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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. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Registro:

Documento: Artículo
Título:A Highly Sensitive Fluorogenic Probe for Imaging Glycoproteins and Mucine Activity in Live Cells in the Near-Infrared Region
Autor:Samaniego Lopez, C.; Hebe Martínez, J.; Uhrig, M.L.; Coluccio Leskow, F.; Spagnuolo, C.C.
Filiación:Departamento de Química Orgánica-CIHIDECAR-CONICET, Facultad de Ciencias ExactasyNaturales, Universidad de Buenos Aires, Int. Guiraldes 2160, Ciudad de Buenos Aires, 1428, Argentina
IQUIBICEN-CONICET, Departamento de Química Biológica, Facultad de Ciencias ExactasyNaturales, Universidad de Buenos Aires, Int. Guiraldes 2160, Ciudad de Buenos Aires, 1428, Argentina
Palabras clave:boronolectin; cyanine; dyes/pigments; fluorescent probes; glycoprotein; Fluorescence; Glycoproteins; Infrared devices; Boronolectin; Cyanine; Dyes/pigments; Excellent solubility; Fluorescent probes; Fluorescent reporter; Near infrared region; Near-infrared emissions; Probes; boron derivative; fluorescent dye; glycoprotein; mucin; chemical structure; chemistry; drug effect; epithelium cell; human; near infrared spectroscopy; procedures; Boron Compounds; Epithelial Cells; Fluorescent Dyes; Glycoproteins; Humans; Molecular Structure; Mucins; Spectroscopy, Near-Infrared
Año:2018
Volumen:24
Número:24
Página de inicio:6344
Página de fin:6348
DOI: http://dx.doi.org/10.1002/chem.201800790
Título revista:Chemistry - A European Journal
Título revista abreviado:Chem. Eur. J.
ISSN:09476539
CODEN:CEUJE
CAS:Boron Compounds; Fluorescent Dyes; Glycoproteins; Mucins
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09476539_v24_n24_p6344_SamaniegoLopez

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Citas:

---------- APA ----------
Samaniego Lopez, C., Hebe Martínez, J., Uhrig, M.L., Coluccio Leskow, F. & Spagnuolo, C.C. (2018) . A Highly Sensitive Fluorogenic Probe for Imaging Glycoproteins and Mucine Activity in Live Cells in the Near-Infrared Region. Chemistry - A European Journal, 24(24), 6344-6348.
http://dx.doi.org/10.1002/chem.201800790
---------- CHICAGO ----------
Samaniego Lopez, C., Hebe Martínez, J., Uhrig, M.L., Coluccio Leskow, F., Spagnuolo, C.C. "A Highly Sensitive Fluorogenic Probe for Imaging Glycoproteins and Mucine Activity in Live Cells in the Near-Infrared Region" . Chemistry - A European Journal 24, no. 24 (2018) : 6344-6348.
http://dx.doi.org/10.1002/chem.201800790
---------- MLA ----------
Samaniego Lopez, C., Hebe Martínez, J., Uhrig, M.L., Coluccio Leskow, F., Spagnuolo, C.C. "A Highly Sensitive Fluorogenic Probe for Imaging Glycoproteins and Mucine Activity in Live Cells in the Near-Infrared Region" . Chemistry - A European Journal, vol. 24, no. 24, 2018, pp. 6344-6348.
http://dx.doi.org/10.1002/chem.201800790
---------- VANCOUVER ----------
Samaniego Lopez, C., Hebe Martínez, J., Uhrig, M.L., Coluccio Leskow, F., Spagnuolo, C.C. A Highly Sensitive Fluorogenic Probe for Imaging Glycoproteins and Mucine Activity in Live Cells in the Near-Infrared Region. Chem. Eur. J. 2018;24(24):6344-6348.
http://dx.doi.org/10.1002/chem.201800790