Facile and general synthesis of photoactivatable xanthene dyes

Angewandte Chemie - International Edition

Volumn 50, Issue 47, 2011, Pages 11206-11209

  Wysocki, Laura M ^a   Grimm, Jonathan B ^a   Tkachuk, Ariana N ^a   Brown, Timothy A ^a   Betzig, Eric ^a   Lavis, Luke D ^a  

^a HOWARD HUGHES MEDICAL INSTITUTE   (United States)

Author keywords

caged compounds; fluorescence; imaging agents; rhodamine; super resolution microscopy

Indexed keywords

CAGED COMPOUNDS; CARBOXY GROUPS; FLEXIBLE STRATEGIES; IMAGING AGENTS; PHOTOACTIVATABLE; RHODAMINE; SUPER-RESOLUTION MICROSCOPY; XANTHENE DYES;

CATALYSIS; FLUORESCENCE;

CHEMISTRY;

CONTRAST MEDIUM; FLUORESCENT DYE; XANTHINE DERIVATIVE;

ANIMAL; ARTICLE; CELL NUCLEUS; CELL STRAIN 3T3; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE MICROSCOPY; MOUSE; PHOTOCHEMISTRY; RADIATION EXPOSURE; SYNTHESIS; ULTRASTRUCTURE;

3T3 CELLS; ANIMALS; CELL NUCLEUS; CONTRAST MEDIA; FLUORESCENT DYES; MICE; MICROSCOPY, FLUORESCENCE; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; XANTHINES;

EID: 81255172807     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201104571     Document Type: Article

References (30)

1. T. J. Mitchison, K. E. Sawin, J. A. Theriot, K. Gee, A. Mallavarapu, G. Marriott, Methods Enzymol. 1998, 291, 63-78
2. L. D. Lavis, R. T. Raines, ACS Chem. Biol. 2008, 3, 142-155
3. M. Fernández-Suárez, A. Ting, Nat. Rev. Mol. Cell Biol. 2008, 9, 929-943
4. D. Puliti, D. Warther, C. Orange, A. Specht, M. Goeldner, Bioorg. Med. Chem. 2011, 19, 1023-1029.
5. E. Betzig, G. H. Patterson, R. Sougrat, O. W. Lindwasser, S. Olenych, J. S. Bonifacino, M. W. Davidson, J. Lippincott-Schwartz, H. F. Hess, Science 2006, 313, 1642-1645.
6. S. T. Hess, T. P. K. Girirajan, M. D. Mason, Biophys. J. 2006, 91, 4258-4272
7. M. J. Rust, M. Bates, X. Zhuang, Nat. Methods 2006, 3, 793-796.
8. J. Fölling, V. Belov, D. Riedel, A. Schonle, A. Egner, C. Eggeling, M. Bossi, S. W. Hell, ChemPhysChem 2008, 9, 321-326
9. V. N. Belov, C. A. Wurm, V. P. Boyarskiy, S. Jakobs, S. W. Hell, Angew. Chem. 2010, 122, 3598-3602
10. Angew. Chem. Int. Ed. 2010, 49, 3520-3523.
11. J. A. Royall, H. Ischiropoulos, Arch. Biochem. Biophys. 1993, 302, 348-355.
12. W.-C. Sun, K. R. Gee, D. H. Klaubert, R. P. Haugland, J. Org. Chem. 1997, 62, 6469-6475.
13. R. P. Haugland, M. T. Z. Spence, I. D. Johnson, Handbook of Fluorescent Probes and Research Chemicals, 6 th ed., Molecular Probes, Eugene, 1996.
14. T. O. Zaikova, A. V. Rukavishnikov, G. B. Birrell, O. H. Griffith, J. F. W. Keana, Bioconjugate Chem. 2001, 12, 307-313.
15. C. Kim, P. Misco, Tetrahedron Lett. 1985, 26, 2027-2030.
16. J. Ottl, D. Gabriel, G. Marriott, Bioconjugate Chem. 1998, 9, 143-151.
17. I. S. Ioffe, V. F. Otten, Zh. Obshch. Khim. 1961, 31, 1511-1516.
18. C. C. Woodroofe, M. H. Lim, W. M. Bu, S. J. Lippard, Tetrahedron 2005, 61, 3097-3105.
19. X. Jin, C. Uttamapinant, A. Y. Ting, ChemBioChem 2011, 12, 65-70.
20. G. A. Krafft, W. R. Sutton, R. T. Cummings, J. Am. Chem. Soc. 1988, 110, 301-303
21. T. J. Mitchison, J. Cell Biol. 1989, 109, 637-652.
22. S. A. McKinney, C. S. Murphy, K. L. Hazelwood, M. W. Davidson, L. L. Looger, Nat. Methods 2009, 6, 131-133.
23. A. Salic, T. J. Mitchison, Proc. Natl. Acad. Sci. USA 2008, 105, 2415-2420.
24. C. Flors, C. N. J. Ravarani, D. Dryden, ChemPhysChem 2009, 10, 2201-2204.
25. F. Persson, P. Bingen, T. Staudt, J. Engelhardt, J. Tegenfeldt, S. W. Hell, Angew. Chem. 2011, 123, 5696-5698
26. Angew. Chem. Int. Ed. 2011, 50, 5581-5583.
27. J. Yao, R. D. Fetter, P. Hu, E. Betzig, R. Tjian, Genes Dev. 2011, 25, 569-580.
28. K. Kolmakov, V. N. Belov, J. Bierwagen, C. Ringemann, V. Müller, C. Eggeling, S. W. Hell, Chem. Eur. J. 2010, 16, 158-166.
29. G. T. Dempsey, M. Bates, W. E. Kowtoniuk, D. R. Liu, R. Y. Tsien, X. Zhuang, J. Am. Chem. Soc. 2009, 131, 18192-18193
30. H. D. Lee, S. J. Lord, S. Iwanaga, K. Zhan, H. Xie, J. C. Williams, H. Wang, G. R. Bowman, E. D. Goley, L. Shapiro, R. J. Twieg, J. Rao, W. E. Moerner, J. Am. Chem. Soc. 2010, 132, 1642-1645.