Novel Scaffolds for Photoswitchable Tools by Robert Tombari

Robert Tombari

UC Davis

Small molecule photoswitches capable of accessing two geometric states are highly desirable, especially if their design is modular and incorporates a pharmacophore tethering site. My team and I have developed novel photoswitchable scaffolds, to which we can append molecules of interest with optimal photophysical properties. The ability to streamline syntheses of photoswitchable compounds allows us to investigate the mechanism of action of various small molecules in biological systems with the high degree of spatial and temporal control that the field of photopharmacology offers.

ABSTRACT

Photoswitches capable of accessing two geometric states are highly desirable, especially if their design is modular and incorporates a pharmacophore tethering site. My team and I utilized azide-alkyne click chemistry to access arylazo-1,2,3-triazoles, a previously unexplored class of azoheteroarenes that exhibit high thermal stabilities and near quantitative bidirectional photoconversion. Our strategy enabled us to access a wide variety of photoswitchable compounds from readily available azides. In a similar fashion, we developed a redox isomerization strategy for synthesizing p-formylazobenzenes from p-nitrobenzyl alcohol, where the resulting azo-aldehydes can be readily converted to photoswitchable compounds with excellent photophysical properties using simple hydrazide click chemistry. The ability to streamline syntheses of photoswitchable compounds with reliably optimal photophysical properties allows us to investigate the mechanism of action of various small molecules in biological systems with the high degree of spatial and temporal control that the field of photopharmacology offers.

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