Detection and mechanistic studies of multicomponent assembly by fluorescence resonance energy transfer

Journal of the American Chemical Society

Volumn 122, Issue 33, 2000, Pages 7876-7882

  Castellano, Ronald K ^a,b   Craig, Stephen L ^a   Nuckolls, Colin ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE;

ARTICLE; CHROMATOPHORE; DIMERIZATION; ENERGY TRANSFER; FLUORESCENCE; HYDROGEN BOND; KINETICS; MECHANICS; MOLECULAR RECOGNITION; SPECTRAL SENSITIVITY; THERMODYNAMICS;

EID: 0034705977     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994397m     Document Type: Article

References (47)

1. (a) Shimizu, K. D.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12403-12407. (b) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326-1329. Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1996, 41, 10002- 10003.
2. (a) Shimizu, K. D.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12403-12407. (b) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326-1329. Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1996, 41, 10002- 10003.
3. (a) Shimizu, K. D.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12403-12407. (b) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326-1329. Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1996, 41, 10002-10003.
4. (a) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496. (b) Mogck, O.; Paulus, E. F.; Böhmer, V.; Thondorf, I.; Vogt, W. Chem. Commun. 1996, 2533-2534. Mogck, O.; Pons, M.; Böhmer, V.; Vogt, W. J. Am. Chem. Soc. 1997, 119, 5706-5712. Böhmer, V.; Mogck, O.; Pons, M.; Paulus, E. F. Reversible Dimerization of Tetraureas Derived From Calix[4]arenes. In NMR in Supramolecular Chemistry; M. Pons, ed.; NATO ASl Ser., Ser. C, Vol. 526; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999; pp 45-60. (e) Vysotsky, M. O.; Thondorf, I.; Böhmer, V. Angew. Chem., Int. Ed. Engl. 2000, 39, 1264- 1267.
5. (a) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489- 8496. (b) Mogck, O.; Paulus, E. F.; Böhmer, V.; Thondorf, I.; Vogt, W. Chem. Commun. 1996, 2533-2534. Mogck, O.; Pons, M.; Böhmer, V.; Vogt, W. J. Am. Chem. Soc. 1997, 119, 5706-5712. Böhmer, V.; Mogck, O.; Pons, M.; Paulus, E. F. Reversible Dimerization of Tetraureas Derived From Calix[4]arenes. In NMR in Supramolecular Chemistry; M. Pons, ed.; NATO ASl Ser., Ser. C, Vol. 526; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999; pp 45-60. (e) Vysotsky, M. O.; Thondorf, I.; Böhmer, V. Angew. Chem., Int. Ed. Engl. 2000, 39, 1264- 1267.
6. (a) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489- 8496. (b) Mogck, O.; Paulus, E. F.; Böhmer, V.; Thondorf, I.; Vogt, W. Chem. Commun. 1996, 2533-2534. Mogck, O.; Pons, M.; Böhmer, V.; Vogt, W. J. Am. Chem. Soc. 1997, 119, 5706-5712. Böhmer, V.; Mogck, O.; Pons, M.; Paulus, E. F. Reversible Dimerization of Tetraureas Derived From Calix[4]arenes. In NMR in Supramolecular Chemistry; M. Pons, ed.; NATO ASl Ser., Ser. C, Vol. 526; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999; pp 45-60. (e) Vysotsky, M. O.; Thondorf, I.; Böhmer, V. Angew. Chem., Int. Ed. Engl. 2000, 39, 1264- 1267.
7. (a) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489- 8496. (b) Mogck, O.; Paulus, E. F.; Böhmer, V.; Thondorf, I.; Vogt, W. Chem. Commun. 1996, 2533-2534. Mogck, O.; Pons, M.; Böhmer, V.; Vogt, W. J. Am. Chem. Soc. 1997, 119, 5706-5712. Böhmer, V.; Mogck, O.; Pons, M.; Paulus, E. F. Reversible Dimerization of Tetraureas Derived From Calix[4]arenes. In NMR in Supramolecular Chemistry; M. Pons, ed.; NATO ASl Ser., Ser. C, Vol. 526; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999; pp 45-60. (e) Vysotsky, M. O.; Thondorf, I.; Böhmer, V. Angew. Chem., Int. Ed. Engl. 2000, 39, 1264- 1267.
8. (a) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489- 8496. (b) Mogck, O.; Paulus, E. F.; Böhmer, V.; Thondorf, I.; Vogt, W. Chem. Commun. 1996, 2533-2534. Mogck, O.; Pons, M.; Böhmer, V.; Vogt, W. J. Am. Chem. Soc. 1997, 119, 5706-5712. Böhmer, V.; Mogck, O.; Pons, M.; Paulus, E. F. Reversible Dimerization of Tetraureas Derived From Calix[4]arenes. In NMR in Supramolecular Chemistry; M. Pons, ed.; NATO ASl Ser., Ser. C, Vol. 526; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999; pp 45-60. (e) Vysotsky, M. O.; Thondorf, I.; Böhmer, V. Angew. Chem., Int. Ed. Engl. 2000, 39, 1264-1267.
9. (a) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671-12672. (b) Castellano, R. K.; Nuckolls, C.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11156-11163.
10. (a) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671-12672. (b) Castellano, R. K.; Nuckolls, C.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11156-11163.
11. (a) Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 7132-7137. (b) Castellano, R. K.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3657-3663. Castellano, R. K.; Nuckolls, C.; Eichhorn, S. H.; Wood, M. R.; Lovinger, A. J.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2603-2606. Castellano, R. K.; Nuckolls, C.; Rebek, J., Jr. Polym. News 2000, 25, 44-52. (e) Nuckolls, C.; Castellano, R. K.; Rebek, J., Jr. Polym. Prepr. 2000, 41, 930-931. (f) Castellano, R. K.; Clark, R.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr., submitted for publication.
12. (a) Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 7132-7137. (b) Castellano, R. K.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3657-3663. Castellano, R. K.; Nuckolls, C.; Eichhorn, S. H.; Wood, M. R.; Lovinger, A. J.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2603-2606. Castellano, R. K.; Nuckolls, C.; Rebek, J., Jr. Polym. News 2000, 25, 44-52. (e) Nuckolls, C.; Castellano, R. K.; Rebek, J., Jr. Polym. Prepr. 2000, 41, 930-931. (f) Castellano, R. K.; Clark, R.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr., submitted for publication.
13. (a) Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 7132-7137. (b) Castellano, R. K.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3657-3663. Castellano, R. K.; Nuckolls, C.; Eichhorn, S. H.; Wood, M. R.; Lovinger, A. J.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2603-2606. Castellano, R. K.; Nuckolls, C.; Rebek, J., Jr. Polym. News 2000, 25, 44-52. (e) Nuckolls, C.; Castellano, R. K.; Rebek, J., Jr. Polym. Prepr. 2000, 41, 930-931. (f) Castellano, R. K.; Clark, R.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr., submitted for publication.
14. (a) Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 7132-7137. (b) Castellano, R. K.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3657-3663. Castellano, R. K.; Nuckolls, C.; Eichhorn, S. H.; Wood, M. R.; Lovinger, A. J.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2603-2606. Castellano, R. K.; Nuckolls, C.; Rebek, J., Jr. Polym. News 2000, 25, 44-52. (e) Nuckolls, C.; Castellano, R. K.; Rebek, J., Jr. Polym. Prepr. 2000, 41, 930-931. (f) Castellano, R. K.; Clark, R.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr., submitted for publication.
15. (a) Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 7132-7137. (b) Castellano, R. K.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3657-3663. Castellano, R. K.; Nuckolls, C.; Eichhorn, S. H.; Wood, M. R.; Lovinger, A. J.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2603-2606. Castellano, R. K.; Nuckolls, C.; Rebek, J., Jr. Polym. News 2000, 25, 44-52. (e) Nuckolls, C.; Castellano, R. K.; Rebek, J., Jr. Polym. Prepr. 2000, 41, 930-931. (f) Castellano, R. K.; Clark, R.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr., submitted for publication.
16. (a) Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 7132-7137. (b) Castellano, R. K.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3657-3663. Castellano, R. K.; Nuckolls, C.; Eichhorn, S. H.; Wood, M. R.; Lovinger, A. J.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2603-2606. Castellano, R. K.; Nuckolls, C.; Rebek, J., Jr. Polym. News 2000, 25, 44-52. (e) Nuckolls, C.; Castellano, R. K.; Rebek, J., Jr. Polym. Prepr. 2000, 41, 930-931. (f) Castellano, R. K.; Clark, R.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr., submitted for publication.
17. Schalley, C. A.; Castellano, R. K.; Brody, M. S.; Rudkevich, D. M.; Siuzdak, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 4568-4579.
18. 3 (295K): Castellano, R. K.; Rebek, J., Jr., unpublished work.
19. For reviews on FRET theory and applications, see: (a) Wu, P.; Brand, L. Anal. Biochem. 1994, 218, 1-13. (b) Clegg, R. M. Curr. Opin. Biotechnol. 1995, 6, 103-110. Selvin, P. R. Methods Eniymol 1995, 246, 300-334. Yang, M.; Millar, D. P. Methods Enzymol. 1997, 278, 417-444. (e) Szöllõsi, J.; Damjanovich, S.; Mátyus, L. Cytometry 1998, 34, 159-179. (f) Tsien, R. Y.; Miyawaki, A. Science 1998, 280, 1954- 1955.
20. For reviews on FRET theory and applications, see: (a) Wu, P.; Brand, L. Anal. Biochem. 1994, 218, 1-13. (b) Clegg, R. M. Curr. Opin. Biotechnol. 1995, 6, 103-110. Selvin, P. R. Methods Eniymol 1995, 246, 300-334. Yang, M.; Millar, D. P. Methods Enzymol. 1997, 278, 417-444. (e) Szöllõsi, J.; Damjanovich, S.; Mátyus, L. Cytometry 1998, 34, 159-179. (f) Tsien, R. Y.; Miyawaki, A. Science 1998, 280, 1954- 1955.
21. For reviews on FRET theory and applications, see: (a) Wu, P.; Brand, L. Anal. Biochem. 1994, 218, 1-13. (b) Clegg, R. M. Curr. Opin. Biotechnol. 1995, 6, 103-110. Selvin, P. R. Methods Eniymol 1995, 246, 300-334. Yang, M.; Millar, D. P. Methods Enzymol. 1997, 278, 417-444. (e) Szöllõsi, J.; Damjanovich, S.; Mátyus, L. Cytometry 1998, 34, 159-179. (f) Tsien, R. Y.; Miyawaki, A. Science 1998, 280, 1954- 1955.
22. For reviews on FRET theory and applications, see: (a) Wu, P.; Brand, L. Anal. Biochem. 1994, 218, 1-13. (b) Clegg, R. M. Curr. Opin. Biotechnol. 1995, 6, 103-110. Selvin, P. R. Methods Eniymol 1995, 246, 300-334. Yang, M.; Millar, D. P. Methods Enzymol. 1997, 278, 417-444. (e) Szöllõsi, J.; Damjanovich, S.; Mátyus, L. Cytometry 1998, 34, 159-179. (f) Tsien, R. Y.; Miyawaki, A. Science 1998, 280, 1954- 1955.
23. For reviews on FRET theory and applications, see: (a) Wu, P.; Brand, L. Anal. Biochem. 1994, 218, 1-13. (b) Clegg, R. M. Curr. Opin. Biotechnol. 1995, 6, 103-110. Selvin, P. R. Methods Eniymol 1995, 246, 300-334. Yang, M.; Millar, D. P. Methods Enzymol. 1997, 278, 417-444. (e) Szöllõsi, J.; Damjanovich, S.; Mátyus, L. Cytometry 1998, 34, 159-179. (f) Tsien, R. Y.; Miyawaki, A. Science 1998, 280, 1954- 1955.
24. For reviews on FRET theory and applications, see: (a) Wu, P.; Brand, L. Anal. Biochem. 1994, 218, 1-13. (b) Clegg, R. M. Curr. Opin. Biotechnol. 1995, 6, 103-110. Selvin, P. R. Methods Eniymol 1995, 246, 300-334. Yang, M.; Millar, D. P. Methods Enzymol. 1997, 278, 417-444. (e) Szöllõsi, J.; Damjanovich, S.; Mátyus, L. Cytometry 1998, 34, 159-179. (f) Tsien, R. Y.; Miyawaki, A. Science 1998, 280, 1954-1955.
25. For a recent example, see: Ha, T.; Zhuang, X.; Kim, H. D.; Orr, J. W.; Williamson, J. R.; Chu, S. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 9077-9082 and references therein.
26. For a recent example, see: Gelfand, C. A.; Plum, G. E.; Mielewczyk, S.; Remeta, D. P.; Breslauer, K. J. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 6113-6118.
27. Within the presumed Förster distance of the FRET dye pair (typically <80 Å). See ref 7a.
28. For energy transfer in other neutral, hydrogen-bonded assemblies, see: (a) Ward, M. D. Chem. Soc. Rev. 1997, 26, 365-375 and references therein, (b) Springs, S. L.; Gosztola, D.; Wasielewski, M. R.; Král, V.; Andrievsky, A.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 2281-2289 and references therein.
29. For energy transfer in other neutral, hydrogen-bonded assemblies, see: (a) Ward, M. D. Chem. Soc. Rev. 1997, 26, 365-375 and references therein, (b) Springs, S. L.; Gosztola, D.; Wasielewski, M. R.; Král, V.; Andrievsky, A.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 2281-2289 and references therein.
30. (a) Gilat, S. L.; Adronov, A.; Fréchet, J. M. J. Angew. Chem., Int. Ed. Engl. 1999, 38, 1422-1427. (b) Gilat, S. L.; Adronov, A.; Fréchet, J. M. J. J. Org. Chem. 1999, 64, 7474-7484. Adronov, A.; Gilat, S. L., Fréchet, J. M. J.; Ohta, K.; Neuwahl, F. V. R.; Fleming, G. R. J. Am. Chem. Soc. 2000, 122, 1175-1185.
31. (a) Gilat, S. L.; Adronov, A.; Fréchet, J. M. J. Angew. Chem., Int. Ed. Engl. 1999, 38, 1422-1427. (b) Gilat, S. L.; Adronov, A.; Fréchet, J. M. J. J. Org. Chem. 1999, 64, 7474-7484. Adronov, A.; Gilat, S. L., Fréchet, J. M. J.; Ohta, K.; Neuwahl, F. V. R.; Fleming, G. R. J. Am. Chem. Soc. 2000, 122, 1175-1185.
32. (a) Gilat, S. L.; Adronov, A.; Fréchet, J. M. J. Angew. Chem., Int. Ed. Engl. 1999, 38, 1422-1427. (b) Gilat, S. L.; Adronov, A.; Fréchet, J. M. J. J. Org. Chem. 1999, 64, 7474-7484. Adronov, A.; Gilat, S. L., Fréchet, J. M. J.; Ohta, K.; Neuwahl, F. V. R.; Fleming, G. R. J. Am. Chem. Soc. 2000, 122, 1175-1185.
33. N-alkylation of coumarin 2 does cause a decrease in molar absorptivity. See ref 12c for details.
34. Throughout all of these experiments ca. 10% of the acceptor emission signal arises from its direct excitation.
35. Control experiments determined the inherent sensitivities of the dyes to DMSO. The emission intensity of both the donor and acceptor controls gradually increased upon titration (at 1% DMSO, 14% increase for the donor, 10% increase for the acceptor). See the Supporting Information for details.
36. For DMSO denaturation experiments monitored by FRET in a biological context, see: Garzon-Rodriguez, W.; Sepulveda-Becerra, M.; Milton, S.; Glabe, C. G. J. Biol. Chem. 1997, 272, 21037-21044.
37. Lomakin, A.; Benedek, G. B.; Castellano, R. K.; Nuckolls, C.; Rebek, J., Jr., unpublished work.
38. Scheerder, J.; Vreekamp, R. H.; Engbersen, J. F. J.; Verboom, W.; van Duynhoven, J. P. M.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 3476-3481.
39. Brody, M. S.; Rebek, J., Jr., unpublished work.
40. Even low concentrations of hydrogen-bonding groups have a dramatic effect on the rates of the assembly processes, e.g., dissociation of 1D·2A in the presence of only 0.3% DMSO occurs in seconds vs hours.
41. For a review of fluorescence-based sensing, see: Prasanna de Silva, A.; Nimal Gunaratne, H. Q.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566. See also (a) Song, X.; Nolan, J.; Swanson, B. I. J. Am. Chem. Soc. 1998, 120, 11514-11515. (b) Chen, C.-T.; Wagner, H.; Still, W. C. Science 1998, 279, 851-853. Rothman, J. H.; Still, W. C. Bioorg. Med. Chem. Lett. 1999, 9, 509-512.
42. For a review of fluorescence-based sensing, see: Prasanna de Silva, A.; Nimal Gunaratne, H. Q.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566. See also (a) Song, X.; Nolan, J.; Swanson, B. I. J. Am. Chem. Soc. 1998, 120, 11514-11515. (b) Chen, C.-T.; Wagner, H.; Still, W. C. Science 1998, 279, 851-853. Rothman, J. H.; Still, W. C. Bioorg. Med. Chem. Lett. 1999, 9, 509-512.
43. For a review of fluorescence-based sensing, see: Prasanna de Silva, A.; Nimal Gunaratne, H. Q.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566. See also (a) Song, X.; Nolan, J.; Swanson, B. I. J. Am. Chem. Soc. 1998, 120, 11514-11515. (b) Chen, C.-T.; Wagner, H.; Still, W. C. Science 1998, 279, 851-853. Rothman, J. H.; Still, W. C. Bioorg. Med. Chem. Lett. 1999, 9, 509-512.
44. For a review of fluorescence-based sensing, see: Prasanna de Silva, A.; Nimal Gunaratne, H. Q.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566. See also (a) Song, X.; Nolan, J.; Swanson, B. I. J. Am. Chem. Soc. 1998, 120, 11514-11515. (b) Chen, C.-T.; Wagner, H.; Still, W. C. Science 1998, 279, 851-853. Rothman, J. H.; Still, W. C. Bioorg. Med. Chem. Lett. 1999, 9, 509-512.
45. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
46. Niu, J.; Lawrence, D. S. J. Biol. Chem. 1997, 272, 1493-1499.
47. See the Supporting Information for synthetic details.