A multicomponent diversity-oriented synthesis of new highly emissive tetracyclic isoquinolines that target specific organelles is described. The title compounds were prepared via a three-step protocol starting with an Ugi fourcomponent reaction, followed by either an intramolecular alkyne hydroarylation and subsequent alkene isomerization or through a Pomeranz−Fritsch-type cyclization with a final intramolecular Heck reaction. Subcellular localization studies of these compounds using green channel confocal microscopy revealed remarkable and distinctive distribution patterns in live cells, showing an unprecedented high selectivity and imaging contrast. The differentiated organelle visualizationincluding localizers for mitochondria, lysosomes, Golgi apparatus, endoplasmic reticulum, and plasma membranewas achieved by varying the nature of the tetracyclic system and substituent pattern, changing the original four-component set in the starting Ugi reaction.

As et of BODIPY-carboranyl dyads synthesizedb ya Sonogashira cross-coupling reaction, where different C-substituted ortho-a nd meta-carboranyl fragments have been linked to aB ODIPY fluorophore is described. Chemical, photophysical and physicochemical analyses are presented, in-cludingN MR and singleX RD experiments, optical absorption/emission studies and partition coefficient(log P)m easurements. These studies, supported by DFT computations (M06-2X/6-31G**), provide an explanation to the largely divergentc ell income that thesef luorescent carboranyl-based fluorophores display,f or which as tructural or physicochemi-cal explanation remainse lusive. By studying the cell uptake efficiency and subcellular localization for our set of dyads on living HeLa cells, we trackedt he origins of these differences to significant variations in their static dipolem oments and partitionc oefficients,w hich tune their ability to interactw ith lipophilic microenvironments in cells. Remarkably, m-carboranyl-BODIPY derivativesw ith ah igherl ipophilicity are much betteri nternalisedb yc ells than their homologous with ocarborane, suggestingt hat m-isomers are potentially better theranostic agents for in vitro bioimaging and boron carriers for boron neutron capture therapy.

A dual-emissive fluorescent probe enabled unique tracking of 1O2-ROS species through a differential mitochondrial–nucleoli localization dynamic.

Mitochondrial voltage dynamics plays a crucial role in cell healthy and disease. Here, a new fluorescent probe to monitor mitochondrial early voltage variations is described. The slowly permeant probe is...