Signal-amplifying resonance energy transfer: A dynamic multichromophore array for allosteric switching

Angewandte Chemie - International Edition

Volumn 46, Issue 37, 2007, Pages 7019-7022

  Riddle, Justin A ^a   Jiang, Xuan ^a   Huffman, John ^a   Lee, Dongwhan ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Cooperative phenomena; FRET (fluorescence resonant energy transfer); Hydrogen bonds; Molecular devices; Signal amplification

Indexed keywords

CHROMOPHORES; ENERGY TRANSFER; HYDROGEN BONDS; MICROARRAYS;

COOPERATIVE PHENOMENA; FRET (FLUORESCENCE RESONANT ENERGY TRANSFER); MOLECULAR DEVICES; SIGNAL AMPLIFICATION;

SIGNAL ANALYSIS;

EID: 34848859226     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701410     Document Type: Article

References (49)

1. a) K. E. van Holde, W. C. Johnson, P. S. Ho, Principles of Physical Biochemistry, 2nd ed., Pearson Prentice Hall, Upper Saddle River, 2006;
2. b) G. Krauss, Biochemistry of Signal Transduction and Regulation, 3rd ed., Wiley-VCH, Weinheim, 2003;
3. c) A. Levitzki, Quantitative Aspects of Allosteric Mechanisms, Springer, Berlin, 1978.
4. a) J.-P. Changeux, S. J. Edelstein, Neuron 1998, 21, 959-980;
5. b) J.-P. Changeux, S. J. Edelstein, Science 2005, 308, 1424-1428.
6. J. D. Badjic, A. Nelson, S. J. Cantrill, W. B. Turnbull, J. F. Stoddart, Acc. Chem. Res. 2005, 38, 723-732.
7. K. A. Connors, Binding Constants, Wiley, New York, 1987.
8. a) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264;
9. b) S. Shinkai, M. Ikeda, A. Sugassaki, M. Takeuchi, Acc. Chem. Res. 2001, 34, 494-503;
10. c) M. Takeuchi, M. Ikeda, A. Sugassaki, S. Shinkai, Acc. Chem. Res. 2001, 34, 865-873;
11. d) L. Kovbasyuk, R. Krämer, Chem. Rev. 2004, 104, 3161-3187, and references therein.
12. A sharp structural transition of macromolecules often involves cooperative folding. Such phase transitions can also be exploited for binary switching; for example, fluorescent side chains can be incorporated as "reporter groups" that are sensitive to changes in the local dielectric constants resulting from structural folding and unfolding. See: S. Uchiyama, Y. Matsumura, A. P. de Silva, K. Iwai, Anal. Chem. 2003, 75, 5926-5935.
13. a) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530;
14. Angew. Chem. Int. Ed. 2000, 39, 3348-3391;
15. b) V. Balzani, M. Venturi, A. Credi, Molecular Devices and Machines: A Journey into the Nanoworld, Wiley-VCH, Weinheim, 2003;
16. c) Functional Molecular Nanostructures (Ed.: A. D. Schlüter), Springer, Berlin, 2005.
17. For recent examples, see: a) J. L. Sessler, E. Tomat, V. M. Lynch, J. Am. Chem. Soc. 2006, 128, 4184-4185;
18. b) R. Wakabayashi, Y. Kubo, O. Hirata, M. Takeuchi, S. Shinkai, Chem. Commun. 2005, 5742-5744;
19. c) O. Hirata, M. Takeuchi, S. Shinkai, Chem. Commun. 2005, 3805-3807;
20. d) H. Kawai, R. Katoono, K. Nishimura, S. Matsuda, K. Fujiwara, T. Tsuji, T. Suzuki, J. Am. Chem. Soc. 2004, 126, 5034-5035;
21. e) S.-Y. Chang, H.-Y. Jang, K.-S. Jeong, Chem. Eur. J. 2004, 10, 4358-4366;
22. f) F. Huang, F. R. Fronczek, H. W. Gibson, J. Am. Chem. Soc. 2003, 125, 9272-9273;
23. g) V. V. Borovkov, J. M. Lintuluoto, H. Sugeta, M. Fujiki, R. Arakawa, Y. Inoue, J. Am. Chem. Soc. 2002, 124, 2993-3006;
24. h) J. L. Sessler, H. Maeda, T. Mizuno, V. M. Lynch, H. Furuta, J. Am. Chem. Soc. 2002, 124, 13 474-13 479;
25. i) J. Raker, T. E. Glass, J. Org. Chem. 2002, 67, 6113-6116;
26. j) M. Ikeda, M. Takeuchi, S. Shinkai, F. Tani, Y. Naruta, S. Sakamoto, K. Yamaguchi, Chem. Eur. J. 2002, 8, 5541-5550;
27. k) M. Takeuchi, T. Shioya, T. M. Swager, Angew. Chem. 2001, 113, 3476-3480;
28. Angew. Chem. Int. Ed. 2001, 40, 3372-3376.
29. n species from a multisite receptor S with n binding sites. To complete the switching cycle depicted in Figure 1 a, this excessive amount of L needs to be quantitatively removed to regenerate free S. This is an operationally nontrivial task and has not been demonstrated before.
30. a) J. R. Lakowicz, Principles of Fluorescence Spectroscopy, 3rd ed., Springer, New York, 2006;
31. b) Resonance Energy Transfer (Eds.: D. L. Andrews, A. A. Demidov), Wiley, Chichester, 1999;
32. c) B. Valeur, Molecular Fluorescence: Principles and Applications, Wiley-VCH, Weinheim, 2002.
33. a) X. Jiang, J. C. Bollinger, D. Lee, J. Am. Chem. Soc. 2006, 128, 11 732-11 733;
34. b) Y.-K. Lim, X. Jiang, J. C. Bollinger, D. Lee, J. Mater. Chem. 2007, 17, 1969-1980;
35. c) J. A. Riddle, S. P. Lathrop, J. C. Bollinger, D. Lee, J. Am. Chem. Soc. 2006, 128, 10 986-10 987;
36. d) J. A. Riddle, J. C. Bollinger, D. Lee, Angew. Chem. 2005, 117, 6847-6851;
37. Angew. Chem. Int. Ed. 2005, 44, 6689-6693;
38. e) E. Opsitnick, D. Lee, Chem, Eur. J. 2007, in press.
39. Supramolecular Dye Chemistry (Ed.: F. Würthner), Springer, Berlin, 2005.
40. R. P. Haugland in The Handbook: A Guide to Fluorescent Probes and Labeling Technologies, 10th ed. (Ed.: M. T. Z. Spence), Invitrogen, Eugene, 2005.
41. See the Supporting Information.
42. CCDC-642093 contains the supplementary crystallographic data for the key precursor of 2 (BODIPY-appended aniline). The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_-request/cif. See also the Supporting Information.
43. -, neither of which reacts with the receptor molecule.
44. 4NF, although alternative geometries can also be considered. See: a) G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, New York, 1997;
45. b) T. Steiner, Angew. Chem. 2002, 114, 50-80;
46. Angew. Chem. Int. Ed. 2002, 41, 48-76.
47. B. W. van der Meer in Resonance Energy Transfer (Eds.: D. L. Andrews, A. A. Demidov), Wiley, Chichester, 1999, pp. 151-172.
48. A. Harriman, G. Izzet, R. Ziessel, J. Am. Chem. Soc. 2006, 128, 10 868-10 875.
49. Additionally, one could also consider the orientation-dependent self quenching of BODIPY as another RET pathway leading to signal amplification. This mechanism is currently under investigation.