Theory and experiment: The synthesis and drug application of "ON-OFF-ON" fluorescent probes for copper and biothiols detection

Abnormal copper ions (Cu ) and biothiols have potential impacts on environmental pollution and human health, so the detection of these substances with high selectivity and sensitivity has become an important research topic. In this study, we designed and synthesized two fluorescent probes (L and L ) based on naphthalene and anthracene derivatives that could specifically detect Cu and biothiols. Owing to the paramagnetic effect of Cu , the strong fluorescent intensity was quenched after the addition of Cu . When biothiols were added to the solution (L-Cu ), the fluorescence intensity was significantly enhanced and recovered. So, the interaction process was accompanied with "ON-OFF-ON" phenomenon in fluorescent intensity. Two complexes (L-Cu ) showed low limit of detection for biothiols (Cys was 3.4 ×10 M and GSH was 2.0 ×10 M) and weak cytotoxicity (< 150 μg/mL). Theoretical investigation analysis revealed that the intramolecular hydrogen bond existed in the structure of probes and the roles of molecular frontier orbitals in molecular interplay. In addition, two probes also showed good applicability in actual drug Atomolan. The GSH content in the tested Atomolan reached over 99.9% of the labeling which was accord with the percentage of pharmacopoeia. Therefore, two probes have the real application value in the detection of Cu , biothiols and drug efficacy in various environments.