Tetrazine as a general phototrigger to turn on fluorophores. Issue 17 (17th April 2020)

• Record Type: Journal Article
• Authors: Loredo, Axel; Tang, Juan; Wang, Lushun; Wu, Kuan-Lin; Peng, Zane; Xiao, Han
• Is Part Of: Chemical science. Volume 11:Issue 17(2020)
• Page Start: 4410
• Page End: 4415
• Publication Date: 2020-04-17
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc01009j
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Tetrazine was demonstrated for the first time as a general phototrigger to design photoactivatable fluorophore probes. Abstract : Light-activated fluorescence affords a powerful tool for monitoring subcellular structures and dynamics with enhanced temporal and spatial control of the fluorescence signal. Here, we demonstrate a general and straightforward strategy for using a tetrazine phototrigger to design photoactivatable fluorophores that emit across the visible spectrum. Tetrazine is known to efficiently quench the fluorescence of various fluorophores via a mechanism referred to as through-bond energy transfer. Upon light irradiation, restricted tetrazine moieties undergo a photolysis reaction that generates two nitriles and molecular nitrogen, thus restoring the fluorescence of fluorophores. Significantly, we find that this strategy can be successfully translated and generalized to a wide range of fluorophore scaffolds. Based on these results, we have used this mechanism to design photoactivatable fluorophores targeting cellular organelles and proteins. Compared to widely used phototriggers ( e.g., o -nitrobenzyl and nitrophenethyl groups), this study affords a new photoactivation mechanism, in which the quencher is photodecomposed to restore the fluorescence upon light irradiation. Because of the exclusive use of tetrazine as a photoquencher in the design of fluorogenic probes, we anticipate that our current study will significantly facilitate the development of novel photoactivatable fluorophores.