Switchable cucurbituril-bipyridine beacons

Chemistry - A European Journal

Volumn 16, Issue 30, 2010, Pages 9056-9067

  Sinha, Mantosh K ^a   Reany, Ofer ^a   Parvari, Galit ^a   Karmakar, Ananta ^a   Keinan, Ehud ^a,b  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Biocatalysis; Cucurbiturils; Fluorescence; Inclusion compounds; Sensors

Indexed keywords

ALDOLASES; BINDING CONSTANT; BIOCATALYSIS; BIOCATALYTIC REACTION; BIPYRIDINES; CHARGE-DIPOLE INTERACTION; CHEMICAL SENSING; CUCURBIT[6]URIL; CUCURBITURILS; DIRECT MEASUREMENT; ELIMINATION REACTION; FLUORESCENCE INTENSITIES; GUEST MOLECULES; INCLUSION COMPLEX; INCLUSION COMPOUNDS; PENICILLIN G ACYLASE; REVERSIBLE BINDING; SWITCHABLE;

AMIDES; COMPLEXATION; DRUG PRODUCTS; KETONES; SENSORS; TRANSITION METALS;

FLUORESCENCE;

2,2' BIPYRIDINE; ANTIBODY ALDOLASE; CUCURBITURIL; DRUG DERIVATIVE; FRUCTOSE BISPHOSPHATE ALDOLASE; IMMUNOGLOBULIN F(AB) FRAGMENT; MACROCYCLIC COMPOUND; PENICILLIN AMIDASE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; METABOLISM;

2,2'-DIPYRIDYL; FLUORESCENCE; FRUCTOSE-BISPHOSPHATE ALDOLASE; IMMUNOGLOBULIN FAB FRAGMENTS; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; PENICILLIN AMIDASE;

EID: 77955457611     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903067     Document Type: Article

References (51)

1. a) W. M. Nau, G. Ghale, A. Hennig, H. Bakirci, D. Bailey, J. Am. Chem. Soc. 2009, 131, 11558;
2. A. Hennig, H. Bakirci, W. M. Nau, Nat. Methods 2007, 4, 629.
3. J. Lagona, P. Mukhopadhyay, S. Chakrabati, L. Isaacs, Angew. Chem. 2005, 117, 4922;
4. Angew. Chem. Int. Ed. 2005, 44, 4844.
5. a) S. Sasmal, M. K. Sinha, E. Keinan, Org. Lett. 2004, 6, 1225;
6. I. Ben Shir, S. Sasmal, T. Mejuch, M. K. Sinha, M. Kapon, E. Keinan, J. Org. Chem. 2008, 73, 8772.
7. a) W. M. Nau, J. Mohanty, Intl. J. Photoenergy 2005, 7, 133;
8. B. D. Wagner, N. Stojanovic, A. I. Day, R. J. Blanch, J. Phys. Chem. B 2003, 107, 10741;
9. C. Marquez, F. Huang, W. M. Nau, IEEE Trans. Nanobiosci. 2004, 39;
10. H.-J. Buschmann, E. Schollmeyer, J. Inclusion Phenom. Mol. Recognit. Chem. 1997, 29, 167.
11. a) N. Saleh, A. L. Koner, W. M. Nau, Angew. Chem. 2008, 120, 5478;
12. Angew. Chem. Int. Ed. 2008, 47, 5398;
13. R. Wang, L. Yuan, D. H. Macartney, Chem. Commun. 2005, 5867;
14. A. Praetorius, D. M. Bailey, T. Schwarzlose, W. M. Nau, Org. Lett. 2008, 10, 4089;
15. A. L. Koner, W. M. Nau, Supramol. Chem. 2007, 19, 55;
16. J. Mohanty, A. C. Bhasikuttan, W. M. Nau, H. Pal, J. Phys. Chem. B 2006, 110, 5132.
17. a) H. Cong, Y.-J. Zhao, S.-F. Xue, Z. Tao, Q.-J. Zhu, J. Mol. Model. 2007, 13, 1221;
18. Z. Limei, Z. Jiannan, Z. Yunqian, Z. Qianjiang, X. Saifen, Z. Tao, Z. Jianxin, Z. Xin, W. Zhanbin, L. Lasheng, A. I. Day, Supramol. Chem. 2008, 1;
19. Y. Zhao, S. Xue, Q. Zhu, Z. Tao, J. Zhang, Z. Wei, L. Long, M. Hu, H. Xiao, A. I. Day, Chin Sci. Bull. 2004, 49, 1111.
20. W. M. Nau, G. Ghale, A. Hennig, H. Bakirci, D. Bailey, J. Am. Chem. Soc. 2009, 131, 11558.
21. a) D. Pappo, T. Mejuch, O. Reany, E. Solel, M. Gurram, E. Keinan, Org. Lett. 2009, 11, 1063;
22. A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586;
23. Angew. Chem. Int. Ed. 1998, 37, 3387.
24. S. Wu, S. Chen, M. Li, J. Xiang, Y. Xiao, L. Yuan, Cryst. Eng. 2007, 10, 907.
25. A. Moissette, Y. Batonneau, C. Bremard, J. Am. Chem. Soc. 2001, 123, 12325.
26. W. Rettig, R. Lapouyade in Topics in Fluorescence Spectroscopy, Vol. 4 (Ed.: J. R. Lakowicz), Plenum Press, New York, 1994, pp. 109-149.
27. W. Rettig, Angew. Chem. 1986, 98, 969;
28. Angew. Chem. Int. Ed. Engl. 1986, 25, 971.
29. S.-S. Sun, A. J. Lees, J. Photochem. Photobiol. A 2001, 140, 157.
30. G. Qian, M. Wang, Mater. Lett. 2002, 56, 71.
31. Photophysics of Aromatic Molecules (Ed.: J. B. Birks), Wiley, New York, 1970, p. 301.
32. K. A. Connors, Binding Constants: The Measurement of Molecular Complex Stability (Ed.: K. A. Connors), Wiley, New York, 1987, p. 27.
33. K. A. Connors, Binding Constants: The Measurement of Molecular Complex Stability (Ed.: K. A. Connors), Wiley, New York, 1987, p. 61.
34. i is the binding constant of the ith ligand (L) to the macromolecule.
35. P. Job, Ann. Chim. 1928, 9, 113.
36. M. R. Eftink in Methods in Enzymology, Vol. 278 (Eds.: L. Brand, M. L. Johnson), Academic Press, New York, 1997, pp. 221-245.
37. a) W. L. Mock, N. Y. Shih, J. Org. Chem. 1986, 51, 4440;
38. M. V. Rekharsky, Y. H. Ko, N. Selvapalam, K. Kim, Y. Inoue, Supramol. Chem. 2007, 19, 39.
39. Advances in Heterocyclic Chemistry (Eds.: A. R. Katritzky, J. M. Lagowski), Academic Press, New York, 1976.
40. K. D. Lay, K. S. Schanze, Coord. Chem. Rev. 1998, 171, 287.
41. K. E. Bethin, T. R. Cimato, M. J. Ettinger, J. Biol. Chem. 1995, 270, 20703.
42. T. Omori, R. Kimizuka, K. Yoshihara, M. Yagi, J. Radioanal. Nucl. Chem. 1984, 87, 260.
43. M. V. Rekharsky, Y. H. Ko, N. Selvapalam, K. Kim, Y. Inoue, Supramol. Chem. 2007, 19, 39.
44. a) W. L. Mock, Top. Curr. Chem. 1995, 175, 1;
45. C. Márquez, R. R. Hudgins, W. M. Nau, J. Am. Chem. Soc. 2004, 126, 5806.
46. J.-P. Goddard, J.-L. Reymond, Trends Biotechnol. 2004, 22, 363.
47. A. Roa, J. L. Garcia, F. Salto, E. Cortes, Biochem. J. 1994, 303, 869.
48. Y. Weiss, A. Shulman, I. Ben Shir, E. Keinan, S. Wolf, Nat. Biotechnol. 2006, 24, 713.
49. H. Nierengarten, J. Rojo, E. Leize, J.-M. Lehn, A. V. Dorsselaer, Eur. J. Org. Chem. 2002, 573.
50. A. T. R. Williams, S. A. Winfield, J. N. Miller, Analyst 1983, 108, 1067.
51. H. E. Zimmerman, J. H. Penn, C. W. Carpenter, Proc. Natl. Acad. Sci. USA 1982, 79, 2128.