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

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

CHEMISTRY-A EUROPEAN JOURNAL

WILEY-V C H VERLAG GMBH

Año: 2018 vol. 24 p. 6344 - 6348

0947-6539

We introduce a novel fluorescent molecular probe 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 meet high rated molecular probes: specificity, excellent solubility in water and off-on near infrared emission. The probe we provide 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.