Rapid Identification of the Receptor‐Binding Specificity of Influenza A Viruses by Fluorogenic Glycofoldamers

Abstract

The re-emergence of influenza raises a global concern that viral pandemics can unpredictably occur. However, effective approaches that can probe the infection risk of influenza viruses for humans are rare. In this work, we develop a glycofoldamer that can rapidly identify the glycan-receptor specificity of influenza viruses in a high-throughput manner. The coupling of glycan receptors that can be recognized by hemagglutinin (a surface protein on the virion capsid of influenza) to a fluorogenic-dye foldamer produces the glycofoldamers with minimal fluorescence in aqueous solution. After interaction with human-infecting virus strains for only five minutes, the fluorescence intensity of the glycofoldamer is remarkably enhanced with a blue-shifted emission peak. The probes have also proven effective for the rapid identification of 1) the human- or bird-infecting properties of influenza viruses in a high-throughput manner and 2) the receptor-specificity switch of a virus strain by mutations.

Photochromism and molecular logic gate operation of a water-compatible bis-glycosyl diarylethene

“…This research paves the way for the development of photocontrolled diagnostic glycoprobes [34][35][36][37][38] for biomedical applications.…”

Bio‐Conjugated Advanced Materials for Targeted Disease Theranostics

“…Numerous examples have been reported on the use of galactose for targeting Hep‐G2 cells (ASGPr‐galactose interactions) . Poly(3‐hexylthiophene‐2,5‐diyl) (P3HT) nanodots assembled with poly(styrene‐ co ‐maleic anhydride) (PSMA) and galactose‐/mannose‐conjugated dicyanomethylene‐4H‐pyran (DCM) was complexed with poly(9,9‐dioctylfluorenyl‐2,7‐diyl) (PFO) before the self‐assembly with galactose‐/mannose‐conjugated DCM fluorophores, with FRET suppressing the fluorescence of PFO while enhancing that of glyco‐DCM, for targeted PNA/Con A detection and cancer cell imaging/PDT in Hep‐G2/MDA‐MB‐231 cells with improved water solubility (Figure 17d).…”

“…A foldable naphthalimide‐based probe with galactose‐containing glycan was able to sense Influenza A virus through binding to glycan receptors. Subsequent binding resulted in the unfolding of the probe and a clear fluorescence recovery . The use of galactose residues have further been proven to interact with the promising cancer biomarkers Erythrina cristagalli agglutinin (ECA) and galectin‐3 .…”

Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

“…Such rate enhancements are particularly important for the formation of neo‐glycoconjugates from carbohydrates of low reactivity (e.g., with GlcNAc at the reducing end). Recently, for example, this technique has enabled the labeling of complex influenza antigen tri‐, tetra‐ and pentasaccharides . We have also successfully utilized aniline‐catalyzed oxime formation to synthesize a range of highly complex neo‐glycoconjugates (Scheme ) …”