Orthogonally-tunable and ER-targeting fluorophores detect avian influenza virus early infection

Abstract

Cell-based assays can monitor virus infection at a single-cell level with high sensitivity and cost-efficiency. For this purpose, it is crucial to develop molecular probes that respond selectively to physiological changes in live cells. We report stimuli-responsive light-emitters built on a T-shaped benzimidazole platform, and consecutive borylation reactions to produce a library of homologs displaying systematic changes in fluorescence quantum yield and environmental sensitivity. We find that certain fluorophores localize selectively at the endoplasmic reticulum, and interact with proteins involved in the stress signaling pathways. Notably, the mono-borylated compound responds selectively to the stress conditions by enhancing fluorescence, and detects avian influenza virus infection at the single-cell level. Our findings demonstrate the unprecedented practical utility of the stress-responsive molecular probes to differentiate cellular states for early diagnosis.

Single‐Benzene Dual‐Emitters Harness Excited‐State Antiaromaticity for White Light Generation and Fluorescence Imaging

“…Such absence of solvatochromic shifts is quite unusual since ESIPT is often coupled with intramolecular charge transfer (ICT) across π-conjugation. [50] While polarity-sensitive dual emission might be beneficial for applications in sensing and imaging, [7,50,51] it could compromise the batch-to-batch color reproducibility of light-emitting devices. In this respect, dual emission without ICT is ideally suited for producing consistent white light.…”

Single‐Benzene Dual‐Emitters Harness Excited‐State Antiaromaticity for White Light Generation and Fluorescence Imaging

“…While polarity‐sensitive dual emission might be beneficial for applications in sensing and imaging, [7, 50, 51] it could compromise the batch‐to‐batch color reproducibility of light‐emitting devices. In this respect, dual emission without ICT is ideally suited for producing consistent white light.…”

Small is Beautiful: Electronic Origin and Synthetic Evolution of Single-Benzene Fluorophores

“…Over the years, we have been making π-extended benzimidazoles as fluorescent sensors, and multidentate ligands for transition metals and main-group elements. − In line with this research theme, attempts were taken to prepare a benzimidazole derivative, 13 , featuring silyl-protected acetylenes as solubility-enhancing groups (Scheme ). Contrary to our expectations, however, the reaction between diamine 12 and chloroacetic acid produced only highly polar products, as indicated by TLC analysis.…”