Design And Bioimaging Of Fluorescent Probe Based On Anthracencecarboximide Chromophore Platform

As one of the important reactive oxygen species?ROS?,hydrogen peroxide is involved with many important physiological processes.The aberrant level of hydrogen peroxide?H₂O₂?in vivo is associated with many diseases.In recent years,drug-induced organ failure has been an important issue for public health.Many literature reports indicate that the pathological process accompanies with rapidly elevated levels of H₂O₂,hence monitoring H₂O₂ level in vivo may be helpful for evaluating the drug-induced pathological process.Thus,efficiently detecting,monitoring and real time imaging of H₂O₂ in live cells and in vivo is of significance.Fluorescence imaging has been employed as a powerful tool to track biomolecules in disease diagnosis and scientific research owing to its high selectivity,sensitivity,real-time assay and in situ monitoring capability.As a new fluorophore,anthracene carboximide has many advantages,such as high fluorescence quantum yield,fluorescence stability,large Stokes shift.Futhermore,anthracene carboximide has relatively long operating wavelengths?excitation and emission?compared with 1,8-Naphthalimide derivatives,which may contribute to the application in vivo.The probe based on anthracene carboximide has the property that photophysical property is dependent on the electron-withdrawing capability of substituent at 6th position of the anthracene ring,In other words,the fluorescence of this probe can be adjusted by altering electron-withdrawing capability of substituent at 6th position of the anthracene ring,and this may offer ieads for the design of probe.Liposome nanoparticle has excellent biocompatibility.Encapsulating the probe into liposome to afford the liposomal nanoprobe has a broad prospect for the fluorescent detection and imaging in vivo.In this paper,based on ICT,we built a ratiometric probe for H₂O₂ by using anthracene carboximide.We synthesized anthracene carboximide as the fluorophore,then introduced the nitrophenyl-dicarbonyl moiety onto the 6th position of the anthracene carboximide,the nitrophenyl-dicarbonyl group can reacted with H₂O₂ specifically.The probe has high selectivity and sensitivity towards H₂O₂ and can quantitatively detect H₂O₂ in low concentration range.The detection limit is determined to be 0.49 ?M.Moreover,the probe possesses relativly long operating wavelengths?absorption: 560 nm,emission: 595 nm?.Futhermore,in order to enhance the application of probe in biosystem and the ability of imaging in vivo,we encapsulated the probe into liposome decorated with PEG to make the long-circulation liposome nanoprobe?NPs-A?.The NPs-A is spherical,the average diameter of NPs-A is about 90 nm;NPs-A is biocompatible,has the little-long circulation in vivo,and is able to image endogenous H₂O₂ in live cells and zebrafish;it can also track the APAP-induced organ damage.This study may offer a helpful and convenient means for investigating the functions of H₂O₂ during related pathological processes.