Protease probes that enable excimer signaling upon scission

Angewandte Chemie - International Edition

Volumn 53, Issue 44, 2014, Pages 11955-11959

  Fischbach, Melanie ^a   Resch Genger, Ute ^b   Seitz, Oliver ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

^b BAM FEDERAL INSTITUTE FOR MATERIALS RESEARCH AND TESTING   (Germany)

Author keywords

Excimers; Fluorescent probes, .; Peptide nucleic acids; Proteases; Time resolved fluorescence

Indexed keywords

BLOOD; FLUORESCENCE; GLYCOSYLATION; LIGHT EMISSION; NUCLEIC ACIDS; PEPTIDES; PYRENE;

EXCIMERS; FLUORESCENT PROBES; PEPTIDE NUCLEIC ACID; PROTEASES; TIME-RESOLVED FLUORESCENCE;

PROBES;

FLUORESCENT DYE; PEPTIDE HYDROLASE;

CHEMISTRY; HUMAN; SIGNAL TRANSDUCTION;

FLUORESCENT DYES; HUMANS; PEPTIDE HYDROLASES; SIGNAL TRANSDUCTION;

EID: 84919363361     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201406909     Document Type: Article

References (49)

1. a) J. Zhang, R. E. Campbell, A. Y. Ting, R. Y. Tsien, Nat. Rev. Mol. Cell Biol. 2002, 3, 906-918;
2. b) L. D. Lavis, R. T. Raines, ACS Chem. Biol. 2008, 3, 142-155;
3. c) H. Kobayashi, M. Ogawa, R. Alford, P. L. Choyke, Y. Urano, Chem. Rev. 2009, 109, 2620-2640.
4. a) A. P. Demchenko, Anal. Biochem. 2005, 343, 1-22;
5. b) S. M. Borisov, O. S. Wolfbeis, Chem. Rev. 2008, 108, 423-461;
6. c) K. Rurack, U. Resch-Genger, Chem. Soc. Rev. 2002, 31, 116-127.
7. a) Z. Xu, N. J. Singh, J. Lim, J. Pan, H. N. Kim, S. Park, K. S. Kim, J. Yoon, J. Am. Chem. Soc. 2009, 131, 15528-15533;
8. b) C. J. Yang, S. Jockusch, M. Vicens, N. J. Turro, W. Tan, Proc. Natl. Acad. Sci. USA 2005, 102, 17278-17283;
9. c) J. Huang, Y. Wu, Y. Chen, Z. Zhu, X. Yang, C. J. Yang, K. Wang, W. Tan, Angew. Chem. Int. Ed. 2011, 50, 401 - 404;
10. Angew. Chem. 2011, 123, 421-424.
11. a) A. A. Martí, X. Li, S. Jockusch, Z. Li, B. Raveendra, S. Kalachikov, J. J. Russo, I. Morozova, S. V. Puthanveettil, J. Ju, N. J. Turro, Nucleic Acids Res. 2006, 34, 3161-3168;
12. b) K. Yamana, Y. Fukunaga, Y. Ohtani, S. Sato, M. Nakamura, W. J. Kim, T. Akaike, A. Maruyama, Chem. Commun. 2005, 2509-2511;
13. c) M. Masuko, H. Ohtani, K. Ebata, A. Shimadzu, Nucleic Acids Res. 1998, 26, 5409-5416;
14. d) P. L. Paris, J. M. Langenhan, E. T. Kool, Nucleic Acids Res. 1998, 26, 3789-3793;
15. e) P. Conlon, C. J. Yang, Y. Wu, Y. Chen, K. Martinez, Y. Kim, N. Stevens, A. A. Marti, S. Jockusch, N. J. Turro, W. Tan, J. Am. Chem. Soc. 2008, 130, 336-342.
16. a) P. Somerharju, Chem. Phys. Lipids 2002, 116, 57-74;
17. b) H.-J. Galla, E. Sackmann, Biochim. Biophys. Acta Biomembr. 1974, 339, 103-115.
18. a) G. Bains, A. B. Patel, V. Narayanaswami, Molecules 2011, 16, 7909-7935;
19. b) S. S. Lehrer, Methods Enzymol. 1997, 278, 286-295;
20. c) K. Yamana, Y. Ohtani, H. Nakano, I. Saito, Bioorg. Med. Chem. Lett. 2003, 13, 3429-3431.
21. a) B. Turk, Nat. Rev. Drug Discovery 2006, 5, 785-799;
22. b) M. Funovics, R.Weissleder, C.-H. Tung, Anal. Bioanal. Chem. 2003, 377, 956-963;
23. c) J. Neefjes, N. P. Dantuma, Nat. Rev. Drug Discovery 2004, 3, 58-69.
24. a) S. Thurley, L. Röglin, O. Seitz, J. Am. Chem. Soc. 2007, 129, 12693-12695;
25. b) K. J. Oh, K. J. Cash, A. A. Lubina, K. W. Plaxco, Chem. Commun. 2007, 4869-4871.
26. a) Y. Hara, T. Fujii, H. Kashida, K. Sekiguchi, X. G. Liang, K. Niwa, T. Takase, Y. Yoshida, H. Asanuma, Angew. Chem. Int. Ed. 2010, 49, 5502 - 5506;
27. Angew. Chem. 2010, 122, 5634-5638;
28. b) H. Kashida, T. Takatsu, T. Fujii, K. Sekiguchi, X. Liang, K. Niwa, T. Takase, Y. Yoshida, H. Asanuma, Angew. Chem. Int. Ed. 2009, 48, 7044 - 7047;
29. Angew. Chem. 2009, 121, 7178-7181;
30. c) R. Häner, S. M. Biner, S. M. Langenegger, T. Meng, V. L. Malinovskii, Angew. Chem. Int. Ed. 2010, 49, 1227 - 1230;
31. Angew. Chem. 2010, 122, 1249-1252.
32. B. Armitage, D. Ly, T. Koch, H. Frydenlund, H. Orum, G. B. Schuster, Biochemistry 1998, 37, 9417-9425.
33. K. F. MacKinnon, D. F. Qualley, S. A. Woski, Tetrahedron Lett. 2007, 48, 8074-8077.
34. a) N. Borkakoti, Prog. Biophys. Mol. Biol. 1998, 70, 73-94;
35. b) M. D. Sternlicht, Z.Werb, Annu. Rev. Cell Dev. Biol. 2001, 17, 463-516;
36. c) T. Klein, R. Bischoff, Amino Acids 2011, 41, 271-290.
37. a) L. E. Littlepage, M. D. Sternlicht, N. Rougier, J. Phillips, E. Gallo, Y. Yu, K. Williams, A. Brenot, J. I. Gordon, Z. Werb, Cancer Res. 2010, 70, 2224-2234;
38. b) M. Egeblad, Z. Werb, Nat. Rev. Cancer 2002, 2, 161-174;
39. c) T. A. Giambernardi, G. M. Grant,G. P. Taylor, R. J. Hay, V. M. Maher, J. J. Mccormick, R. J. Klebe, Matrix Biol. 1998, 16, 483-496;
40. d) M. Pacheco, M. Mourao, E. Mantovani, I. Nishimoto, M. Mitzi Brentani, Clin. Exp. Metastasis 1998, 16, 577-585;
41. e) E. L. Rosenthal, L. M. Matrisian, Head Neck 2006, 28, 639-648;
42. f) T. Rath, M. Roderfeld, J. r. Graf, S. Wagner, A.-K. Vehr, C. Dietrich, A. Geier, E. Roeb, Inflamm. Bowel Dis. 2006, 12, 1025-1035;
43. g) T. Masaki, H. Matsuoka, M. Sugiyama, N. Abe, A. Goto, A. Sakamoto, Y. Atomi, Br. J. Cancer 2001, 84, 1317-1321;
44. h) E. Roeb, M. Arndt, B. Jansen, V. Schumpelick, S. Matern, Int. J. Colorectal Dis. 2004, 19, 518-524.
45. a) J. O. McIntyre, B. Fingleton, K. S. Wells, D. W. Piston, C. C. Lynch, S. Gautam, L. M. Matrisian, Biochem. J. 2004, 377, 617-628;
46. b) A. R. Welch, C. M. Holman, M. F. Browner, M. R. Gehring, C.-C. Kan, H. E. Van Wart, Arch. Biochem. Biophys. 1995, 324, 59-64;
47. c) Y.-P. Kim, Y.-H. Oh, E. Oh, S. Ko, M.-K. Han, H.-S. Kim, Anal. Chem. 2008, 80, 4634-4641;
48. d) G. Liu, J. Wang, D. S. Wunschel, Y. Lin, J. Am. Chem. Soc. 2006, 128, 12382-12383.
49. J. Maurel, C. Nadal, X. Garcia-Albeniz, R. Gallego, E. Carcereny, V. Almendro, M. Mármol, E. Gallardo, J. Maria Augé, R. Longarón, A. Martínez-Fernandez, R. Molina, A. Castells, P. Gascón, Int. J. Cancer 2007, 121, 1066-1071.