Modular and tunable chemosensor scaffold for divalent zinc

Journal of the American Chemical Society

Volumn 125, Issue 35, 2003, Pages 10591-10597

  Shults, Melissa D ^a   Pearce, Dierdre A ^a   Imperiali, Barbara ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHETIC PEPTIDES;

CHELATION; CHEMICAL SENSORS; FLUORESCENCE; STOICHIOMETRY;

ZINC;

ZINC;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; BIOSENSOR; COMPLEX FORMATION; DERIVATIZATION; DISSOCIATION CONSTANT; PANCREAS ISLET BETA CELL; PHASE TRANSITION; STOICHIOMETRY; SYNAPTIC TRANSMISSION; TISSUE DISTRIBUTION;

AMINO ACIDS; BIOSENSING TECHNIQUES; CATIONS, DIVALENT; FLUORENES; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; KINETICS; OLIGOPEPTIDES; QUINOLINES; SPECTROMETRY, FLUORESCENCE; SULFONAMIDES; ZINC;

EID: 0042355634     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0355980     Document Type: Article

References (52)

1. (a) Vallee, B. L.; Falchuk, K. H. Physiol. Rev. 1993, 73, 79-118.
2. (b) Fraústo da Silva, J. J. R.; Williams, R. J. P. The Biological Chemistry of the Elements: The Inorganic Chemistry of Life, 2nd ed.; Oxford University Press: Oxford, 2001.
3. Beyersmann, D.; Haase, H. BioMetals 2001, 14, 331-341.
4. (a) Frederickson, C. J.; Bush, A. I. BioMetals 2001, 14, 353-366.
5. (b) Frederickson, C. J.; Suh, S. W.; Silva, D.; Frederickson, C. J.; Thompson, R. B. J. Nutr. 2000, 130, 1471S-1483S.
6. (c) Cuajungco, M. P.; Lees, G. J. Neurobiol. Dis. 1997, 4, 137-169.
7. (a) Formby, B.; Schmid-Formby, F.; Grodsky, G. M. Diabetes 1984, 33, 229-234.
8. (b) Grodsky, G. M.; Schmid-Formby, F. Endocrinology 1985, 117, 704-710.
9. (a) Kimura, E.; Aoki, S. BioMetals 2001, 14, 191-204.
10. (b) Burdette, S. C.; Lippard, S. J. Coord. Chem. Rev. 2001, 216, 333-361.
11. See references within Canzoniero, L. M. T.; Sensi, S. L.; Choi, D. W. Neurobiol. Dis. 1997, 4, 275-279 and within ref 5a.
12. (a) Walkup, G. K.; Burdette, S. C.; Lippard, S. J.; Tsien, R. Y. J. Am. Chem. Soc. 2000, 122, 5644-5645.
13. (b) Burdette, S. C.; Walkup, G. K.; Spingler, B.; Tsien, R. Y.; Lippard, S. J. J. Am. Chem. Soc. 2001, 123, 7831-7841.
14. (c) Burdette, S. C.; Frederickson, C. J.; Bu, W. M.; Lippard, S. J. J. Am. Chem. Soc. 2003, 125, 1778-1787.
15. (a) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2000, 122, 12 399-12 400.
16. (b) Hirano, T.; Kikuchi, K.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2002, 124, 6555-6562.
17. (c) Ueno, S.; Tsukamoto, M.; Hirano, T.; Kikuchi, K.; Yamada, M. K.; Nishiyama, N.; Nagano, T.; Matsuki, N.; Ikegaya, Y. J. Cell Biol. 2002, 158, 215-220.
18. (a) Gee, K. R.; Zhou, Z.-L.; Qian, W.-J.; Kennedy, R. J. Am. Chem. Soc. 2002, 124, 776-778.
19. (b) Gee, K. R.; Zhou, Z.-L.; Ton-That, D.; Sensi, S. L.; Weiss, J. H. Cell Calcium 2002, 31, 245-251.
20. (c) Qian, W.-J.; Gee, K. R.; Kennedy, R. T. Anal. Chem. 2003, 75, 3136-3143.
21. (a) Fierke, C. A.; Thompson, R. B. BioMetals 2001, 14, 205-222.
22. (b) Thompson, R. B.; Peterson, D.; Mahoney, W.; Cramer, M.; Maliwal, B. P.; Suh, S. W.; Frederickson, C.; Fierke, C.; Herman, P. J. Neurosci. Methods 2002, 118, 63-75.
23. Maruyama, S.; Kikuchi, K.; Hirano, T.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2002, 124, 10 650-10 651.
24. Thompson, R. B.; Cramer, M. L.; Bozym, R.; Fierke, C. A. J. Biomed. Optics 2002, 7, 555-560.
25. (a) Walkup, G. K.; Imperiali, B. J. Am. Chem. Soc. 1996, 118, 3053-3054.
26. (b) Walkup, G. K.; Imperiali, B. J. Am. Chem. Soc. 1997, 119, 3443-3450.
27. Walkup, G. K.; Imperiali, B. J. Org. Chem. 1998, 63, 6727-6731.
28. Jotterand, N.; Pearce, D. A.; Imperiali, B. J. Org. Chem. 2001, 66, 3224-3228.
29. Koike, T.; Abe, T.; Takahashi, M.; Ohtani, K.; Kimura, E.; Shiro, M. J. Chem. Soc., Dalton Trans., 2002, 1764-1768.
30. Thompson, R. B.; Maliwal, B. P.; Feliccia, V. L.; Fierke, C. A.; McCall, K. Anal. Chem. 1998, 70, 4717-4723.
31. (a) Torrado, A.; Walkup, G. K.; Imperiali, B. J. Am. Chem. Soc. 1998, 120, 609-610.
32. (b) Torrado, A.; Imperiali, B. J. Org. Chem. 1996, 61, 8940-8948.
33. (a) Pearce, D. A.; Walkup, G. K.; Imperiali, B. Bioorg. Med. Chem. Lett. 1998, 8, 1963-1968.
34. (b) Godwin, H. A.; Berg, J. M. J. Am. Chem. Soc. 1996, 118, 6514-6515.
35. Franz, K.; Nitz, M.; Imperiali, B. ChemBioChem 2003, 4, 265-271.
36. (a) Wadia, J. S.; Dowdy, S. F. Curr. Opin. Biotech. 2002, 13, 52-56.
37. (b) Lindgren, M.; Hällbrink, M.; Prochiantz, A.; Langel, Ü. Trends Pharmacol. Sci. 2000, 21, 99-103.
38. Pearce, D. A.; Jotterand, N.; Carrico, I. S.; Imperiali, B. J. Am. Chem. Soc. 2001, 123, 5160-5161.
39. (a) Cheng, R. P.; Fisher, S. L.; Imperiali, B. J. Am. Chem. Soc. 1996, 118, 11 349-11 356.
40. (b) Imperiali, B.; Kapoor, T. M. Tetrahedron 1993, 49, 3501-3510.
41. (a) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12 414-12 415.
42. (b) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350.
43. O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3-13.
44. Fujii, K.; Ikai, Y.; Mayumi, T.; Oka, H.; Suzuki, M.; Harada, K. Anal. Chem. 1997, 69, 3346-3352.
45. The preference for L-enantiomer formation with the catalyst O-(9)-allyl-N-9-anthracenyl methylcinchonidium bromide is well-established over a wide range of electrophiles. See refs 24 and 25.
46. Some variation between peptide sequences in the extinction coefficients was observed due to the error associated with the stock solution concentration determined by QAA. The error in this measurement is at least 10%. The values are detailed in the Supporting Information.
47. SPECFIT/32 for Windows (version 3.0), Spectrum Software Associates, Marlborough, MA.
48. Connors, K. A. Binding Constants: The Measurement of Molecular Complex Stability; John Wiley and Sons: New York, 1987.
49. 2+ relative to the "softer" imidazole ligand may be due to its increased negative charge and/or its ability to bind as a bidentate ligand.
50. Seitz, W. R. CRC Critical Reviews in Analytical Chemistry; CRC Press: Boca Raton, FL, 1980; pp 367-404.
51. Outten, C. E.; O'Halloran, T. V. Science 2001, 292, 2488-2492.
52. Rae T. D.; Schmidt, P. J.; Pufahl, R. A.; Culotta, V. C.; O'Halloran, T. V. Science 1999, 284, 805-808.