Polymethine cyanine dyes in β-cyclodextrin solution: Multiple equilibria and chemical oxidation

Journal of Physical Organic Chemistry

Volumn 23, Issue 10, 2010, Pages 893-903

  Barros, Teresa C ^a   Toma, Sergio H ^b   Toma, Henrique E ^b   Bastos, Erick L ^c   Baptista, Mauricio S ^b,d  

^a PAULISTA UNIVERSITY   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c UNIVERSIDADE FEDERAL DO ABC   (Brazil)

^d Department of Biochemistry ^*  (Brazil)

Author keywords

chemical oxidation; cyclodextrin; inclusion complex; near infrared dyes

Indexed keywords

ABSORPTION AND FLUORESCENCE SPECTROSCOPY; CD COMPLEX; CD CONCENTRATIONS; CHEMICAL OXIDATION; ELECTROCHEMICAL TECHNIQUES; FRONTIER ORBITAL ANALYSIS; INCLUSION COMPLEX; INDOCYANINE GREEN; INTERMEDIATE SPECIE; MULTIPLE EQUILIBRIUM; NEAR-INFRARED DYES; ONE-ELECTRON OXIDATION; OXIDIZING AGENTS; POLYMETHINE CYANINES; SECOND-ORDER RATE CONSTANTS; SEMI-EMPIRICAL CALCULATION; VIS ABSORPTION;

ABSORPTION; ABSORPTION SPECTROSCOPY; BLEACHING; CLEANING; CYCLIC VOLTAMMETRY; DYES; FLUORESCENCE SPECTROSCOPY; HYDROGEN PEROXIDE; INFRARED DEVICES; OLIGOMERS; OXIDATION; RATE CONSTANTS;

REACTION INTERMEDIATES;

EID: 78649683098     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1692     Document Type: Conference Paper

References (74)

1. A. R. Oseroff, G. Ara, K. S. Wadwa, T. Dahl, in Photodynamic Therapy of Neoplastic Disease, Vol. 1 (Ed.: D. Kessel), CRC Press, Boston, 1990, p. 291.
2. G. Patonay, M. D. Antoine, Anal. Chem. 1991, 63, 321A.
3. A. Mishra, R. K. Behera, P. K. Behera, B. K. Mishra, G. B. Behera, Chem. Rev. 2000, 100, 1973.
4. M. Wainwright, Photosensitisers in Biomedicine, John Wiley & Sons Ltd., Chichester, 2009.
5. R. J. Williams, M. Lipowska, G. Patonay, L. Strekowski, Anal. Chem. 1993, 65, 601.
6. K. Kadonosono, N. Itoh, E. Uchio, S. Nakamura, S. Ohno, Arch. Ophtamol. 2000, 118, 1116.
7. C. Haritoglou, S. Neubauer Aljoscha, A. Gandorfer, M. Thiel, A. Kampik, Am. J. Ophthalmol. 2003, 136, 389.
8. S. Fickweiler, R.-M. Szeimies, W. Baeumler, P. Steinbach, S. Karrer, A. E. Goetz, C. Abels, F. Hofstaedter, M. Landthaler, J. Photochem. Photo-biol., B 1997, 38, 178.
9. A. J. Gomes, L. O. Lunardi, J. M. Marchetti, C. N. Lunardi, A. C. Tedesco, Photomed. Laser Surg. 2006, 24, 514.
10. K. Skrivanova, J. Skorpikova, J. Svihalek, V. Mornstein, R. Janisch, J. Photochem. Photobiol., B 2006, 85, 150.
11. N. A. Karp, K. S. Lilley, Proteomics 2005, 5, 3105.
12. H.-L. Huang, T. Stasyk, S. Morandell, H. Dieplinger, G. Falkensammer, A. Griesmacher, M. Mogg, M. Schreiber, I. Feuerstein, C. W. Huck, G. Stecher, G. K. Bonn, L. A. Huber, Electrophoresis 2006, 27, 1641.
13. D. Wijte, A. L. de Jong, M. A. E. Mol, B. L. M. van Baar, A. J. R. Heck, J. Proteome Res. 2006, 5, 2033.
14. J. Raez, D. R. Blais, Y. Zhang, R. A. Alvarez-Puebla, J. P. Bravo-Vasquez, J. P. Pezacki, H. Fenniri, Langmuir 2007, 23, 6482.
15. D. Kessel, Y. Luo, J. Photochem. Photobiol., B 1998, 42, 89.
16. D. J. Ball, Y. Luo, D. Kessel, J. Griffiths, S. B. Brown, D. I. Vernon, J. Photochem. Photobiol., B 1998, 42, 159.
17. D. Gabrielli, E. Belisle, D. Severino, A. J. Kowaltowski, M. S. Baptista, Photochem. Photobiol. 2004, 79, 227.
18. B. I. Shapiro, Russ. Chem. Rev. 2006, 75, 433.
19. R. Guether, M. V. Reddington, Tetrahedron Lett. 1997, 38, 6167.
20. C. Roos, V. Buss, J. Inclusion Phenom. 1997, 27, 49.
21. G. Patonay, J. S. Kim, R. Kodagahally, L. Strekowski, Appl. Spectrosc. 2005, 59, 682.
22. A. H. Herz, Adv. Colloid Interface Sci. 1977, 8, 237.
23. W. West, S. Pearce, J. Phys. Chem. 1965, 69, 1894.
24. W. G. Herkstroeter, P. A. Martic, S. Farid, J. Am. Chem. Soc. 1990, 112, 3583.
25. T. V. S. Rao, J. B. Huff, C. Bieniarz, Tetrahedron 1998, 54, 10627.
26. H. C. Junqueira, D. Severino, L. G. Dias, M. S. Gugliotti, M. S. Baptista, Phys. Chem. Chem. Phys. 2002, 4, 2320.
27. D. Severino, H. C. Junqueira, M. Gugliotti, D. S. Gabrielli, M. S. Baptista, Photochem. Photobiol. 2003, 77, 459.
28. C. Reichardt, J. Phys. Org. Chem. 1995, 8, 761.
29. M. D. Joesten, J. L. Wood, World of Chemistry, Harcourt College Publishers, Orlando, 1996.
30. G. N. Kalinkova, Int. J. Pharm. 1999, 187, 1.
31. I. Tabushi, Y. Kuroda, Adv. Catal. 1983, 32, 417.
32. R. Breslow, S. D. Dong, Chem. Rev. 1998, 98, 1997.
33. O. S. Tee, Adv. Phys. Org. Chem. 1994, 29, 1.
34. K. Kano, Y. Itoh, H. Kitagishi, T. Hayashi, S. Hirota, J. Am. Chem. Soc. 2008, 130, 8006.
35. G. W. Byers, S. Gross, P. M. Henrichs, Photochem. Photobiol. 1976, 23, 37.
36. J. E. H. Buston, J. R. Young, H. L. Anderson, Chem. Commun. 2000, 905.
37. A. Ruebner, Z. Yang, D. Leung, R. Breslow, Proc. Natl Acad. Sci. U. S. A. 1999, 96, 14692.
38. K. A. Connors, Binding Constants: The Measurement of Molecular Complex Stability, John Wiley & Sons, New York, 1987.
39. H. A. Benesi, J. H. Hildebrand, J. Am. Chem. Soc. 1949, 71, 2703.
40. J. S. Kim, R. Kodagahally, L. Strekowski, G. Patonay, Talanta 2005, 67, 947.
41. U. Rösch, S. Yao, R. Wortmann, F. Würthner, Angew. Chem., Int. Ed. 2006, 45, 7026.
42. G. B. Rocha, R. O. Freire, A. M. Simas, J. J. P. Stewart, J. Comput. Chem. 2006, 27, 1101.
43. L. Liu, Q.-X. Guo, Inclusion Phenom. Macrocyclic Chem. 2004, 50, 95.
44. S. Chelli, M. Majdoub, M. Jouini, S. Aeiyach, F. Maurel, K. I. Cha-ne-Ching, P.-C. Lacaze, J. Phys. Org. Chem. 2007, 20, 30.
45. C. S. Oliveira, E. L. Bastos, E. L. Duarte, R. Itri, M. S. Baptista, Langmuir 2006, 22, 8718.
46. A. Klamt, G. Schueuermann, J. Chem. Soc., Perkin Trans. 2 1993, 799.
47. G. Schueuermann, Quant. Struct. Act. Relat. 1990, 9, 326.
48. J. J. P. Stewart, MOPAC 2009 version, 9.351W ed., Stewart Computational Chemistry, Colorado Springs, 2009.
49. H.-J. Schneider, F. Hacket, V. Rüdiger, H. Ikeda, Chem. Rev. 1998, 98, 1755.
50. K. B. Lipkowitz, Chem. Rev. 1998, 98, 1829.
51. V. Jiménez, J. B. Alderete, E. J. Delgado, J. Belmar, J. Gav́n, Struct. Chem. 2006, 17, 217.
52. K. Kasatani, M. Ohashi, H. Sato, Carbohydr. Res. 1989, 192, 197.
53. M. Ohashi, K. Kasatani, H. Shinohara, H. Sato, J. Am. Chem. Soc. 1990, 112, 5824.
54. K. Fukuzumi, N. Ikeda, J. Am. Oil Chem. Soc. 1971, 48, 384.
55. S. Krishnan, D. G. Kuhn, G. A. Hamilton, J. Am. Chem. Soc. 1977, 99, 8121.
56. J. Winkler, E. R. Smith, R. G. Compton, J. Colloid Interface Sci. 1997, 195, 229.
57. T. Hihara, Y. Okada, Z. Morita, Dyes Pigm. 2000, 46, 181.
58. T. Hihara, Y. Okada, M. Zenzo, Dyes Pigm. 2003, 59, 201.
59. K. Fukui, T. Yonezawa, C. Nagata, Bull. Chem. Soc. Jpn 1954, 27, 423.
60. J. Wang, Analytical Electrochemistry, 2nd edn, John Wiley & Sons, New York, 2000.
61. R. Philip, A. Penzkofer, W. Baeumler, R. M. Szeimies, C. Abels, J. Photochem. Photobiol., A 1996, 96, 137.
62. R. S. Hays, G. P. Hobbs, M. Kourouma, J. J. Ries, T. M. Ste. Marie, S. K. M. Sherwood, R. G. Landolt, J. Mol. Catal. A: Chem. 1998, 129, L123.
63. V. Buss, Angew. Chem., Int. Ed. 1991, 30, 869.
64. K. Kasatani, M. Ohashi, M. Kawasaki, H. Sato, Chem. Lett. 1987, 1633.
65. E. D. Moritz, M. R. V. Sahyun, J. Photochem. Photobiol., A 2005, 169, 211.
66. K. Bredereck, C. Schumacher, Dyes Pigm. 1993, 21, 45.
67. J. Oakes, P. Gratton, I. Weil, J. Chem. Soc., Dalton Trans. 1997, 3805.
68. J. Oakes, G. Welch, P. Gratton, J. Chem. Soc., Dalton Trans. 1997, 3811.
69. J. Oakes, P. Gratton, R. Clark, I. Wilkes, J. Chem. Soc., Perkin Trans. 2 1998, 2569.
70. J. Oakes, P. Gratton, J. Chem. Soc., Perkin Trans. 2 1998, 2201.
71. G. R. Hodges, J. R. Lindsay Smith, J. Oakes, J. Chem. Soc., Perkin Trans. 2 1998, 617.
72. S. M. Dellegar, S. A. Murphy, A. E. Bourne, J. C. DiCesare, G. H. Purser, Biochem. Biophys. Res. Commun. 1999, 257, 431.
73. S. Marmor, J. Org. Chem. 1963, 28, 250.
74. G. Bouillon, C. Lick, K. Schank, in The Chemistry of Peroxides (Ed.: S. Patai), 1983, p. 279.