Journal
BIOSENSORS-BASEL
Volume 12, Issue 12, Pages -Publisher
MDPI
DOI: 10.3390/bios12121149
Keywords
bacteriochlorin; naphthalimide; photodynamic therapy; fluorescence imaging; theranostics; resonance energy transfer; glutathione
Funding
- Russian Federation President Grant for Young Scientists
- RSF project [MK-4878.2021.1.3]
- [21-73-20158]
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In this study, we report a new conjugate BChl-S-S-NI that can be cleaved into individual functional fragments by the intracellular enzyme glutathione (GSH). The conjugate exhibits efficient energy transfer and fluorescence recovery in solution. The photoinduced activity and imaging properties of the conjugate were investigated with promising results.
Herein, we report a new conjugate BChl-S-S-NI based on the second-generation photosensitizer bacteriochlorin e6 (BChl) and a 4-styrylnaphthalimide fluorophore (NI), which is cleaved into individual functional fragments in the intracellular medium. The chromophores in the conjugate were cross-linked by click chemistry via a bis(azidoethyl)disulfide bridge which is reductively cleaved by the intracellular enzyme glutathione (GSH). A photophysical investigation of the conjugate in solution by using optical spectroscopy revealed that the energy transfer process is realized with high efficiency in the conjugated system, leading to the quenching of the emission of the fluorophore fragment. It was shown that the conjugate is cleaved by GSH in solution, which eliminates the possibility of energy transfer and restores the fluorescence of 4-styrylnaphthalimide. The photoinduced activity of the conjugate and its imaging properties were investigated on the mouse soft tissue sarcoma cell line S37. Phototoxicity studies in vitro show that the BChl-S-S-NI conjugate has insignificant dark cytotoxicity in the concentration range from 15 to 20,000 nM. At the same time, upon photoexcitation, it exhibits high photoinduced activity.
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