Anion binding to a ferric porphyrin complexed with per-O-methylated β-cyclodextrin in aqueous solution

Journal of the American Chemical Society

Volumn 126, Issue 46, 2004, Pages 15202-15210

  Kano, Koji ^a   Kitagishi, Hiroaki ^a   Tamura, Shigeto ^a   Yamada, Akihisa ^a  

^a DOSHISHA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRATION; HYDROPHILICITY; HYDROPHOBICITY; IRON COMPOUNDS; NEGATIVE IONS; ORGANOMETALLICS; THERMODYNAMICS;

ANION BINDING; CYCLODEXTRINS; FERRIC PORPHYRIN; LEWIS BASICITY;

POLYSACCHARIDES;

5,10,15,20 TETRAKIS(4 SULFONATOPHENYL)PORPHINATO IRON; ANION; BETA CYCLODEXTRIN DERIVATIVE; BROMIDE; CHLORIDE ION; FERRIC ION; FLUORIDE ION; HEPTAKIS(2,3,6 O TRIMETHYL) BETA CYCLODEXTRIN; IRON COMPLEX; NITRATE; PERCHLORATE; PHOSPHATE; PORPHYRIN DERIVATIVE; SULFATE; THIOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; AQUEOUS SOLUTION; ARTICLE; BINDING KINETICS; COMPLEX FORMATION; ELECTRON SPIN RESONANCE; HYDROPHILICITY; HYDROPHOBICITY; METHYLATION; PH; PKA; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; THERMODYNAMICS;

ANIONS; BETA-CYCLODEXTRINS; CALORIMETRY; FERRIC COMPOUNDS; HYDROGEN-ION CONCENTRATION; HYDROPHOBICITY; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; METHYLATION; PORPHYRINS; SOLUTIONS; SPECTROPHOTOMETRY, ULTRAVIOLET; THERMODYNAMICS; WATER;

EID: 9344232790     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045472i     Document Type: Article

References (86)

1. (a) Kendrew, J. C.; Bodo, G.; Dintzis, H. M.; Parrish, R. G.; Wyckoff, H.; Phillips, D. C. Nature (London) 1958, 181, 662-666.
2. (b) Kendrew, J. C.; Dickerson, R. E.; Strandberg, B. E.; Hart, R. G.; Davis, D. R.; Phillips, D. C.; Shore, V. C. Nature (London) 1960, 185, 422-427.
3. (c) Kendrew, J. C. Science 1963, 139, 1259-1266.
4. (a) Perutz, M. F.; Rossmann, M. G.; Cullis, A. F.; Muirhead, H.; Will, G.; North, A. C. T. Nature (London) 1960, 185, 416-422.
5. (b) Cullis, A. F.; Muirhead, H.; Perutz, M. F.; Rossmann, M. G.; North, A. C. T. Proc. R. Soc. London, Ser. A 1962, 265, 161-187.
6. (c) Perutz, M. F. Science 1963, 140, 863-869.
7. (a) Collman, J. P.; Gagne, R. R.; Halbert, T. R.; Marchon, J. C.; Reed, C. A. J. Am. Chem. Soc. 1973, 95, 7868-7870.
8. (b) Collman, J. P. Acc. Chem. Res. 1977, 10, 265-272.
9. Momenteau, M.; Reed, C. A. Chem. Rev. 1994, 94, 659-698.
10. Collman, J. P.; Boulatov, R.; Sunderland, C. J.; Fu, L. Chem. Rev. 2004, 104, 561-588.
11. Kano, K.; Nishiyabu, R. In Advances in Supramolecular Chemistry; Gokel, G. W., Ed.; Cerberus Press: South Miami, FL, 2003; Vol. 9, Chapter 2, pp 39-69.
12. Kano, K.; Tanaka, N.; Minamizono, H.; Kawakita, Y. Chem. Lett. 1996, 925-926.
13. Komatsu, T.; Hayakawa, S.; Tsuchida, E.; Nishide, H. Chem. Commun. 2003, 50-51.
14. Zhou, H.; Groves, J. T. Biophys. Chem. 2003, 105, 639-648.
15. (a) Kuroda, Y.; Hiroshige, T.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1990, 1594-1595.
16. (b) Kuroda, Y.; Hiroshige, T.; Sera, T.; Shiroiwa, Y.; Tanaka, H.; Ogoshi, H. J. Am. Chem. Soc. 1989, 111, 1912-1913.
17. (a) Yang, J.; Breslow, R. Angew. Chem., Int. Ed. 2000, 39, 2692-2694.
18. (b) Breslow, R.; Yan, J.; Belvedere, S. Tetrahedron Lett. 2002, 43, 363-365.
19. (c) Breslow, R.; Yand, J.; Yan, J. Tetrahedron 2002, 58, 653-659.
20. (d) Yang, J.; Gabriele, B.; Belvedere, S.; Huang, Y.; Breslow, R. J. Org. Chem. 2002, 67, 5057-5067.
21. Weber, L.; Imiolczyk, I.; Haufer, G.; Rehorek, D.; Hennig, H. J. Chem. Soc., Chem. Commun. 1992, 301-303.
22. (a) Breslow, R. Chemtracts 2002, 15, 59-68.
23. (b) Breslow, R.; Zhang, X.; Xu, R.; Maletic, M.; Merger, R. J. Am. Chem. Soc. 1996, 118, 11678-11679.
24. (c) Breslow, R.; Zhang, X.; Huang, Y. J. Am. Chem. Soc. 1997, 119, 4535-4536.
25. (d) Breslow, R.; Gabriele, B.; Yang, J. Tetrahedron Lett. 1998, 39, 2887-2890.
26. (a) French, R. R.; Wirz, J.; Woggon, W.-D. Helv. Chim. Acta 1998, 81, 1521-1527.
27. (b) French, R. R.; Holzer, P.; Leuenberger, M. G.; Woggon, W.-D. Angew. Chem., Int. Ed. 2000, 39, 1267-1269.
28. (a) Manka, J. S.; Lawrence, D. S. Tetrahedron Lett. 1989, 30, 7341-7344.
29. (b) Manka, J. S.; Lawrence, D. S. J. Am. Chem. Soc. 1990, 112, 2440-2442.
30. (c) Dick, D. L.; Rao, T. V. S.; Sukumaran, D.; Lawrence, D. S. J. Am. Chem. Soc. 1992, 114, 2664-2669.
31. (a) Ribo, J. M.; Farrera, J.-A.; Valero, M. L.; Virgili, A. Tetrahedron 1995, 51, 3705-3712.
32. (b) Hamai, S.; Koshiyama, T. J. Photochem. Photobiol. 1999, 127, 135-141.
33. (a) Mosseri, S.; Mialocq, J. C.; Perly, B.; Hambright, P. J. Phys. Chem. 1991, 95, 4659-4663.
34. (b) Sur, S. K.; Bryant, R. G. J. Phys. Chem. 1995, 99, 4900-4905.
35. Kano, K.; Nishiyabu, R.; Asada, T.; Kuroda, Y. J. Am. Chem. Soc. 2002, 124, 9937-9944.
36. Carofiglio, T.; Fornasier, R.; Lacchini, V.; Rosso, C.; Tonellato, U. Tetrahedron Lett. 1996, 8019-8022.
37. Kano, K.; Nishiyabu, R.; Yamazaki, T.; Yamazaki, I. J. Am. Chem. Soc. 2003, 125, 10625-10634.
38. Reed, C. A. Inorg. Chim. Acta 1997, 263, 95-97.
39. Shikama, K. Chem. Rev. 1998, 98, 1357-1373.
40. Satoh, Y.; Shikama, K. J. Biol. Chem. 1981, 256, 10272-10275.
41. For a recent paper on anion binding to metMb, see: De Rosa, M. C.; Bertonati, C.; Giardina, B.; Di Stasio, E.; Enrico, B. A. Biochim. Biophys. Acta 2002, 1594, 341-352.
42. For recent reviews, see: (a) Best, M. D.; Tobey, S. L.; Anslyn, E. V. Coord. Chem. Rev. 2003, 240, 3-15.
43. (b) Martinez-Manes, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419-4476.
44. (c) Beer, P. D.; Hayes, E. J. Coord. Chem. Rev. 2003, 240, 167-189.
45. (d) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516.
46. (e) Sessler, J. L.; Tvermoes, N. A.; Davis, J.; Anzenbacher, P., Jr.; Jursikov, K.; Sato, W.; Seidel, D.; Lunch, V.; Black, C. B.; Try, A.; Andrioletti, B.; Hemmi, G.; Mody, T. D.; Magda, D. J.; Krai, V. Pure Appl. Chem. 1999, 71, 2009-2018.
47. (a) Schmidtchen, F. D. Angew. Chem. 1977, 89, 751-752.
48. (b) Schmidtchen, F. P. Pure Appl. Chem. 1989, 61, 1535-1546.
49. (c) Metz, B.; Rosalky, J. M.; Weiss, R. J. Chem. Soc., Chem. Commun. 1976, 533-534.
50. (d) Lehn, J.-M.; Sonveaux, E.; Willard, A. K. J. Am. Chem. Soc. 1978, 100, 4914-4916.
51. (e) Hosseini, M. W.; Lehn, J.-M. J. Am. Chem. Soc. 1982, 104, 3525-3527.
52. (f) Tobey, S. L.; Jones, B. D.; Anslyn, E. V. J. Am. Chem. Soc. 2003, 125, 4026-4027.
53. (g) Lee, D. H.; Im, J. H.; Son, S. U.; Chung, Y. K.; Hong, J.-I. J. Am. Chem. Soc. 2003, 125, 7752-7753.
54. (h) Metzger, A.; Lynch, V. M.; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 862-865.
55. (a) Fleischer, E. B.; Palmer, J. M.; Srivastava, T. S.; Chatterjee, A. J. Am. Chem. Soc. 1971, 93, 3162-3167.
56. (b) Sutler, J. R.; Hambright, P.; Chock, P. B.; Krishnamurthy, M. Inorg. Chem. 1974, 13, 2764-2765.
57. (c) Goff, H.; Morgan, L. O. Inorg. Chem. 1976, 15, 3180-3181.
58. (c) MeLendon, G.; Bailey, M. Inorg. Chem. 1979, 18, 2120-2123.
59. (d) El-Awady, A. A.; Wilkins, P. C.; Wilkins, R. A. Inorg. Chem. 1985, 24, 2053-2057.
60. (e) Barley, M. H.; Takeuchi, K.; Meyer, T. J. J. Am. Chem. Soc. 1986, 108, 5876-5885.
61. (a) Lexa, D.; Momenteau, M.; Saveant, J.-M.; Xu, F. Inorg. Chem. 1985, 24, 122-127.
62. (b) Almersson, O.; Adalsteinsson, H.; Bruice, T. C. J. Am. Chem. Soc. 1995, 117, 4524-4532.
63. Sur, S. K.; Bryant, R. G. J. Phys. Chem. 1995, 99, 7172-7179.
64. Dorough, G. D.; Miller, J. R.; Hunennekens, F. M. J. Am. Chem. Soc. 1951, 73, 4315-4320.
65. Connors, K. A. Binding Constants; John Wiley & Sons: New York, 1987; Chapter 2.
66. ITC Data Analysis in Origin - Tutorial Guide; MicroCal: Northampton, MA, 1998; pp 76-78.
67. Sheidt, W. R.; Reed, C. A. Chem. Rev. 1981, 81, 543-555.
68. Ivanca, M. A.; Lappin, A. G.; Scheidt, W. R. Inorg. Chem. 1991, 30, 711-718.
69. Boersma, A. D.; Goff, H. M. Inorg. Chem. 1982, 21, 581-586.
70. Aime, S.; Fasano, M.; Paoletti, S.; Cutruzzola, F.; Desideri, A.; Bolognesi, M.; Rizzi, M.; Ascenzi, P. Biophys. J. 1996, 70, 482-488.
71. (a) Sessler, J. L.; Seidel, D. Angew. Chem., Int. Ed. 2003, 42, 5134-5175.
72. (b) Sessler, J. L.; Camiolo, S.; Gale, P. A. Coord. Chem. Rev. 2003, 240, 17-55.
73. (c) Gale, P. A.; Anzenbacher, P., Jr.; Sessler, J. L. Coord. Chem. Rev. 2001, 222, 57-102.
74. (d) Sessler, J. L. Acc. Chem. Res. 2001, 34, 989-997.
75. Král, V.; Furuta, H.; Shreder, K.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1595-1607.
76. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140-5141.
77. Rudkevich, D. M.; Shivanyuk, A. N.; Brzozka, Z.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2124-2126.
78. (a) Jagessar, R. C.; Burns, D. H. Chem. Commun. 1997, 1685-1686.
79. (b) Jagessar, R. C.; Shang, M.; Scheidt, W. R.; Burns, D. H. J. Am. Chem. Soc. 1998, 120, 11684-11692.
80. (c) Lee, C.; Lee, D. H.; Hong, J.-I. Tetrahedron Lett. 2001, 42, 8665-8668.
81. Takeuchi, M.; Shioya, T.; Swager, T. M. Angew. Chem., Int. Ed. 2001, 40, 3372-3376.
82. Sachs, J. N.; Woolf, T. B. J. Am. Chem. Soc. 2003, 125, 8742-8743.
83. (a) Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875-1917.
84. (b) Kano, K.; Kitae, T.; Shimofuri, Y.; Tanaka, N.; Mineta, Y. Chem.-Eur. J. 2000, 6, 2705-2713.
85. Kano, K.; Kitagishi, H.; Kodera, M.; Hirota, S. Angew. Chem. Int. Ed. In press.
86. Adler, A. D.; Longo, F. R.; Rampas, F.; Kim, J. J. Inorg. Nucl. Chem. 1970, 23, 2443-2445.