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Hydrazide–Hydrazone Small Molecules as AIEgens: Illuminating Mitochondria in Cancer Cells
Author(s) -
Patil Sohan,
Pandey Shalini,
Singh Amit,
Radhakrishna Mithun,
Basu Sudipta
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901074
Subject(s) - hydrazide , hela , hydrazone , chemistry , small molecule , cancer cell , mitochondrion , biocompatible material , organelle , biophysics , molecule , aggregation induced emission , cytotoxicity , cyanine , fluorescence , nanotechnology , cell , biochemistry , materials science , cancer , biology , stereochemistry , in vitro , medicine , genetics , physics , organic chemistry , quantum mechanics , biomedical engineering
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.