1616735-75-1Relevant academic research and scientific papers
Mechanism-Based Fluorogenic trans-Cyclooctene–Tetrazine Cycloaddition
Vázquez, Arcadio,Dzijak, Rastislav,Dra?ínsky, Martin,Rampmaier, Robert,Siegl, Sebastian J.,Vrabel, Milan
supporting information, p. 1334 - 1337 (2017/01/24)
The development of fluorogenic reactions which lead to the formation of fluorescent products from two nonfluorescent starting materials is highly desirable, but challenging. Reported herein is a new concept of fluorescent product formation upon the inverse electron-demand Diels–Alder reaction of 1,2,4,5-tetrazines with particular trans-cyclooctene (TCO) isomers. In sharp contrast to known fluorogenic reagents the presented chemistry leads to the rapid formation of unprecedented fluorescent 1,4-dihydropyridazines so that the fluorophore is built directly upon the chemical reaction. Attachment of an extra fluorophore moiety is therefore not needed. The photochemical properties of the resulting dyes can be easily tuned by changing the substitution pattern of the starting 1,2,4,5-tetrazine. We support the claim with NMR measurements and rationalize the data by computational study. Cell-labeling experiments were performed to demonstrate the potential of the fluorogenic reaction for bioimaging.
In situ synthesis of alkenyl tetrazines for highly fluorogenic bioorthogonal live-cell imaging probes
Wu, Haoxing,Yang, Jun,Seckute, Jolita,Devaraj, Neal K.
supporting information, p. 5805 - 5809 (2014/06/10)
In spite of the wide application potential of 1,2,4,5-tetrazines, particularly in live-cell and in vivo imaging, a major limitation has been the lack of practical synthetic methods. Here we report the in situ synthesis of (E)-3-substituted 6-alkenyl-1,2,4
