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Phosphorescence lifetime imaging microscopy (PLIM) combined with an oxygen (O 2 )-sensitive luminescent probe allows for high-resolution O 2  imaging of living tissues. Herein, we present phosphorescent Ir(III) complexes, (btp) 2 Ir(acac-DM) ( Ir-1 ) and (btp-OH) 3 Ir ( Ir-2 ), as useful O 2  probes for PLIM measurement. These small-molecule probes were efficiently taken up into cultured cells and accumulated in specific organelles. Their excellent cell-permeable properties allowed for efficient staining of three-dimensional cell spheroids, and thereby phosphorescence lifetime measurements enabled the evaluation of the O 2  level and distribution in spheroids, including the detection of alterations in O 2  levels by metabolic stimulation with an effector. We took PLIM images of hepatic tissues of living mice by intravenously administrating these probes. The PLIM images clearly visualized the O 2  gradient in hepatic lobules with cellular-level resolution, and the O 2  levels were derived based on calibration using cultured cells; the phosphorescence lifetime of  Ir-1  gave reasonable O 2  levels, whereas  Ir-2  exhibited much lower O 2  levels. Intravenous administration of NH 4 Cl to mice caused the hepatic tissues to experience hypoxia, presumably due to O 2  consumption to produce ATP required for ammonia detoxification, suggesting that the metabolism of the probe molecule might affect liver O 2  levels.

In vivo O2 imaging in hepatic tissues by phosphorescence lifetime imaging microscopy using Ir(III) complexes as intracellular probes