A Highly Sensitive Fluorogenic Probe for Imaging Glycoproteins and Mucine Activity in Live Cells in the Near‐Infrared Region

Cecilia Samaniego Lopez; Jimena Hebe Martínez; María Laura Uhrig; Federico Coluccio Leskow; Carla Cecilia Spagnuolo

Index: 10.1002/chem.201800790

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Abstract

A novel fluorescent molecular probe is reported, which is able to detect glycoproteins, especially mucins, with high sensitivity and with a turn‐on response along with a large Stokes shift (>130 nm), within the biologically active window. The probe contains an aminotricarbocyanine as the fluorescent reporter with a linked benzoboroxole as the recognition unit, which operates through a dynamic covalent reaction between the boronic hemiester residue of the receptor and cis‐diols of the analyte. The superior selectivity of the probe is displayed by the labeling of mucins present in Calu‐3 cells. The new benzoboroxole fluorescent derivative gathers together key properties to make it a highly rated molecular probe: specificity, excellent solubility in water, and off–on near infrared emission. This probe is expected to be an excellent tool for imaging intracellular mucin to evaluate mucus‐related diseases as well as a sensing strategy towards glycosylated structures with a high potential for theranostics approaches in biological samples.