New Luminescent Cyclometalated Iridium(III) Diimine Complexes as Biological Labeling Reagents

Inorganic Chemistry

Volumn 42, Issue 21, 2003, Pages 6886-6897

  Lo, Kenneth Kam Wing ^a   Chung, Chi Keung ^a   Lee, Terence Kwok Ming ^a   Lui, Lok Hei ^a   Tsang, Keith Hing Kit ^a   Zhu, Nianyong ^b  

^a CITY UNIVERSITY OF HONG KONG   (Hong Kong)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 METHYLPHENYL)PYRIDINE; 2 PHENYLPYRIDINE; 2 PHENYLQUINOLINE DERIVATIVE; 3 METHYL 1 PHENYLPYRAZOLE; 4 AMINO 2,2' BIPYRIDINE; 4 IODOACETAMIDO 2,2' BIPYRIDINE; 4 ISOTHIOCYANATO 2,2' BIPYRIDINE; 5 AMINO 1,10 PHENANTHROLINE; 5 IODOACETAMIDO 1,10 PHENANTHROLINE; 5 ISOTHIOCYANATO 1,10 PHENANTHROLINE; AVIDIN; BENZO[H]QUINOLINE; DIGOXIN ANTIBODY; IODOACETAMIDE; IRIDIUM COMPLEX; ISOTHIOCYANIC ACID; LIGAND; METAL; PYRAZOLE DERIVATIVE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL LABELING; CHEMICAL REACTION; CRYSTAL STRUCTURE; ELECTROCHEMICAL ANALYSIS; IRRADIATION; LUMINESCENCE; MOLECULAR BIOLOGY; MOLECULAR RECOGNITION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMISTRY; INDICATORS AND REAGENTS; IRIDIUM; LUMINESCENCE; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 0142072139     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic0346984     Document Type: Article

References (85)

1. See, for example: (a) Hermanson, G. T. Bioconjugate Techniques; Academic Press: San Diego, CA, 1996.
2. (b) Kessler, C. Nonradioactive Labeling and Detection of Biomolecules, 2nd ed.; Springer: Heidelberg, Germany, 1999.
3. See, for example: Sammes, P. G.; Yahioglu, G. Nat. Prod. Rep. 1996, 13, 1.
4. See, for example: (a) Gray, H. B.; Winkler, J. R. Annu. Rev. Biochem. 1996, 65, 537.
5. (b) Erkkila, K. E.; Odom, D. T.; Barton, J. K. Chem. Rev. 1999, 99, 2777.
6. (c) Cohen, S. M.; Lippard, S. J. Prog. Nucleic Acid Res. 2001, 67, 93.
7. (d) Beilstein, A. E.; Tierney, M. T.; Grinstaff, M. W. Comments Inorg. Chem. 2000, 22, 105.
8. (e) Terpetschnig, E.; Szmacinski, H.; Lakowicz, J. R. Methods Enzymol. 1997, 278, 295.
9. (f) Perrin, D. M.; Mazumder, A.; Sigman, D. S. Prog. Nucleic Acid Res. 1996, 52, 123.
10. (g) Winkler, J. R.; Gray, H. B. Chem. Rev. 1992, 92, 369.
11. (a) Watts, R. J. Inorg. Chem. 1981, 20, 2302.
12. (b) Sprouse, S.; King, K. A.; Spellane, P. J.; Watts, R. J. J. Am. Chem. Soc. 1984, 106, 6647.
13. (c) Ohsawa, Y.; Sprouse, S.; King, K. A.; DeArmond, M. K.; Hanck, K. W.; Watts, R. J. J. Phys. Chem. 1987, 91, 1047.
14. (d) Garces, F. O.; King, K. A.; Watts, R. J. Inorg. Chem. 1988, 27, 3464.
15. (e) Wilde, A. P.; Watts, R. J. J. Phys. Chem. 1991, 95, 622.
16. (f) Wilde, A. P.; King, K. A.; Watts, R. J. J. Phys. Chem. 1991, 95, 629.
17. (g) Dedeian, K.; Djurovich, P. I.; Garces, F. O.; Carlson, G.; Watts, R. J. Inorg. Chem. 1991, 30, 1685.
18. (h) Djurovich, P. I.; Watts, R. J. Inorg. Chem. 1993, 32, 4681.
19. (i) Schmid, B.; Garces, F. O.; Watts, R. J. Inorg. Chem. 1994, 33, 9.
20. (a) Serroni, S.; Juris, A.; Campagna, S.; Venturi, M.; Denti, G.; Balzani, V. J. Am. Chem. Soc. 1994, 116, 9086.
21. (b) Calogero, G.; Giuffrida, G.; Serroni, S.; Ricevuto, V.; Campagna, S. Inorg. Chem. 1995, 34, 541.
22. (c) Mamo, A.; Stefio, I.; Parisi, M. F.; Credi, A.; Venturi, M.; Di Pietro, C.; Campagna, S. Inorg. Chem. 1997, 36, 5947.
23. (d) Di Marco, G.; Lanza, M.; Mamo, A.; Stefio, I.; Di Pietro, C.; Romeo, G.; Campagna, S. Anal. Chem. 1998, 70, 5019.
24. (e) Neve, F.; Crispini, A.; Campagna, S.; Serroni, S. Inorg. Chem. 1999, 38, 2250.
25. (f) Griffiths, P. M.; Loiseau, F.; Puntoriero, F.; Serroni, S.; Campagna, S. Chem. Commun. 2000, 2297.
26. (g) Neve, F.; Crispini, A.; Loiseau, F.; Campagna, S. J. Chem. Soc., Dalton Trans. 2000, 1399.
27. (h) Neve, F.; Crispini, A. Eur. J. Inorg. Chem. 2000, 1039.
28. (i) Neve, F.; Crispini, A.; Serroni, S.; Loiseau, F.; Campagna, S. Inorg. Chem. 2001, 40, 1093.
29. (a) Vogler, L. M.; Scott, B.; Brewer, K. J. Inorg. Chem. 1993, 32, 898.
30. (b) Bridgewater, J. S.; Vogler, L. M.; Molnar, S. M.; Brewer, K. J. Inorg. Chim. Acta 1993, 208, 179.
31. (c) Molnar, S. M.; Nallas, G.; Bridgewater, J. S.; Brewer, K. J. J. Am. Chem. Soc. 1994, 116, 5206.
32. (a) Didier, P.; Ortmans, I.; Kirsch-De Mesmaeker, A.; Watts, R. J. Inorg. Chem. 1993, 32, 5239.
33. (b) Ortmans, I.; Didier, P.; Kirsch-De Mesmaeker, A. Inorg. Chem. 1995, 34, 3695.
34. (a) Collin, J.-P.; Dixon, I. M.; Sauvage, J.-P.; Williams, J. A. G.; Barigelletti, F.; Flamigni, L. J. Am. Chem. Soc. 1999, 121, 5009.
35. (b) Dixon, I. M.; Collin, J.-P.; Sauvage, J.-P.; Flamigni, L.; Encinas, S.; Barigelletti, F. Chem. Soc. Rev. 2000, 29, 385.
36. (c) Dixon, I. M.; Collin, J.-P.; Sauvage, J.-P.; Barigelletti, F.; Flamigni, L. Angew. Chem., Int. Ed. 2000, 39, 1292.
37. (d) Flamigni, L.; Dixon, I. M.; Collin, J.-P.; Sauvage, J.-P. Chem. Commun. 2000, 2479.
38. (e) Dixon, I. M.; Collin, J.-P.; Sauvage, J.-P.; Flamigni, L. Inorg. Chem. 2001, 40, 5507.
39. (a) Colombo, M. G.; Güdel, H. U. Inorg. Chem. 1993, 32, 3081.
40. (b) Colombo, M. G.; Hauser, A.; Güdel, H. U. Inorg. Chem. 1993, 32, 3088.
41. (c) Colombo, M. G.; Brunold, T. C.; Riedener, T.; Güdel, H. U.; Förtsch, M.; Bürgi, H.-B. Inorg. Chem. 1994, 33, 545.
42. (d) Colombo, M. G.; Hauser, A.; Güdel, H. U. Topics Curr. Chem. 1994, 171, 143.
43. (a) Lamansky, S.; Djurovich, P.; Murphy, D.; Abdel-Razzaq, F.; Kwong, R. ; Tsyba, I.; Bortz, M.; Mui, B.; Bau, R.; Thompson, M. E. Inorg. Chem. 2001, 40, 1704.
44. (b) Lamansky, S.; Djurovich, P.; Murphy, D.; Abdel-Razzaq, F.; Lee, H.-E.; Adachi, C.; Burrows, P. E.; Forrest, S. R.; Thompson, M. E. J. Am. Chem. Soc. 2001, 123, 4304.
45. (c) Gao, R.; Ho, D. G.; Hernandez, B.; Selke, M.; Murphy, D.; Djurovich, P. I.; Thompson, M. E. J. Am. Chem. Soc. 2002, 124, 14828.
46. (a) Licini, M.; Williams, J. A. G. Chem. Commun. 1999, 1943.
47. (b) Goodall, W.; Williams, J. A. G. J. Chem. Soc., Dalton Trans. 2000, 2893.
48. Ayala, N. P.; Flynn, C. M., Jr.; Sacksteder, L.; Demas, J. N.; DeGraff, B. A. J. Am. Chem. Soc. 1990, 112, 3837.
49. (a) van Diemen, J. H.; Haasnoot, J. G.; Hage, R.; Müller, E.; Reedijk, J. Inorg. Chim. Acta 1991, 181, 245.
50. (b) van Diemen, J. H.; Hage, R.; Haasnoot, J. G.; Lempers, H. E. B.; Reedijk, J.; Vos, J. G.; De Cola, L.; Barigelletti, F.; Balzani, V. Inorg. Chem. 1992, 31, 3518.
51. Maestri, M.; Balzani, V.; Deuschel-Cornioley, C.; von Zelewsky, A. Adv. Photochem. 1992, 17, 1.
52. (a) Lo, K. K. W.; Ng, D. C. M.; Chung, C. K. Organometallics 2001, 20, 4999.
53. (b) Lo, K. K. W.; Chung, C. K.; Ng, D. C. M.; Zhu, N. New J. Chem. 2002, 26, 81.
54. (c) Lo, K. K. W.; Chung, C. K.; Zhu, N. Chem. Eur. J. 2003, 9, 475.
55. (a) Baldo, M. A.; Thompson, M. E.; Forrest, S. R. Nature 2000, 403, 750.
56. (b) Watanabe, T.; Nakamura, K.; Kawami, S.; Fukuda, Y.; Tsuji, T.; Wakimoto, T.; Miyaguchi, S.; Yahiro, M.; Yang, M.-J.; Tsutsui, T. Synth. Met. 2001, 122, 203.
57. (c) Ostrowski, J. C.; Robinson, M. R.; Heeger, A. J.; Bazan, G. C. Chem. Commun. 2002, 784.
58. (d) Beeby, A.; Bettington, S.; Samuel, I. D. W.; Wang, Z. J. Mater. Chem. 2003, 13, 80.
59. See for example: (a) Riaz, K.; Forker, A. D. Drugs 1998, 55, 747.
60. (b) Dasgupta, A. Am. J. Clin. Pathol. 2002, 118, 132.
61. (c) Kjeldsen, K.; Norgaard, A.; Gheorghiade, M. Cardiovasc. Res. 2002, 55, 710.
62. Fava, C.; Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 2001, 12, 2731.
63. (a) Ellis, C. D.; Margerum, L. D.; Murray, R. W.; Meyer, T. J. Inorg. Chem. 1983, 22, 1283.
64. (b) Bachas, L. G.; Cullen, L.; Hutchins, R. S.; Scott, D. L. J. Chem. Soc., Dalton Trans. 1997, 1571.
65. (a) Jobbagy, A.; Kiraly, K. Biochim. Biophys. Acta 1966, 124, 166.
66. (b) Strottmann, J. M.; Robinson, J. B., Jr.; Stellwagen, E. Anal. Biochem. 1983, 132, 334.
67. Bradford, M. M. Anal. Biochem. 1976, 72, 248.
68. See, for example: (a) Drost, R. H.; Plomp, T. A.; Teunissen, A. J.; Maas, A. H. J.; Maes, R. A. A. Clin. Chim. Acta 1977, 79, 557.
69. (b) Pinnaduwage, P.; Huang, L. Clin. Chem. 1988, 34, 268.
70. See, for example: (a) Barbieri, U.; Gandolfi, C. Clin. Chim. Acta 1977, 77, 257.
71. (b) Bergdähl, B.; Molin, L. Clin. Biochem. 1981, 14, 67.
72. (c) Hinds, J. A.; Pincombe, C. F.; Morris, H.; Duffy, P. Clin. Chem. 1986, 32, 16.
73. (d) Hubl, W.; Daxenbichler, G.; Meissner, D.; Thiele, H. J. Clin. Chem. 1988, 34, 2521.
74. (e) Helsingius, P.; Hemmilä, I.; Lövgren, T. Clin. Chem. 1986, 32, 1767.
75. (f) Papanastasiou-Diamandi, A.; Conway, K.; Diamandis, E. P. J. Pharm. Sci. 1989, 78, 617.
76. (g) Blackburn, G. F.; Shah, H. P.; Kenten, J. H.; Leland, J.; Kamin, R. A.; Link, J.; Peterman, J.; Powell, M. J.; Shah, A.; Talley, D. B.; Tyagi, S. K.; Wilkins, E.; Wu, T.-G.; Massey, R. J. Clin. Chem. 1991, 37, 1534.
77. Bulter, V. P.; Tse-Eng, D. Methods in Enzymology; Academic Press: San Diego, CA, 1982; Vol, 84, p 558.
78. Stevens, P. W.; Henry, M. R.; Kelso, D. M. Nucleic Acids Res. 1999, 27, 1719.
79. Jones, R. A.; Roney, B. D.; Sasse, W. H. F.; Wade, K. O. J. Chem. Soc. B 1967, 106.
80. Del Guerzo, A.; Demeunynck, M.; Lhomme, J.; Kirsch-De Mesmaeker, A. Inorg. Chem. Commun. 1998, 1, 339.
81. Takalo, H.; Mukkala, V.-M.; Mikola, H.; Liitti, P.; Hemmilä, I. Bioconjugate Chem. 1994, 5, 278.
82. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991.
83. Nakamaru, K. Bull. Chem. Soc. Jpn. 1982, 55, 2697.
84. DENZO: Otwinowski, Z.; Minor, W. Methods in Enzymology; Academic Press: San Diego, CA, 1997: Vol. 276, p 307.
85. SHELXS-97 and SHELXL-97: Sheldrick, G. M. Programs for Crystal Structure Analysis (Release 97-2); University of Göttingen: Göttingen, Germany.