Development of ratiometric fluorescent probe for zinc ion based on indole fluorophore

Tetrahedron Letters

Volumn 50, Issue 12, 2009, Pages 1345-1347

  Taki, Masayasu ^a   Watanabe, Yasumasa ^a   Yamamoto, Yukio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

High affinity; Indole; Ratiometric probe; Zinc ion

Indexed keywords

FLUORESCENT DYE; PYRIDINE DERIVATIVE; ZINC ION;

ARTICLE; BINDING AFFINITY; COMPLEX FORMATION;

EID: 59049086538     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.026     Document Type: Article

References (47)

1. de Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., Huxley A.J.M., McCoy C.P., Rademacher J.T., and Rice T.E. Chem. Rev. 97 (1997) 1515-1566
2. Valeur B. Molecular Fluorescence: Principles and Applications (2002), Wiley-VCH, Weinheim, New York
3. Domaille D.W., Que E.L., and Chang C.J. Nat. Chem. Biol. 3 (2008) 168-175
4. Que E.L., Domaille D.W., and Chang C. J. Chem. Rev. 108 (2008) 1517-1549
5. Grynkiewicz G., Poenie M., and Tsien R.Y. J. Biol. Chem. 260 (1985) 3440-3450
6. Lippard S.J., and Berg J.M. Principles of Bioinorganic Chemistry (1994), University Science Books, Mill Valley, CA
7. Sensi S.L., Canzoniero L.M.T., Yu S.P., Ying H.S., Koh J.Y., Kerchner G.A., and Choi D.W. J. Neurosci. 17 (1997) 9554-9564
8. Coleman J.E. Curr. Opin. Chem. Biol. 2 (1998) 222-234
9. Frederickson C.J. Int. Rev. Neurobiol. 31 (1989) 145-238
10. Frederickson C.J., Koh J.Y., and Bush A.I. Nat. Rev. Neurosci. 6 (2005) 449-462
11. Gyulkhandanyan A.V., Lu H.F., Lee S.C., Bhattacharjee A., Wijesekara N., Fox J.E.M., MacDonald P.E., Chimienti F., Dai F.F., and Wheeler M.B. J. Biol. Chem. 283 (2008) 10184-10197
12. Edstrom A.M.L., Malm J., Frohm B., Martellini J.A., Giwercman A., Morgelin M., Cole A.M., and Sorensen O.E. J. Immunol. 181 (2008) 3413-3421
13. Frederickson C.J., Kasarskis E.J., Ringo D., and Frederickson R.E. J. Neurosci. Methods 20 (1987) 91-103
14. Zalewski P.D., Forbes I.J., and Betts W.H. Biochem. J. 296 (1993) 403-408
15. Mikata Y., Yamanaka A., Yamashita A., and Yano S. Inorg. Chem. 47 (2008) 7295-7301
16. Burdette S.C., Walkup G.K., Spingler B., Tsien R.Y., and Lippard S.J. J. Am. Chem. Soc. 123 (2001) 7831-7841
17. Hirano T., Kikuchi K., Urano Y., and Nagano T. J. Am. Chem. Soc. 124 (2002) 6555-6562
18. Gee K.R., Zhou Z.L., Qian W.J., and Kennedy R. J. Am. Chem. Soc. 124 (2002) 776-778
19. Taki M., Wolford J.L., and O'Halloran T.V. J. Am. Chem. Soc. 126 (2004) 712-713
20. Henary M.M., Wu Y.G., and Fahrni C.J. Chem.-Eur. J. 10 (2004) 3015-3025
21. Lim N.C., and Bruckner C. Chem. Commun. (2004) 1094-1095
22. Komatsu K., Urano Y., Kojima H., and Nagano T. J. Am. Chem. Soc. 129 (2007) 13447-13454
23. Koike T., Watanabe T., Aoki S., Kimura E., and Shiro M. J. Am. Chem. Soc. 118 (1996) 12696-12703
24. Hanaoka K., Kikuchi K., Kojima H., Urano Y., and Nagano T. J. Am. Chem. Soc. 126 (2004) 12470-12476
25. Van Dongen E., Dekkers L.M., Spijker K., Meijer E.W., Klomp L.W.J., and Merkx M. J. Am. Chem. Soc. 128 (2006) 10754-10762
26. Bozym R.A., Thompson R.B., Stoddard A.K., and Fierke C.A. ACS Chem. Biol. 1 (2006) 103-111
27. Evers T.H., Appelhof M.A.M., de Graaf-Heuvelmans P., Meijer E.W., and Merkx M. J. Mol. Biol. 374 (2007) 411-425
28. Evers T.H., Appelhof M.A.M., Meijer E.W., and Merkx M. Protein Eng. Des. Sel. 21 (2008) 529-536
29. Jiang P.J., and Guo Z.J. Coord. Chem. Rev. 248 (2004) 205-229
30. Kikuchi K., Komatsu K., and Nagano T. Curr. Opin. Chem. Biol. 8 (2004) 182-191
31. Carol P., Sreejith S., and Ajayaghosh A. Chem. Asian J. 2 (2007) 338-348
32. Gee K.R., Zhou Z.L., Ton-That D., Sensi S.L., and Weiss J.H. Cell Calcium 31 (2002) 245-251
33. Maruyama S., Kikuchi K., Hirano T., Urano Y., and Nagano T. J. Am. Chem. Soc. 124 (2002) 10650-10651
34. Woodroofe C.C., and Lippard S.J. J. Am. Chem. Soc. 125 (2003) 11458-11459
35. Chang C.J., Jaworski J., Nolan E.M., Sheng M., and Lippard S.J. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 1129-1134
36. Ajayaghosh A., Carol P., and Sreejith S. J. Am. Chem. Soc. 127 (2005) 14962-14963
37. Kiyose K., Kojima H., Urano Y., and Nagano T. J. Am. Chem. Soc. 128 (2006) 6548-6549
38. Bredas J.L., Perry J.W., and Fahrni C.J. J. Am. Chem. Soc. 129 (2007) 11888-11889
39. Sreejith S., Divya K.P., and Ajayaghosh A. Chem. Commun. (2008) 2903-2905
40. Li Z.F., Xiang Y., and Tong A. Anal. Chim. Acta 619 (2008) 75-80
41. Potter S.M., Wang C.M., Garrity P.A., and Fraser S.E. Gene 173 (1996) 25-31
42. Raju B., Murphy E., Levy L.A., Hall R.D., and London R.E. Am. J. Physiol. 256 (1989) C540-C548
43. Chen C.A., Yeh R.H., and Lawrence D.S. J. Am. Chem. Soc. 124 (2002) 3840-3841
44. Haugland R.P. Handbook of Fluorescent Probes and Research Products. 9th ed. (2003), Molecular Probes, Eugene, OR
45. Kay A.R. J. Neurosci. 23 (2003) 6847-6855
46. Outten C.E., and O'Halloran T.V. Science 292 (2001) 2488-2492
47. Changela A., Chen K., Xue Y., Holschen J., Outten C.E., O'Halloran T.V., and Mondragon A. Science 301 (2003) 1383-1387