Fluorogenic 1,3-dipolar cycloaddition reaction between 9-azidomethylanthracenes and acetylenes and fluorescent properties study

CHED 577

Blake M. Hodges, bmhodges@gmail.com, Fang Xie, xie@mail.chem.sc.edu, and Qian Wang, wang@mail.chem.sc.edu. Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter St., Columbia, SC 29208
One major application of bioconjugation techniques is to attach signaling molecules to bio-entities for bioimaging and diagnosis applications. In general, excess labeling molecules should be removed after conjugation reactions in order to avoid the interference of the signaling events. However, it is very difficult to perform such purification operations for imaging in the intracellular environment.

We utilized the 1,3-dipolar cycloaddition reaction to combine 9-azidomethylanthracene derivatives, which have very poor fluorescence, with a variety of acetylene compounds. The quantum yield values of both the starting materials and products were measured and compared in order to evaluate the “trigger-on" effect of the fluorogenic property of this cycloaddition reaction. Our results showed that the products generally have very high quantum yields while the starting materials display very low fluorescent properties and quantum efficiency. Therefore, this reaction can potentially be used in the in vivo labeling applications for the biomedical applications.