Diversity-Oriented Synthesis of Highly Fluorescent Fused Isoquinolines for Specific Subcellular Localization.

Yoarhy A Amador-Sánchez, Andrés Aguilar-Granda, Ricardo Flores-Cruz, Davir González-Calderón, Cynthia Orta, Braulio Rodríguez-Molina, Arturo Jiménez-Sánchez, Luis D Miranda

The Journal of organic chemistry 2020 Jan 17

filter terms:

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 four-component 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.

Citation

Yoarhy A Amador-Sánchez, Andrés Aguilar-Granda, Ricardo Flores-Cruz, Davir González-Calderón, Cynthia Orta, Braulio Rodríguez-Molina, Arturo Jiménez-Sánchez, Luis D Miranda. Diversity-Oriented Synthesis of Highly Fluorescent Fused Isoquinolines for Specific Subcellular Localization. The Journal of organic chemistry. 2020 Jan 17;85(2):633-649