A coumarin-based fluorescent chemosensor as a Sn indicator and a fluorescent cellular imaging agent

Abstract

In the present study, fluorogenic coumarin-based probes (1–3) through condensation of 4-hydroxy coumarin with malondialdehyde bis(diethyl acetal)/triethyl orthoformate were prepared. The absorption and fluorescence emission properties of 2b and 3 in different solvents were studied, and a considerable solvatochromic effect was observed. The sensitivity of chemosensors 2b and 3 toward various cations and anions was investigated. It was revealed that compound 3 had a distinct selectivity toward Sn²⁺, possibly via a chelation enhanced quenching mechanism. The fluorescence signal was quenched over the concentration range of 6.6–120 μM, with an LOD value of 3.89 μM. The cytotoxicity evaluation of 3 against breast cancer cell lines demonstrated that the chemosensor was nontoxic and could be used successfully in cellular imaging. The probe responded to tin ions not only via fluorescence quenching, but also through colorimetric signal change. The change in optical properties was observed in ambient conditions and inside living cells.