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To improve the potency of Heptamethine cyanines (Hcyanines) in cancer research, we designed and synthesized two novel Hcyanines based theranostic probes,  IR794-Morph  and  IR794-Morph-Mpip , to enhance cancer cell internalization and targeting. In acidic conditions that resemble to tumour environment, both  IR794  derivatives exhibited broad NIR absorption band (704‒794 nm) and fluorescence emission (798‒828 nm) that is suitable for deep seated tumour imaging. Moreover, in vitro study revealed that  IR794-Morph-Mpip  exhibited better cancer targetability towards various cancer cell lines under physiological and slightly acidic conditions compared to normal cells.  IR794-Morph-Mpip  was fast internalized into the cancer cells within the first 5 min and mostly localized in lysosomes and mitochondria. In addition, the internalized signal was brighter when the cells were in the hypoxic environment. Furthermore, cellular uptake mechanism of both  IR794  dyes, investigated via flow cytometry, revealed that endocytosis through OATPs receptors and clathrin-mediated endocytosis were the main routes. Moreover,  IR794-Morph-Mpip , displayed anti-cancer activity towards all tested cancer cell types with IC 50  below 7 μM (at 6 h incubation), which is approximately three times lower than that of the normal cells. Therefore, increasing protonated cites in tumour environment of Hcyanines together with incorporating morpholine in the molecule can enhance structure-inherent targeting of these dyes.

Effect of morpholine and charge distribution of cyanine dyes on cell internalization and cytotoxicity