Abstract:
New fluorinated biarsenical derivatives with improved optical properties based on highly photostable analogs of fluorescein were recently introduced. The photophysical parameters of the triplet excited states as well as photosensitized oxidation reactions of these dyes were determined in order to investigate the influence of molecular structure on the exceptional photostability of these fluorophores. The lack of correspondence between triplet quantum yields and lifetimes with the photobleaching rates of some of the fluorophores of the series suggests that differential reactivities of the excited states with ground state oxygen accounts for the different photodegradation resistances. The UV-visible absorption and emission spectra of the fluorinated fluoresceins and their biarsenical derivatives were evaluated using a TD-DFT/BP86/6-31G** approach, taking bulk solvent effects into account by means of the polarizable continuum model. The calculated properties are in good agreement with experimental data. The S 0→S1 vertical excitation energies in the gas phase and in water were obtained with the optimized geometries of the excited states. This type of calculation could be used in the rational design of new dyes. © 2009 The American Society of Photobiology.
Registro:
Documento: |
Artículo
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Título: | Photostability and spectral properties of fluorinated fluoresceins and their biarsenical derivatives: A combined experimental and theoretical study |
Autor: | Spagnuolo, C.C.; Massad, W.; Miskoski, S.; Menendez, G.O.; García, N.A.; Jares-Erijman, E.A. |
Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de Río Cuarto, Río Cuarto, Argentina
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Año: | 2009
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Volumen: | 85
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Número: | 5
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Página de inicio: | 1082
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Página de fin: | 1088
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DOI: |
http://dx.doi.org/10.1111/j.1751-1097.2009.00565.x |
Título revista: | Photochemistry and Photobiology
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Título revista abreviado: | Photochem. Photobiol.
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ISSN: | 00318655
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CODEN: | PHCBA
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00318655_v85_n5_p1082_Spagnuolo |
Referencias:
- Griffin, B.A., Adams, S.R., Tsien, A.R., Specific covalent labeling of recombinant protein molecules inside live cells (1998) Science, 281, pp. 269-272
- Adams, S.R., Campbell, R.E., Gross, L.A., Martin, B.R., Walkup, G.K., Yao, Y., Llopis, J., Tsien, R.Y., New biarsenical ligands and tetracysteine motifs for protein labeling in vitro and in vivo: Synthesis and biological applications (2002) J. Am. Chem. Soc., 124, pp. 6063-6076
- Tsien, R.Y., Waggoner, A., (1995) Fluorophores for Confocal Microscopy., , Plenum Press. New York
- Spagnuolo, C.C., Vermeij, R.J., Jares-Erijman, E.A., Improved photostable FRET-competent biarsenical-tetracysteine probes based on fluorinated fluoresceins (2006) J. Am. Chem. Soc., 128, pp. 12040-12041
- Sun, W., Gee, K.R., Klaubert, D.H., Haugland, R.P., Synthesis of fluorinated fluoresceins (1997) J. Org. Chem., 62, pp. 6469-6475
- Renikuntla, B.R., Rose, H.C., Eldo, J., Waggoner, A.S., Armitage, B.A., Improved photostability and fluorescence properties through polyfluorination of a cyanine dye (2004) Org. Lett., 6, pp. 909-912
- Valeur, B., (2002) Molecular Fluorescence: Principles and Applications., , Wiley-VCH. Weinheim
- Gandin, E., Lion, Y., Van De Vorst, A., Quantum yield of singlet oxygen production by xanthene derivatives (1983) Photochem. Photobiol., 37, pp. 271-278
- Amat-Guerri, F., López-González, M.M.C., Martínez- Utrilla, R., Sastre, R., Singlet oxygen photogeneration by ionized and un-ionized derivatives of rose bengal and eosin y in diluted solutions (1990) J. Photochem. Photobiol. A, 53, pp. 199-210
- Jovin, T.M., Arndt-Jovin, D.J., Marriott, G., Clegg, R.M., Robert-Nicaud, M., Schormann, T., Distance, wavelength and time: The versatile 3rd dimensions in light emission microscopy (1990) Optical Microscopy for Biology, pp. 575-602. , Edited by. B. H. K. Jacobson Wiley-Liss. New York
- Massad, W.A., Bertolotti, S.G., Romero, M., Garcia, N.A., A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species. the case of phenylephrine (2005) J. Photochem. Photobiol. B, Biol., 80, pp. 130-138
- Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, Jr.J.A., Pople, J.A., (2003) Revision A.1., , Gaussian, Inc. Pittsburgh, PA
- Runge, E., Gross, E.K.U., Density-functional theory for time-dependent systems (1984) Phys. Rev. Lett., 52, pp. 997-1000
- Cossi, M., Barone, V., Time-dependent density functional theory for molecules in liquid solutions (2001) Chem. Phys., 115, pp. 4708-4717
- Sun, W., Gee, K.R., Haugland, R.P., Synthesis of novel fluorinated coumarins: Excellent UV-light excitable fluorescent dyes (1998) Bioorg. Med. Chem. Lett., 8, pp. 3107-3110
- Lindqvist, L., A flash photolysis study of fluorescein (1960) Ark. Kemi, 16, pp. 79-138
- Song, L., Hennink, E.J., Young, T., Tanke, H.J., Photobleaching kinetics of fluorescein in quantitative fluorescence microscopy (1995) Biophys. J., 68, pp. 2588-2600
- Criado, S., Pajares, A., Gianotti, J., Stettler, G., Escalada, J.P., Bertolotti, S., Amat-Guerri, F., Garcia, N.A., Kinetic study of the riboflavin-sensitised photooxygenation of two hydroxyquinolines of biological interest (2003) J. Photochem. Photobiol. B, Biol., 71, pp. 19-25
- Martin, B.R., Giepmans, B.N.G., Adams, S.R., Tsien, R.Y., Mammalian cell-based optimization of the biarsenical-binding tetracysteine motif for improved fluorescence and affinity (2005) Nat. Biotechnol., 23, pp. 1308-1314
- Jacquemin, D., Preat, J., Wathelet, V., Fontaine, F., Perpéte, E.A., Thioindigo dyes: Highly accurate visible spectra with TD-DFT (2006) J. Am. Chem. Soc., 128, pp. 2072-2083
- Georgieva, I., Trendafilova, N., Aquino, A., Lischka, H., Excited state properties of 7-hydroxy-4-methylcoumarin in the gas phase and in solution. A theoretical study (2005) J. Phys. Chem. A, 109, pp. 11860-11869
Citas:
---------- APA ----------
Spagnuolo, C.C., Massad, W., Miskoski, S., Menendez, G.O., García, N.A. & Jares-Erijman, E.A.
(2009)
. Photostability and spectral properties of fluorinated fluoresceins and their biarsenical derivatives: A combined experimental and theoretical study. Photochemistry and Photobiology, 85(5), 1082-1088.
http://dx.doi.org/10.1111/j.1751-1097.2009.00565.x---------- CHICAGO ----------
Spagnuolo, C.C., Massad, W., Miskoski, S., Menendez, G.O., García, N.A., Jares-Erijman, E.A.
"Photostability and spectral properties of fluorinated fluoresceins and their biarsenical derivatives: A combined experimental and theoretical study"
. Photochemistry and Photobiology 85, no. 5
(2009) : 1082-1088.
http://dx.doi.org/10.1111/j.1751-1097.2009.00565.x---------- MLA ----------
Spagnuolo, C.C., Massad, W., Miskoski, S., Menendez, G.O., García, N.A., Jares-Erijman, E.A.
"Photostability and spectral properties of fluorinated fluoresceins and their biarsenical derivatives: A combined experimental and theoretical study"
. Photochemistry and Photobiology, vol. 85, no. 5, 2009, pp. 1082-1088.
http://dx.doi.org/10.1111/j.1751-1097.2009.00565.x---------- VANCOUVER ----------
Spagnuolo, C.C., Massad, W., Miskoski, S., Menendez, G.O., García, N.A., Jares-Erijman, E.A. Photostability and spectral properties of fluorinated fluoresceins and their biarsenical derivatives: A combined experimental and theoretical study. Photochem. Photobiol. 2009;85(5):1082-1088.
http://dx.doi.org/10.1111/j.1751-1097.2009.00565.x