Naphthalimide and Carbazole Based Mechanochromic Molecular Dyads and Triads for Selective Lysosome Imaging.

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Chemistry - An Asian Journal Pub Date : 2025-01-16 DOI:10.1002/asia.202401386

Akkarakkaran Thayyil Muhammed Munthasir, Poonam Rani, Pandi Dhanalakshmi, Silvano Geremia, Neal Hickey, Pakkirisamy Thilagar

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Abstract

In this study, we report the design and development of a stable fluorescent probe that is selectively localized in the cytosol of Hela cells. We designed two probes, 1 and 2, with D-π-A (carbazole (Cbz)-vinyl-naphthalimide (NPI)) and A-π-D-π-A (NPI-vinyl-Cbz-vinyl-NPI) architecture, respectively. Probes 1 and 2 exhibit broad photoluminescence (PL) spectra ranging from green (550 nm) to far-red (800 nm) in solutions and aggregated states. In the solid-state, the PL of these probes shows a bathochromic shift, which can be attributed to intermolecular interactions. In a water-rich medium, Probe 1, with a single NPI moiety, shows aggregation-caused quenching (ACQ) but retains a moderate quantum yield of 13.7 % (Φ_soln=61.4 %). On the other hand, probe 2, with two NPI units, showed aggregation-induced enhanced emission AIEE, where the PLQY is increased nearly 4 times (Φ_soln=3.5 %, Φ_agg=12.8 %). In-vitro cell studies revealed that these probes are non-toxic and effectively stain cells in green and red channels. Notably, Probe 1 demonstrated excellent cellular uptake and selectivity for lysosome, with a Pearson overlap coefficient of 0.91.

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基于萘酰亚胺和咔唑的机械变色分子二联体和三联体用于选择性溶酶体成像。

在这项研究中，我们报道了一种稳定的荧光探针的设计和开发，它可以选择性地定位在Hela细胞的细胞质中。我们设计了两种探针1和2，分别具有D-π-A(咔唑（Cbz)-乙烯基-萘酰亚胺（NPI））和A-π-D-π-A （NPI-乙烯基-Cbz-乙烯基-NPI）结构。探针1和2在溶液和聚集状态下表现出从绿色（550 nm）到远红色（800 nm）的宽光致发光（PL）光谱。在固体中，这些探针的PL显示出一种色移，这可以归因于分子间的相互作用。在富水介质中，探针1具有单个NPI片段，表现出聚集引起的猝灭（ACQ），但保持了中等量子产率13.7% （Фsoln = 61.4%）。另一方面，具有两个NPI单元的探针2显示出聚集诱导的增强发射AIEE，其中PLQY增加了近4倍（Фsoln = 3.5%， Фagg = 12.8%）。体外细胞研究表明，这些探针是无毒的，并有效地在绿色和红色通道染色细胞。值得注意的是，探针1对溶酶体表现出良好的细胞摄取和选择性，Pearson重叠系数为0.91。

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).