Molecular Chemiluminescent Probes with a Very Long Near‐Infrared Emission Wavelength for in Vivo Imaging

Abstract

Chemiluminescence imaging is imperative for diagnostics and imaging due to its intrinsically high sensitivity. To improve in vivo detection of biomarkers, chemiluminophores that simultaneously possess near‐infrared (NIR) emission and modular structures amenable to construction of activatable probes are highly desired; however, these are rare. Herein, we report two chemiluminophores with record long NIR emission (>750 nm) via integration of dicyanomethylene‐4H‐benzothiopyran or dicyanomethylene‐4H‐benzoselenopyran with dioxetane unit. Caging of the chemiluminophores with different cleavable moieties produces NIR chemiluminescence probes (NCPs) that only produce signals upon reaction with reactive oxygen species or enzymes, for example, β‐galactosidase, with a tissue‐penetration depth of up to 2 cm. Thus, this study provides NIR chemiluminescence molecular scaffolds applicable for in vivo turn‐on imaging of versatile biomarkers in deep tissues.

Seeking Illumination: The Path to Chemiluminescent 1,2-Dioxetanes for Quantitative Measurements and In Vivo Imaging

“…The acrylic acid group improves aqueous solubility, but HyCL-4-AM features improved cellular uptake. Huang and co-workers , have developed a series of near-infrared 1,2-dioxetane probes using a formyl ester trigger for peroxynitrite detection. The near-infrared emission can image deeper in tissue and the different trigger is likely to have a disparate selectivity from the isatin-based PNCL probe.…”

Progresses in Fluorescence Imaging Guidance for Bone and Soft Tissue Sarcoma Surgery

“…The activatable fluorescent probes for tumor cells consist of two parts. One is the activation of intracellular enzymes, such as b-galactosidase bioactivation (24) and glutathione (GSH) bioactivation (25). And the other one is the activation of fluorescence by the tumor cell hypoxia environment (26).…”

Amphiphilic Molecules Exhibiting Zwitterionic Excited-State Intramolecular Proton Transfer and Near-Infrared Emission for the Detection of Amyloid β Aggregates in Alzheimer’s Disease

“…56 In addition, to expand the functionality of these molecules, the phenol group could be readily capped with a variety of triggers that could be reactive only in presence of specific analytes, to generate various reactivity-based imaging agents. 57,58 Further studies regarding the effect of the number of nitrogen atoms on the macrocycle and the substituents on the amino group are currently ongoing in our group.…”