Rhodamines NN: A novel class of caged fluorescent dyes

Angewandte Chemie - International Edition

Volumn 49, Issue 20, 2010, Pages 3520-3523

  Belov, Vladimir N ^a   Wurm, Christian A ^a   Boyarskiy, Vadim P ^a   Jakobs, Stefan ^a   Hell, Stefan W ^a  

^a MAX PLANCK INSTITUTE FOR BIOPHYSICAL CHEMISTRY   (Germany)

Author keywords

Caged compounds; Diazo compounds; Fluorescence; Imaging agents; Rhodamines

Indexed keywords

ACID CHLORIDES; DIAZO COMPOUNDS; DIAZOMETHANES; FLUORESCENCE IMAGING; FLUORESCENT DYES; FLUORESCENT MARKERS;

CHLORINE COMPOUNDS;

FLUORESCENCE;

FLUORESCENT DYE; RHODAMINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SPECTROPHOTOMETRY; SYNTHESIS;

FLUORESCENT DYES; MOLECULAR STRUCTURE; RHODAMINES; SPECTROPHOTOMETRY;

EID: 77952411563     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201000150     Document Type: Article

References (54)

1. For reviews on photocleavable (protecting) groups, see Ref. [ac]: a) V. N. Rajasekharan Pillai, Synthesis 1980, 1-26;
2. b) C. G. Bochet, J. Chem. Soc. Perkin Trans. 1 2002, 125-142;
3. c) A. P. Pelliccioli, J. Wirz, Photochem. Photobiol. Sci. 2002, 7, 441-458;
4. d) J. Lippincott-Schwartz, E. Snapp, A. Kenworthy, Nat. Rev. Mol. Cell Biol. 2001, 2, 444-456;
5. e) D. S. Lidke, B. S. Wilson, Trends Cell Biol. 2009, 19, 566-574;
6. f) R.A. Neher, M. Mitkovski, F. Kirchhoff, E. Neher, F. Theis, A. Zeung, Biophys J. 2009, 96, 3791-3800;
7. for very recent data on photoactivable azido fluorogens, see S. J. Lord, H. D. Lee, R. Samuel, R. Weber, N. Liu, N. R. Conley, M. A. Thompson, R. J. Twieg, W. E. Moerner, J. Phys. Chem. B 2010, DOI: 10.1021./jp907080r.
8. a) K. H. Knauer, R. Gleiter, Angew. Chem. 1977, 89, 116-117;
9. Angew. Chem. Int. Ed, Engl. 1977, 16, 113-113;
10. b) H. Willwohl, J. Wolfrum, R. Gleiter, Laser Chem. 1989, 10, 63-72;
11. c) J. Fölling, V. Belov, R. Kunetsky, R. Medda, A. Schönle, A. Egner, C. Eggeling, M. Bossi, S. W. Hell, Angew. Chem. 2007, 119, 6382-6386;
12. Angew. Chem. Int. Ed. 2007, 46, 6266-6270;
13. d) M. Bossi, J. Fölling, V. N. Belov, V. P. Boyarskiy, R. Medda, A. Egner, C. Eggeling, A. Schönle, S. W. Hell, Nano Lett. 2008, 8, 2463-2468;
14. e) V. N. Belov, M. L. Bossi, J. Fölling, V. P. Boyarskiy, S. W. Hell, Chem. Eur. J. 2009, 15, 10762-10776.
15. M. Andresen, A. C. Stiel, J. Fölling, D. Wenzel, A. Schönle, A. Egner, C. Eggeling, S. W. Hell, S. Jakobs, Nat. Biotechnol. 2008, 26, 1035-1040.
16. a) A. S. Schönle, S.W. Hell, Nat. Biotechnol. 2007, 25, 1234-1235;
17. a) M. Beija, C. A. M. Afonso, J. M. G. Martinho, Chem. Soc. Rev. 2009, 38, 2410-2433;
18. b) M.S.T. Gonçalves, Chem. Rev. 2009, 109, 190-212;
19. c) R. P. Haugland, A Guide to Fluorescent Probes and Labelling Technologies, Invitrogen, Carlsbad, 2005, pp. 11-37;
20. for the use of rhodamines in bioconjugation procedures, see d) G. T. Hermanson, Bioconjugate Techniques, Academic Press, Amsterdam, 2008, pp. 415-427.
21. a) Rhodamine Q: T. J. Mitchison, K. E. Sawin, J. A. Theriot, K. Gee, A. Mallavarapu, Methods Enzymol. 1998, 291, 63-78;
22. K. R. Gee, E. S. Weinberg, D. J. Kozlowski, Bioorg. Med. Chem. Lett. 2001, 11, 2181-2183;
23. b) rhodamine 110: L. D. Lavis, T.-Y. Chao, R. T. Raines, ACS Chem. Biol. 2006, 1, 252-260;
24. J. Ottl, D. Gabriel, G. Marriott, Bioconjugate Chem. 1998, 9, 143-151.
25. a) W.-H. Li, Y. R. Zhao, US 7304168, 2007;
26. b) Y. R. Zhao, Q. Zheng, K. Dakin, K. Xu, M. Martinez, W.-H. Li, J. Am. Chem. Soc. 2004, 126, 4653-4663.
27. a) R. P. Haugland, K. R. Gee, US 5635608, 1997;
28. b) T. Kobayashi, Y. Urano, M. Kamiya, T. Ueno, H. Kojima, T. Nagano, J. Am. Chem. Soc. 2007, 129, 6696-6697;
29. c) G. A. Krafft, W. R. Sutton, R. T. Cummings, J. Am. Chem. Soc. 1988, 110, 301-303.
30. Synthesis and properties of caged fluorescent 2-amidothioxanthones - compounds structurally similar to fluorescein or rhodamines- were also reported: J. R. R. Majjigapu, A. N. Kurchan, R. Kattani, T. P. Gustafson, A. G. Kutateladze, J. Am. Chem. Soc. 2005, 127, 12458-12459.
31. Branching at the a position facilitates the uncaging reaction; see Ref. [8a].
32. A. Banerjee, C. Grewer, L. Ramakrishnan, J. Jäger, A. Gameiro, H.-G. A. Breitinger, K. R. Gee, B. K. Carpenter, G. P. Hess, J. Org. Chem. 2003, 68, 8361-8367;
33. see: M. Matsuzaki, G. C. R. Ellis-Davies, T. Nemoto, Y. Miyashita, M. lino, H. Kasai, Nat. Neurosa. 2001, 4, 1086-1092.
34. P. Stegmaier, J. M. Alonso, A. Del Campo, Langmuir 2008, 24, 11872-11879.
35. O. D. Fedoryak, T. M. Dore, Org. Lett. 2002, 4, 3419-3422.
36. a) T. Furuta, S. S.-H. Wang, J. L. Dantzker, T. M. Dore, W. J. Bybee, E. M. Callaway, W. Denk, R. Y. Tsien, Proc. Natl Acad. Sci. USA 1999, 96, 1193-2000;
37. b) H. Ando, T. Furuta, R. Y. Tsien, H. Okamoto, Nat. Genet. 2001, 28, 317-325;
38. c) W. Lin, D.S. Lawrence, J. Org. Chem. 2002, 67, 2723-2726;
39. d) H.J. Montgomery, B. Perdicakis, D. Fishlock, G. A. Lajoie, E. Jervis, J. G. Guillemette, Bioorg. Med. Chem. 2002, 10, 1919-1927.
40. See the Supporting Information for details and experimental procedures.
41. For a review on the Wolff rearrangement, see a) W. Kirmse, Eur. J. Org. Chem. 2002, 2193-2256;
42. b) N. Hashimoto, T. Aoyama, T. Shioiri, Tetrahedron Lett. 1980, 21, 4619-4622.
43. fl = 0.68).
44. R. Juskaitis, T. Wilson, J. Microsc 1999, 195, 17-22.
45. S. W. Hell, V. N. Belov, V. P. Boyarskiy, C. A. Wurm, S. Jakobs, C. Geisler (Max-Planck-Innovation GmbH), PCT/EP/2009/006578, 2009.
46. T. Gronemeyer, G. Godin, K. Johnsson, Curr. Opin. Biotechnol. 2005, 16, 453-458.
47. a) "Far-Field Optical Nanoscopy": S. W. Hell in Single Molecule Spectroscopy in Chemistry, Physics and Biology (Eds.: A. Grälslund, R. Rigler, J. Widengren), Springer, Berlin, 2009, pp. 365-398;
48. b) S. W. Hell, Science 2007, 316, 1153-1158;
49. c) M. Fernández-Suárez, A. Y. Ting, Nat. Rev. Mol. Cell Biol. 2008, 9, 929-943;
50. d) D. Evanko, Nat. Methods 2009, 6, 19-20;
51. e) S. W. Hell, Nat. Methods 2009, 6, 24-32;
52. f) X, Zhuang, Nat. Photonics 2009, 3, 365-367;
53. g) J. Lippincott-Schwartz, S. Manley, Nat. Methods 2009, 6, 21-23;
54. h) B. Huang, M. Bates, X. Zhuang, Annu. Rev. Biochem. 2009, 78, 993-1016.