Photodynamic and photothermal synergistic behavior of triphenylamine-porphyrin nanoparticles for DNA interaction, cellular cytotoxicity and localization

Abstract

In this paper, amphiphilic conjugated triphenylamine-porphyrins TPA-Por-TPA and TPA-Por were designed and synthesized. The water-soluble nanostructures TPA-Por-TPA NPs and TPA-Por NPs spontaneously assembled after π–π stacking, which can be changed by improving the internal transfer ability of electrons. The intercalation and external binding modes of these free porphyrins and nanoporphyrins interacting with ct-DNA were confirmed by UV–vis and fluorescence spectroscopy. Reactive oxygen species (ROS) production was studied by 2′,7′-dichlorofluorescein diacetate, demonstrating that the rate of production of ROS is TPA-Por-TPA NPs > TPA-Por-TPA > TPA-Por NPs > TPA-Por. In addition, the structure of the NP enhanced the acceptor–donor conjugated structure, resulting in fluorescence quenching and promoting non-radiative heat generation. The photothermal conversion efficiencies of the TPA-Por-TPA NPs and TPA-Por NPs were measured and calculated to be 34.89% and 37.99%, respectively. At the same time, the three nanomaterials showed good photocytotoxicity, and the IC50 of the TPA-Por-TPA NPs and TPA-Por NPs was 32.18 and 36.62 μg ml−1, respectively, at 10 min after laser irradiation. The cellular uptake and subcellular localization of these NPs were further evaluated through a confocal laser scanning microscope. The results showed that the conjugated NPs have good biocompatibility properties in the cancer cells. These properties make it possible for triphenylamine porphyrin NPs to become photosensitizers for the photodynamic and photothermal synergistic treatment of tumors, and have potential prospects for applications in cancer diagnosis and treatment.