Abstract
Nitroxyl, which was acknowledged as a vital constituent among the reactive nitrogen species, poses significant challenges when it comes to its swift and precise identification and measurement. Recently, a kind of BODIPY-DAP-Cu(II)-conjugate fluorescent probes has been broadly used to detect nitroxyl. However, the impact of varying linker chain lengths on the physicochemical attributes and imaging performance of dipyrromethene boron difluoride–based fluorescent probes remained uncertain. In this study, we engineered three new dipyrromethene boron difluoride–based nitroxyl fluorescent probes CuII[BD1] (3.88 Å), CuII[BD2] (5.02 Å), CuII[BD3] (6.67 Å), CuII[BD4] (10.77 Å) which were composed of dipyrromethene boron difluoride as fluorescence indicator and a tripodal-DPA-Cu(II) unit as nitroxyl recognition site, using increasing lengths of linker chain. The new probe CuII[BD3] (6.67 Å) showed fast response (within 1 min) toward nitroxyl with remarkable sensitivity, capable of detecting as low as 0.25 μM, superior specificity for nitroxyl, and relative stability under physiological pH condition. Furthermore, the probe CuII[BD3] was applied to bioimaging of nitroxyl in rat blood. In conclusion, those results revealed that the imaging characteristics of dipyrromethene boron difluoride derivatives were significantly influenced by the length of the linker chain. The fluorescence detection efficiency increases with the growth of the linker chains within 6.67 Å. Consequently, these probes hold promise as valuable chemical instruments for probing the detailed functions and mechanisms of nitroxyl within biological organisms and offered an innovative approach for the construction of dipyrromethene boron difluoride–based nitroxyl fluorescent probes.
Published Version
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