Chitosan-naphthalimide probes for dual channel recognition of HClO and H 2 S in cells and their application in photodynamic therapy

The combination of bio-imaging with photodynamic therapy (PDT) to accomplish theranostics is promising in cancer treatment. Three chitosan-naphthalimide probes were studied in this work. 4-(5-Bromothiophen-2-yl)-1,8-naphthalic anhydride was first synthesized, and then reacted with chitosan to obtain the macromolecules (CS-N-Br). The recognition group thiomorpholine or its derivatives were introduced into CS-N-Br to obtain nano-probes (CS-N-ML, CS-N-BSZ, CS-N-FSQ) eventually. The studies revealed that CS-N-ML and CS-N-FSQ exhibit high selectivity and can specifically recognize HClO and H S. CS-N-ML and CS-N-FSQ can perform exogenous and endogenous confocal imaging of HClO and H S in cells also. CS-N-ML's ability to target lysosomes positions indicated it could act as a lysosome-specific probe. It was discovered that the probes generate superoxide anions (O ) via a Type I mechanism. This discovery endows the probes with high photosensitizing activity even under hypoxic conditions. There is a positive correlation between the extent of the conjugated system and the photosensitivity of the probes, indicating that an enhanced conjugation leads to increased photosensitivity. Upon light irradiation, the probes generate ROS within HeLa cells. These results suggested that these probes can achieve theranostics for diseases associated with abnormal levels of HClO and H S.