Synthesis, photophysical and electrochemical properties, and biological labeling studies of cyclometalated iridium(III) bis(pyridylbenzaldehyde) complexes: Novel luminescent cross-linkers for biomolecules

Chemistry - A European Journal

Volumn 9, Issue 2, 2003, Pages 475-483

  Lo, Kenneth Kam Wing ^a   Chung, Chi Keung ^a   Zhu, Nianyong ^b  

^a CITY UNIVERSITY OF HONG KONG   (Hong Kong)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Avidin; Cross linker; Iridium; Luminescence; X ray diffraction

Indexed keywords

ALDEHYDES; AMINES; IRIDIUM; LUMINESCENCE; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

BIOCONJUGATES;

ELECTROCHEMISTRY;

ALDEHYDE DERIVATIVE; IRIDIUM COMPLEX;

AMINATION; ARTICLE; COMPLEX FORMATION; CROSS LINKING; CRYSTAL STRUCTURE; ELECTROCHEMISTRY; ENERGY; LOW TEMPERATURE; LUMINESCENCE; SYNTHESIS;

AVIDIN; BENZALDEHYDES; BINDING, COMPETITIVE; CROSS-LINKING REAGENTS; CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMISTRY; IRIDIUM; LUMINESCENT MEASUREMENTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY, ATOMIC;

EID: 0037455153     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390050     Document Type: Article

References (71)

1. See for example: a) G. T. Hermanson. Bioconjugate Techniques; Academic Press. San Diego, CA, 1996;
2. b) C. Kessler, Nonradioactive Labeling and Detection of Biomolecules, 2nd Ed, Springer, Heidelberg, Germany, 1999.
3. See for example: a) M. N. Gupta, ACS Sym. Ser. 1993, 516, 307;
4. b) C. P. Govardhan, Curr. Opin. Biotech. 1999, 10, 331.
5. a) D. Mornet, K. Ue, P. Chaussepied, M. F. Morales, Eur. J. Biochem. 1986, 159, 555;
6. b) J.-S. Kim, R. T. Raines, Anal. Biochem. 1995, 225, 174;
7. c) H. Bhattacharjee, B. P. Rosen, J. Biol. Chem. 1996, 271, 24465;
8. d) A. Sinz, K. Wang, Biochemistry 2001, 40, 7903.
9. a) J. J. Kang, A. Tarcsafalvi, A. D. Carlos, E. Fujimoto, Z. Shahrokh, B. J. M. Thevenin, S. B. Shohet, N. Ikemoto, Biochemistry 1992, 31, 3288;
10. b) B. J. M. Thevenin, Z. Shahrokh, R. L. Williard, E. K. Fujimoto, J. J. Kang, N. Ikemoto, S. B. Shohet, Eur. J. Biochem. 1992, 206, 471;
11. c) K. K. Sharma, H. Kaur, K. Kester, Biochem. Bioph. Res. Co. 1997, 239, 217.
12. See for example: a) J. R. Winkler, H. B. Gray, Chem. Rev. 1992, 92, 369;
13. b) D. M. Perrin, A. Mazumder, D. S. Sigman, Prog. Nucleic Acid Res. 1996, 52, 123;
14. c) E. Terpetschnig, H. Szmacinski, J. R. Lakowicz, Methods Enzymol. 1997, 278, 295;
15. d) A. E. Beilstein, M. T. Tierney, M. W Grinstaff, Comments Inorg. Chem. 2000, 22, 105;
16. e) S. M. Cohen, S. J. Lippard, Prog. Nucleic Acid Res. 2001, 67, 93.
17. a) F. D. Lewis, S. A. Helvoigt, R. L. Letsinger, Chem. Commun. 1999, 327;
18. b) I. Vargas-Baca, D. Mitra, H. J. Zulyniak, J. Banerjee, H. F. Sleiman, Angew. Chem. 2001, 113, 4765; Angew. Chem. Int. Ed. 2001. 40, 4629.
19. b) I. Vargas-Baca, D. Mitra, H. J. Zulyniak, J. Banerjee, H. F. Sleiman, Angew. Chem. 2001, 113, 4765; Angew. Chem. Int. Ed. 2001. 40, 4629.
20. a) R. J. Watts, Inorg. Chem. 1981, 20, 2302;
21. b) S. Sprouse, K. A. King, P. J. Spellane, R. J. Watts, J. Am. Chem. Soc. 1984, 106, 6647;
22. c) Y. Ohsawa, S. Sprouse, K. A. King, M. K. DeArmond, K. W. Hanck, R. J. Watts, J. Phys. Chem. 1987, 91, 1047;
23. d) F. O. Garces, K. A. King, R. J. Watts, Inorg. Chem. 1988, 27, 3464;
24. e) A. P. Wilde, R. J. Watts, J. Phys. Chem. 1991, 95, 622;
25. f) A. P. Wilde, K. A. King, R. J. Watts, J. Phys. Chem. 1991, 95, 629;
26. g) K. Dedeian, P. I. Djurovich, F. O. Garces, G. Carlson, R. J. Watts. Inorg. Chem. 1991, 30, 1685;
27. h) P. I. Djurovich, R. J. Watts, Inorg. Chem. 1993, 32, 4681;
28. i) B. Schmid, F. O. Garces, R. J. Watts, Inorg. Chem. 1994, 33, 9.
29. a) S. Serroni, A. Juris, S. Campagna, M. Venturi, G. Denti, V. Balzani, J. Am. Chem. Soc. 1994, 116, 9086;
30. b) G. Calogero, G. Giuffrida, S. Serroni, V. Ricevuto, S. Campagna, Inorg. Chem. 1995, 34, 541;
31. c) A. Mamo, I. Stefio, M. F. Parisi, A. Credi, M. Venturi, C. Di Pietro, S. Campagna, Inorg. Chem. 1997, 36, 5947;
32. d) G. Di Marco, M. Lanza, A. Mamo, I. Stefio, C. Di Pietro, G. Romeo, S. Campagna, Anal. Chem. 1998, 70, 5019;
33. e) F. Neve, A. Crispini, S. Campagna, S. Serroni, Inorg. Chem. 1999, 38, 2250;
34. f) P. M. Griffiths, F. Loiseau, F. Puntoriero, S. Serroni, S. Campagna, Chem. Commun. 2000, 2297;
35. g) F. Neve, A. Crispini, F. Loiseau, S. Campagna, J. Chem. Soc. Dalton Trans. 2000, 1399;
36. h) F. Neve, A. Crispini, Eur. J. Inorg. Chem. 2000, 1039;
37. i) F. Neve, A. Crispini, S. Serroni, F. Loiseau, S. Campagna, Inorg. Chem. 2001, 40, 1093.
38. a) L. M. Vogler, B. Scott, K. J. Brewer, Inorg. Chem. 1993, 32, 898;
39. b) S. M. Molnar, G. Nallas, J. S. Bridgewater, K. J. Brewer, J. Am. Chem. Soc. 1994, 116, 5206;
40. c) J. S. Bridgewater, L. M. Vogler, S. M. Molnar, K. J. Brewer, Inorg. Chim. Acta 1993, 208, 179.
41. a) P. Didier, I. Ortmans, A. Kirsch-De Mesmaeker, R. J. Watts, Inorg. Chem. 1993, 32, 5239;
42. b) I. Ortmans, P. Didier, A. Kirsch-De Mesmaeker. Inorg. Chem. 1995, 34, 3695.
43. a) I. M. Dixon, J.-P. Collin, J.-P. Sauvage, L. Flamigni, S. Encinas, F. Barigelletti, Chem. Soc. Rev. 2000, 29, 385;
44. b) J.-P Collin, I. M. Dixon, J.-P. Sauvage, J. A. G. Williams, F. Barigelletti, L. Flamigni, J. Am. Chem. Soc. 1999, 127, 5009;
45. c) I. M. Dixon, J.-P. Collin, J.-P. Sauvage, F. Barigelletti, L. Flamigni, Angew. Chem. 2000, 112, 1348; Angew. Chem. Int. Ed. 2000, 39, 1292;
46. c) I. M. Dixon, J.-P. Collin, J.-P. Sauvage, F. Barigelletti, L. Flamigni, Angew. Chem. 2000, 112, 1348; Angew. Chem. Int. Ed. 2000, 39, 1292;
47. d) L. Flamigni, I. M. Dixon, J.-P. Collin, J.-P. Sauvage, Chem. Commun. 2000, 2479;
48. e) I. M. Dixon, J.-P. Collin, J.-P. Sauvage, L. Flamigni, Inorg. Chem. 2001, 40, 5507.
49. a) M. G. Colombo, H. U. Güdel, Inorg. Chem. 1993, 32, 3081;
50. b) M. G. Colombo, A. Hauser, H.U. Güdel, Inorg. Chem. 1993, 32, 3088;
51. c) M. G. Colombo, T. C. Brunold, T. Riedener, H. U. Güdel, M. Förtsch, H.-B. Bürgi, Inorg. Chem. 1994, 33, 545;
52. d) M. G. Colombo, A. Hauser, H. U. Güdel, Topics Curr. Chem. 1994, 177, 143.
53. a) S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, R. Kwong, I. Tsyba, M. Bortz, B. Mui, R. Bau, M. E. Thompson, Inorg. Chem. 2001, 40, 1704;
54. b) S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, H.-E. Lee, C. Adachi, P. E. Burrows, S. R. Forrest, M. E. Thompson, J. Am. Chem. Soc. 2001, 123, 4304.
55. a) M. Licini, J. A. G. Williams, Chem. Commun. 1999, 1943;
56. b) W. Goodall, J. A. G. Williams, J. Chem. Soc. Dalton Trans. 2000, 2893.
57. N. P. Ayala, C. M. Flynn, Jr., L. Sacksteder, J. N. Demas, B. A. DeGraff, J. Am. Chem. Soc. 1990, 112, 3837.
58. J. H. Van Diemen, J. G. Haasnoot, R. Hage, E. Müller, J. Reedijk, Inorg. Chim. Acta 1991, 181, 245.
59. M. Maestri, V. Balzani, C. Deuschel-Cornioley, A. von Zelewsky, Adv. Photochem. 1992, 17, 1.
60. a) K. K.-W. Lo, D. C.-M. Ng, C.-K. Chung, Organometallics 2001, 20, 4999;
61. b) K. K.-W. Lo, C.-K. Chung, D. C.-M. Ng, N. Zhu, New J. Chem. 2002, 26, 81.
62. S. Gould, C. Earl, B. P. Sullivan, T. J. Meyer, J. Electroanal. Chem. 1993, 350, 143.
63. L. Wallace, D. P. Rillema, Inorg. Chem. 1993, 32, 3836.
64. M. Wilchek, E. A. Bayer, Method Enzymol. vol. 184, Academic Press, San Diego, 1990.
65. M. M. Bradford, Anal. Biochem. 1976, 72, 248.
66. P. W. Stevens, M. R. Henry, D. M. Kelso, Nucleic Acids Res. 1999, 27, 1719.
67. J. N. Demas, G. A. Crosby, J. Phys. Chem. 1971, 75, 991.
68. K. Nakamaru, Bull. Chem. Soc. Jpn., 1982, 55, 2697.
69. DENZO: Z. Otwinowski, W. Minor, Method Enzymol. vol. 276, Academic Press, San Diego, 1997, p. 307.
70. SIR97: A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115.
71. SHELXL-97: G. M. Sheldrick, Programs for Crystal Structure Analysis (Release 97-2), University of Götingen, Germany.