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

UHRIG, MARÍA LAURA; MARTÍNEZ, JIMENA HEBE; COLUCCIO LESKOW, FEDERICO; SAMANIEGO LOPEZ, CECILIA; SPAGNUOLO, CARLA CECILIA

CHEMISTRY-A EUROPEAN JOURNAL

WILEY-V C H VERLAG GMBH

Año: 2018

0947-6539

We introduce a novel fluorescent molecular probe able to detect glycoproteins, especiallymucins, with high sensitivity and with a turn-on response along with a large Stokes shift (>130nm), within the biologically active window. The probe contains an aminotricarbocyanine as thefluorescent reporter with a linked benzoboroxole as the recognition unit, which operates througha dynamic covalent reaction between the boronic hemiester residue of the receptor and cis-diolsof the analyte. The superior selectivity of the probe is displayed by the labeling of mucinspresent in Calu-3 cells. The new benzoboroxole fluorescent derivative gathers together keyproperties to meet high rated molecular probes: specificity, excellent solubility in water and offonnear infrared emission. The probe we provide is expected to be an excellent tool for imagingintracellular mucin to evaluate mucus related diseases as well as a sensing strategy towardsglycosylated structures with a high potential for theranostics approaches in biological samples.