Abstract:
We designed a strategy to activate fluorescence under the influence of optical stimulations based on the intermolecular transfer of protons. Specifically, the illumination of a 2-nitrobenzyl derivative at an activating wavelength is accompanied by the release of hydrogen bromide. In turn, the photogenerated acid encourages the opening of an oxazine ring embedded within a halochromic compound. This structural transformation extends the conjugation of an adjacent coumarin fluorophore and enables its absorption at an appropriate excitation wavelength. Indeed, this bimolecular system offers the opportunity to activate fluorescence in liquid solutions, within rigid matrixes and inside micellar assemblies, relying on the interplay of activating and exciting beams. Furthermore, this strategy permits the permanent imprinting of fluorescent patterns on polymer films, the monitoring of proton diffusion within such materials in real time on a millisecond time scale, and the acquisition of images with spatial resolution at the nanometer level. Thus, our operating principles for fluorescence activation can eventually lead to the development of valuable photoswitchable probes for imaging applications and versatile mechanisms for the investigation of proton transport. © 2012 American Chemical Society.
Registro:
Documento: |
Artículo
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Título: | Fluorescence photoactivation by intermolecular proton transfer |
Autor: | Swaminathan, S.; Petriella, M.; Deniz, E.; Cusido, J.; Baker, J.D.; Bossi, M.L.; Raymo, F.M. |
Filiación: | Laboratory for Molecular Photonics, Department of Biology, University of Miami, 1301 Memorial Drive, Coral Gables, FL 33146-0431, United States Laboratory for Molecular Photonics, Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, FL 33146-0431, United States INQUIMAE, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
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Palabras clave: | 2-nitrobenzyl; Excitation wavelength; Hydrogen bromide; Imaging applications; Intermolecular transfer; Liquid solution; Micellar assemblies; Nanometer level; Operating principles; Optical stimulation; Photo-switchable; Photoactivation; Proton diffusion; Proton transport; Real time; Spatial resolution; Structural transformation; Time-scales; Chemical activation; Polymer films; Fluorescence; hydrobromic acid; proton; article; chemistry; fluorescence; photochemistry; Fluorescence; Hydrobromic Acid; Photochemical Processes; Protons |
Año: | 2012
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Volumen: | 116
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Número: | 40
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Página de inicio: | 9928
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Página de fin: | 9933
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DOI: |
http://dx.doi.org/10.1021/jp307787w |
Título revista: | Journal of Physical Chemistry A
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Título revista abreviado: | J Phys Chem A
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ISSN: | 10895639
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CODEN: | JPCAF
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CAS: | hydrobromic acid, 10035-10-6; proton, 12408-02-5, 12586-59-3; Hydrobromic Acid, 10035-10-6; Protons
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10895639_v116_n40_p9928_Swaminathan |
Referencias:
- Murphy, D.B., (2001) Fundamentals of Light Microscopy and Electronic Imaging, , Wiley Liss: New York
- Lakowicz, J.R., (2006) Principles of Fluorescence Spectroscopy, , Springer: New York
- Mitchison, T.J., Sawin, K.E., Theriot, J.A., Gee, K., Mallavarapu, A., (1998) Methods Enzymol, 291, pp. 63-78
- Pelliccioli, A.P., Wirz, J., (2002) Photochem. Photobiol. Sci., 1, pp. 441-458
- Goeldner, M., Givens, R., (2005) Dynamic Studies in Biology: Phototriggers, Photoswitches and Caged Biomolecules, , Wiley VCH: Weinheim, Germany
- Puliti, D., Warther, D., Orange, C., Specht, A., Goeldner, M., (2011) Bioorg. Med. Chem., 19, pp. 1023-1029
- Wysocki, L.M., Davis, L.D., (2011) Curr. Opin. Chem. Biol., 15, pp. 752-759
- Li, W.-H., Zhneg, G., (2012) Photochem. Photobiol. Sci., 11, pp. 460-471
- Krafft, G.A., Cummings, R.T., Dizio, J.P., Furukawa, R.H., Brvenik, L.J., Sutton, W.R., War, B.R., (1986) Nucleocytoplasmic Transport, pp. 35-52. , Peters, R., Trendelenburg, M., Eds.; Springer-Verlag: Berlin, Germany
- Adams, S.R., Tsien, R.Y., (1993) Annu. Rev. Physiol., 55, pp. 755-784
- Politz, J.C., (1999) Trends Cell Biol, 9, pp. 284-287
- Lippincott-Schwartz, J., Altan-Bonnet, N., Patterson, G.H., (2003) Nat. Cell Biol., 5, pp. S7-S14
- Lippincott-Schwartz, J., Patterson, G.H., (2003) Science, 300, pp. 87-91
- Manley, S., Gillette, J.M., Lippincott-Schwartz, J., (2010) Methods Enzymol., 475, pp. 109-120
- Ellis-Davies, G.C., (2007) Nat. Methods, 4, pp. 619-628
- Johnson, I., Spence, M.T.Z., (2010) The Molecular Probes Handbook: A Guide to Fluorescent Probes and Labeling Technologies, , 11th Ed.; Life Technologies: Carlsbad CA
- Hell, S.W., (2003) Nat. Biotechnol., 21, pp. 1347-1355
- Hell, S.W., (2007) Science, 316, pp. 1153-1158
- Hell, S.W., (2009) Nat. Methods, 6, pp. 24-32
- Sauer, M., (2005) Proc. Natl. Acad. Sci. U.S.A., 105, pp. 9433-9434
- Van De Linde, S., Wolter, S., Sauer, M., (2011) Aust. J. Chem., 64, pp. 503-511
- Van De Linde, S., Heilemann, M., Sauer, M., (2012) Annu. Rev. Phys. Chem., 63, pp. 519-540
- Fernández-Suárez, M., Ting, A.Y., (2008) Nat. Rev. Mol. Cell. Biol., 9, pp. 929-943
- Bates, M., Huang, B., Zhuang, X., (2008) Curr. Opin. Chem. Biol., 12, pp. 505-514
- Huang, B., Bates, M., Zhuang, X., (2009) Annu. Rev. Biochem., 78, pp. 993-1016
- Vaughan, J.C., Zhuang, X., (2011) Nat. Biotechnol., 29, pp. 880-881
- Hess, S.T., Gould, T.J., Gunewardene, M., Bewersdorf, J., Mason, M.D., (2009) Methods Mol. Biol. 2009, pp. 483-522
- Toomre, D., Bewersdorf, J., (2010) Annu. Rev. Cell Dev. Biol., 26, pp. 285-314
- Vogelsang, J., Steinhauer, C., Forthmann, C., Stein, I.H., Person-Skergo, B., Cordes, T., Tinnefeld, P., (2010) ChemPhysChem, 11, pp. 2475-2490
- Ha, T., Tinnefeld, P., (2012) Annu. Rev. Phys. Chem., 63, pp. 595-617
- Thompson, M.A., Biteen, J.S., Lord, S.J., Conley, N., Moerner, W.E., (2010) Methods Enzymol., 475, pp. 27-59
- Moerner, W.E., (2012) J. Microsc., 246, pp. 213-220
- Cusido, J., Impellizzeri, S., Raymo, F.M., (2011) Nanoscale, 3, pp. 59-70
- Raymo, F.M., Giordani, S., (2001) Org. Lett., 3, pp. 3475-3478
- Raymo, F.M., Alvarado, R.J., Giordani, S., Cejas, M.A., (2003) J. Am. Chem. Soc., 125, pp. 2361-2364
- Giordani, S., Cejas, M.A., Raymo, F.M., (2004) Tetrahedron, 60, pp. 10973-10981
- Silvi, S., Arduini, A., Pochini, A., Secchi, A., Tomasulo, M., Raymo, F.M., Baroncini, M., Credi, A., (2007) J. Am. Chem. Soc., 129, pp. 13378-13379
- Silvi, S., Constable, E.C., Housecroft, C.E., Beves, J.E., Dunphy, E.L., Tomasulo, M., Raymo, F.M., Credi, A., (2009) Chem.-Eur. J., 15, pp. 178-185
- Silvi, S., Constable, E.C., Housecroft, C.E., Beves, J.E., Dunphy, E.L., Tomasulo, M., Raymo, F.M., Credi, A., (2009) Chem. Commun., pp. 1484-1486
- Deniz, E., Sortino, S., Raymo, F.M., (2010) J. Phys. Chem. Lett., 1, pp. 3506-3509
- Deniz, E., Tomasulo, M., Cusido, J., Yildiz, I., Petriella, M., Bossi, M.L., Sortino, S., Raymo, F.M., (2012) J. Phys. Chem. C, 116, pp. 6058-6068
- Houlihan, M., Shugard, A., Gooden, R., Reichmanis, E., (1988) Macromolecules, 21, pp. 2001-2006
- Yildiz, I., Impellizzeri, S., Deniz, E., McCaughan, B., Callan, J.F., Raymo, F.M., (2011) J. Am. Chem. Soc., 133, pp. 871-879
- Cusido, J., Battal, M., Deniz, E., Yildiz, I., Sortino, S., Raymo, F.M., (2012) Chem. Eur. J., 18, pp. 10399-10407
- Egner, A., Geisler, C., Von Middendorf, C., Bock, H., Wenzel, D., Medda, R., Andresen, M., Eggeling, C., (2007) Biophys. J., 93, pp. 3285-3290
Citas:
---------- APA ----------
Swaminathan, S., Petriella, M., Deniz, E., Cusido, J., Baker, J.D., Bossi, M.L. & Raymo, F.M.
(2012)
. Fluorescence photoactivation by intermolecular proton transfer. Journal of Physical Chemistry A, 116(40), 9928-9933.
http://dx.doi.org/10.1021/jp307787w---------- CHICAGO ----------
Swaminathan, S., Petriella, M., Deniz, E., Cusido, J., Baker, J.D., Bossi, M.L., et al.
"Fluorescence photoactivation by intermolecular proton transfer"
. Journal of Physical Chemistry A 116, no. 40
(2012) : 9928-9933.
http://dx.doi.org/10.1021/jp307787w---------- MLA ----------
Swaminathan, S., Petriella, M., Deniz, E., Cusido, J., Baker, J.D., Bossi, M.L., et al.
"Fluorescence photoactivation by intermolecular proton transfer"
. Journal of Physical Chemistry A, vol. 116, no. 40, 2012, pp. 9928-9933.
http://dx.doi.org/10.1021/jp307787w---------- VANCOUVER ----------
Swaminathan, S., Petriella, M., Deniz, E., Cusido, J., Baker, J.D., Bossi, M.L., et al. Fluorescence photoactivation by intermolecular proton transfer. J Phys Chem A. 2012;116(40):9928-9933.
http://dx.doi.org/10.1021/jp307787w