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Hydrazide-Hydrazone Small Molecules as AIEgens: Illuminating Mitochondria in Cancer Cells
- Source :
- Chemistry (Weinheim an der Bergstrasse, Germany). 25(35)
- Publication Year :
- 2019
-
Abstract
- 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.
- Subjects :
- Cell Survival
Biocompatible Materials
Mitochondrion
010402 general chemistry
Hydrazide
01 natural sciences
Catalysis
law.invention
Cell Line
HeLa
chemistry.chemical_compound
Organophosphorus Compounds
Confocal microscopy
law
Humans
Computer Simulation
Cytotoxicity
Fluorescent Dyes
biology
010405 organic chemistry
Organic Chemistry
Optical Imaging
Hydrazones
General Chemistry
Fibroblasts
biology.organism_classification
Fluorescence
Small molecule
0104 chemical sciences
Mitochondria
chemistry
Cancer cell
Biophysics
HeLa Cells
Subjects
Details
- ISSN :
- 15213765
- Volume :
- 25
- Issue :
- 35
- Database :
- OpenAIRE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Accession number :
- edsair.doi.dedup.....4a5eb1a8fbea8f5f99b39c68bce0afbe