Modulation of prototropic activity and rotational relaxation dynamics of a cationic biological photosensitizer within the motionally constrained bio-environment of a protein

Journal of Physical Chemistry B

Volumn 115, Issue 34, 2011, Pages 10322-10334

  Paul, Bijan Kumar ^a   Guchhait, Nikhil ^a  

^a UNIVERSITY OF CALCUTTA   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANISOTROPY; BINDING ENERGY; BODY FLUIDS; CIRCULAR DICHROISM SPECTROSCOPY; DICHROISM; FLUORESCENCE; PHOTOSENSITIZERS; RELAXATION PROCESSES;

AQUEOUS BUFFER; BIEXPONENTIAL; BINDING INTERACTION; BIO-ENVIRONMENT; BOVINE SERUM ALBUMINS; CANCER CELLS; CARBOLINES; CATIONIC DRUGS; DOCKING SIMULATIONS; DRUG MOLECULES; EMISSION PROFILE; FLUORESCENCE ANISOTROPY DECAY; HARMANE; HELICAL CONTENT; INTERACTION SITE; MOLAR RATIO; MOTIONAL RESTRICTIONS; NATURALLY OCCURRING; NEGATIVE CHARGE; ROTATIONAL RELAXATIONS; SENSITIVITY OF THE PROBE; STEADY-STATE FLUORESCENCE; STRUCTURAL CONTENT; TIME-RESOLVED FLUORESCENCE; TRANSPORT PROTEINS;

PROTEINS;

EID: 80052220838     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp2015275     Document Type: Article

References (85)

1. Coronilla, A. S.; Carmona, C.; Munoz, M. A.; Balon, M. J. Fluoresc. 2009, 19, 1025-1035
2. Abramovitch, R. A.; Spencer, I. D. Adv. Heterocycl. Chem. 1964, 3, 79-207
3. Wolfbeis, O. S.; Furlinger, E.; Wintersteiger, R. Montash. Chem. 1982, 113, 509-517
4. Allen, J. R. F.; Holmstedt, B. R. Phytochemistry 1980, 19, 1573-1982
5. Balon, M.; Munoz, M. A.; Guardado, P.; Hidalgo, J.; Carmona, C. Trends Photochem. Photobiol. 1994, 3, 117-138
6. Bloom, H.; Barchas., J.; Sandler, M.; Usdin, E. Progress in Clinical and Biological Research. Beta-carbolines and Tetrahydroisoquinolines; Alan R. Liss Inc.: New York, 1982; Vol 90.
7. Braestrup, C.; Nielsen, M.; Olsen, C. E. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 2288-2292
8. Carlini, E. A. Pharmacol., Biochem. Behav. 2003, 75, 501-512
9. Meester, C. Mutat. Res. 1995, 339, 139-153
10. Tamura, S.; Konakahara, T.; Komatsu, H.; Ozaki, T.; Ohta, Y.; Takeuchi, H. Heterocycles 1998, 48, 2477-2480
11. Balon, M.; Munoz, M. A.; Carmona, C.; Guardado, P.; Galan, M. Biophys. Chem. 1999, 80, 41-52
12. Cao, R.; Peng, W.; Chen, H.; Ma, Y.; Liu, X.; Hou, X.; Guan, H.; Xu, A. Biochem. Biophys. Res. Commun. 2005, 338, 1557-1563
13. Hudson, J. B.; Towers, G. H. Pharmacol. Ther. 1991, 49, 81-122
14. Shimoi, K.; Kawabata, H.; Tomita, I. Mutat. Res. 1992, 268, 287-295
15. Guan, H.; Liu, X.; Peng, W.; Cao, R.; Ma, Y.; Chen, H.; Xu, A. Biochem. Biophys. Res. Commun. 2006, 342, 894-901
16. Wang, S.; Gao, R.; Zhou, F.; Selke, M. J. Mater. Chem. 2004, 14, 487-493
17. Allison, R. R.; Downie, G. H.; Cuenca, R.; Hu, X.-H.; Childs, C. J. H.; Sibata, C. H. Photodiag. Photodyn. Ther. 2004, 1, 27-42
18. Levy, J. G. Semin. Oncol. 1994, 21, 4-10
19. Dolmans, D. E. J. G. J.; Fukumura, D.; Jain, R. K. Nat. Rev. Cancer 2003, 3, 380-387
20. Varela, A. P.; Miguel, M. G.; Maçanita, A. L.; Becker, R. S.; Burrows, H. D. J. Phys. Chem. 1995, 99, 16093-16100
21. Reyman, D.; Pardo, A.; Poyato, J. M. L. J. Phys. Chem. 1994, 98, 10408-10411
22. Henderson, B.; Dougherty, T., Eds. Photodynamic Therapy: Basic Principles and Clinical Applications; Marcel Dekker Inc.: New York, 1992.
23. Chae, K. H.; Ham, H. S. Bull. Korean Chem. Soc. 1987, 7, 478-479
24. He, X. M.; Carter, D. C. Nature 1992, 358, 209-215
25. Chakraborty, T.; Chakraborty, I.; Moulik, S. P.; Ghosh, S. Langmuir 2009, 25, 3062-3074
26. Peters, T. Serum albumin. Advances in Protein Chemistry; Academic Press: New York, 1985; pp 161-245, Vol. 37.
27. Abou-Zied, O. K.; Al-Shihi, O. I. K. J. Am. Chem. Soc. 2008, 130, 10793-10801
28. Abou-Zied, O. K. J. Phys. Chem. B 2007, 111, 9879-9885
29. Brown, J. R. Albumin Structure, Function and Uses; Rosenoer, V. M.; Oratz, M.,; Rothschild, M. A., Eds.; Pergamon Press: Oxford, 1977, 27.
30. Carter, D. C.; Ho, J. X. Adv. Protein Chem. 1994, 45, 153-159
31. Wu, F.-Y.; Ji, Z.-J.; Wu, Y.-M.; Wan, X.-F. Chem. Phys. Lett. 2006, 424, 387-393
32. Zhong, D.; Douhal, A.; Zewail, A. H. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 14056-1461
33. Kamal, J. K. A.; Zhao, L.; Zewail., A. H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 13411-13416
34. Pavdridge, W. M. Am. J. Physiol. 1987, 252, 157-164
35. Mallick, A.; Chattopadhyay, N. Photochem. Photobiol. 2005, 81, 419-424
36. Lakowicz, J. R. Priniples of Fluorescence Spectroscopy, 3 rd ed.; Plenum: New York, 2006.
37. Gelamo, E. L.; Tabak, M. Spectrochim. Acta 2000, 56, 2255-2271
38. Gelamo, E. L.; Silva, C. H. T. P.; Imasato, H.; Tabak, M. Biochim. Biophys. Acta 2002, 1594, 84-99
39. Paul, B. K.; Samanta, A.; Guchhait, N. J. Phys. Chem. B 2010, 114, 6183-6196
40. Frisch, M. J. Gaussian 03, revision B.03; Gaussian, Inc.: Pittsburgh, PA, 2003.
41. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. J. Comput. Chem. 1998, 19, 1639-1662 and references therein
42. Hetenyi, C.; van der Spoel, D. FEBS Lett. 2006, 580, 1447-1450
43. De Lano, W. L. The PyMOL Molecular Graphics System; De Lano Scientific: San Carlos, CA, USA, 2002.
44. Tomas Vert, F.; Zabala Sanchez, I.; Olba Torrent, A. J. Photochem. 1983, 23, 355-368
45. Wolfbeis, O. S.; Furlinger, E.; Wintersteiger, R. Monatsh. Chem. 1982, 113, 509-517
46. Hayashi, K.; Nagao, M.; Gugimara, T. Nucleic Acid Res. 1977, 4, 3679-3685
47. Gonzalez, M. M.; Arnbjerg, J.; Denofrio, M. P.; Erra-Balsells, R.; Ogilby, P. R.; Cabrarizo, F. M. J. Phys. Chem. A 2009, 113, 6648-6656
48. Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703-2707
49. Singh, R. B.; Mahanta, S.; Guchhait, N. Chem. Phys. Lett. 2008, 463, 183-188
50. Ding, F.; Liu, W.; Liu, F.; Li, Z.-Y.; Sun, Y. J. Fluoresc. 2009, 19, 783-791
51. Reichardt, C. Chem. Rev. 1994, 94, 2319-2358
52. Bhattacharya, B.; Nakka, S.; Guruprasad, L.; Samanta, A. J. Phys. Chem. B 2009, 113, 2143-2150
53. Berezin, M. Y.; Achilefu, S. Chem. Rev. 2010, 110, 2641-2684
54. Ingersoll, C. M.; Strollo, C. M. J. Chem. Educ. 2007, 84, 1313-1315
55. Demchenko, A. P. Luminescence 2002, 17, 19-42
56. Guz., A.; Wasylewski, Z. J. Protein Chem. 1994, 13, 393-399
57. Samanta, A. J. Phys. Chem. B 2006, 110, 13704-13716 and references therein
58. Maglia, G.; Jonckheer, A.; Maeyer, M. D.; Frere, J.-M.; Engelborghs, Y. Protein Sci. 2008, 17, 352-361
59. Reviews in Fluorescence; Geddes, C. D.; Lakowicz, J. R., Eds.; Kluwer-Plenum: New York, 2004. The appearance of Leonardo da Vinci's Universal.
60. Berg, J. M.; Tymoczko, J. L.; Stryer, L. Biochemistry, 5 th ed.; Devlin, T. M., Ed.; W. H. Freeman and Company: New York, 2002.
61. Garcia-Zubiri, I. X.; Burrows, H. D.; de Melo, J. S. S.; Pina, J.; Monteserin, M.; Tapia, M. J. Photochem. Photobiol. 2007, 83, 1455-1464
62. Chakraborty, A.; Seth, D.; Setua, P.; Sarkar, N. J. Chem. Phys. 2008, 128, 204510-204519
63. Paul, B. K.; Guchhait, N. J. Phys. Chem. B 2010, 114, 12528-12540
64. Dutt, G. B. J. Phys. Chem. B 2005, 109, 4923-4928
65. Dutt, G. B. J. Chem. Phys. 2003, 119, 11971-11976
66. Paul, B. K.; Guchhait, N. J. Colloid Interface Sci. 2011, 353, 237-247
67. Quitevis, E. L.; Marcus, A. H.; Fayer, M. D. J. Chem. Phys. 1993, 97, 5792-5769
68. Kinosita, K.; Kawato, S.; Ikegami, A. Biophys. J. 1977, 20, 289-305
69. Schames, J. R.; Hecnchman, R. H.; Siegel, J. S.; Sotriffer, C. A.; Ni, H.; McCammon, J. A. J. Med. Chem. 2004, 47, 1879-1881
70. McKenna, C. E.; Kashemirov, B. A.; Upton, T. G.; Batra, V. K.; Goodman, M. F.; Pedersen, L. C.; Beard, W. A.; Wilson, S. H. J. Am. Chem. Soc. 2007, 129, 15412-15413
71. Hetenyi, C.; van der Spoel, D. Protein Sci. 2002, 11, 1729-1737
72. Pineda, O.; Farras, J.; Maccari, L.; Manetti, F.; Botta, M.; Vilarrasa, J. Med. Chem. Lett. 2004, 14, 4825-4829
73. Campbell, S. J.; Gold, N. D.; Jackson, R. M.; Westhead, D. R. Curr. Opin. Struct. Biol. 2003, 13, 389-395
74. Moriyama, Y.; Takeda, K. Langmuir 2005, 21, 5524-5528
75. Moriyama, Y.; Takeda, K. Langmuir 1999, 15, 2003-2008
76. Moriyama, Y.; Watanabe, E.; Kobayashi, K.; Harano, H.; Inui, E.; Takeda, K. J. Phys. Chem. B 2008, 112, 16585-16589
77. Hu, Y.-J.; Ou-Yang, Y.; Dai, C.-M.; Liu, Y.; Xiao, X.-H. Biomacromolecules 2010, 11, 106-112
78. Wu, X.; Narsimhan, G. Biochim. Biophys. Acta 2008, 1784, 1694-1701
79. Zsila, F.; Bikadi, Z.; Simonyi, M. Biochem. Pharmacol. 2003, 65, 447-456
80. Dufour, C.; Dangles, O. Biochim. Biophys. Acta 2005, 1721, 164-173
81. Jiang, Y. L. Bioorg. Med. Chem. 2008, 16, 6406-6414
82. Tayyab, S.; Ahmad, B.; Kumar, Y.; Khan, M. M. Int. J. Biol. Macromol. 2002, 30, 17-22
83. Sulkowska, A.; Bojko, B.; Rownicka, J.; Pentak, D.; Sulkowska, W. J. Mol. Struct. 2003, 651, 237-243
84. Beauchemin, R.; Nsoukpoe-Kossi, C. N.; Thomas, T. J.; Thomas, T.; Carpentier, R.; Tajmir-Riahi, H. A. Biomacromolecules 2007, 8, 3177-3183
85. Nsoukpoe-Kossi, C. N.; Sedaghat-Herati, R.; Ragi, C.; Hotchandani, S.; Tajmir-Riahi, H. A. Int. J. Biol. Macromol. 2007, 40, 484-490