In situ synthesis of alkenyl tetrazines for highly fluorogenic bioorthogonal live-cell imaging probes

Angewandte Chemie - International Edition

Volumn 53, Issue 23, 2014, Pages 5805-5809

  Wu, Haoxing ^a   Yang, Jun ^a   Šečkute, Jolita ^a   Devaraj, Neal K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

bioorthogonal reaction; cellular imaging; cycloaddition; fluorophores; heterocycles

Indexed keywords

CYCLOADDITION; FLUORESCENCE; FLUOROPHORES; PROBES;

BIOORTHOGONAL REACTIONS; CASCADE REACTIONS; CELLULAR IMAGING; FLUORESCENT PROBES; FLUOROGENIC PROBES; HETEROCYCLES; SYNTHETIC METHODOLOGY; SYNTHETIC METHODS;

ORGANIC POLYMERS;

ALKENE; FLUORESCENT DYE; HETEROCYCLIC COMPOUND;

ANIMAL; CHEMISTRY; CYCLOADDITION; FEMALE; HUMAN; MALE; TUMOR CELL LINE;

ALKENES; ANIMALS; CELL LINE, TUMOR; CYCLOADDITION REACTION; FEMALE; FLUORESCENT DYES; HETEROCYCLIC COMPOUNDS; HUMANS; MALE;

EID: 84901773363     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201400135     Document Type: Article

References (54)

1. G. Clavier, P. Audebert, Chem. Rev. 2010, 110, 3299-3314
2. N. K. Devaraj, R. Weissleder, Acc. Chem. Res. 2011, 44, 816-827
3. G. Budin, K. S. Yang, T. Reiner, R. Weissleder, Angew. Chem. 2011, 123, 9550-9553
4. Angew. Chem. Int. Ed. 2011, 50, 9378-9381.
5. D. E. Chavez, S. K. Hanson, J. M. Veauthier, D. A. Parrish, Angew. Chem. 2013, 125, 7014-7017
6. Angew. Chem. Int. Ed. 2013, 52, 6876-6879
7. J. Yang, J. Seckute, C. M. Cole, N. K. Devaraj, Angew. Chem. 2012, 124, 7594-7597
8. Angew. Chem. Int. Ed. 2012, 51, 7476-7479
9. A. Hamasaki, J. M. Zimpleman, I. Hwang, D. L. Boger, J. Am. Chem. Soc. 2005, 127, 10767-10770
10. W. Kaim, Coord. Chem. Rev. 2002, 230, 127-139
11. Z. Li, J. F. Ding, N. H. Song, J. P. Lu, Y. Tao, J. Am. Chem. Soc. 2010, 132, 13160-13161
12. N. Saracoglu, Tetrahedron 2007, 63, 4199-4236.
13. K. S. Yang, G. Budin, T. Reiner, C. Vinegoni, R. Weissleder, Angew. Chem. 2012, 124, 6702-6707
14. Angew. Chem. Int. Ed. 2012, 51, 6598-6603
15. T. Plass, S. Milles, C. Koehler, J. Szymanski, R. Mueller, M. Wiessler, C. Schultz, E. A. Lemke, Angew. Chem. 2012, 124, 4242-4246
16. Angew. Chem. Int. Ed. 2012, 51, 4166-4170
17. K. Lang, L. Davis, J. Torres-Kolbus, C. J. Chou, A. Deiters, J. W. Chin, Nat. Chem. 2012, 4, 298-304.
18. N. K. Devaraj, S. Hilderbrand, R. Upadhyay, R. Mazitschek, R. Weissleder, Angew. Chem. 2010, 122, 2931-2934
19. Angew. Chem. Int. Ed. 2010, 49, 2869-2872.
20. J. C. T. Carlson, L. G. Meimetis, S. A. Hilderbrand, R. Weissleder, Angew. Chem. 2013, 125, 7055-7058
21. Angew. Chem. Int. Ed. 2013, 52, 6917-6920.
22. I. D. L. Albert, T. J. Marks, M. A. Ratner, J. Am. Chem. Soc. 1997, 119, 6575-6582
23. P. Audebert, S. Sadki, F. Miomandre, G. Clavier, Electrochem. Commun. 2004, 6, 144-147
24. P. Audebert, S. Sadki, F. Miomandre, G. Clavier, M. C. Vernieres, M. Saoud, P. Hapiot, New J. Chem. 2004, 28, 387-392
25. W. B. Ma, Y. Q. Wu, D. H. Gu, F. X. Gan, J. Mol. Struct. 2006, 774, 13-18.
26. J. Yang, M. R. Karver, W. Li, S. Sahu, N. K. Devaraj, Angew. Chem. 2012, 124, 5312-5315
27. Angew. Chem. Int. Ed. 2012, 51, 5222-5225.
28. G. D. Byrkit, G. A. Michalek, Ind. Eng. Chem. 1950, 42, 1862-1875.
29. N. Leconte, A. Keromnes-Wuillaume, F. Suzenet, G. Guillaumet, Synlett 2007, 204-210
30. Z. Novák, A. Kotschy, Org. Lett. 2003, 5, 3495-3497.
31. A. C. Knall, C. Slugovc, Chem. Soc. Rev. 2013, 42, 5131-5142.
32. S. Pican, V. Lapinte, J. F. Pilard, E. Pasquinet, L. Beller, L. Fontaine, D. Poullain, Synlett 2009, 731-734.
33. C. F. B. Praquin, P. D. Koning, P. J. Peach, R. M. Howard, S. L. Spencer, Org. Process Res. Dev. 2011, 15, 1124-1129
34. G. K. S. Prakash, P. V. Jog, H. S. Krishnan, G. A. Olah, J. Am. Chem. Soc. 2011, 133, 2140
35. A. S. Saiyed, A. V. Bedekar, Tetrahedron Lett. 2010, 51, 6227-6231.
36. V. P. Mehtaa, E. V. Van der Eycken, Chem. Soc. Rev. 2011, 40, 4925-4936.
37. J. P. Stambuli, S. R. Stauffer, K. H. Shaughnessy, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 2677-2678
38. M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298
39. Q. Shelby, N. Kataoka, G. Mann, J. Hartwig, J. Am. Chem. Soc. 2000, 122, 10718-10719
40. N. Kataoka, Q. Shelby, J. P. Stambuli, J. Hartwig, J. Org. Chem. 2002, 67, 5553-5566.
41. T. Lifka, H. Meier, J. Prakt. Chem./Chem.-Ztg. 1995, 337, 641-646.
42. J. Seckute, J. Yang, N. K. Devaraj, Nucleic Acids Res. 2013, 41, e 148
43. K. Lang, L. Davis, S. Wallace, M. Mahesh, D. J. Cox, M. L. Blackman, J. M. Fox, J. W. Chin, J. Am. Chem. Soc. 2012, 134, 10317-10320
44. J. Schoch, M. Wiessler, A. Jaschke, J. Am. Chem. Soc. 2010, 132, 8846-8847.
45. M. R. Karver, R. Weissleder, S. A. Hilderbrand, Bioconjugate Chem. 2011, 22, 2263-2270.
46. C. M. Cole, J. Yang, J. Seckute, N. K. Devaraj, ChemBioChem 2013, 14, 205-208.
47. C. Dumas-Verdes, F. Miomandre, E. Lepicier, O. Galangau, T. T. Vu, G. Clavier, R. Meallet-Renault, P. Audebert, Eur. J. Org. Chem. 2010, 2525-2535.
48. G. Ulrich, C. Goze, M. Guardigli, A. Roda, R. Ziessel, Angew. Chem. 2005, 117, 3760-3764
49. Angew. Chem. Int. Ed. 2005, 44, 3694-3698.
50. A. Loudet, K. Burgess, Chem. Rev. 2007, 107, 4891-4932.
51. A. Burghart, L. H. Thoresen, J. Chen, K. Burgess, F. Bergstrom, L. B. A. Johansson, Chem. Commun. 2000, 2203-2204
52. G. S. Jiao, L. H. Thoresen, K. Burgess, J. Am. Chem. Soc. 2003, 125, 14668-14669.
53. J. Yang, Y. Liang, J. Seckute, K. N. Houk, N. K. Devaraj, Chem. Eur. J. 2014, 20, 3365- 3375.
54. N. K. Devaraj, G. M. Thurber, E. J. Keliher, B. Marinelli, R. Weissleder, Proc. Natl. Acad. Sci. USA 2012, 109, 4762-4767.