biostudies-literatureBrondsted FNIH Office of the DirectorNational Cancer InstituteNCI NIH HHSNational Institute of General Medical SciencesNIGMS NIH HHSNIH HHSe202303038https://www.ebi.ac.uk/biostudies/studies/S-EPMC10926271biostudies-literatureUnknown30(1)Photoacoustic imaging (PAI) is an emerging imaging technique that uses pulsed laser excitation with near-infrared (NIR) light to elicit local temperature increases through non-radiative relaxation events, ultimately leading to the production of ultrasound waves. The classical xanthene dye scaffold has found numerous applications in fluorescence imaging, however, xanthenes are rarely utilized for PAI since they do not typically display NIR absorbance. Herein, we report the ability of Nebraska Red (NR) xanthene dyes to produce photoacoustic (PA) signal and provide a rational design approach to reduce the hydrolysis rate of ester containing dyes, affording cell permeable probes. To demonstrate the utility of this approach, we construct the first cell permeable rhodamine-based, turn-on PAI imaChemistry (Weinheim an der Bergstrasse, Germany)Single Atom Stabilization of Phosphinate Ester-Containing Rhodamines Yields Cell Permeable Probes for Turn-On Photoacoustic Imaging.PMC10926271UM1CA186644P30CA16059R35GM148221OD030409S10 OD030409UM1 CA186644P30 CA016059R35 GM148221Fang YGrant SStains CIBrondsted FLi LZhou XfalseSingle Atom Stabilization of Phosphinate Ester-Containing Rhodamines Yields Cell Permeable Probes for Turn-On Photoacoustic Imaging.Photoacoustic imaging (PAI) is an emerging imaging technique that uses pulsed laser excitation with near-infrared (NIR) light to elicit local temperature increases through non-radiative relaxation events, ultimately leading to the production of ultrasound waves. The classical xanthene dye scaffold has found numerous applications in fluorescence imaging, however, xanthenes are rarely utilized for PAI since they do not typically display NIR absorbance. Herein, we report the ability of Nebraska Red (NR) xanthene dyes to produce photoacoustic (PA) signal and provide a rational design approach to reduce the hydrolysis rate of ester containing dyes, affording cell permeable probes. To demonstrate the utility of this approach, we construct the first cell permeable rhodamine-based, turn-on PAI ima2024-01-01T00:00:00Z2024 Jan2025-04-18T14:23:21.978Z2025-04-07T00:30:15.16ZS-EPMC109262713785293510.1002/chem.202303038