Department of Chemistry, Indian Institute of Science Education and Research (IISER)-Pune, Dr. Homi Bhabha Road, Pashan, Pune, Maharashtra, 411008, India.
Department of Chemistry, Indian Institute of Technology (IIT)-Gandhinagar, Palaj, Gandhinagar, Gujarat, 382355, India.
Chemistry. 2019 Jun 21;25(35):8229-8235. doi: 10.1002/chem.201901074. Epub 2019 May 17.
Aggregation-induced-emission luminogens (AIEgens) have gained considerable attention as interesting tools for several biomedical applications, especially for bioimaging due to their brightness and photostability. Numerous AIEgens have been developed for lighting up the subcellular organelles to understand their forms and functions not only healthy but also unhealthy states, such as in cancer cells. However, there is lack of easily synthesizable, biocompatible small molecules for illuminating mitochondria (powerhouses) inside cells. To address this issue, an easy and short synthesis of new biocompatible hydrazide-hydrazone-based small molecules with remarkable aggregation-induced emission (AIE) properties is described. These small-molecule AIEgens showed hitherto unobserved AIE properties due to dual intramolecular H-bonding confirmed by theoretical calculation, pH- and temperature-dependent fluorescence and X-ray crystallographic studies. Confocal microscopy showed that these AIEgens were internalized into the HeLa cervical cancer cells without showing any cytotoxicity. One of the AIEgens was tagged with a triphenylphosphine (TPP) moiety, which successfully localized in the mitochondria of HeLa cells in a selective way compared to L929 noncancerous fibroblast cells. These unique hydrazide-hydrazone-based biocompatible AIEgens can serve as powerful tools to illuminate multiple subcellular organelles to elucidate their forms and functions in cancer cells for next-generation biomedical applications.
聚集诱导发光化合物（AIEgens）因其亮度和光稳定性而成为多种生物医学应用的有趣工具，尤其是在生物成像方面。已经开发出许多 AIEgens 来照亮亚细胞细胞器，以了解它们的形态和功能，不仅在健康状态下，而且在不健康状态下，如癌细胞中。然而，缺乏易于合成、生物相容的小分子来照亮细胞内的线粒体（动力工厂）。为了解决这个问题，描述了一种简单而短的合成新的生物相容的酰腙基小分子的方法，这些小分子具有显著的聚集诱导发光（AIE）性质。这些小分子 AIEgens 由于通过理论计算、pH 和温度依赖性荧光以及 X 射线晶体学研究证实的双重分子内氢键而表现出前所未有的 AIE 性质。共焦显微镜显示，这些 AIEgens 被内化到 HeLa 宫颈癌细胞中，而没有显示出任何细胞毒性。其中一种 AIEgen 被标记上三苯基膦（TPP）部分，与非癌细胞 L929 成纤维细胞相比，它能够以选择性的方式定位于 HeLa 细胞的线粒体中。这些基于酰腙的独特生物相容的 AIEgens 可以作为强大的工具，照亮多个亚细胞细胞器，以阐明它们在癌细胞中的形态和功能，用于下一代生物医学应用。
