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Functional aza-boron dipyrromethenes for subcellular imaging and organelle-specific photodynamic therapy
- Wang, Qiong, Ng, Dennis K. P., Lo, Pui-Chi
- Journal of materials chemistry 2018 v.6 no.20 pp. 3285-3296
- adenocarcinoma, apoptosis, breast neoplasms, colon, confocal microscopy, hepatoma, human cell lines, humans, hydrophilicity, image analysis, inhibitory concentration 50, irradiation, lysosomes, mitochondria, morpholine, neoplasm cells, photochemotherapy, photosensitizing agents, singlet oxygen, uterine cervical neoplasms
- Two hydrophilic aza-boron dipyrromethene (aza-BODIPY) derivatives have first been designed and synthesised for subcellular imaging. With a triphenylphosphonium or morpholine substituent, these probes show high affinity towards the mitochondria or lysosomes of a range of cancer cell lines, including human cervical cancer HeLa cells, hepatocellular carcinoma HepG2 cells, breast cancer MCF-7 cells and colon adenocarcinoma HT29 cells as revealed by confocal microscopy. By introducing two bromo groups into the aza-BODIPY skeleton, which can promote intersystem crossing by the heavy-atom effect, the resulting compounds become efficient singlet-oxygen generators and can serve as organelle-specific photosensitisers for photodynamic therapy (PDT). Upon irradiation, both compounds are photocytotoxic. The lysosome-targeted derivative exhibits higher cellular uptake and more efficient reactive oxygen species generation inside HeLa cells, resulting in higher PDT efficacy with an IC₅₀ value of 0.48 μM and cell death mainly through apoptosis.