Small photoactivatable molecules for controlled fluorescence activation in living cells

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 3, 2011, Pages 1023-1029

  Puliti, David ^a   Warther, David ^a   Orange, Clelia ^a   Specht, Alexandre ^a   Goeldner, Maurice ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Caged fluorescence; Cellular imaging; Photolabile linkers; Two photon uncaging

Indexed keywords

CELL PROTEIN; FLUORESCENT DYE; SMALL PHOTOACTIVATABLE MOLECULE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CELL ACTIVATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; COVALENT BOND; ELECTRON TRANSPORT; FEMALE; FLUORESCENCE; HUMAN; HUMAN CELL; LIGHT; PHOTOACTIVATION; PROTEIN ANALYSIS; PROTEIN TARGETING; SIGNAL TRANSDUCTION; ULTRAVIOLET RADIATION;

FLUORESCENCE; GREEN FLUORESCENT PROTEINS; PHOTOCHEMICAL PROCESSES; PROTEINS; STAINING AND LABELING;

EID: 79551499208     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.07.011     Document Type: Article

References (74)

1. For recent reviews see: R.Y. Tsien Angew. Chem., Int. Ed. 48 2009 5612
2. N.C. Shaner, G.H. Patterson, and M.W. Davidson J. Cell Sci. 120 2007 4247
3. J. Lippincott-Schwartz, and G.H. Patterson Science 297 2002 1873
4. F.V. Subach, G.H. Patterson, S. Manley, J.M. Gillette, J. Lippincott-Schwartz, and V.V. Verkhusha Nat. Methods 6 2009 153
5. For a recent review see: J. Lippincott-Schwartz, and G.H. Patterson Trends Cell Biol. 11 2009 555
6. V. Sharma, and D.S. Lawrence Angew. Chem., Int. Ed. 48 2009 7290
7. J.F. Callan, A.P. Silva, and D.C. Magri Tetrahedron 61 2005 8551
8. K. Rurack Spectrochim. Acta, Part A 57 2001 2161
9. A.P. de Silva, T.S. Moody, and G.D. Wright Analyst 134 2009 2385
10. L.D. Lavis, and R.T. Raines ACS Chem. Biol. 3 2008 142
11. G. Mayer, and A. Heckel Angew. Chem., Int. Ed. 45 2006 4900
12. D.D. Young, and A. Deiters Org. Biomol. Chem. 5 2007 999
13. A. Specht, F. Bolze, Z. Osram, J.-F. Nicoud, and M. Goeldner HFSP J. 3 2009 255
14. M. Goeldner, R. Givens, Dynamic Studies in Biology: Phototriggers, Photoswitches and Caged Biomolecules 2005 Wiley-VCH
15. H.-M. Lee, D.R. Larson, and D.S. Lawrence ACS Chem. Biol. 4 2009 409
16. M.A. Priestman, and D.S. Lawrence Biochim. Biophys. Acta 1084 2010 547
17. J.C. Politz Trends Cell Biol. 9 1990 284
18. G.A. Krafft, W.R. Sutton, and R.T. Cummings J. Am. Chem. Soc. 110 1988 301
19. J. Ottl, D. Gabriel, and G. Marriott Bioconjugate Chem. 9 1998 143
20. T.J. Mitchison, K.E. Sawin, J.A. Theriot, K. Gee, and A. Mallavaparu Methods Enzymol. 291 1998 63
21. Y. Zhao, Q. Zheng, K. Dakin, K. Xu, M.L. Martinez, and W.-H. Li J. Am. Chem. Soc. 126 2004 4653
22. T. Kobayashi, Y. Urano, M. Kamiya, T. Ueno, H. Kojima, and T. Nagano J. Am. Chem. Soc. 129 2007 6696
23. C. Orange, A. Specht, D. Puliti, E. Sakr, T. Furuta, B. Winsor, and M. Goeldner Chem. Commun. 2008 1217
24. A. Specht, J.-S. Thomann, K. Alarcon, W. Wittayanan, D. Ogden, T. Furuta, Y. Kurakawa, and M. Goeldner ChemBioChem 7 2006 1690
25. S.J. Lord, N.R. Conley, H.D. Lee, R. Samuel, N. Liu, R.J. Twieg, and W.E. Moerner J. Am. Chem. Soc. 130 2008 9204
26. S.J. Lord, N.R. Conley, H.D. Lee, S.Y. Nishimura, A.K. Pomerantz, K.A. Willets, Z. Lu, H. Wang, N. Liu, R. Samuel, R. Weber, A. Semyonov, M. He, R.J. Twieg, and W.E. Moerner ChemPhysChem 10 2009 55
27. V.N. Belov, M.L. Bossi, J. Fölling, V. Boyarskiy, and S.W. Hell Chem. Eur. J. 15 2009 10762
28. V.N. Belov, A.A. Wurm, V.P. Boyarskiy, S. Jakobs, and S.W. Hell Angew. Chem., Int. Ed. 49 2010 3520
29. G. Gramlich, and W.M. Nau Org. Lett. 1 1999 603
30. J.R.R. Majjigapu, A.N. Kurchan, R. Kottani, T.P. Gustafson, and A.G. Kutateladze J. Am. Chem. Soc. 127 2005 12458
31. N. Gagey, M. Emond, P. Neveu, C. Benbrahim, B. Goetz, I. Aujard, J.-B. Baudin, and L. Jullien Org. Lett. 10 2008 2341
32. J.A. Blake, M. Lukeman, and J.C. Scaiano J. Am. Chem. Soc. 131 2009 4127
33. N. Gagey, P. Neveu, and L. Jullien Angew. Chem., Int. Ed. 46 2007 2467
34. G.C.R. Ellis-Davis Nat. Methods 4 2007 619
35. D. Warther, S. Gug, A. Specht, F. Bolze, J.-F. Nicoud, A. Mourot, and M. Goeldner Bioorg. Med. Chem. 18 2010 7753
36. T. Furuta, S.S.-A. Wang, J.L. Dantzker, T.M. Dore, W.J. Bybee, E.M. Callaway, W. Denk, and R.Y. Tsien Proc. Natl. Acad. Sci. U.S.A. 96 1999 1193
37. W. Denk, J.H. Strickler, and W.W. Webb Science 248 1990 73
38. N.S. Makarov, M. Drobizhev, and A. Rebane Opt. Express 16 2008 4029
39. S. Gug, S. Charon, A. Specht, K. Alarcon, D. Ogden, B. Zietz, J. Léonard, S. Haacke, F. Bolze, J.-F. Nicoud, and M. Goeldner ChemBioChem 9 2008 1303
40. S. Gug, F. Bolze, A. Specht, C. Bourgogne, M. Goeldner, and J.-F. Nicoud Angew. Chem., Int. Ed. 47 2008 9525
41. D. Warther, F. Bolze, J. Léonard, S. Gug, A. Specht, D. Puliti, X.-H. Sun, P. Kessler, Y. Lutz, J.-L. Vonesch, B. Winsor, J.-F. Nicoud, and M. Goeldner J. Am. Chem. Soc. 132 2010 2585
42. T. Ueno, Y. Urano, K. Setsukinai, H. Takakusa, H. Kojima, K. Kikuchi, K. Ohkubo, S. Fukuzumi, and T. Nagano J. Am. Chem. Soc 126 2004 14079
43. J.R. Lakowicz Principles of Fluorescence Spectroscopy 3rd ed. 2006 Springer ISBN-10:0-387-31278-1, ISBN-13:978-0-387-31278-1
44. A. Weller Pure Appl. Chem. 16 1968 115
45. R.A. Marcus Annu. Rev. Phys. Chem. 15 1964 155
46. L. Yi, H. Li, L. Sun, L. Liu, C. Zhang, and Z. Xi Angew. Chem., Int. Ed. 48 2009 4034
47. T. Matsumoto, Y. Urano, T. Shoda, H. Kojima, and T. Nagano Org. Lett. 9 2007 3375
48. J. Guy, K. Caron, S. Dufresne, S.W. Michnick, W.G. Skene, and J.W. Keillor J. Am. Chem. Soc. 129 2007 11969
49. E.D. Matayoshi, G.T. Wang, G.A. Krafft, and J. Erickson Science 247 1990 954
50. J.-P. Pellois, M.E. Hahn, and T.W. Muir J. Am. Chem. Soc. 261 2004 7170
51. H.-M. Lee, M.A. Priestman, and D.S. Lawrence J. Am. Chem. Soc. 132 2010 1446
52. Maurel, D.; Banala, S.; Laroche, T.; Johnsson, K. ACS Chem. Biol. doi:10.1021/cb1000229.
53. G. Marriott, and M. Heidecker Biochemistry 35 1996 3170
54. T. Sakata, Y. Yan, and G. Marriott Proc. Natl. Acad. Sci. U.S.A. 102 2005 4759
55. S. Mao, R.K.P. Benninger, C. Petchprayoon, D. Jackson, C.J. Easley, D.W. Piston, and G. Mariott Biophys. J. 94 2008 4515
56. N. Johnsson, and K. Johnsson ACS Chem. Biol. 2 2007 31
57. H.M. O'Hare, K. Johnsson, and A. Gautier Curr. Opin. Struct. Biol. 17 2007 488
58. D.L. Beene, D.A. Dougherty, and H.A. Lester Curr. Opin. Neurobiol. 13 2003 264
59. C.J. Noren, S.J. Anthony-Cahill, M.C. Griffith, and P.G. Schultz Science 244 1989 182
60. A. Stromgaard, A.A. Jensen, and K. Stromgaard ChemBioChem 5 2004 909
61. E.M. Sletten, and C.R. Bertozzi Angew. Chem., Int. Ed. 48 2009 6974
62. T.S. Young, I. Ahmad, J.A. Yin, and P.G. Schultz J. Mol. Biol. 395 2010 361
63. B.A. Griffin, S.R. Adams, and R.Y. Tsien Science 28 1998 269
64. S.R. Adams, R.E. Campbell, L.A. Gross, B.R. Martin, G.K. Walkup, Y. Yao, J. Llopis, and R.Y. Tsien J. Am. Chem. Soc. 124 2002 6063
65. G. Gaietta, T.J. Deerinck, S.R. Adams, J. Bouwer, O. Tour, D.W. Laird, G.E. Sosinsky, R.Y. Tsien, and M.H. Ellisman Science 296 2002 503
66. B.J. Wilkins, X. Yang, and T.A. Cropp Bioorg. Med. Chem. Lett. 19 2009 4296
67. T.L. Halo, J. Appelbaum, E.M. Hobert, D.M. Balkin, and A. Schepartz J. Am. Chem. Soc. 131 2009 438
68. E.G. Guignet, R. Hovius, and H. Vogel Nat. Biotechnol. 22 2004 440
69. M. Kamoto, N. Umezawa, N. Kato, and T. Higuchi Chem. Eur. J. 14 2008 8004
70. T. Gronemeyer, G. Godin, and K. Johnsson Curr. Opin. Biotechnol. 16 2005 453
71. S. Lata, M. Gavutis, R. Tampe, and J. Piehler J. Am. Chem. Soc. 128 2006 2365
72. C.T. Hauser, and R.Y. Tsien Proc. Natl. Acad. Sci. U.S.A. 104 2007 3693
73. S. Mizukami, S. Watanabe, Y. Hori, and K. Kikuchi J. Am. Chem. Soc. 131 2009 5016
74. Y. Hori, H. Ueno, S. Mizukami, and K. Kikuchi J. Am. Chem. Soc. 131 2009 16610