Artículo

Arce, V.B.; Scotto, J.; Allegretti, P.E.; Melo, M.A.; Airoldi, C.; Salum, M.L.; Erra-Balsells, R.; Pis Diez, R.; Mártire, D.O. "Combined experimental and computational investigation of the fluorescence quenching of riboflavin by cinnamic alcohol chemisorbed on silica nanoparticles" (2014) Journal of Physical Chemistry C. 118(28):15348-15355
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Abstract:

Riboflavin (vitamin B2) is usually present in water courses, lakes, and seas and acts as a photosensitizer in the photo-oxidation of a range of contaminants. However, little is known about the interaction of this compound with aromatics sorbed on silica sediments or on suspended silica particles. This article describes the modification and characterization of silica nanoparticles by condensation of the silanol groups of the particles with E-cinnamic alcohol. The reaction was confirmed by Fourier transform infrared spectroscopy (FTIR), solid-state 13C and 29Si cross-polarization magic angle spinning (CPMAS) NMR, reduction of the specific surface area measured by BET, thermal analysis, and fluorescence spectroscopy. Toxicity to the marine bacteria Vibrio fischeri of the modified particles was also measured. Riboflavin fluorescence was quenched in aqueous medium in the presence of dissolved E-cinnamic alcohol or in suspensions of the modified particles. The results are interpreted in terms of formation of 1:1 complexes between the ground states of riboflavin and the free or adsorbed cinnamic alcohol. Density functional theory (DFT) calculations in aqueous medium support the existence of the complex and explain the observed quenching of riboflavin fluorescence upon addition of cinnamic alcohol without affecting the emission maximum of riboflavin. © 2014 American Chemical Society.

Registro:

Documento: Artículo
Título:Combined experimental and computational investigation of the fluorescence quenching of riboflavin by cinnamic alcohol chemisorbed on silica nanoparticles
Autor:Arce, V.B.; Scotto, J.; Allegretti, P.E.; Melo, M.A.; Airoldi, C.; Salum, M.L.; Erra-Balsells, R.; Pis Diez, R.; Mártire, D.O.
Filiación:Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas, Universidad Nacional de la Plata, Casilla de Correo 16, Sucursal 4, 1900 La Plata, Argentina
Centro de Investigaciones Ópticas, CONICET la Plata-CIC, CC 3, 1897 Gonnet, La Plata, Argentina
LADECOR, Departamento de Química, Universidad Nacional de la Plata, 1900 La Plata, Argentina
Chemistry Institute, University of Campinas, P.O. Box 6154, 13084-971 Campinas, São Paulo, Brazil
CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, 3 Piso, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Centro de Química Inorgánica, Facultad de Ciencias Exactas, Universidad Nacional de la Plata, CC 962, 1900 La Plata, Argentina
Palabras clave:Fluorescence; Fluorescence spectroscopy; Fourier transform infrared spectroscopy; Magic angle spinning; Photosensitizers; Quenching; Silica; Suspended sediments; Thermoanalysis; Computational investigation; Cross polarizations; Fluorescence quenching; Marine bacterium; Riboflavin (Vitamin B2); Silica nanoparticles; Silica particles; Vibrio fischeri; Suspensions (fluids)
Año:2014
Volumen:118
Número:28
Página de inicio:15348
Página de fin:15355
DOI: http://dx.doi.org/10.1021/jp504919c
Título revista:Journal of Physical Chemistry C
Título revista abreviado:J. Phys. Chem. C
ISSN:19327447
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_19327447_v118_n28_p15348_Arce

Referencias:

  • Sikorska, E., Khmelinskii, I., Komasa, A., Koput, J., Ferreira, L.F.V., Herance, J.R., Bourdelande, J.L., Sikorski, M., Spectroscopy and photophysics of flavin related compounds: Riboflavin and iso-(6,7)-riboflavin (2005) Chemical Physics, 314 (1-3), pp. 239-247. , DOI 10.1016/j.chemphys.2005.03.005, PII S0301010405000820
  • Datta, S., Mukhopadhyay, C., Bhattacharya, S., Bose, S.K., Studies on the riboflavin-resorcinol interaction in an aqueous medium and its pH dependence (2005) Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 62 (1-3), pp. 721-728. , DOI 10.1016/j.saa.2005.02.047, PII S1386142505000946
  • Duurkens, R.H., Tol, M.B., Geertsma, E.R., Permentier, H.P., Slotboom, D.J., Flavin binding to the high affinity riboflavin transporter RibU (2007) Journal of Biological Chemistry, 282 (14), pp. 10380-10386. , http://www.jbc.org/cgi/reprint/282/14/10380, DOI 10.1074/jbc.M608583200
  • Bieger, B., Essen, L.-O., Oesterhelt, D., Crystal structure of halophilic dodecin: A novel, dodecameric flavin binding protein from Halobacterium salinarum (2003) Structure, 11 (4), pp. 375-385. , DOI 10.1016/S0969-2126(03)00048-0
  • Van Den Berg, P.A.W., Feenstra, K.A., Mark, A.E., Berendsen, H.J.C., Visser, A.J.W.G., Dynamic conformations of flavin adenine dinucleotide: Simulated molecular dynamics of the flavin cofactor related to the time-resolved fluorescence characteristics (2002) Journal of Physical Chemistry B, 106 (34), pp. 8858-8869. , DOI 10.1021/jp020356s
  • Datta, S., Mukhopadhyay, C., Bose, S.K., Molecular complex formation between riboflavin and salicylate in an aqueous medium (2003) Bulletin of the Chemical Society of Japan, 76 (9), pp. 1729-1734. , DOI 10.1246/bcsj.76.1729
  • Zeng, K., Hwang, H.-M., Zhang, Y., Yu, H., Identification of 6-aminochrysene photoproducts and study of the effect of a humic acid and riboflavin on its photolysis (2003) Journal of Photochemistry and Photobiology B: Biology, 72 (1-3), pp. 95-100. , DOI 10.1016/j.jphotobiol.2003.09.006
  • García, N.A., Amat-Guerri, F., Photodegradation of Hydroxylated N-Heteroaromatic Derivatives in Natural-like Aquatic Environments. A Review of Kinetic Data of Pesticide Model Compounds (2005) Chemosphere, 59, pp. 1067-1082
  • Escalada, J.P., Pajares, A., Gianotti, J., Biasutti, A., Criado, S., Molina, P., Massad, W., García, N.A., Photosensitized Degradation in Water of the Phenolic Pesticides Bromoxynil and Dichlorophen in the Presence of Riboflavin, as a Model of their Natural Photodecomposition in the Environment (2011) J. Hazard. Mater., 186, pp. 466-472
  • Remucal, C.K., McNeill, K., Photosensitized Amino Acid Degradation in the Presence of Riboflavin and its Derivatives (2011) Environ. Sci. Technol., 45, pp. 5230-5237
  • Wiesner, M.R., Lowry, G.V., Jones, K.L., Hochella, M.F., Di Giulio, R.T., Casman, E., Bernhardt, E.S., Decreasing Uncertainties in Assessing Environmental Exposure, Risk, and Ecological Implications of Nanomaterials (2009) Environ. Sci. Technol., 43, pp. 6458-6462
  • Vione, D., Maddigapu, P.R., De Laurentiis, E., Minella, M., Pazzi, M., Maurino, V., Minero, C., Richard, C., Modelling the Photochemical Fate of Ibuprofen in Surface Waters (2011) Water Res., 45, pp. 6725-6736
  • Escalada, J.P., Arce, V.B., Porcal, G.V., Biasutti, M.A., Criado, S., García, N.A., Mártire, D.O., The effect of Dichlorophen Binding to Silica Nanoparticles on its Photosensitized Degradation in Water (2014) Water Res., 50, pp. 229-236
  • Escalada, J.P., Arce, V.B., Carlos, L., Porcal, G.V., Biasutti, M.A., Criado, S., García, N.A., Mártire, D.O., Photodegradation Routes of the Herbicide Bromoxynil in Solution and Sorbed on Silica Nanoparticles (2014) Environ. Sci.: Processes Impacts, 16, pp. 858-865
  • Becerril, E., Lamas, J.P., Sanchez-Prado, L., Llompart, M., Lores, M., García-Jares, C., Analysis of Regulated Suspected Allergens in Waters (2010) Talanta, 83, pp. 464-474
  • Li, C.C., Chen, Y.T., Lin, Y.T., Sie, S.F., Chen-Yang, Y.W., Mesoporous Silica Aerogel as a Drug Carrier for the Enhancement of the Sunscreen Ability of Benzophenone-3 (2014) Colloids Surf., B, 115, pp. 191-196
  • Noomane, A., Hbaieb, S., Bolzinger, M., Briançon, S., Chevalier, Y., Kalfat, R., Effectiveness of Grafting Modes of Methoxycinnamate Sunscreen onto Silica Particles (2014) Colloids Surf., A, 441, pp. 653-663
  • Mori, T., Inoue, Y., (2005) C=C Photoinduced Isomerization Reactions, p. 417. , Griesbeck, A. G. Mattay, J. Synthetic Organic Photochemistry; Marcel Dekker: New York
  • Arce, V.B., Bertolotti, S.G., Oliveira, F.J.V.E., Airoldi, C., Gonzalez, M.C., Allegretti, P.E., Mártire, D.O., Safranine-t Triplet-State Quenching by Modified Silica Nanoparticles (2011) J. Phys. Chem. C, 115, pp. 18122-18130
  • Arce, V.B., Bertolotti, S.G., Oliveira, F.J.V.E., Airoldi, C., Arques, A., Santos-Juanes, L., Gonzalez, M.C., Mártire, D.O., Triplet State of 4-Methoxybenzyl Alcohol Chemisorbed on Silica Nanoparticles (2012) Photochem. Photobiol. Sci., 11, pp. 1032-1040
  • Valeur, B., (2002) Molecular Fluorescence. Principles and Applications, , Wiley-VCH: Weinheim, Germany
  • Kirby, E.P., Steiner, R.F., Influence of Solvent and Temperature upon the Fluorescence of Indole Derivatives (1970) J. Phys. Chem., 74, pp. 4480-4490
  • Ruiz, A.E., Caregnato, P., Arce, V.B., Schiavoni, M.D.L.M., Mora, V.C., Gonzalez, M.C., Allegretti, P.E., Martire, D.O., Synthesis and characterization of butoxylated silica nanoparticles. Reaction with benzophenone triplet states (2007) Journal of Physical Chemistry C, 111 (21), pp. 7623-7628. , DOI 10.1021/jp0710640
  • Hohenberg, P., Kohn, W., Inhomogeneous Electron Gas (1964) Phys. Rev., 136, pp. 864-B871
  • Kohn, W., Sham, L.J., Self-Consistent Equations Including Exchange and Correlation Effects (1965) Phys. Rev., 140, pp. 1133-A1138
  • Parr, R.G., Yang, W., (1989) Density Functional Theory of Atoms and Molecules, , University Press: Oxford, U.K
  • Grimme, S., Semiempirical GGA-type density functional constructed with a long-range dispersion correction (2006) Journal of Computational Chemistry, 27 (15), pp. 1787-1799. , DOI 10.1002/jcc.20495
  • Dreuw, A., Head-Gordon, M., Single-reference ab initio methods for the calculation of excited states of large molecules (2005) Chemical Reviews, 105 (11), pp. 4009-4037. , DOI 10.1021/cr0505627
  • Elliott, P., Furche, F., Burke, K., Excited States from Time-Dependent Density Functional Theory (2009) Rev. Comput. Chem., 26, pp. 91-165
  • Adamo, C., Barone, V., Toward Reliable Density Functional Methods without Adjustable Parameters: The PBE0 model (1999) J. Chem. Phys., 110, pp. 6158-6170
  • Weigend, F., Ahlrichs, R., Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy (2005) Physical Chemistry Chemical Physics, 7 (18), pp. 3297-3305. , DOI 10.1039/b508541a
  • Rappoport, D., Furche, F., Property-optimized Gaussian Basis Sets for Molecular Response Calculations (2010) J. Chem. Phys., 133, pp. 134105-134111
  • Barone, V., Cossi, M., Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model (1998) Journal of Physical Chemistry A, 102 (11), pp. 1995-2001
  • Cossi, M., Rega, N., Scalmani, G., Barone, V., Energies, Structures, and Electronic Properties of Molecules in Solution with the C-PCM Solvation Model (2003) J. Comput. Chem., 24, pp. 669-681
  • Marenich, A.V., Cramer, C.J., Truhlar, D.G., Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions (2009) J. Phys. Chem. B, 113, pp. 6378-6396
  • (2011), GAMESS-US, version 11, August, (R1); Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Montgomery, J.A., General Atomic and Molecular Electronic Structure System (1993) J. Comput. Chem., 14, pp. 1347-1363
  • Gordon, M.S., Schmidt, M.W., (2005) Theory and Applications of Computational Chemistry, the First Forty Years, pp. 1167-1189. , Dykstra, C. E. Frenking, G. Kim, K. S. Scuseria, G. E. Elsevier: Amsterdam, The Netherlands
  • Allouche, A.R., Gabedit-A Graphical User Interface for Computational Chemistry Softwares (2011) J. Comput. Chem., 32, pp. 174-182
  • De Farias, R.F., Airoldi, C., Thermogravimetry as a reliable tool to estimate the density of silanols on a silica gel surface (1998) Journal of Thermal Analysis and Calorimetry, 53 (3), pp. 751-756
  • Fubini, B., Fenoglio, I., Tomatis, M., Turci, F., Effect of Chemical Composition and State of the Surface on the Toxic Response to High Aspect Ratio Nanomaterials (2011) Nanomedicine, 6, pp. 899-920
  • Salerno, M.B., Logan, B.E., Velegol, D., Importance of Molecular Details in Predicting Bacterial Adhesion to Hydrophobic Surfaces (2004) Langmuir, 20, pp. 10625-10629
  • Konschin, H., Sundholm, F., Sundholm, G., Fluorescence Characteristics of Lignin Model Compounds (1976) Acta Chem. Scand., Ser. B, 30, pp. 262-266
  • Salum, M.L., Robles, C.J., Erra-Balsells, R., Photoisomerization of Ionic Liquids Ammonium Cinnamates: One-Pot Synthesis-Isolation of Z -Cinnamic Acids (2010) Org. Lett., 12, pp. 4808-4811
  • Klaumünzer, B., Kröner, D., Saalfrank, P., (TD-) DFT Calculation of Vibrational and Vibronic Spectra of Riboflavin in Solution (2010) J. Phys. Chem. B, 114, pp. 10826-10834
  • Moore, W.M., McDaniels, J.C., Hen, J.A., The Photochemistry of Riboflavin VI. The Photophysical Properties of Isoalloxazines (1977) Photochem. Photobiol., 25, pp. 505-512
  • Gutman, D.E., Complex Formation Influence on Reaction Rate I. Effect of Caffeine on Riboflavin Base-Catalyzed Degradation Rate (1962) J. Pharm. Sci., 51, pp. 1162-1167
  • Boys, S.F., Bernardi, F., Calculation of Small Molecular Interactions by Differences of Separate Total Energies-Some Procedures with Reduced Errors (1970) Mol. Phys., 19, pp. 553-566
  • Bader, R.F.W., (1990) Atoms in Molecules-A Quantum Theory, , Oxford University Press: New York

Citas:

---------- APA ----------
Arce, V.B., Scotto, J., Allegretti, P.E., Melo, M.A., Airoldi, C., Salum, M.L., Erra-Balsells, R.,..., Mártire, D.O. (2014) . Combined experimental and computational investigation of the fluorescence quenching of riboflavin by cinnamic alcohol chemisorbed on silica nanoparticles. Journal of Physical Chemistry C, 118(28), 15348-15355.
http://dx.doi.org/10.1021/jp504919c
---------- CHICAGO ----------
Arce, V.B., Scotto, J., Allegretti, P.E., Melo, M.A., Airoldi, C., Salum, M.L., et al. "Combined experimental and computational investigation of the fluorescence quenching of riboflavin by cinnamic alcohol chemisorbed on silica nanoparticles" . Journal of Physical Chemistry C 118, no. 28 (2014) : 15348-15355.
http://dx.doi.org/10.1021/jp504919c
---------- MLA ----------
Arce, V.B., Scotto, J., Allegretti, P.E., Melo, M.A., Airoldi, C., Salum, M.L., et al. "Combined experimental and computational investigation of the fluorescence quenching of riboflavin by cinnamic alcohol chemisorbed on silica nanoparticles" . Journal of Physical Chemistry C, vol. 118, no. 28, 2014, pp. 15348-15355.
http://dx.doi.org/10.1021/jp504919c
---------- VANCOUVER ----------
Arce, V.B., Scotto, J., Allegretti, P.E., Melo, M.A., Airoldi, C., Salum, M.L., et al. Combined experimental and computational investigation of the fluorescence quenching of riboflavin by cinnamic alcohol chemisorbed on silica nanoparticles. J. Phys. Chem. C. 2014;118(28):15348-15355.
http://dx.doi.org/10.1021/jp504919c