An anticancer-active imidazole analogue as a fluorescent sensor: sensitive and selective detection of Cu 2+ ions
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An anticancer‑active imidazole analogue as a fluorescent sensor: sensitive and selective detection of Cu2+ ions Krishnaswamy Savithri1 · Rathinasabapathi Prabhakaran1 · Manickam Paulpandi2 · Israel V. M. V. Enoch3 · Palathurai Subramaniam Mohan1 Received: 29 March 2020 / Accepted: 7 May 2020 © Springer Nature Switzerland AG 2020
Abstract A highly sensitive and selective imidazole-based fluorescent “on–off” probe, (2-(4,5-bis((E)-4-methoxystyryl)-1H-imidazol2-yl) phenol) (BMIP), is synthesized and characterized. The fluorescence of the compound is quenched by C u2+ ions, contrary 2+ to the response at the addition of other metal ions. Further, the color change due to C u ion addition is noticeable with 2+ 2+ naked eyes. A 1:1 stoichiometry of BMIP/Cu is observed. An excellent C u sensing with high quantum efficiency of the compound was successfully utilized to probe the cancer cells by using fluorescence microscopy. In addition, the compound is tested for its in vitro anti-proliferative activity against human liver and lung cancer cell lines. The in vitro study demonstrated the efficiency of BMIP against selected cancer cells, with an inhibitory concentration ( IC50) of 12 ± 1.0 µM, 11 ± 1.0 µM lung and liver cancer cells, respectively. The occurrence of apoptotic bodies indicated that the cell death induced by BMIP through activation of apoptotic pathway. Overall, our findings signify that BMIP is one of the most promising drugs holding significant pharmaceutical potential in cancer treatment.
Introduction Sensing metal ions to ease the job of biologists and environmental scientists has become crucial, and thus research on designing and developing newer sensors is on the rise [1]. A chemosensor should not cause any negative side effects if tested in vivo. An added advantage of the sensor molecule is a possession of medicinal property. Among metal ions that cause adverse effects on the environment and the health of human beings is Cu(II). Copper is one of the predominant metals present in plants, animals and microorganisms [2]. Levels of aerosol copper in the environment are often Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11243-020-00396-7) contains supplementary material, which is available to authorized users. * Palathurai Subramaniam Mohan [email protected] 1
Department of Chemistry, Bharathiar University, Coimbatore, Tamil Nadu, India
2
Disease Proteomics Laboratory, Department of Zoology, Bharathiar University, Coimbatore, Tamil Nadu, India
3
Centre for Nanoscience and Genomics, Karunya Institute of Technology and Sciences (Deemed-to-be University), Coimbatore, Tamil Nadu 641114, India
used as an indication of industrial activity. The functions of Cu(II) ions in human body include a range of physiological processes like bone formation, cellular energy generation, activation of oxygen transport and signal transduction [3]. Excess of copper in human body has connection with Alzheimer’s disease [4]. Therefore, it is of paramount im
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