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Abstract:

We report molecular dynamics simulation results of equilibrium and dynamical characteristics pertaining to the solvation of the dye coumarin 153 (C 153) trapped within hydrophobic cavities of di- and trimethylated β-cyclodextrins (CD) in aqueous solutions. We found that stable configurations of the encapsulated probe are characterized by a slanted docking, in which the plane of the C153 lies mostly parallel to one of the glucose units of the CD. "In and out" dynamical modes of the encapsulated probe present very small amplitudes. The rotational dynamics of the trapped coumarin can be cast in terms of a simple model that includes diffusive motions within a local restrictive environment coupled to the overall rotational motion of the CD. We have examined the early stages of the solvation response of the environment following a vertical excitation of the probe. Regardless of the degree of CD methylation, the water dynamical response seems to be completed within 2-3 ps and does not differ substantially from that observed for nonencapsulated probes. The CD response is characterized by a single, subpicosecond relaxation that involves intramolecular motions. We also explored dynamical modes that could account for the recently reported persistence of Stokes shifts in the nanosecond time domain. In all cases, the only sources of ultraslow dynamics that we detected were those associated with gauche-trans interconversions in primary hydroxyl chains of the CD, which do not seem to be directly connected to the electronic excitation of the probe. © 2008 American Chemical Society.

Registro:

Documento: Artículo
Título:Exploring the picosecond time domain of the solvation dynamics of coumarin 153 within β-cyclodextrins
Autor:Rodriguez, J.; Martí, J.; Guardia, E.; Laria, D.
Filiación:Departamento de Física, Comisión Nacional de Energia Atómica, Avenida Libertador 8250, 1429, Buenos Aires, Argentina
Departamento de Quimica Inorganica, Analitica y Quimica-Fisica e INQUIMAE, Facultad de Ciencias Exactas y Naturales, Pabellón II, 1428, Buenos Aires, Argentina
Departament de Fisica i Enginyeria Nuclear, Universitat Politecnica de Catalunya, B4-B5 Campus Nord, 08034, Barcelona, Spain
Palabras clave:Cyclodextrins; Data storage equipment; Electric excitation; Glucose; Hydrophobicity; Molecular dynamics; Quantum chemistry; Solutions; Solvation; Time domain analysis; Aqueous solutions; Coumarin 153; Cyclodextrins (CD); Diffusive motions; Dynamical characteristics; Dynamical response; Early stages; Electronic excitations; Hydrophobic cavities; Hydroxyl chains; Interconversions; Intra-molecular motion; Molecular dynamics simulation; Picosecond time domain; Rotational dynamics; Rotational motions; Simple modeling; Solvation dynamics; Solvation response; Stokes shifts; Subpicosecond; Time domain OCT; Vertical excitation; Dynamics
Año:2008
Volumen:112
Número:30
Página de inicio:8990
Página de fin:8998
DOI: http://dx.doi.org/10.1021/jp8023765
Título revista:Journal of Physical Chemistry B
Título revista abreviado:J Phys Chem B
ISSN:15206106
CODEN:JPCBF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15206106_v112_n30_p8990_Rodriguez

Referencias:

  • For comprehensive information about cyclodextrins, see the special issue Chem. Rev. 1998, 98; Kano, K., Kato, Y., Kodera, N., (1996) J. Chem. Soc., Perkin Trans, 2, p. 1211
  • Kuwabara, T., Shiba, K., Ozawa, M., Miyajima, N., Yasutada, S., (2006) Tetrahedron Lett, 47, p. 4433
  • Clark, J.L., Peinado, J., Stezowski, J.J., Void, R.L., Huang, Y., Hoatson, G.L., (2006) J. Phys. Chem. B, 110, p. 26375
  • Menuel, S., Duval, R.E., Cue, D., Mutzenhardt, P., Marsura, A., (2007) New J. Chem, 31, p. 995
  • Bhattacharyya, K., (2003) Acc. Chem. Res, 36, p. 95
  • Sen, P., Roy, D., Mondai, S.K., Sahu, K., Ghosh, S., Bhattacharyya, K., (2005) J. Phys. Chem. A, 109, p. 9716
  • Douhal, A., Fiebig, T., Chachisvilis, M., Zewail, A.H., (1998) J. Phys. Chem. A, 102, p. 1657
  • Douhal, A., (2004) Chem. Rev, 104, p. 1955
  • Douhal, A., (2005) J. Photochem. Photobiol, A, 173, p. 229
  • Reija, B., Al-Soufi, W., Novo, M., Tato, J.V., (2005) J. Phys. Chem. B, 109, p. 1364
  • Okazaki, M., Kuwata, K., (1984) J. Phys. Chem, 88, p. 4181
  • Uccello-Barretta, G., Chiavacci, C., Bertucci, C., Salvadoi, P., (1993) Carbohydr. Res, 243, p. 1
  • Behr, J.P., Lehn, J.M., (1976) J. Am. Chem. Soc, 98, p. 1743
  • Pistolis, G., Balomenou, I., (2006) J. Phys. Chem. B, 110, p. 16428
  • Singh, M.K., Pal, H., Koti, A.S.R., Sapre, A.V., (2004) J. Phys. Chem. A, 108, p. 1465
  • El-Kemary, M., Organero, J.A., Santos, L., Douhal, A., (2006) J. Phys. Chem. B, 110, p. 14128
  • Sen, S., Sukul, D., Dutta, P., Bhattacharyya, K., (2001) J. Phys. Chem. A, 105, p. 10635
  • Vajda, S., Jimenez, R., Rosenthal, S.J., Fidlert, V., Fleming, G.R., Castner Jr, E.Q., (1995) J. Chem. Soc., Faraday. Trans, 91, p. 867
  • Balabai, N., Linton, B., Napper, A., Priyadarshy, S., Sukharevsky, A.P., Waldeck, D.H., (1998) J. Phys. Chem. B, 102, p. 9617
  • Roy, D., Mondai, J., Sahu, K., Ghosh, S., Sen, P., Bhattacharyya, K., (2005) J. Phys. Chem. A, 109, p. 7359
  • Das, P., Chakrabarty, A., Haldar, B., Mallick, A., Chattopadhyay, N., (2007) J. Chem. Phys. B, 111, p. 7401
  • Sen, P., Roy, D., Mondal, S.K., Sahu, K., Ghosh, S., Bhattacharyya, K., (2005) J. Phys. Chem. A, 109, p. 9716
  • Harzeba, W., Walker, G.C., Johnson, A.E., Barbara, P.F., (1991) Chem. Phys, 152, p. 57
  • Horng, M.-L., Gardecki, J.A., Papazyan, A., Maroncelli, M., (1995) J. Phys. Chem, 99, p. 17311
  • Horng, M.-L., Gardecki, J.A., Maroncelli, M., (1997) J. Phys. Chem. A, 101, p. 1030
  • Chakrabarty, D., Chakraborty, A., Seth, D., Hazra, P., Sarkar, N., (2005) Chem. Phys. Lett, 412, p. 255
  • Harza, P., Chakraborty, D., Sarkar, N., (2003) Chem. Phys. Lett, 371, p. 553
  • Chakrabarty, D., Chakraborty, A., Seth, D., Hazra, P., Sarkar, N., (2004) Chem. Phys. Lett, 397, p. 469
  • Jin, H., Baker, G.A., Arzhantsev, S., Dong, J., Maroncelli, M., (2007) J. Phys. Chem, 111, p. 7191. , and references therein
  • Hazra, P., Chakrabarty, D., Chakraborty, A., Sarkar, N., (2004) Biochem. Biophys. Res. Commun, 314, p. 543
  • Kometani, N., Hoshihara, Y., Yonezawa, Y., Kajimoto, O., Hara, K., Ito, N., (2004) J. Phys. Chem. A, 108, p. 9479
  • Baumann, R., Ferrante, C., Kneuper, E., Deeg, F.-W., Bräuchle, C., (2003) J. Phys. Chem. A, 107, p. 2422
  • Nandi, N., Bagchi, B., (1996) J. Phys. Chem, 100, p. 13914
  • Nandi, N., Bagchi, B., (1997) J. Phys. Chem. A, 101, p. 10954
  • Pizzitutti, F., Marchi, M., Sterpone, F., Rossky, P.J., (2007) J. Phys. Chem. B, 111, p. 7584
  • Bhattacharyya, K., Bagchi, B., (2000) J. Phys. Chem. A, 104, p. 10603
  • Lipkowitz, K.B., (1998) Chem. Rev, 98, p. 1829. , and references therein. For a comprhensive review article on simulation studies of cyclodextrins, see
  • Yu, Y., Chipot, C., Cai, W., Shao, X., (2006) J. Phys. Chem. B, 110, p. 6372
  • Naidoo, K.J., Chen, J.Y.-J., Jansson, J.L.M., Widmalm, G., Maliniak, A., (2004) J. Phys. Chem. B, 108, p. 4236
  • Manunza, B., Deiana, S., Pintore, M., Gessab, C., (1997) J. Mol. Struct. (THEOCHEM), 419, p. 133
  • Starikov, E.V., Bräsicke, K., Knapp, E.W., Saenger, W., (2001) Chem. Phys. Lett, 336, p. 504
  • Koehler, J.R.H., Saenger, W., van Gunsteren, W.F., (1988) Eur. Biophys. J, 16, p. 153
  • Koehler, J.R.H., Saenger, W., van Gunsteren, W.F.J., (1988) Mol. Biol, 203, p. 241
  • Varady, J., Wu, X., Wang, S., (2002) J. Phys. Chem. B, 106, p. 4863
  • Heine, T., Dos Santos, H.F., Patchkovski, S., Duarte, H.A., (2007) J. Phys. Chem. A, 111, p. 5648
  • Raffaini, G., Ganazzoli, F., (2007) Chem. Phys, 333, p. 128
  • Oana, M., Tintaru, A., Gavriliu, D., Maior, O., Hillebrand, M., (2002) J. Phys. Chem. B, 106, p. 257
  • Engelsen, S.B., Hervédu Penhoat, C., Pérez, S., (1995) J. Phys. Chem, 99, p. 13334. , See, for example
  • Shikata, T., Takahashi, R., Satokawa, Y., (2007) J. Phys. Chem. B, 111, p. 12239
  • Kumar, P.V., Maroncelli, M., (1995) J. Chem. Phys, 103, p. 3038
  • Baumann, R., Ferrante, C., Kneuper, E., Deeg, F.-W., Bräuchte, C., (2003) J. Phys. Chem. A, 107, p. 2422
  • Martins, L., Tamashiro, A., Laria, D., Skaf, M.S., (2003) J. Chem. Phys, 118, p. 5955
  • Martins, L., Skaf, M., (2003) Chem. Phys. Lett, 370, p. 683
  • Cichos, F., Brown, R., Rempel, U., von Borzyskowski, C., (1999) J. Phys. Chem. A, 103, p. 2506
  • Re, M., Laria, D., (1997) J. Phys. Chem, 101, p. 10494
  • Tamashiro, A., Rodriguez, J., Laria, D., (2002) J. Phys. Chem. A, 106, p. 215
  • Day, T.J.F., Patey, G.N., (1999) J. Chem. Phys, 110, p. 10937
  • Laria, D., Skaf, M.S., (1999) J. Chem. Phys, 111, p. 300
  • Fonseca, T., Ladanyi, B., (1991) J. Phys. Chem, 95, p. 2116
  • Ladanyi, B., Maroncelli, M., (1998) J. Chem. Phys, 709, p. 3204
  • Thompson, W.H., (2002) J. Chem. Phys, 117, p. 6618
  • Thompson, W.H., (2004) J. Chem. Phys, 120, p. 8125
  • Gomez, J.A., Thompson, W.H., (2004) J. Chem. Phys. B, 108, p. 20144
  • Berendsen, H.J.C., Postma, J.P.M., van Gunsteren, W.F., Hermans, J., (1981) In lntermolecular Forces; Pullman, B, p. 331. , Ed, Reidel: Dordrecht, The Netherlands
  • Berweger, C.D., van Gunsteren, W.F., Müller-Plathe, F., (1995) Chem. Phys. Lett, 232, p. 429
  • Moylan, C.R., (1994) J. Phys. Chem, 98, p. 13513
  • Baumann, W., Nagy, Z., (1993) Pure Appl. Chem, 65, p. 1729
  • Atomic coordinates for β-CD can be, , http://xray.bmc.uu.se/hicup/BCD, found at
  • Koehler, J.R.H., Saenger, W., van Gunsteren, W.F., (1987) Eur. Biophys. J, 15, p. 197
  • Koehler, J.R.H., Saenger, W., van Gunsteren, W.F., (1987) Eur. Biophys. J, 15, p. 211
  • Lawtrakul, L., Viernstein, H., Wolschann, P., (2003) Int. J. Pharm, 256, p. 33
  • Yua, H., Amannb, M., Hanssona, T., Köhlerb, J., Wichb, G., van Gunsteren, W.F., (2004) Carbohydr. Res, 339, p. 1697
  • Luzhkov, V., Åqvist, J., (1998) J. Am. Chem. Soc, 120, p. 6131
  • Darden, T.A., York, D.M., Pedersen, L.G., (1993) J. Chem. Phys, 98, p. 10089
  • Essmann, U., Perera, L., Berkowitz, M.L., Darden, T., Lee, H., Pedersen, L.G., (1995) J. Chem. Phys, 103, p. 8577
  • Rodriguez, J., Rico, D.H., Dommeniani, L., Laria, D., (2008) J. Phys. Chem. B, 112, pp. 7522-7529
  • Betzel, C., Saenger, W., Hingerty, B.E., Brown, G.M., (1974) J. Am. Chem. Soc, 96, p. 3630
  • Fleming, G.R., Morris, J.M., Robinson, G.W., (1976) Chem. Phys, 17, p. 91
  • Lipari, G., Szabo, A., (1980) Biophys. J, 30, p. 489
  • Schröder, G., Alexiev, U., Grubmüller, H., (2005) Biophys. J, 89, p. 3757
  • Kinosita Jr., K., Kawato, S., Ikegami, A., (1977) Biophys. J, 20, p. 289
  • Kawato, S., Kinosita Jr, K., (1981) Biophys. J, 36, p. 111
  • Chandler, D., (1987) Introduction to Modern Statistical Mechanics, , Oxford University Press: New York, Chapt. 8
  • Maroncelli, M., (1993) J. Mol Liq, 57, p. 1. , For review articles on solvation dynamics, see for example a
  • Barbara, P.F., Jarzeba, W., (1990) Adv. Photochem, 75, p. 1
  • Bagchi, B., (1989) Annu. Rev. Phys. Chem, 40, p. 115
  • Hynes, J.T., (1994) Ultrafast Dynamics of Chemical Systems, p. 345. , Simon, J. D, Ed, Kluwer: Dordrecht, The Netherlands
  • Liu, L., Guo, Q.-X., (2002) J. Inclusion Phenom. Macrocyclic Chem, 42, p. 1

Citas:

---------- APA ----------
Rodriguez, J., Martí, J., Guardia, E. & Laria, D. (2008) . Exploring the picosecond time domain of the solvation dynamics of coumarin 153 within β-cyclodextrins. Journal of Physical Chemistry B, 112(30), 8990-8998.
http://dx.doi.org/10.1021/jp8023765
---------- CHICAGO ----------
Rodriguez, J., Martí, J., Guardia, E., Laria, D. "Exploring the picosecond time domain of the solvation dynamics of coumarin 153 within β-cyclodextrins" . Journal of Physical Chemistry B 112, no. 30 (2008) : 8990-8998.
http://dx.doi.org/10.1021/jp8023765
---------- MLA ----------
Rodriguez, J., Martí, J., Guardia, E., Laria, D. "Exploring the picosecond time domain of the solvation dynamics of coumarin 153 within β-cyclodextrins" . Journal of Physical Chemistry B, vol. 112, no. 30, 2008, pp. 8990-8998.
http://dx.doi.org/10.1021/jp8023765
---------- VANCOUVER ----------
Rodriguez, J., Martí, J., Guardia, E., Laria, D. Exploring the picosecond time domain of the solvation dynamics of coumarin 153 within β-cyclodextrins. J Phys Chem B. 2008;112(30):8990-8998.
http://dx.doi.org/10.1021/jp8023765