Ultrafast photodynamics of drugs in nanocavities: Cyclodextrins and human serum albumin protein

Langmuir

Volumn 28, Issue 17, 2012, Pages 6746-6759

  Martín, Cristina ^a   Gil, Michał ^a   Cohen, Boiko ^a   Douhal, Abderrazzak ^a  

^a UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC SYSTEM; BIOLOGICAL WATER; BIOLOGICALLY RELEVANT MOLECULES; CAVITANDS; CIS-TRANS ISOMERIZATION; CONFORMATIONAL CHANGE; ELECTRONIC DISTRIBUTION; GUEST MOLECULES; HOST GUEST INTERACTIONS; HUMAN SERUM ALBUMINS; MOLECULAR SYSTEMS; NANO-CAVITIES; NANOCARRIERS; PHOTO-STABILITY; STRUCTURAL ASPECTS; TIME RESOLVED TECHNIQUE; TWISTING MOTION; ULTRA-FAST; ULTRA-FAST DYNAMICS;

CHARGE TRANSFER; CYCLODEXTRINS; ISOMERIZATION; MOLECULES; RATE CONSTANTS;

DRUG INTERACTIONS;

CYCLODEXTRIN; DRUG; DRUG CARRIER; PROTON; SERUM ALBUMIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON TRANSPORT; HUMAN; KINETICS; LIGHT; METHODOLOGY; MOTION; NANOTECHNOLOGY; PROTEIN CONFORMATION; STEREOISOMERISM;

CYCLODEXTRINS; DRUG CARRIERS; ELECTRON TRANSPORT; HUMANS; KINETICS; LIGHT; MODELS, MOLECULAR; MOTION; NANOTECHNOLOGY; PHARMACEUTICAL PREPARATIONS; PROTEIN CONFORMATION; PROTONS; SERUM ALBUMIN; STEREOISOMERISM;

EID: 84860458329     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la2049713     Document Type: Article

References (75)

1. Zewail, A. H. Femtochemistry: atomic-scale dynamics of the chemical bond J. Phys. Chem. A 2000, 104, 5660-5694
2. Douhal, A. Ultrafast guest dynamics in cyclodextrin nanocavities Chem. Rev. 2004, 104, 1955-1976
3. Douhal, A. Breaking, making, and twisting of chemical bonds in gas, liquid, and nanocavities Acc. Chem. Res. 2004, 37, 349-355
4. Peters, T., Jr. All about Albumin: Biochemistry, Genetics, and Medical Applications; Academic Press: San Diego, 1996.
5. Zhong, D.; Douhal, A.; Zewail, A. H. Femtosecond studies of protein-ligand hydrophobic binding and dynamics: Human serum albumin Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 14056-14061 (Pubitemid 32016528)
6. Kamal, J. K. A.; Zhao, L.; Zewail, A. H. Ultrafast hydration dynamics in protein unfolding: human serum albumin Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 13411-13416 (Pubitemid 39238416)
7. Qiu, W.; Zhang, L.; Okobiah, O.; Yang, Y.; Wang, L.; Zhong, D.; Zewail, A. H. Ultrafast solvation dynamics of human serum albumin: Correlations with conformational transitions and site-selected recognition J. Phys. Chem. B 2006, 110, 10540-10549 (Pubitemid 43952951)
8. Cal, K.; Centkowska, K. Use of cyclodextrins in topical formulations: practical aspects Eur. J. Pharm. Biopharm. 2008, 68, 467-478 (Pubitemid 351318207)
9. El-Kemary, M.; Organero, J. A.; Santos, L.; Douhal, A. Effect of cyclodextrin nanocavity confinement on the photorelaxation of the cardiotonic drug milrinone J. Phys. Chem. B 2006, 110, 14128-14134 (Pubitemid 44187970)
10. Marconi, G.; Monti, S.; Manoli, F.; Degli Esposti, A.; Mayer, B. A circular dichroism and structural study of the inclusion complex artemisinin-β-cyclodextrin Chem. Phys. Lett. 2004, 383, 566-571
11. Douhal, A.; Sanz, M.; Tormo, L. Femtochemistry of orange II in solution and in chemical and biological nanocavities Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 18807-18812 (Pubitemid 43049526)
12. Cohen, B.; Alvarez, C. M.; Carmona, N. A.; Organero, J. A.; Douhal, A. Proton-transfer reaction dynamics within the human serum albumin protein J. Phys. Chem. B 2011, 115, 7637-7647
13. Bransburg-Zabary, S.; Nachliel, E.; Gutman, M. Gauging of the PhoE channel by a single freely diffusing proton Biophys. J. 2002, 83, 2987-3000 (Pubitemid 36041923)
14. Moilanen, D. E.; Spry, D. B.; Fayer, M. D. Water dynamics and proton transfer in nafion fuel cell membranes Langmuir 2008, 24, 3690-3698 (Pubitemid 351575153)
15. Mondal, S. K.; Sahu, K.; Sen, P.; Roy, D.; Ghosh, S.; Bhattacharyya, K. Excited state proton transfer of pyranine in a γ-cyclodextrin cavity Chem. Phys. Lett. 2005, 412, 228-234 (Pubitemid 41085115)
16. Sen Mojumdar, S.; Mondal, T.; Das, A. K.; Dey, S.; Bhattacharyya, K. Ultrafast and ultraslow proton transfer of pyranine in an ionic liquid microemulsion. J. Chem. Phys. 2010, 132, 194505.
17. Gepshtein, R.; Leiderman, P.; Huppert, D.; Project, E.; Nachliel, E.; Gutman, M. Proton antenna effect of the γ-cyclodextrin outer surface, measured by excited state proton transfer J. Phys. Chem. B 2006, 110, 26354-26364 (Pubitemid 46133358)
18. Pines, E.; Pines, D. In Ultrafast Hydrogen Bonding Dynamics and Proton Transfer Processes in the Condensed Phase; Elsaesser, T.; Bakker, H. J., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2002; pp 155-184.
19. Pines, E.; Magnes, B. -Z.; Lang, M. J.; Fleming, G. R. Direct measurement of intrinsic proton transfer rates in diffusion-controlled reactions Chem. Phys. Lett. 1997, 281, 413-420 (Pubitemid 127337917)
20. Genosar, L.; Cohen, B.; Huppert, D. Ultrafast direct photoacid-base reaction J. Phys. Chem. A 2000, 104, 6689-6698
21. Rini, M.; Magnes, B.-Z.; Pines, E.; Nibbering, E. T. J. Real-time observation of bimodal proton transfer in acid-base pairs in water Science (Washington, DC) 2003, 301, 349-352 (Pubitemid 36877065)
22. Mohammed, O. F.; Pines, D.; Dreyer, J.; Pines, E.; Nibbering, E. T. J. Chemistry: sequential proton transfer through water bridges in acid-base reactions Science 2005, 310, 83-86 (Pubitemid 41434539)
23. Cox, M. J.; Bakker, H. J. Parallel proton transfer pathways in aqueous acid-base reactions. J. Chem. Phys. 2008, 128, 174501.
24. Spry, D. B.; Goun, A.; Fayer, M. D. Deprotonation dynamics and stokes shift of pyranine (HPTS) J. Phys. Chem. A 2007, 111, 230-237 (Pubitemid 46278941)
25. Adamczyk, K.; Premont-Schwarz, M.; Pines, D.; Pines, E.; Nibbering, E. T. J. Real-time observation of carbonic acid formation in aqueous solution Science 2009, 326, 1690-1694
26. Leiderman, P.; Genosar, L.; Huppert, D. Excited-state proton transfer: indication of three steps in the dissociation and recombination process J. Phys. Chem. A 2005, 109, 5965-5977 (Pubitemid 41048752)
27. Mondal, S. K.; Sahu, K.; Ghosh, S.; Sen, P.; Bhattacharyya, K. Excited-state proton transfer from pyranine to acetate in γ-cyclodextrin and hydroxypropyl γ-cyclodextrin J. Phys. Chem. A 2006, 110, 13646-13652 (Pubitemid 46133376)
28. Carmona, N. A.; Cohen, B.; Organero, J. A.; Douhal, A. Excited state intermolecular proton and energy transfer of 1-hydroxypyrene interacting with the human serum albumin protein. J. Photochem. Photobiol., A DOI: 10.1016/j.photochem.2011.10.024.
29. Milosavljevic, B. H.; Thomas, J. K. The photophysics of 1-hydroxypyrene, the acidity of its singlet excited state, and the nature of its photoionization process in polar media Photochem. Photobiol. Sci. 2002, 1, 100-104 (Pubitemid 37069715)
30. Lukeman, M. L. M.; Burns, M. D.; Wan, P. Excited state intramolecular proton transfer in 1-hydroxypyrene Can. J. Chem. 2011, 89, 433-440
31. Mohammed, O. F.; Dreyer, J.; Magnes, B. Z.; Pines, E.; Nibbering, E. T. J. Solvent-dependent photoacidity state of pyranine monitored by transient mid-infrared spectroscopy ChemPhysChem 2005, 6, 625-636 (Pubitemid 40579966)
32. Spry, D. B.; Goun, A.; Bell, C. B., III; Fayer, M. D. Identification and properties of the 1La and 1Lb states of pyranine. J. Chem. Phys. 2006, 125, 144514.
33. Ferrer, M. L.; Duchowicz, R.; Carrasco, B.; Garcia de la Torre, J.; Acuña, A. U. The conformation of serum albumin in solution: a combined phosphorescence depolarization-hydrodynamic modeling study Biophys. J. 2001, 80, 2422-2430 and references therein. (Pubitemid 32402004)
34. Lochbrunner, S.; Wurzer, A. J.; Riedle, E. Ultrafast excited-state proton transfer and subsequent coherent skeletal motion of 2-(2′-hydroxyphenyl) benzothiazole J. Chem. Phys. 2000, 112, 10699-10702
35. Garcia-Ochoa, I.; Lopez, M.-A. D.; Vinas, M. H.; Santos, L.; Ataz, E. M.; Amat-Guerri, F.; Douhal, A. Probing hydrophobic nanocavities in chemical and biological systems with a fluorescent proton-transfer dye Chem.-Eur. J. 1999, 5, 897-901 (Pubitemid 129504638)
36. Chang, C.-W.; Lu, Y.-C.; Wang, T.-T.; Diau, E. W.-G. Photoisomerization dynamics of azobenzene in solution with S1 excitation: A femtosecond fluorescence anisotropy study J. Am. Chem. Soc. 2004, 126, 10109-10118 (Pubitemid 39079433)
37. Cusati, T.; Granucci, G.; Persico, M. Photodynamics and time-resolved fluorescence of azobenzene in solution: A mixed quantum-classical simulation J. Am. Chem. Soc. 2011, 133, 5109-5123
38. Yui, H.; Takei, M.; Hirose, Y.; Sawada, T. Ultrafast transient lens spectroscopy of photoisomerization dynamics of azocompounds in confined nanospace of cyclodextrins Rev. Sci. Instrum. 2003, 74, 907-909
39. Lochbrunner, S.; Schultz, T.; Schmitt, M.; Shaffer, J. P.; Zgierski, M. Z.; Stolow, A. Dynamics of excited-state proton transfer systems via time-resolved photoelectron spectroscopy J. Chem. Phys. 2001, 114, 2519-2522 (Pubitemid 32873868)
40. Organero, J. A.; Tormo, L.; Douhal, A. Caging ultrafast proton transfer and twisting motion of 1-hyroxyl-2-acetonapthone Chem. Phys. Lett. 2002, 363, 409-414
41. Organero, J. A.; Martin, C.; Cohen, B.; Douhal, A. Chemical and biological caging effects on the relaxation of a proton-transfer dye Langmuir 2008, 24, 10352-10357
42. Sancar, A. Structure and function of DNA photolyase and cryptochrome blue-light photoreceptors Chem. Rev. 2003, 103, 2203-2237
43. Brazard, J.; Usman, A.; Lacombat, F.; Ley, Ch.; Martin, M. M.; Plaza, P. New insights into the ultrafast photophysics of oxidized and reduced FAD in solution J. Phys. Chem. A 2011, 115, 3251-3262
44. Kao, Y. -T.; Tan, C.; Song, S.-H.; Oztürk, N.; Li, J.; Wang, L.; Sancar, A.; Zhong, D. Ultrafast dynamics and anionic active states of the flavin cofactor in cryptochrome and photolyase J. Am. Chem. Soc. 2008, 130, 7695-7701 (Pubitemid 351842134)
45. Zhao, R.-K.; Lukacs, A.; Haigney, A.; Brust, R.; Greetham, G. M.; Towrie, M.; Tonge, P. J.; Meech, S. R. Ultrafast transient mid IR to visible spectroscopy of fully reduced flavins Phys. Chem. Chem. Phys. 2011, 13, 17642-17648
46. Miskolczy, Z.; Biczok, L.; Görner, H. Tautomerization of lumichrome promoted by supramolecular complex formation with cucurbit[7]uril J. Photochem. Photobiol., A 2009, 207, 47-51
47. Marchena, M.; Gil, M.; Martin, C.; Organero, J. A.; Sanchez, F.; Douhal, A. Stability and photodynamics of lumichrome structures in water at different pHs and in chemical and biological caging media J. Phys. Chem. B 2011, 115, 2424-2435
48. Gil., M.; Wang, Y.; Douhal, A. Ultrafast dynamics of lumichrome in solution and in chemical and biological caging media. J. Photochem. Photobiol., A DOI:10.1016/j.photochem.2012.10.017.
49. Tormo, L.; Organero, J. A.; Cohen, B.; Martin, C.; Santos, L.; Douhal, A. Dynamical and structural changes of an anesthetic analogue in chemical and biological nanocavities J. Phys. Chem. B 2008, 112, 13641-13647
50. Kandoth, N.; Choudhury, S. D.; Mohanty, J.; Bhasikuttan, A. C.; Pal, H. Inhibiting intramolecular electron transfer in flavin adenine dinucleotide by host-guest interaction: a fluorescence study J. Phys. Chem. B 2010, 114, 2617-2626
51. Douhal, A.; Sanz, M.; Tormo, L.; Organero, J. A. Femtochemistry of inter- and intramolecular hydrogen bonds ChemPhysChem. 2005, 6, 419-423 (Pubitemid 40477724)
52. Ameer-Beg, S.; Ormson, S. M.; Brown, R. G.; Matousek, P.; Towrie, M.; Nibbering, E. T. J.; Foggi, P.; Neuwahl, V. R. Ultrafast measurements of excited state intramolecular proton transfer (ESIPT) in room temperature solutions of 3-hydroxyflavone and derivatives J. Phys. Chem. A 2001, 105, 3709-3718
53. Douhal, A.; Sanz, M.; Carranza, M. A.; Organero, J. A.; Santos, L. Femtosecond observation of intramolecular charge- and proton-transfer reactions in a hydroxyflavone derivative Chem. Phys. Lett. 2004, 394, 54-60
54. Tormo, L.; Douhal, A. Caging anionic structure of a proton transfer dye in a hydrophobic nanocavity with a cooperative H-bonding J. Photochem. Photobiol., A 2005, 173, 358-364 (Pubitemid 40935811)
55. 2+ complexes J. Phys. Chem. A 1998, 102, 5907-5914 (Pubitemid 128604894)
56. Chou, P.-T.; Pu, S.-C.; Cheng, Y.-M.; Yu, W.-S.; Hung, F.-T.; Hu, W.-P. Femtosecond dynamics on excited-state proton/charge-transfer reaction in 4′- N, N -diethylamino-3-hydroxyflavone. The role of dipolar vectors in constructing a rational mechanism J. Phys. Chem. A 2005, 109, 3777-3787 (Pubitemid 40680388)
57. Organero, J. A.; Tormo, L.; Sanz, M.; Roshal, A.; Douhal, A. Complexation effect of γ-cyclodextrin on a hydroxyflavone derivative: formation of excluded and included anions J. Photochem. Photobiol., A 2007, 188, 74-82
58. Tormo, L.; Organero, J. A.; Douhal, A. Effect of nanocavity confinement on the relaxation of anesthetic analogues: relevance to encapsulated drug photochemistry J. Phys. Chem. B 2005, 109, 17848-17854 (Pubitemid 41445320)
59. Altomare, C.; Cellamare, S.; Summo, L.; Fossa, P.; Mosti, L.; Carotti, A. Ionization behaviour and tautomerism-dependent lipophilicity of pyridine-2(1H)-one cardiotonic agents Bioorg. Med. Chem. 2000, 8, 909-916 (Pubitemid 30336387)
60. El-Kemary, M.; Organero, J. A.; Douhal, A. Fast relaxation dynamics of the cardiotonic drug milrinone in water solutions J. Med. Chem. 2006, 49, 3086-3091 (Pubitemid 43830508)
61. Gil, M.; Douhal, A. Femtosecond dynamics in ionic structures of a heart medicine Chem. Phys. Lett. 2006, 432, 106-109 (Pubitemid 44737442)
62. Robertson, D. W.; Beedle, E. E.; Swartzendruber, J. K.; Jones, N. D.; Elzey, T. K.; Kauffman, R. F.; Wilson, H.; Hayes, J. S. Bipyridine cardiotonics: the three-dimensional structures of amrinone and milrinone J. Med. Chem. 1986, 29, 635-640 (Pubitemid 16034668)
63. Bordner, J.; Hammen, P. D.; Whipple, E. B. Deuterium isotope effects on carbon-13 NMR shifts and the tautomeric equilibrium in N-substituted pyridyl derivatives of piroxicam J. Am. Chem. Soc. 1989, 111, 6572-6578
64. Yoon, M.; Choi, H. N.; Kwon, H. W.; Park, K. H. Solvent dependence of absorption and fluorescence spectra of piroxicam. A possible intramolecular proton transfer in the excited state Bull. Korean Chem. Soc. 1988, 9, 171-175
65. Gil, M.; Douhal, A. Femtosecond dynamics of piroxicam structures in solutions J. Phys. Chem. A 2008, 112, 8231-8237
66. Andrade, S. M.; Costa, S. M. B.; Pansu, R. The influence of water on the photophysical and photochemical properties of piroxicam in AOT/iso-octane/water reversed micelles Photochem. Photobiol. 2000, 71, 405-412
67. El-Kemary, M.; Gil, M.; Douhal, A. Relaxation dynamics of piroxicam structures within human serum albumin protein J. Med. Chem. 2007, 50, 2896-2902 (Pubitemid 46980860)
68. Bree, F.; Urien, S.; Nguyen, P.; Albengres, E.; Tillement, J. P. Eur. A re-evaluation of the HSA-piroxicam interaction J. Drug Metab. Pharmacokinet. 1990, 15, 303-307
69. Antoniades, C.; Tousoulis, D.; Koumallos, N.; Marinou, K.; Stefanadis, C. Levosimendan: beyond its simple inotropic effect in heart failure Pharmacol. Ther. 2007, 114, 184-197 (Pubitemid 46561532)
70. Cohen, B.; Organero, J. A.; Santos, L.; Padial, L. R.; Douhal, A. Exploring the ground and excited states structural diversity of levosimendan, a cardiovascular calcium sensitizer J. Phys. Chem. B 2010, 114, 14787-14795
71. Hunt, N. T. 2D-IR spectroscopy: ultrafast insights into biomolecule structure and function Chem. Soc. Rev. 2009, 38, 1837-1848
72. Bredenbeck, J.; Helbing, J.; Kolano, C.; Hamm, P. Ultrafast 2D-IR spectroscopy of transient species ChemPhysChem 2007, 8, 1747-1756
73. Frontiera, R. R.; Fang, C.; Dasgupta, J.; Mathies, R. A. Probing structural evolution along multidimensional reaction coordinates with femtosecond stimulated Raman spectroscopy Phys. Chem. Chem. Phys. 2012, 14, 405-414
74. Novo, M.; Granadero, D.; Bordello, J.; Al-Soufi, W. Host-guest association studied by fluorescence correlation spectroscopy J. Inclusion Phenom. Macrocyclic Chem. 2011, 70, 259-268
75. Das, D. K.; Mondal, T.; Mandal, A. K.; Bhattacharyya, K. Binding of organic dyes with human serum albumin: a single-molecule study Chem.-Asian J. 2011, 6, 3097-3103