Consecutive signal amplification for DNA detection based on de novo fluorophore synthesis and host-guest chemistry

Angewandte Chemie - International Edition

Volumn 51, Issue 18, 2012, Pages 4479-4483

  Chen, Xiao Hua ^a   Roloff, Alexander ^a   Seitz, Oliver ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

DNA detection; DNA templated catalysis; fluorescence; host guest interactions

Indexed keywords

BENZYLIDENE; DNA DETECTION; DNA-TEMPLATE; HOST GUEST INTERACTIONS; HOSTGUEST CHEMISTRY; PHOSPHONIUM SALTS; SIGNAL AMPLIFICATIONS; SYNTHETIC RECEPTORS; WITTIG REACTION;

ALDEHYDES; FLUORESCENCE; SIGNAL PROCESSING;

DNA;

DNA; FLUORESCENT DYE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

DNA; FLUORESCENT DYES; MOLECULAR STRUCTURE;

EID: 84860132285     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201108845     Document Type: Article

References (61)

1. T. N. Grossmann, A. Strohbach, O. Seitz, ChemBioChem 2008, 9, 2185-2192
2. S. K. Silverman, Angew. Chem. 2010, 122, 7336-7359
3. Angew. Chem. Int. Ed. 2010, 49, 7180-7201
4. X. Li, D. R. Liu, Angew. Chem. 2004, 116, 4956-4979
5. Angew. Chem. Int. Ed. 2004, 43, 4848-4870
6. D. Summerer, A. Marx, Angew. Chem. 2002, 114, 93-95
7. Angew. Chem. Int. Ed. 2002, 41, 89-90
8. D. M. Kolpashchikov, Chem. Rev. 2010, 110, 4709-4723
9. J. Scheuermann, D. Neri, ChemBioChem 2010, 11, 931-937.
10. Z. C. Ma, J. S. Taylor, Proc. Natl. Acad. Sci. USA 2000, 97, 11159-11163
11. J. Brunner, A. Mokhir, R. Krämer, J. Am. Chem. Soc. 2003, 125, 12410-12411
12. I. Boll, R. Krämer, J. Brunner, A. Mokhir, J. Am. Chem. Soc. 2005, 127, 7849-7856
13. H. Abe, Y. Kondo, H. Jinmei, N. Abe, K. Furukawa, A. Uchiyama, S. Tsuneda, K. Aikawa, I. Matsumoto, Y. Ito, Bioconjugate Chem. 2008, 19, 327-333
14. S. Ficht, C. Dose, O. Seitz, ChemBioChem 2005, 6, 2098-2103
15. A. Erben, T. N. Grossmann, O. Seitz, Angew. Chem. 2011, 123, 2880-2884
16. Angew. Chem. Int. Ed. 2011, 50, 2828-2832.
17. Z. Ma, J. S. Taylor, Bioorg. Med. Chem. 2001, 9, 2501-2510
18. S. Sando, E. T. Kool, J. Am. Chem. Soc. 2002, 124, 2096- 2097
19. H. Abe, E. T. Kool, J. Am. Chem. Soc. 2004, 126, 13980-13986
20. J. Cai, X. Li, J. S. Taylor, Org. Lett. 2005, 7, 751-754
21. C. Dose, S. Ficht, O. Seitz, Angew. Chem. 2006, 118, 5495-5499
22. Angew. Chem. Int. Ed. 2006, 45, 5369-5373
23. T. N. Grossmann, O. Seitz, J. Am. Chem. Soc. 2006, 128, 15596-15597
24. C. Dose, O. Seitz, Bioorg. Med. Chem. 2008, 16, 65-77
25. T. N. Grossmann, O. Seitz, Angew. Chem. 2008, 120, 7228-7231
26. Angew. Chem. Int. Ed. 2008, 47, 7119-7122
27. A. Shibata, H. Abe, M. Ito, Y. Kondo, S. Shimizu, K. Aikawa, Y. Ito, Chem. Commun. 2009, 6586-6588
28. D. J. Kleinbaum, E. T. Kool, Chem. Commun. 2010, 46, 8154-8156
29. D. K. Prusty, A. Herrmann, J. Am. Chem. Soc. 2010, 132, 12197-12199
30. S. Dutta, A. Mokhir, Chem. Commun. 2011, 47, 1243-1245.
31. J. F. Cai, X. X. Li, X. Yue, J. S. Taylor, J. Am. Chem. Soc. 2004, 126, 16324-16325
32. Z. L. Pianowski, N. Winssinger, Chem. Commun. 2007, 3820-3822
33. R. M. Franzini, E. T. Kool, ChemBioChem 2008, 9, 2981-2988
34. K. Furukawa, H. Abe, J. Wang, M. Uda, H. Koshino, S. Tsuneda, Y. Ito, Org. Biomol. Chem. 2009, 7, 671-677
35. Z. Pianowski, K. Gorska, L. Oswald, C. A. Merten, N. Winssinger, J. Am. Chem. Soc. 2009, 131, 6492-6497
36. R. M. Franzini, E. T. Kool, J. Am. Chem. Soc. 2009, 131, 16021-16023
37. G. Katarzyna, K. Ioanna, T. Ulrich, N. Winssinger, Chem. Sci. 2011, 2, 1969-1975.
38. Y. Huang, J. M. Coull, J. Am. Chem. Soc. 2008, 130, 3238-3239
39. K. Meguellati, G. Koripelly, S. Ladame, Angew. Chem. 2010, 122, 2798-2802
40. Angew. Chem. Int. Ed. 2010, 49, 2738-2742.
41. Z. J. Gartner, M. W. Kanan, D. R. Liu, Angew. Chem. 2002, 114, 1874-1878
42. Angew. Chem. Int. Ed. 2002, 41, 1796-1800
43. Z. J. Gartner, R. Grubina, C. T. Calderone, D. R. Liu, Angew. Chem. 2003, 115, 1408-1413
44. Angew. Chem. Int. Ed. 2003, 42, 1370-1375.
45. E. Arunkumar, C. C. Forbes, B. D. Smith, Eur. J. Org. Chem. 2005, 4051-4059
46. G. L. Duveneck, E. V. Sitzmann, K. B. Eisenthal, N. J. Turro, J. Phys. Chem. 1989, 93, 7166-7170
47. C. A. Stanier, M. J. O'Connell, W. Clegg, H. L. Anderson, Chem. Commun. 2001, 493-494
48. J. Terao, A. Tang, J. J. Michels, A. Krivokapic, H. L. Anderson, Chem. Commun. 2004, 56-57.
49. A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515-1566.
50. Greater signal increases were obtained when cyclodextrin was added after the DNA-templated reaction rather than included in the reaction mixture.
51. For comparison, a fluorogenic hybridization probe would require 2500-fold fluorescence intensification upon binding to an equimolar amount of target to achieve the same signal enhancement as 0.001 equivalent template.
52. R. Breslow, N. Greenspoon, T. Guo, R. Zarzycki, J. Am. Chem. Soc. 1989, 111, 8296-8297
53. P, Suresh, K. Pitchumani, J. Photochem. Photobiol. A 2009, 206, 40-45.
54. For example, it has been reported that antibodies can have a high binding affinity for stilbenes and lead to enhancements of stilbene emission
55. A. Simeonov, M. Matsushita, E. A. Juban, E. H. Z. Thompson, T. Z. Hoffman, A. E. Beuscher, M. J. Taylor, P. Wirsching, W. Rettig, J. K. McCusker, R. C. Stevens, D. P. Millar, P. G. Schultz, R. A. Lerner, K. D. Janda, Science 2000, 290, 307-313
56. F. Tian, E. W. Debler, D. P. Millar, A. A. Deniz, I. A. Wilson, P. G. Schultz, Angew. Chem. 2006, 118, 7927-7929
57. Angew. Chem. Int. Ed. 2006, 45, 7763-7765.
58. See the Supporting Information for the details of the PCR, DNA sequence of target, and primers used.
59. S. Ficht, A. Mattes, O. Seitz, J. Am. Chem. Soc. 2004, 126, 9970-9981.
60. H. Li, R. M. Franzini, C. Bruner, E. T. Kool, ChemBioChem 2010, 11, 2132-2137.
61. 2-fold enhancement in fluorescence during templated Staudinger reactions in the presence of 1 equivalent target was reported:, R. M. Franzini, E. T. Kool, Chem. Eur. J. 2011, 17, 2168-2175.