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 |
Referencias:
- Carter, T.S., Mooibroek, T.J., Stewart, P.F.N., Crump, M.P., Galan, M.C., Davis, A.P., (2016) Angew. Chem. Int. Ed., 55, pp. 9311-9315
- (2016) Angew. Chem., 128, pp. 9457-9461
- Sun, W., Guo, S., Hu, C., Fan, J., Peng, X., (2016) Chem. Rev., 116, pp. 7768-7817
- Zhang, X.-T., Liu, G.-J., Ning, Z.-W., Xing, G.-W., (2017) Carbohydr. Res., 452, pp. 129-148
- Samaniego Lopez, C., Lago Huvelle, M.A., Uhrig, M.L., Coluccio Leskow, F., Spagnuolo, C.C., (2015) Chem. Commun., 51, pp. 4895-4898
- Bérubé, M., Dowlut, M., Hall, D.G., (2008) J. Org. Chem., 73, pp. 6471-6479
- Dowlut, M., Hall, D.G., (2006) J. Am. Chem. Soc., 128, pp. 4226-4227
- Schumacher, S., Katterle, M., Hettrich, C., Paulke, B.-R., Pal, A., Hall, D.G., Scheller, F.W., Gajovic-Eichelmann, N., (2011) J. Mol. Recognit., 24, pp. 953-959
- Liu, C.T., Tomsho, J.W., Benkovic, S.J., (2014) Bioorg. Med. Chem., 22, pp. 4462-4473
- Adamczyk-Woźniak, A., Borys, K.M., Sporzyński, A., (2015) Chem. Rev., 115, pp. 5224-5247
- Strekowski, L., Lipowska, M., Patonay, G., (1992) J. Org. Chem., 57, pp. 4578-4580
- Menéndez, G.O., Pichel, M.E., Spagnuolo, C.C., Jares-Erijman, E.A., (2013) Photochem. Photobiol. Sci., 12, pp. 236-240
- Menéndez, G.O., Samaniego López, C., Jares-Erijman, E.A., Spagnuolo, C.C., (2013) Photochem. Photobiol., 89, pp. 1354-1361
- Sindrewicz, P., Lian, L.-Y., Yu, L.-G., (2016) Front. Oncol., 6, p. 79
- Zhang, Q., Wang, F., Wu, Y.-S., Zhang, K.-K., Lin, Y., Zhu, X.-Q., Lv, J.-Q., Huang, Y.-P., (2015) Oncol. Lett., 9, pp. 1231-1235
- Shen, B.Q., Finkbeiner, W.E., Wine, J.J., Mrsny, R.J., Widdicombe, J.H., (1994) Am. J. Physiol. Lung Cell. Mol. Physiol., 266, p. L493
- Callaghan Rose, M., Voynow, J.A., (2006) Physiol. Rev., 86, pp. 245-278
- Shumilov, D., Popov, A., Fudala, R., Akopova, I., Gryczynski, I., Borejdo, J., Gryczynski, Z., Grygorczyk, R., (2014) Methods, 66, pp. 312-324
- Kreda, S.M., Okada, S.F., van Heusden, C.A., O'Neal, W., Gabriel, S., Abdullah, L., Davis, C.W., Lazarowski, E.R., (2007) J. Physiol., 584, pp. 245-259
- Kreda, S.M., Seminario-Vidal, L., van Heusden, C.A., O'Neal, W., Jones, L., Boucher, R.C., Lazarowski, E.R., (2010) J. Physiol., 588, pp. 2255-2267
- Stewart, C.E., Torr, E.E., Mohd Jamili, N.H., Bosquillon, C., Sayers, I., (2012) J. Allergy, 2012, p. 943982
- Adler, K., Tuvim, M., Dickey, B., (2013) Front. Endocrinol., 4, p. 129
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