Analytica chimica acta · 2026
Ratiometric near-infrared fluorescent probe for imaging Peroxynitrite fluxes in rheumatoid arthritis and drug-induced liver injury models.
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Li Rong, Wang Ruifang, Li Minglu, Zhang Liyun
Аннотация
BACKGROUND: Peroxynitrite (ONOO-) plays a pivotal role in the pathogenesis of Rheumatoid arthritis (RA) and drug-induced liver injury (DILI), with its dynamic accumulation closely associated with disease progression. To effectively monitor the level of ONOO- in biological system, fluorescent probes offer distinct advantages for ONOO-, including high spatiotemporal resolution, non-invasive imaging capability, and exceptional sensitivity for detecting transient ONOO- fluctuations in living systems. These probes enable real-time visualization of ONOO- in inflamed joints or drug-stressed livers, facilitating early diagnosis and therapeutic monitoring.
RESULTS: Thus, a novel mitochondria-targeted ratiometric near-infrared (NIR) fluorescent probe, DXD, was designed and synthesized via the condensation reaction of a diphenylamino-substituted xanthene with dicyanoisophorone. The incorporation of a dicyanoisophorone bridging unit enabled emission redshift into the NIR region, while a phenylboronic acid recognition group conferred rapid and selective responsiveness to ONOO-. DXD exhibited a markedly larger Stokes shift and faster response kinetics for ONOO-. Importantly, the original emission peak of DXD at 734 nm gradually decreased, while a new peak at 618 nm progressively emerged and intensified, enabling ratiometric detection of ONOO-. Functionally, DXD enabled selective monitoring of dynamic fluctuations in both endogenous and exogenous ONOO- in live cells. It is noteworthy that ONOO- concentrations were significantly elevated in RA and DILI models compared to normal mice, providing important imaging evidence for the role of ONOO- in disease progression.
SIGNIFICANCE: Detecting ONOO- levels using fluorescent probes is critically important because ONOO- acts as a key pathogenic mediator in both RA and DILI models, driving inflammation, autoimmunity, and tissue damage. Furthermore, its real-time monitoring serves as an early and sensitive biomarker for disease progression, often showing changes before traditional clinical indicators.
RESULTS: Thus, a novel mitochondria-targeted ratiometric near-infrared (NIR) fluorescent probe, DXD, was designed and synthesized via the condensation reaction of a diphenylamino-substituted xanthene with dicyanoisophorone. The incorporation of a dicyanoisophorone bridging unit enabled emission redshift into the NIR region, while a phenylboronic acid recognition group conferred rapid and selective responsiveness to ONOO-. DXD exhibited a markedly larger Stokes shift and faster response kinetics for ONOO-. Importantly, the original emission peak of DXD at 734 nm gradually decreased, while a new peak at 618 nm progressively emerged and intensified, enabling ratiometric detection of ONOO-. Functionally, DXD enabled selective monitoring of dynamic fluctuations in both endogenous and exogenous ONOO- in live cells. It is noteworthy that ONOO- concentrations were significantly elevated in RA and DILI models compared to normal mice, providing important imaging evidence for the role of ONOO- in disease progression.
SIGNIFICANCE: Detecting ONOO- levels using fluorescent probes is critically important because ONOO- acts as a key pathogenic mediator in both RA and DILI models, driving inflammation, autoimmunity, and tissue damage. Furthermore, its real-time monitoring serves as an early and sensitive biomarker for disease progression, often showing changes before traditional clinical indicators.