Photophysics of a series of efficient fluorescent pH probes for dual-emission-wavelength measurements in aqueous solutions

Chemistry - A European Journal

Volumn 12, Issue 4, 2006, Pages 1097-1113

  Charier, Sandrine ^a   Ruel, Odile ^a   Baudin, Jean Bernard ^a   Alcor, Damien ^a   Allemand, Jean François ^a   Meglio, Adrien ^a   Jullien, Ludovic ^a   Valeur, Bernard ^b,c  

^a ECOLE NORMALE SUPÉRIEURE   (France)

^b Bioinformatique et Chimie Moléculaire   (France)

^c Ecole Normale Superieure de Cachan   (France)

Author keywords

Fluorescent probes; Nitrogen heterocycles; pOH jump molecules; Sensors; Structure activity relationships

Indexed keywords

DERIVATIVES; FLUORESCENCE; LIGHT ABSORPTION; PH EFFECTS; PHOTOCHEMICAL REACTIONS; PHOTONS; SOLUTIONS;

FLUORESCENT PROBES; NITROGEN HETEROCYCLES; POH-JUMP MOLECULES; STRUCTURE-ACTIVITY RELATIONSHIPS;

NITROGEN COMPOUNDS;

EID: 31344460620     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200500619     Document Type: Article

References (60)

1. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Plenum Press, New York, 1999.
2. B. Valeur, Molecular Fluorescence Principles and Applications, Wiley-VCH, Weinheim, 2002.
3. For a review, see: W. E. Moerner, J. Phys. Chem. B 2002, 106, 910-927.
4. W. Denk, J. H. Strickler, W. W. Webb, Science 1990, 248, 73-76.
5. C. Xu, W. Zipfel, J. B. Shear, R. M. Williams, W. W. Webb, Proc. Natl. Acad. Sci. USA 1996, 93, 10763-10768.
6. R. M. Williams, W. R. Zipfel, W. W. Webb, Curr. Opin. Chem. Biol. 2001, 5, 603-608.
7. S. W. Hell, Nat. Biotechnol. 2003, 11, 1347-1355.
8. M. Göppert-Mayer, Ann. Phys. 1931, 9, 273-294.
9. D. M. Friedrich, J. Chem. Educ. 1982, 59, 472-481.
10. Z. Diwu, C.-S. Chen, C. Zhang, D.H. Klaubert, R. P. Haugland, Chem. Biol. 1999, 6, 411-418.
11. D. E. Metzler, Biochemistry The Chemical Reactions of Living Cells, Vol. 1, 2nd ed., Harcourt-Academic Press, Burlington, Massachusetts, 2001, p. 295.
12. J. E. Whitaker, R. P. Haugland, F. G. Prendergast, Anal. Biochem. 1991, 194, 330-344.
13. S. Charier, O. Ruel, J.-B. Baudin, D. Alcor, J.-F. Allemand, A. Meglio, L. Jullien, Angew. Chem. 2004, 116, 4889-4892;
14. Angew. Chem. Int. Ed. Engl. 2004, 43, 4785-4788.
15. T. Förster, Z. Elektrochem. Angew. Phys. Chem. 1950, 54, 42-46.
16. a) A. Weller, Z. Elektrochem. 1952, 56, 662-668;
17. b) A. Weller, Z. Phys. Chem. (Muenchen Ger.) 1955, 3, 238-254;
18. c) A. Weller, Z. Phys. Chem. (Muenchen Ger.) 1958, 17, 224-245.
19. Molecular Luminescence Spectroscopy, Methods and Applications, Part 2 (Ed.: S. G. Schulman), Wiley-Interscience. New York, Chichester, Brisbane, Toronto, Singapore, 1988, pp. 461-510.
20. For a recent reference, see: D. Moscovitch, O. Noivirt, A. Mezer, E. Nachliel, T. Mark, M. Gutman, G. Fibich, Biophys. J. 2004, 87, 47-57.
21. J. H. Hall, J. Y. Chien, J. M. Kaufman, P. T. Litak, J. K. Adams, R. A. Henry, R. A. Hollins, J. Heterocycl. Chem. 1992, 29, 1245-1273.
22. H. J. Lin, P. Herman, J. S. Kang, J. R. Lakowicz, Anal. Biochem. 2001, 294, 118-125. Note that the molecular formula for DND-160 (2-(4-pyridyl)-5-{[4- (2-dimelhylaminoethylaminocarbarnoyl)methoxy]-phenyljoxazole} given in this paper is a 5-(4-pyridyl)-2-(4′-methoxyphenyl)oxazole derivative. In fact, we checked on the Molecular Probes Web site and obtained direct confirmation from this company that the product referenced DND-160 and investigated by these authors was indeed a 2-(4-pyridyl)-5-(4′-methoxyphenyl)oxazole.
23. R. G. Haugland, Handbook of Fluorescent Probes and Research Products, 9th ed., 2002.
24. N. DiCesare, J. R. Lakowicz, Chem. Commun. 2001, 2022-2023.
25. C. Xu, W. W. Webb, J. Opt. Soc. Am. B 1996, 13, 481-491.
26. D. D. Perrin, Dissociation Constants of Organic Bases in Aqueous Solution: Supplement 1972, Butterworths, London, 1972.
27. D. G. Ott, F. N. Hayes, V. N. Kerr, J. Am. Chem. Soc. 1956, 78, 1941-1944.
28. M. Eigen, Angew. Chem. 1963, 75, 489-508.
29. M. Eigen, W. Kruse, G. Maas, L. de Mayer, Progress in Reaction Kinetics, Vol. 2 (Ed.: G. Porter). Pergamon Press, Oxford, 1964, pp. 287-318.
30. C. Tanford, J. G. Kirkwood, J. Am. Chem. Soc. 1957, 79, 5333-5339.
31. C. Tanford, J. Am. Chem. Soc. 1957, 79, 5340-5347.
32. L. Jullien, H. Cottet, B. Hamelin, A. Jardy, J. Phys. Chem. B 1999, 103, 10866-10875.
33. E. Fluhler, V. G. Burnham, L. M. Loew, Biochemistry 1985, 24, 5149-5755.
34. G. Hulbener, A. Lambacher, P. Fromherz, J. Phys. Chem. B 2003, 107, 7896-7902.
35. S. Yamaguchi, T. Shirasaka, S. Akiyama, K. Tamao, J. Am. Chem. Soc. 2002, 124, 8816-8817.
36. W. E. Feely, E. M. Beavers, J. Am. Chem. Soc. 1959, 81, 4004-4007.
37. J. T. Laydon, J. C. Lee, L. M. Hillegass, D. E. Griswold, J. J. Breton, M. C. Chabot-Fletcher, J. L. Adams, J. Med. Chem. 1996, 39, 3929-3937.
38. E. E. Glover, M. Yorke, J. Chem. Soc. C 1971, 3280-3285.
39. K. M. Doxsee, M. Feigel, K. D. Stewart, J. W. Canary, C. B. Knobler, D. J. Cram, J. Am. Chem. Soc. 1987, 109, 3098-3107.
40. P. Hamel, D. Riendeau, C. Brideau, C. C. Chan, S. Desmarais, D. Delorme, D. Dube, Y. Ducharme, D. Ethier, E. 43 Grimm, J. P. Falgueyret, J. Guay, T. R. Jones, E. Kwong, M. McAuliffe, C. S. McFarlane, H. Piechuta, M. Roumi, P. Tagari, R. N. Young, Y. Girard, J. Med. Chem. 1997, 40, 2866-2875.
41. D. G. Ott, F. N. Hayes, V. N. Kerr, J. Am. Chem. Soc. 1960, 82, 186-189.
42. C. A. Reichardt, Solvents and Solvent Effects in Organic Chemistry. 3rd ed., VCH, Weinheim, 2003.
43. D. Laage, W. H. Thompson, M. Blanchard-Descc, J. T. Hynes, J. Phys. Chem. A 2003, 107, 6032-6046.
44. Z. Diwu, Y. Lu, C. Zhang, D. H. Klaubert, R. P. Haugland, Photochem. Photobiol. 1997, 66, 424-431.
45. N. DiCesare, J. R. Lakowicz, J. Phys. Chem. A 2001, 105, 6834-6840.
46. E. Cogné-Laage, J.-F. Allemand, O. Ruel, J.-B. Baudin, V. Croquette, M. Blanchard-Desce, L. Jullien, Chem. Eur. J. 2004, 10, 1445-1455.
47. F of the investigated cascade blue derivative provided by the Molecular Probes Company under comparable conditions.
48. M. H. V. Werts, S. Gmouh, O. Mongin, T. Pons, M. Blanchard-Desce, J. Am. Chem. Soc. 2004, 126, 16294-16295.
49. S. J. K. Pond, O. Tsutsumi, M. Rumi, O. Kwon, E. Zojer, J.-L. Brédas, S. R. Marder, J. W. Perry, J. Am. Chem. Soc. 2004, 126, 9291-9306.
50. H. M. Kim, M.-Y. Jeong, H. C. Ahn, S.-J. Jeon, B. R. Cho, J. Org. Chem. 2004, 69, 5749-5751.
51. L. M. Tolbert, K. M. Solntsev, Acc. Chem. Res. 2002, 35, 19-27.
52. a of the three components.
53. H. Eyring, J. Walter, G. E. Kimball, Quantum Chemistry, 10th ed., Wiley, New York, 1961.
54. D. G. Ott, F. N. Hayes, E. Hansbury, V. N. Kerr, J. Am. Chem. Soc. 1957, 79, 5448-5454.
55. a) H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1985, 32, 95-101;
56. b) H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1985, 32, 257-264;
57. c) H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1985, 32, 1133-1139;
58. d) H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1986, 33, 943-951.
59. C. Frugoni, Gazz. Chim. Ital. 1957, 87, 403-407.
60. J. N. Demas, G. A. Crosby, J. Phys. Chem. 1971, 75, 991-1024.