Engineering bisquinolinium/thiazole orange conjugates for fluorescent sensing of G-quadruplex DNA

Angewandte Chemie - International Edition

Volumn 48, Issue 12, 2009, Pages 2188-2191

  Yang, Peng ^b   De Cian, Anne ^b   Teulade Fichou, Marie Paule ^a   Mergny, Jean Louis ^b   Monchaud, David ^a  

^a INSTITUT CURIE   (France)

^b MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

Author keywords

DNA; Fluorescence probes; G quadruplex; Guanine

Indexed keywords

FLEXIBLE LINKERS; FLUORESCENCE PROBES; FLUORESCENCE PROPERTIES; FLUORESCENT PROBES; FLUORESCENT SENSING; G-QUADRUPLEX; GUANINE; GUANINE-QUADRUPLEXES; RIGID SCAFFOLDS;

DNA; GENES; NUCLEIC ACIDS; POSITIVE IONS; PROBES;

FLUORESCENCE;

BENZOTHIAZOLE DERIVATIVE; DNA; FLUORESCENT DYE; GUANINE QUADRUPLEX; PDC M TO 2; PDC-M-TO 2; QUINOLINE DERIVATIVE; THIAZOLE ORANGE;

ARTICLE; CHEMISTRY; FLUORESCENCE; FLUORESCENCE RESONANCE ENERGY TRANSFER;

BENZOTHIAZOLES; DNA; FLUORESCENCE; FLUORESCENCE RESONANCE ENERGY TRANSFER; FLUORESCENT DYES; G-QUADRUPLEXES; QUINOLINES; QUINOLINIUM COMPOUNDS;

EID: 61949444534     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805613     Document Type: Article

References (49)

1. a) S. Burge, G. N. Parkinson, P. Hazel, A. K. Todd, S. Neidle, Nucleic Acids Res. 2006, 34, 5402;
2. b) D. J. Patel, A. T. Phan, V. Kuryavyi, Nucleic Acids Res. 2007, 35, 7429;
3. c) J. Dai, M. Carver, D. Yang, Biochimie 2008, 90, 1172.
4. For some recent reviews, see: a) L. Oganesian, T. M. Bryan, BioEssays 2007, 29, 155;
5. b) N. Maizels, Nat. Struct. Biol. 2006, 13, 1055;
6. c) M. Fry, Front. Biosci. 2007, 12, 4336;
7. d) A. De Cian, L. Lacroix, C. Douarre, N. Temine-Smaali, C. Trentesaux, J.-F. Riou, J.-L. Mergny, Biochimie 2008, 90, 131;
8. e) L. Kelland, Clin. Cancer Res. 2007, 13, 4960.
9. a) C. Schaffitzel, I. Berger, J. Postberg, J. Hanes, H. J. Lipps, A. Pluckthun, Proc. Natl. Acad. Sci. USA 2001, 98, 8572;
10. b) J. C. Darnell, K. B. Jensen, P. Jin, V. Brown, S. T. Warren, R. B. Darnell, Cell 2001, 107, 489;
11. c) M. L. Duquette, P. Handa, J. A. Vincent, A. F. Taylor, N. Maizels, Gen. Dev. 2004, 18, 1618;
12. d) K. Paeschke, T. Simonsson, J. Postberg, D. Rhodes, H. J. Lipps, Nat. Struct. Mol. Biol. 2005, 12, 847;
13. e) M. L. Duquette, P. Handa, J. A. Vincent, A. F. Taylor, N. Maizels, Genes Dev. 2004, 18, 1618;
14. f) J. Eddy, N. Maizels, Nucleic Acids Res. 2006, 34, 3887.
15. C. Granotier, G. Pennarun, L. Riou, F. Hoffshir, L. R. Gauthier, A. De Cian, D. Gomez, E. Mandine, J.-F. Riou, J.-L. Mergny, P. Mailliet, B. Dutrillaux, F. D. Boussin, Nucleic Acids Res. 2005, 33, 4182.
16. a) C. A. M. Seidel, A. Schulz, M. H. M. Sauer, J. Phys. Chem. 1996, 100, 5541;
17. b) F. D. Lewis, R. B. Letsinger, M. R. Wasielewski, Acc. Chem. Res. 2001, 34, 159;
18. c) T. Heinlein, J.-P. Knemeyer, O. Piestert, M. Sauer, J. Phys. Chem. B 2003, 107, 7957.
19. a) H. Arthanari, S. Basu, T. L. Kawano, P. H. Bolton, Nucleic Acids Res. 1998, 26, 3724;
20. b) F. Koeppel, J.-F. Riou, A. Laoui, P. Mailliet, P. B. Arimondo, D. Labit, O. Petitgenet, C. Hélène, J.-L. Mergny, Nucleic Acids Res. 2001, 29, 1087;
21. c) C.-C. Chang, C.-W. Chien, Y.-H. Lin, C.-C. Kang, T.-C. Chang, Nucleic Acids Res. 2007, 35, 2846;
22. d) C. Allain, D. Monchaud, M.-P. Teulade-Fichou, J. Am. Chem. Soc. 2006, 128, 11890.
23. a) T. Lemarteleur, D. Gomez, R. Paterski, E. Mandine, P. Mailliet, J.-F. Riou, Biochem. Biophys. Res. Commun. 2004, 323, 802;
24. b) G. Pennarun, C. Granotier, L. R. Gauthier, D. Gomez, F. Hoffschir, E. Mandine, J.-F. Riou, J.-L. Mergny, P. Mailliet, F. D. Boussin, Oncogene 2005, 24, 2917;
25. c) A. De Cian, E. DeLemos, J.-L. Mergny, M.-P. Teulade-Fichou, D. Monchaud, J. Am. Chem. Soc. 2007, 129, 1856;
26. d) A. De Cian, G. Cristofari, P. Reichenbach, E. De Lemos, D. Monchaud, M.-P. Teulade-Fichou, K. Shin-ya, L. Lacroix, J. Lingner, J.-L. Mergny, Proc. Natl. Acad. Sci. USA 2007, 104, 17347;
27. e) D. Monchaud, P. Yang, L. Lacroix, M.-P. Teulade-Fichou, J.-L. Mergny, Angew. Chem. 2008, 120, 4936;
28. Angew. Chem. Int. Ed. 2008, 47, 4858.
29. For general articles related to TO, see: a) T. L. Netzel, K. Nafisi, M. Zhao, J. R. Lenhard, I. Johnson, J. Phys. Chem. 1995, 99, 17936;
30. b) J. Nygren, N. Svanik, M. Kubista, Biopolymers 1998, 46, 39;
31. c) J. T. Petty, J. A. Bordelon, M. E. Robertson, J. Phys. Chem. B 2000, 104, 7221;
32. d) K. C. Hannah, B. A. Armitage, Acc. Chem. Res. 2004, 37, 845;
33. e) V. Karunakaran, J. L. Pérez Lustres, L. Zhao, N. P. Emsting, O. Seitz, J. Am. Chem. Soc. 2006, 128, 2954; for recent examples of TO-related engineered dye, see:
34. f) N. Svanvik, G. Westma, D. Wang, M. Kubista, Anal. Biochem. 2000, 281, 26;
35. g) E. J. Fechter, B. Olenyuk, P. B. Dervan, J. Am. Chem. Soc. 2005, 127, 16685;
36. h) D. V. Jarikote, O. Köhler, E. Socher, O. Seitz, Eur. J. Org. Chem. 2005, 3187;
37. i) R. Lartia, U. Asseline, Chem. Eur. J. 2006, 12, 2270;
38. j) J. Brunner, J. K. Barton, Biochemistry 2006, 45, 12295;
39. k) J. R. Carreon, K. M. Stewart, K. P. Mahon Jr. , S. Shin, S. O. Kelley, Bioorg. Med. Chem. Lett. 2007, 17, 5182;
40. l) S. Ikeda, T. Kubota, K. Kino, A. Okamoto, Bioconjugate Chem. 2008, 19, 1719;
41. m) F. Menacher, M. Rubner, S. Berndl, H.-A. Wagenknecht, J. Org. Chem. 2008, 73, 4263.
42. A. De Cian, L. Guittat, M. Kaiser, B. Saccà, S. Amrane, A. Bourdoncle, P. Alberti, M.-P. Teulade-Fichou, L. Lacroix, J.-L. Mergny, Methods 2007, 42, 183.
43. a) J. L. Huppert, Biochimie 2008, 90, 1140;
44. b) Y. Qin, L. H. Hurley, Biochimie 2008, 90, 1149;
45. c) J. Dash, P. S. Shirude, S. Balasubramanian, Chem. Commun. 2008, 3055.
46. M.-P. Teulade-Fichou, C. Carrasco, L. Guittat, C. Bailly, P. Alberti, J.-L. Mergny, A. David, J.-M. Lehn, W. D. Wilson, J. Am. Chem. Soc. 2003, 125, 4732.
47. For some recent reviews, see: a) D. Monchaud, M.-P. Teulade-Fichou, Org. Biomol. Chem. 2008, 6, 627;
48. b) J. H. Tan, L. Q. Gu, J. Y. Wu, Mini-Rev. Med. Chem. 2008, 8, 1163;
49. c) A. Arola, R. Vilar, Curr. Top. Med. Chem. 2008, 8, 1405.