBM and PyBM both have low cytotoxicity and good photostability, and are able to light up HepG2 cells efficiently. In addition, APBM shows excellent LDs targeting ability, and it is successfully used to discriminate normal cells and cancer cells, and monitor the dynamics of LDs under different nutritional conditions, and the interactions with mitochondria.
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.
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