α,α-Dicyanoolefin-Based Chemiluminophore with Conical Intersection for High-Contrast Imaging of Peroxynitrite in Ulcerative Colitis

Abstract

Chemiluminescence (CL) imaging has been extensively investigated owing to its advantages, such as the lack of an external excitation source, low background signal, and high selectivity. Despite these advantages, existing CL probes for peroxynitrite (ONOO–) detection are often hindered by complex synthetic routes and a propensity for false-positive signals. This study presents a novel CL probe DCM-C based on an α,α-dicyanoolefin skeleton to address these issues. DCM-C features a concise two-step synthesis and enables highly selective ONOO– detection with a superior signal-to-background ratio (SBR) of 552-fold. Both experimental and DFT theoretical calculation results indicate that CL depends on the α,α-dicyanoolefin skeleton through conical intersection. DCM-C is successfully used to image ONOO– in living cells with low cytotoxicity and monitor the ONOO– changes in a mouse model of ulcerative colitis (UC) with high contrast. This study provides an innovative strategy for developing high-sensitivity detection tools for ONOO– and has great potential for the early diagnosis and treatment processes of ulcerative colitis.