Design and synthesis of a new class of membrane-permeable triazaborolopyridinium fluorescent probes

Journal of the American Chemical Society

Volumn 133, Issue 17, 2011, Pages 6780-6790

  Hapuarachchige, Sudath ^a   Montaño, Gilbert ^a   Ramesh, Chinnasamy ^a   Rodriguez, Delany ^a   Henson, Lauren H ^a   Williams, Casey C ^a   Kadavakkollu, Samuel ^a   Johnson, Dennis L ^a   Shuster, Charles B ^a   Arterburn, Jeffrey B ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALEXA FLUOR; ALLOSTERIC INHIBITOR; CELL MEMBRANE PERMEABILITY; CELL-BASED; DYE MOIETIES; DYE STRUCTURE; FLUORESCENT DYES; FLUORESCENT PROBES; HYDRAZONES; IMAGING AGENT; INTRACELLULAR PROTEINS; KINESINS; LIVE-CELL IMAGING; MEMBRANE-PERMEABLE; NEUTRAL-CHARGE; PHOTOPHYSICAL; PYRIDYL; SMALL MOLECULES; STOKES SHIFT; WATER SOLUBILITIES;

AMINO ACIDS; CELL MEMBRANES; CYTOLOGY; FLUORESCENCE;

PROBES;

2 HYDRAZINYLPYRIDINE; CYSTEINE; KINESIN; KINESIN SPINDLE PROTEIN; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; TRIAZABOROLOPYRIDINIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; FLUORESCENCE; MEMBRANE PERMEABILITY; SYNTHESIS;

CELL MEMBRANE; CELL MEMBRANE PERMEABILITY; FLUORESCENT DYES; HELA CELLS; HUMANS; PYRIDINIUM COMPOUNDS; PYRIDONES;

EID: 79955392791     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2005175     Document Type: Article

References (41)

1. Zhang, J.; Campbell, R. E.; Ting, A. Y.; Tsien, R. Y. Nat. Rev. Mol. Cell Biol. 2002, 3, 906-918
2. Lavis, L. D.; Raines, R. T. ACS Chem. Biol. 2008, 3 (3) 142-155
3. Walter, N. G.; Huang, C. Y.; Manzo, A. J.; Sobhy, M. A. Nature Methods 2008, 5 (6) 475-489
4. Tinnefeld, P.; Sauer, M. Angew. Chem., Int. Ed. 2005, 44, 2642-2671
5. Goncalves, M. S. T. Chem. Rev. 2009, 109, 190-212
6. Kobayashi, H.; Ogawa, M.; Alford, R.; Choyke, P. L.; Urano, Y. Chem. Rev. 2010, 110, 2620-2640
7. Loudet, A.; Burgess, K. Chem. Rev. 2007, 107 (11) 4891-4932
8. Kim, E.; Koh, M.; Ryu, J.; Park, S. B. J. Am. Chem. Soc. 2008, 130, 12206-12207
9. Abet, V.; Nuñez, A.; Mendicuti, F.; Burgos, C.; Alvarez-Builla, J. J. Org. Chem. 2008, 73, 8800-8807
10. Ozhalici-Unal, H.; Pow, C. L.; Marks, S. A.; Jesper, L. D.; Silva, G. L.; Shank, N. I.; Jones, E. W.; Burnette, J. M.; Berget, P. B.; Armitage, B. A. J. Am. Chem. Soc. 2008, 130 (38) 12620-12621
11. Alexander, M. D. ChemBioChem 2006, 7, 409-416
12. Ramesh, C.; Bryant, B.; Nayak, T.; Revankar, C. M.; Anderson, T.; Carlson, K. E.; Katzenellenbogen, J. A.; Sklar, L. A.; Norenberg, J. P.; Prossnitz, E. R.; Arterburn, J. B. J. Am. Chem. Soc. 2006, 128, 14476-14477
13. Nayak, T. K.; Hathaway, H. J.; Ramesh, C.; Arterburn, J. B.; Dai, D.; Sklar, L. A.; Norenberg, J. P.; Prossnitz, E. R. J. Nucl. Med. 2008, 49 (6) 978-986
14. Dubs, P.; Bourel-Bonnet, L.; Subra, G.; Blanpain, A.; Melnyk, O.; Pinel, A. M.; Gras-Masse, H.; Martinez, J. J. Comb. Chem. 2007, 9, 973-981
15. Kurpiers, T.; Mootz, H. D. Angew. Chem., Int. Ed. 2009, 48, 1729-1731
16. Dilek, O.; Bane, S. L. Tetrahedron Lett. 2008, 49, 1413-1416
17. Tang, W.; Xiang, Y.; Tong, A. J. Org. Chem. 2009, 74, 2163-2166
18. Dirksen, A.; Yegneswaran, S.; Dawson, P. E. Angew. Chem., Int. Ed. 2010, 49, 2023-2027
19. SoluLink: http://www.solulink.com/productindex.php.
20. Umezawa, K.; Nakamura, Y.; Makino, H.; Citterio, D.; Suzuki, K. J. Am. Chem. Soc. 2008, 130, 1550-1551
21. Zhang, G.; Chen, J.; Payne, S.; Kooi, S. E.; Demas, J. N.; Fraser, C. L. J. Am. Chem. Soc. 2007, 129, 8942-8943
22. Gorman, A.; Killoran, J.; O'Shea, C.; Kenna, T.; Gallagher, W. M.; O'Shea, D. F. J. Am. Chem. Soc. 2004, 126, 10619-10631
23. Zhou, Y.; Xiao, Y.; Chi, S.; Qian, X. Org. Lett. 2008, 10, 633-636
24. Han, J.; Loudet, A.; Barhoumi, R.; Burghardt, R. C.; Burgess, K. J. Am. Chem. Soc. 2009, 131, 1642-1643
25. Tasior, M.; O'Shea, D. F. Bioconjugate Chem. 2010, 21, 1130-1133
26. Chang, P. V.; Prescher, J. A.; Hangauer, M. J.; Bertozzi, C. R. J. Am. Chem. Soc. 2007, 129, 8400-8401
27. Shao, F.; Weissleder, R.; Hilderbrand, S. A. Bioconjugate Chem. 2008, 19, 2487-2491
28. Tsou, L. K.; Zhang, M. M.; Hang, H. C. Org. Biomol. Chem. 2009, 7, 5055-5058
29. Jewett, J. C.; Sletten, E. M.; Bertozzi, C. R. J. Am. Chem. Soc. 2010, 132, 3688-3690
30. Tahtaoui, C.; Thomas, C.; Rohmer, F.; Klotz, P.; Duportail, G.; Mély, Y.; Bonnet, D.; Hibert, M. J. Org. Chem. 2007, 72, 269-272
31. Debonis, S.; Skoufias, D. A.; Lebeau, L.; Lopez, R.; Robin, G.; Margolis, R. L.; Wade, R. H.; Kozielski, F. Mol. Cancer Ther. 2004, 3, 1079-1090
32. Debonis, S.; Skoufias, D. A.; Indorato, R. L.; Liger, F.; Marquet, B.; Laggner, C.; Joesph, B.; Kozielski, F. J. Med. Chem. 2008, 51, 1115-1125
33. Ogo, N.; Oishi, S.; Matsuno, K.; Sawada, J.; Fujii, N.; Asai, A. Bioorg. Med. Chem. Lett. 2007, 17, 3921-3924
34. Brier, S.; Lemaire, D.; DeBonis, S.; Forest, E.; Kozielski, F. Biochemistry 2004, 43, 13072-13082
35. Skoufias, D. A.; Debonis, S.; Saoudi, Y.; Lebeau, L; Crevel, I.; Cross, R.; Wade, R. H; Hackney, D.; Kozielski, F. J. Biol. Chem. 2006, 281, 17559-17569
36. Peterson, J. R.; Mitchison, T. J. Chem. Biol. 2002, 9, 1275-1295
37. Verbrugge, S.; Lechner, B.; Woehlke, G.; Peterman, E. J. G. Biophys. J. 2009, 97, 173-182
38. Johnson, I. Histochem. J. 1998, 30, 123-140
39. Puckett, C. A.; Barton, J. K. J. Am. Chem. Soc. 2009, 131, 8738-8739
40. Lemcke, S.; Hönnscheidt, C.; Waschatko, G.; Bopp, A.; Lütjohann, D.; Bertram, N.; Gehrig-Burger, K. Mol. Cell. Endocrinol. 2010, 314, 31-40
41. Rickert, E. L.; Oriana, S.; Hartman-Frey, C.; Long, X.; Webb, T. T.; Nephew, K. P.; Weatherman, R. V. Bioconjugate Chem. 2010, 21, 903-910