Engineering of Highly Luminescent Lanthanide Tags Suitable for Protein Labeling aad Time-Resolved Luminescence Imaging

Journal of the American Chemical Society

Volumn 126, Issue 15, 2004, Pages 4888-4896

  Weibel, Nicolas ^a   Charbonnière, Loïc J ^a   Guardigli, Massimo ^b   Roda, Aldo ^b   Ziessel, Raymond ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; CHROMOPHORES; COMPLEXATION; ESTERS; EUROPIUM COMPOUNDS; IMAGING TECHNIQUES; LUMINESCENCE; MASS SPECTROMETERS; PROTEINS; TERBIUM COMPOUNDS; TITRATION; ULTRAVIOLET SPECTROPHOTOMETERS;

COVALENT LINKING; LANTHANIDE TAGS; SPECTROPHOTOMETRIC TITRATIONS;

SYNTHESIS (CHEMICAL);

2,2' BIPYRIDINE DERIVATIVE; 6 METHYLENE 6' CARBOXY 2,2' BIPYRIDINE; AMINE; BOVINE SERUM ALBUMIN; CARBOXYLIC ACID; CATION; CHLORIDE; COORDINATION COMPOUND; EUROPIUM; FLUORESCEIN; FUNCTIONAL GROUP; GADOLINIUM; GLUTAMIC ACID; HYDROGEN; LANTHANIDE; LIGAND; METAL ION; NITROGEN; PROTEIN; SODIUM DERIVATIVE; SUCCINIMIDE DERIVATIVE; TERBIUM; UNCLASSIFIED DRUG; WATER;

ANALYTIC METHOD; ARTICLE; CHEMICAL ENGINEERING; CHEMICAL LABELING; CHROMATOPHORE; COMPLEX FORMATION; COVALENT BOND; ELEMENTAL ANALYSIS; HYDRATION; INFRARED SPECTROSCOPY; LUMINESCENCE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MICROSCOPY; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; SOLUBILITY; STOICHIOMETRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

GLUTAMATES; LANTHANOID SERIES ELEMENTS; LUMINESCENT PROTEINS; MAGNETIC RESONANCE SPECTROSCOPY; PYRIDINES; SERUM ALBUMIN, BOVINE; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 1842862933     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja031886k     Document Type: Article

References (74)

1. Tanke, H. J. J. Microsc. 1989, 155, 405.
2. García-Parajó, M.; Verrman, J.-A.; Bouwhuis, R.; Vallée, R.; van Hulst, N. F. Chem. Phys. Chem. 2001, 2, 347.
3. Hemmilä, I.; Harju, R. In Bioanalytical Applications of Labeling Technologies; Hemmilä, I., Ståhlberg, T.; Mottram, P., Eds.; Walac Oy and EG&G Cie Pb: 1995; Chapter 5, p 83.
4. Fleming, G. R.; Knight, A. W. E.; Morris, J. M.; Morrison, R. J. S.; Robinson, G. W. J. Am. Chem. Soc. 1977, 99, 4306.
5. (a) Hennink, E. J.; de Haas, R.; Verwoerd, N. P.; Tanke, H. J. Cytometry 1996, 24, 312.
6. (b) de Haas, R. R.; van Gijlswijk, R. P. M.; van der Tol, E. B.; Veuskens, J.; van Gijssel, H. E.; Tijdens, R. B.; Bonnet, J.; verwoerd, N. P.; Tanke, H. J. J. Histochem. Cytochem. 1999, 47, 183.
7. (a) Bedlek-Anslow, J. M.; Hubner, J. P.; Carroll, B. F.; Schanze, K. S. Langmuir 2000, 16, 9137.
8. (b) Puklin, E.; Carlson, B.; Gouin, S.; Costin, C.; Green, E.; Ponomarev, S.; Tanji, H.; Gouterman, M. J. Appl. Polym. Sci. 2000, 77, 2795.
9. (c) Amao, Y.; Miyashita, T.; Okura, I. Anal. Chim. Acta 2000, 421, 167.
10. Maranto, A. R. Science 1982, 21, 953.
11. (a) Wieder, I. In Immunofluorescence and Related Staining Techniques; Proceedings of the VIth International Conference on Immunofluorescence and Related Staining Techniques; Knapp, W., Holubar, K., Wick, G., Eds.; Elsevier/North-Holland Biomedical Press: Amsterdam, 1978; p 67.
12. (b) Mayer, A.; Neuenhofer, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 1044.
13. Charbonnière, L. J.; Guardigli, M.; Cesario, M.; Roda, A.; Sabbatini, N.; Ziessel, R. J. Am. Chem. Soc. 2001, 123, 2436.
14. (a) Hemmilä, I.; Dakubu, S.; Mukkala, V.-M.; Siitari, H.; Lövgren, T. Anal. Biochem. 1984, 137, 335.
15. (b) Evangelista, R. A.; Pollak, A.; Allore, B.; Templeton, E. F.; Morton, R. C.; Diamandis, E. P. Clin. Biochem. 1988, 21, 173.
16. (a) Marriott, G.; Clegg, R. M.; Ardnt-Jovin, D. J.; Jovin, T. M. Biophys. J. 1991, 60, 1374.
17. (b) Seveus, L.; Väisälä, M.; Syrjänen, S.; Sandberg, M.; Kuusisto, A.; Harju, R.; Salo, J.; Hemmilä, I.; Kojola, H.; Soini, E. Cytometry 1992, 13, 329.
18. (c) Marriott, G.; Heidecker, M.; Diamandis, E. P.; Yan-Marriott, Y. Biophys. J. 1994, 67, 957.
19. Verwoerd, N. P.; Hennink, E. J.; Bonnet, J.; van der Geest, C. R. G.; Tanke, H. J. Cytometry 1994, 16, 113.
20. See, for examples: (a) Frontiers in Lanthanide Chemistry. Chem. Rev. 2002, 102.
21. (b) Yam, V. W.-W.; Lo, K. K.-W. Coord. Chem. Rev. 1998, 184, 157.
22. (c) Woods, M.; Kovacs, Z.; Sherry, A. D. J. Supramol. Chem. 2002, 2, 1.
23. Hemmilä, I.; Webb, S. Drug Discovery Today 1997, 2, 373.
24. (a) Piguet, C.; Bünzli, J.-C. G. Chem. Soc. Rev. 1999, 28, 347.
25. (b) Rodriguez-Ubis, J. C.; Sedano, R.; Barroso, G.; Juanes, O.; Brunet, E. Helv. Chim. Acta 1997, 80, 86.
26. Sabbatini, N.; Guardigli, M.; Lehn, J.-M. Coord. Chem. Rev. 1993, 123, 201.
27. (a) Alpha, B.; Lehn, J.-M.; Mathis, G. Angew. Chem., Int. Ed. Engl. 1987, 26, 266.
28. (b) Bodar-Houillon, F.; Marsura, A. New J. Chem. 1996, 20, 1041.
29. (c) Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Giorgi, C.; Fusi, V.; Masotti, A.; Valtancoli, B.; Roque, A.; Pina, F. Chem. Commun. 2000, 561.
30. For recent examples, see: (a) Chen, J. Selvin, P. R. J. Photochem. Photobiol., A 2000, 135, 27.
31. (b) Quici, S.; Marzanni, G.; Cavazzini, M.; Anelli, P. L.; Botta, M.; Gianolio, E.; Accorsi, G.; Armaroli, N.; Barigelletti, F. Inorg. Chem. 2002, 41, 2777.
32. (c) Clarkson, I. M.; Beeby, A.; Bruce, J. I.; Govenlock, L. J.; Lowe, M. P.; Mathieu, C. E.; Parker, D.; Senanayake, K. New J. Chem. 2000, 24, 377.
33. (d) Senegas, J.; Bernardinelli, G.; Imbert, D.; Bünzli, J.-C. G.; Morgantini, P.-Y.; Weber, J.; Piguet, C. Inorg. Chem. 2003, 42, 4680.
34. For recent examples, see: (a) Griffin, J. M. M.; Skwierawska, A. M.; Manning, H. C.; Marx, J. N.; Bornhop, D. J. Tetrahedron Lett. 2001, 42, 3823.
35. (b) Bornhop, D. J.; Hubbard, D. S.; Houlne, M. P.; Adair, C.; Kiefer, G. E.; Pence, B. C.; Morgan, D. L. Anal. Chem. 1999, 71, 2607.
36. (a) Charbonnière, L. J.; Ziessel, R. F.; Cesario, M.; Prangé, T.; Guardigli, M.; Roda, A.; Nierengarten, H. J. Supramol. Chem. 2003, 15, 277.
37. (b) Bünzli, J.-C. G.; Charbonnière, L. J.; Ziessel, R. J. Chem. Soc., Dalton Trans. 2000, 1917.
38. Charbonnière, L. J.; Ziessel, R. F. Helv. Chim. Acta 2003, 86, 3402.
39. Charbonnière, L. J.; Ziessel, R. F.; Weibel, N. H.; Guardigli, M. ; Roda, A. French Patent N° 03 09158.
40. Adams, R.; Miyano, S. J. Am. Chem. Soc. 1954, 76, 3168.
41. Jutzi, P.; Gilige, U. J. Organomet. Chem. 1983, 246, 163.
42. Houghton, M. A.; Bilyk, A.; Harding, M. M.; Turner, P.; Hambley, T. W. J. Chem. Soc., Dalton Trans. 1997, 2725.
43. Mameri, S.; Charbonnière, L. J.; Ziessel, R. F. Synthesis 2003, 17, 2713.
44. Weigl, M.; Wünsch, B. Tetrahedron 2002, 58, 1173.
45. El-ghayoury, A.; Ziessel, R. J. Org. Chem. 2000, 65, 7757.
46. (b) Charbonnière, L.; Weibel, N.; Ziessel, R. J. Org. Chem. 2002, 67, 3933.
47. Silverstein, R. M.; Bassler, G. C. Identification spectrométrique des composés organiques; Gauthier-Villars: Paris, 1968.
48. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th ed.; Wiley: New York, 1986; p 231.
49. Itoh, K.; Bernstein, H. J. Can. J. Chem. 1956, 34, 170.
50. (a) Bertini, I.; Lucchinat, C. NMR of Paramagnetic Molecules in Biological Systems; Benjamin/Cummings Publishing Co. Inc.: Menlo Park, CA, 1986.
51. (b) Renaud, F.; Piguet, C.; Bernardinelli, G.; Bünzli, J.-C. G.; Hopfgartner, G. J. Am. Chem. Soc. 1999, 121, 9326.
52. Sabbatini, N.; Guardigli, M.; Manet, I. In Advances in Photochemistry; Neckers, D. C., Volman, D. H., von Bunau, G., Eds.; John Wiley & Sons: New York, 1997; Vol. 23, p 213.
53. Bünzli, J.-C. G. In Lanthanide Probes in Life, Chemical and Life Sciences; Bunzli, J.-C. G., Choppin, G. R., Eds.; Elsevier: Amsterdam, 1989; p 228.
54. (a) Horrocks, W. De W., Jr.; Sudnick, D. R. J. Am. Chem. Soc. 1979, 101, 334.
55. (b) Horrocks, W. De W., Jr.; Sudnick, D. R. Acc. Chem. Res. 1981, 14, 384.
56. Beeby, A.; Clarkson, I. M.; Dickins, R. S.; Faulkner, S.; Parker, D.; Royle, L.; S. De Sousa, A.; Williams, J. A. G.; Woods, M. J. Chem. Soc., Perkin Trans. 2 1999, 493.
57. Supkowski, R.; Horrocks, W. De W., Jr. Inorg. Chim. Acta 2002, 340, 44.
58. Latva, M.; Takalo, H.; Mukkala, V.-M.; Matachescu, C.; Rodriguez-Ubis, J. C.; Kankare, J. J. Lumin. 1997, 75, 149.
59. Wu, S. L.; Horrocks, W. De W., Jr. Anal. Chem. 1996, 68, 394.
60. Smith, R. M.; Martell, A. E. Critical Stability Constants; Plenum Press: New York, 1974; Vol. 1, p 204.
61. Hermanson, G. T. Bioconjugate Techniques; Academic Press: New York, 1996.
62. Goodno, C. C.; Swaisgood, H. E.; Catignani, G. L. Anal. Biochem. 1981, 115, 203.
63. Sabbatini, N.; Guardigli, M.; Lehn, J.-M.; Mathis, G. J. Alloys Compd. 1992, 180, 363.
64. Mathis, G. Biological Applications of Rare Earth Cryptates. In Rare Earth, Cursos de Verano de El Escorial; Saez, R., Caro, P., Eds.; Editorial Complutense: 1998; pp 285-297.
65. Beeby, A.; Botchway, S. W.; Clarkson, I. M.; Faulkner, S.; Parker, A. W. ; Parker, D.; Williams, J. A. G. J. Photochem. Photobiol., B 2000, 57, 83.
66. (a) Blomberg, K.; Hurskainen, P.; Hemmilä, I. Clin. Chem. 1999, 45, 855.
67. (b) Tsuji, A.; Sato, Y.; Hirano, M.; Suga, T.; Koshimoto, H.; Taguchi, T.; Ohsuka, S. Biophys. J. 2001, 81, 501.
68. (a) Quin, Q.-P.; Lövgren, T.; Petterson, K. Anal. Chem. 2001, 73, 1521.
69. (b) Scorilas, A.; Diamandis, E. P. Clin. Biochem. 2000, 33, 345.
70. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1988.
71. Haas, Y.; Stein, G. J. Phys. Chem. 1971, 75, 3668.
72. Nakamaru, K. Bull. Chem. Soc. Jpn. 1982, 55, 2697.
73. Meech, S. R.; Phillips, D. J. Photochem. 1983, 23, 193.
74. Roda, A.; Guardigli, M.; Pasini P. In Bioluminescence and Chemiluminescence 2000; Proceedings of the 11th International Symposium on Bioluminescence and Chemiluminescence; Case, J. F., Herring, P. J., Robison, B. H., Haddock, S. H. D., Kricka, L. J., Stanley, P. E., Eds.; World Scientific Publishing Co.: Singapore, 2001; p 493.