A novel lysosomal targeted near-infrared probe for ratio detection of carbon monoxide in cells and in vivo.

[Display omitted] • Based on dicyanoisophorone skeleton a near-infrared fluorescent probe was prepared and used to detect CO with high selectivity. • Two emission channels ratiometric fluorescence changes can be observed through adjusting the ICT effect of probe by CO. • The design of the probe enables it to be used for detecting CO in lysosomal subcellular organelles and further validated through cell co-localization imaging experiments. • The probe can be used to detect the endogenous and exogenous CO in Hela cells and could be used in living mice. • The probe is capable of detecting endogenous and exogenous CO through cell imaging experiments and has been successfully used in living mice. Carbon monoxide (CO) as an endogenous gas signaling molecule possesses important physiological functions and is of great significance in the treatment of various diseases. Real-time tracking of CO in living organisms has become a research hotspot in recent years. This article presents a lysosomal targeted near-infrared ratio fluorescence probe (TBM-CO) for selective detection of CO based on the dicyanoisophorone skeleton and morpholine fragment. The probe TBM-CO with weak ICT effect can be transformed to precursor TBM-NH 2 with strong ICT effect by the traditional Tsuji-Trost reaction procession in the presence of Pd2+ ions. The mechanism was proved by DFT calculation or the MS and HPLC results respectively. In the near-infrared region an obvious ratio fluorescence intensity change (F 686 / F 616) is observed in vitro spectral experiments. The concentration titration experiments indicate that there is a good liner relationship between the ratio fluorescence intensity and the concentration in the range of 0 to 50 μM (R2 = 0.996) and the detection limit is calculated as 0.38 μM. The cell fluorescence imaging and co-localization experiments further demonstrate that TBM-CO is able to detect the exogenous and endogenous CO in lysosomal subcellular organelle. Finally, it was used to detect the changes of CO concentration in living mice successfully. In short, a probe with three advantages of near-infrared emission, ratiometric fluorescence and organelle targeting was reported and used to detect CO successfully in cells and in living mice. [ABSTRACT FROM AUTHOR]