Reversing the discovery paradigm: A new approach to the combinatorial discovery of fluorescent chemosensors

Journal of the American Chemical Society

Volumn 127, Issue 29, 2005, Pages 10124-10125

  Mello, Jesse V ^a   Finney, Nathaniel S ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CADMIUM; CALCIUM ION; CESIUM ION; COPPER ION; LEAD; LITHIUM ION; MAGNESIUM ION; MERCURY; POTASSIUM ION; SODIUM ION; ZINC ION;

ARTICLE; COMBINATORIAL CHEMISTRY; FLUORESCENCE; HYDROPHOBICITY; METAL BINDING; MOLECULAR INTERACTION; SENSOR; SOLID STATE; STEADY STATE;

AMINO ACIDS; BIOSENSING TECHNIQUES; CATIONS, DIVALENT; FLUORENES; FLUORESCENT DYES; MERCURY; PYRIDINES;

EID: 22944437475     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja043682p     Document Type: Article

References (43)

1. For representative reviews of fluorescent chemosensors. see: (a) Rurack, K.; Resch-Genger, U. Chem. Soc. Rev. 2002, 31, 116-127.
2. (b) Lavigne, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 2001, 40, 3118-3130.
3. (c) Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3-40.
4. Overviews of peptide-containing combinatorial libraries for the discovery of new molecular recognition phenomena: (a) Wennemers, H. Chimia 2003, 57, 237-240.
5. (b) Tunnemann, R.; Jung, G. Nachr. Chem. 2000, 48, 453-457.
6. (c) Still, W. C. Acc. Chem. Res. 1996, 29, 155.
7. Czarnik, A. W. Chem. Biol. 1995, 2, 423.
8. For the few examples of combinatorial approaches to fluorescent chemosensor development, see: (a) Chen, C.-T.; Wagner, H.; Still, W. C. Science 1998, 279, 851-853.
9. (b) Rothman, J. H.; Still, W. C. Bioorg. Med. Chem. Lett. 1999, 9, 509-512.
10. (c) Schneider, S. E.; O'Neil, S. N.; Anslyn, E. V. J. Am. Chem. Soc. 2000, 122, 542-543.
11. (d) Singh, A.; Yao, Q.; Tong, L.; Clark Still, W.; Sames, D. Tetrahedron Lett. 2000, 41, 9601-9605.
12. (f) Iorio, E. J.; Shao, Y.; Chen, C.-T.; Wagner, H.; Still, W. C. Bioorg Med. Chem. Lett. 2001, 11, 1635-1638.
13. Photoinduced electron transfer (PET), by far the most common signaling mechanism, requires only simple molecules but is restricted to binding domains containing anilinic or benzylic nitrogen atoms. Energy transfer signaling (FRET, e.g.) is permissive in terms of binding domain structure but requires large changes in interchromophore distance, thereby requiring complex architectures such as proteins or partial protein sequences. Displacement-based assays, in which substrate binding displaces a fluorophore fall between these two extremes. For examples, see ref 1. For an expanded discussion, see ref 6f.
14. (a) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2001, 123, 1260-1261.
15. (b) Mello, J. V.; Finney, N. S. Angew. Chem., Int. Ed. 2001, 40, 1536-1438.
16. (c) McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2002, 124, 1178-1179.
17. (d) McFarland, S. A.; Finney, N. S. Chem. Commun. 2003, 388-389.
18. (e) Fang, A. G.; Mello, J. V.; Finney, N. S. Org. Lett. 2003, 5, 967-970.
19. (f) Fang, A. G.; Mello, J. V.; Finney, N. S. Tetrahedron 2004, 60, 11075-11087.
20. For other work on biaryl conformational restriction as a signaling mechanism, see: (a) Takeuchi, M.; Yoda, S.; Imada, T.; Shinkai, S. Tetrahedron 1997, 53, 8335-8348.
21. (b) Costero, A. M.; Andreu, R.; Monrabal, E.; Martinez-Manez, R.; Sancenon, F.; Soto, J. J. Chem. Soc., Dalton Trans. 2002, 1769.
22. (c) Lee, D. H.; Im, J. H.; Lee, J. H.; Hong, J. I. Tetrahedron Lett. 2002, 43, 9637.
23. (d) Cody, J.; Fahrni, C. J. Tetrahedron 2004, 60, 11099-11107.
24. See Supporting Information for complete details.
25. (a) Johnson, C. R.; Zhang, B. Tetrahedron Lett. 1995, 36, 9253-9256.
26. (b) Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624-2626.
27. For influential examples of seemingly simple combinatorial libraries of metal chelators, see: (a) Burger, M. T.; Still, W. C. J. Org. Chem. 1995, 60, 7382.
28. (b) Frances, M. B.; Finney, N. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8983-8984.
29. Li, H.; Jiang, X.; Ye, Y.-h.; Fan, C.; Romoff, T.; Goodman, M. Org. Lett. 1999, 1, 91-94.
30. Under the O'Bu cleavage conditions we observed cleavage of the fluorophore from the resin; thus, the O'Bu groups were left in place. Phenylthiourea-terminated library elements were left protected to avoid Edman degradation under acidic conditions.
31. 1H NMR).
32. + was also evaluated in triethanolamine buffer. For a discussion of metals for which fluorescent detection would be valuable, see ref 1 and citations therein.
33. The addition of excess ethanedithiol reverses the increase in emission, demonstrating reversibility of Hg(II) binding. This result was confirmed in solution with 2, and 2 could be recovered unchanged from Hg(II) titrations by preparative TLC.
34. 2+.
35. 2+ is scattered blue light from the illumination source. The quantum yield of 2 in the absence of Hg(II) is ∼.01 with ε ≈ 12,000.
36. Other examples of "turn on" fluorescent chemosensors for aqueous Hg(II): (a) Ono, A.; Togashi, H. Angew. Chem., Int. Ed. 2004, 43, 4300-4302.
37. (b) Guo, X.; Qian, X.; Jia, L. J. Am. Chem. Soc. 2004, 126, 2272-2273.
38. (c) Nolan, E. M.; Lippard, S. J. J. Am. Chem. Soc. 2003, 125, 14270-14271.
39. (d) Rurack, K.; Kollmannsberger, M.; Resch-Genger, U.; Daub, J. J. Am. Chem. Soc. 2000, 122, 968-969.
40. (e) Prodi, L.; Bargossi, C.; Montalti, M.; Zaccheroni, N.; Su, N.; Bradshaw, J. S.; Izatt, R. M.; Savage, P. B. J. Am. Chem. Soc. 2000, 122, 6769-6770.
41. (a) Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L. Chem. Rev. 1991, 91, 1721-2085.
42. (b) Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L. Chem. Rev. 1995, 95, 2529-2586.
43. 2+ results from contact-mediated spin-orbit coupling (McClure, D. S. J. Chem. Phys. 1952, 20, 682-686), underscoring a key advantage of the spatial segregation of fluorophore and binding domain.