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

• Published in: Chemistry : a European journal Vol. 24; no. 24; pp. 6344 - 6348
• Main Authors: Samaniego Lopez, Cecilia, Hebe Martínez, Jimena, Uhrig, María Laura, Coluccio Leskow, Federico, Spagnuolo, Carla Cecilia
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 25-04-2018
• Subjects: Biological activity; Biological properties; Biological samples; boronolectin; Chemistry; cyanine; Diols; dyes/pigments; Fluorescence; fluorescent probes; glycoprotein; Glycoproteins; Mucin; Mucins; Mucus; Near infrared radiation; cyanine; dyes/pigments; glycoprotein; boronolectin; fluorescent probes
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201800790

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.
Boronolectin based Near‐IR fluorescent probe: a benzoboroxol‐tricarbocyanine based probe with large Stokes shift, fluorogenic response and high selectivity for glycoproteins was developed. The performance of the dye was demonstrated in live epithelial cells by imaging mucin granules. It was possible to detect differences in morphology and localization of mucin within the cells. The novel probe is expected to be a useful tool for bioanalytical imaging of glycostructures.