Artículo

Menéndez, G.O.; Lõpez, C.S.; Jares-Erijman, E.A.; Spagnuolo, C.C. "A versatile near-infrared asymmetric tricarbocyanine for zinc ion sensing in water" (2013) Photochemistry and Photobiology. 89(6):1354-1361
El editor solo permite decargar el artículo en su versión post-print desde el repositorio. Por favor, si usted posee dicha versión, enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

We have synthesized a near-infrared emissive asymmetric tricarbocyanine conveniently functionalized to improve bioconjugation. The leading structure contains a versatile derivatization point at the meso position for facile radical-nucleophilic aromatic substitution. We have evaluated a DPEN (N,N-di(2-picolyl)ethylendiamine) derivative of this dye as a highly selective sensor for zinc (II) in aqueous medium, which performs in an appropriate sensitivity range for biological studies. The probe was successfully conjugated to a protein-ligand model with high affinity and specificity (biotin-streptavidin technology) rendering an excellent performance of sensing. In a general strategy to obtain sensitive probes combining fluorescent nanoparticles and molecular fluorophores, a preliminary design of a supramolecular assembly derived from the conjugation of the molecular sensor to quantum dots (QDs) was also investigated. The advantages and problems of FRET-based sensors are also discussed. © 2013 The American Society of Photobiology.

Registro:

Documento: Artículo
Título:A versatile near-infrared asymmetric tricarbocyanine for zinc ion sensing in water
Autor:Menéndez, G.O.; Lõpez, C.S.; Jares-Erijman, E.A.; Spagnuolo, C.C.
Filiación:CIHIDECAR-CONICET, Dpto. de Química Orgánica, Ciudad Autónoma de Buenos Aires, Argentina
Palabras clave:carbocyanine; water; zinc; carbon nuclear magnetic resonance; chemistry; electrospray mass spectrometry; fluorescence resonance energy transfer; proton nuclear magnetic resonance; Carbocyanines; Carbon-13 Magnetic Resonance Spectroscopy; Fluorescence Resonance Energy Transfer; Proton Magnetic Resonance Spectroscopy; Spectrometry, Mass, Electrospray Ionization; Water; Zinc
Año:2013
Volumen:89
Número:6
Página de inicio:1354
Página de fin:1361
DOI: http://dx.doi.org/10.1111/php.12160
Título revista:Photochemistry and Photobiology
Título revista abreviado:Photochem. Photobiol.
ISSN:00318655
CODEN:PHCBA
CAS:water, 7732-18-5; zinc, 7440-66-6, 14378-32-6; Carbocyanines; Water; Zinc
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00318655_v89_n6_p1354_Menendez

Referencias:

  • Akers, W.J., Xu, B., Lee, H., Sudlow, G.P., Fields, G.B., Achilefu, S., Edwards, W.B., Detection of MMP-2 and MMP-9 activity in vivo with a triple-helical peptide optical probe (2012) Bioconjug. Chem., 23, pp. 656-663
  • Okuda, K., Okabe, Y., Kadonosono, T., Ueno, T., Youssif, B.G.M., Kizaka-Kondoh, S., Nagasawa, H., 2-Nitroimidazole-tricarbocyanine conjugate as a near-infrared fluorescent probe for in vivo imaging of tumor hypoxia (2012) Bioconjug. Chem., 23, pp. 324-329
  • Samanta, A., Vendrell, M., Yun, S.-W., Guan, Z., Xu, Q.-H., Chang, Y.-T., A photostable near-infrared protein labeling dye for in vivo imaging (2011) Chem. Asian J., 6, pp. 1353-1357
  • Xu, K., Sun, S., Li, J., Li, L., Qiang, M., Tang, B., A near-infrared fluorescent probe for monitoring ozone and imaging in living cells (2012) Chem. Commun., 48, pp. 684-686
  • Kiyose, K., Kojima, H., Urano, Y., Nagano, T., Development of a ratiometric fluorescent zinc ion probe in near-infrared region, based on tricarbocyanine chromophore (2006) J. Am. Chem. Soc., 128, pp. 6548-6549
  • Li, P., Duan, X., Chen, Z., Liu, Y., Xie, T., Fang, L., Li, X., Tang, B., A near-infrared fluorescent probe for detecting copper(II) with high selectivity and sensitivity and its biological imaging applications (2011) Chem. Commun., 47, pp. 7755-7757
  • Yang, Y., Cheng, T., Zhu, W., Xu, Y., Qian, X., Highly selective and sensitive near-infrared fluorescent sensors for cadmium in aqueous solution (2011) Org. Lett., 13, pp. 264-267
  • Zhu, M., Yuan, M., Liu, X., Xu, J., Lv, J., Huang, C., Liu, H., Zhu, D., Visible near-infrared chemosensor for mercury ion (2008) Org. Lett., 10, pp. 1481-1484
  • Vallee, B.L., Falchuk, K.H., The biochemical basis of zinc physiology (1993) Physiol. Rev., 73, pp. 79-118
  • Liu, Z., Zhang, C., Chen, Y., He, W., Guo, Z., An excitation ratiometric Zn2+ sensor with mitochondria-targetability for monitoring of mitochondrial Zn2+ release upon different stimulations (2012) Chem. Commun., 48, pp. 8365-8367
  • Woo, H., You, Y., Kim, T., Jhon, G.-J., Nam, W., Fluorescence ratiometric zinc sensors based on controlled energy transfer (2012) J. Mater. Chem., 22, pp. 17100-17112
  • Kumar Pathak, R., Kumar Hinge, V., Rai, A., Panda, D., Pulla Rao, C., Imino-phenolic-pyridyl conjugates of calix[4]arene (L1 and L2) as primary fluorescence switch-on sensors for Zn2+ in solution and in HeLa cells and the recognition of pyrophosphate and ATP by [ZnL2] (2012) Inorg. Chem., 51, pp. 4994-5005
  • Xie, G., Xi, P., Wang, X., Zhao, X., Huang, L., Chen, F., Wu, Y., Zeng, Z., A highly zinc(ii)-selective fluorescent sensor based on 8-aminoquinoline and its application in biological imaging (2011) Eur. J. Inorg. Chem., 2011, pp. 2927-2931
  • You, Y., Tomat, E., Hwang, K., Atanasijevic, T., Nam, W., Jasanoff, A.P., Lippard, S.J., Manganese displacement from Zinpyr-1 allows zinc detection by fluorescence microscopy and magnetic resonance imaging (2010) Chem. Commun., 46, pp. 4139-4141
  • Cao, J., Zhao, C., Wang, X., Zhang, Y., Zhu, W., Target-triggered deprotonation of 6-hydroxyindole-based BODIPY: Specially switch on NIR fluorescence upon selectively binding to Zn2+ (2012) Chem. Commun., 48, pp. 9897-9899
  • Xu, Y., Pang, Y., Zn2+-triggered excited-state intramolecular proton transfer: A sensitive probe with near-infrared emission from bis(benzoxazole) derivative (2011) Dalton Trans., 40, pp. 1503-1509
  • Menendez, G.O., Pichel, M.E., Spagnuolo, C.C., Jares-Erijman, E.A., NIR fluorescent biotinylated cyanine dye: Optical properties and combination with quantum dots as a potential sensing device (2013) Photochem. Photobiol. Sci., 12, pp. 236-240
  • Ruedas-Rama, M.J., Hall, E.A.H., Azamacrozuhcycle activated quantum dot for zinc ion detection (2008) Anal. Chem., 80, pp. 8260-8268
  • Buccella, D., Horowitz, J.A., Lippard, S.J., Understanding zinc quantification with existing and advanced ditopic fluorescent Zinpyr sensors (2011) J. Am. Chem. Soc., 133, pp. 4101-4114
  • Kurishita, Y., Kohira, T., Ojida, A., Hamachi, I., Organelle-localizable fluorescent chemosensors for site-specific multicolor imaging of nucleoside polyphosphate dynamics in living cells (2012) J. Am. Chem. Soc., 134, pp. 18779-18789
  • Kiyose, K., Aizawa, S., Sasaki, E., Kojima, H., Hanaoka, K., Terai, T., Urano, Y., Nagano, T., Molecular design strategies for near-infrared ratiometric fluorescent probes based on the unique spectral properties of aminocyanines (2009) Chem. Eur. J., 15, pp. 9191-9200
  • Peng, X., Yang, Z., Wang, J., Fan, J., He, Y., Song, F., Wang, B., Yan, M., Fluorescence ratiometry and fluorescence lifetime imaging: Using a single molecular sensor for dual mode imaging of cellular viscosity (2011) J. Am. Chem. Soc., 133, pp. 6626-6635
  • Peng, X., Song, F., Lu, E., Wang, Y., Zhou, W., Fan, J., Gao, Y., Heptamethine cyanine dyes with a large stokes shift and strong fluorescence: A paradigm for excited-state intramolecular charge transfer (2005) J. Am. Chem. Soc., 127, pp. 4170-4171
  • Hirano, T., Kikuchi, K., Urano, Y., Higuchi, T., Nagano, T., Highly zinc-selective fluorescent sensor molecules suitable for biological applications (2000) J. Am. Chem. Soc., 122, pp. 12399-12400
  • Hirano, T., Kikuchi, K., Urano, Y., Nagano, T., Improvement and biological applications of fluorescent probes for zinc, ZnAFs (2002) J. Am. Chem. Soc., 124, pp. 6555-6562
  • Chipon, B., Clavé, G., Bouteiller, C., Massonneau, M., Renard, P.-Y., Romieu, A., Synthesis and post-synthetic derivatization of a cyanine-based amino acid. Application to the preparation of a novel water-soluble nir dye (2006) Tetrahedron Lett., 47, pp. 8279-8284
  • Hirata, T., Kogiso, H., Morimoto, K., Miyamoto, S., Taue, H., Sano, S., Muguruma, N., Nagao, Y., Synthesis and reactivities of 3-indocyanine-green-acyl-1,3-thiazolidine- 2-thione (icg-att) as a new near-infrared fluorescent-labeling reagent (1998) Bioorg. Med. Chem., 6, pp. 2179-2184
  • Lin, Y., Weissleder, R., Tung, C.H., Novel near-infrared cyanine fluorochromes: Synthesis, properties, and bioconjugation (2002) Bioconjugate Chem., 13, pp. 605-610
  • Park, J.W., Kim, Y., Lee, K.J., Kim, D.J., Novel cyanine dyes with vinylsulfone group for labeling biomolecules (2012) Bioconjugate Chem., 23, pp. 350-362
  • Southwick, P.L., Ernst, L.A., Tauriello, E.W., Parker, S.R., Mujumdar, R.B., Mujumdar, S.R., Clever, H.A., Waggoner, A.S., Cyanine dye labeling reagents-carboxymethylindocyanine succinimidyl esters (1990) Cytometry, 11, pp. 418-430
  • Pham, W., Medarova, Z., Moore, A., Synthesis and application of a water-soluble near-infrared dye for cancer detection using optical imaging (2005) Bioconjugate Chem., 16, pp. 735-740
  • Narayanan, N., Patonay, G., A new method for the synthesis of heptamethine cyanine dyes - Synthesis of new near-infrared fluorescent labels (1995) J. Org. Chem., 60, pp. 2391-2395
  • Johnson, I.D., Life, T., Haugland, R.P., Spence, M.T.Z., (2010) The Molecular Probes Handbook: A Guide to Fluorescent Probes and Labeling Technologies, , 11th edition. Life Technologies Corporation, Washington, DC

Citas:

---------- APA ----------
Menéndez, G.O., Lõpez, C.S., Jares-Erijman, E.A. & Spagnuolo, C.C. (2013) . A versatile near-infrared asymmetric tricarbocyanine for zinc ion sensing in water. Photochemistry and Photobiology, 89(6), 1354-1361.
http://dx.doi.org/10.1111/php.12160
---------- CHICAGO ----------
Menéndez, G.O., Lõpez, C.S., Jares-Erijman, E.A., Spagnuolo, C.C. "A versatile near-infrared asymmetric tricarbocyanine for zinc ion sensing in water" . Photochemistry and Photobiology 89, no. 6 (2013) : 1354-1361.
http://dx.doi.org/10.1111/php.12160
---------- MLA ----------
Menéndez, G.O., Lõpez, C.S., Jares-Erijman, E.A., Spagnuolo, C.C. "A versatile near-infrared asymmetric tricarbocyanine for zinc ion sensing in water" . Photochemistry and Photobiology, vol. 89, no. 6, 2013, pp. 1354-1361.
http://dx.doi.org/10.1111/php.12160
---------- VANCOUVER ----------
Menéndez, G.O., Lõpez, C.S., Jares-Erijman, E.A., Spagnuolo, C.C. A versatile near-infrared asymmetric tricarbocyanine for zinc ion sensing in water. Photochem. Photobiol. 2013;89(6):1354-1361.
http://dx.doi.org/10.1111/php.12160