Reversible off-on fluorescence probe for hypoxia and imaging of hypoxia-normoxia cycles in live cells

Journal of the American Chemical Society

Volumn 134, Issue 48, 2012, Pages 19588-19591

  Takahashi, Shodai ^a   Piao, Wen ^a   Matsumura, Yuriko ^b   Komatsu, Toru ^a   Ueno, Tasuku ^a   Terai, Takuya ^a   Kamachi, Toshiaki ^b   Kohno, Masahiro ^b   Nagano, Tetsuo ^a   Hanaoka, Kenjiro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b Tokyo Institute of Technology ^*  (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORBANCES; BIOREDUCTIONS; CYANINE DYES; FLUORESCENCE PROBES; LIVE CELL; RESONANCE ENERGY TRANSFER;

ENERGY TRANSFER; PROBES;

FLUORESCENCE;

2 AMINOANTHRAQUINONE; ANTHRAQUINONE DERIVATIVE; CYANINE DYE 5; MALACHITE GREEN; UNCLASSIFIED DRUG;

ARTICLE; CELL HYPOXIA; CHEMICAL STRUCTURE; ENERGY TRANSFER; FLUORESCENCE; FORSTER RESONANCE ENERGY TRANSFER; OXIDATION;

ANOXIA; ANTHRAQUINONES; CELL LINE, TUMOR; FLUORESCENCE RESONANCE ENERGY TRANSFER; FLUORESCENT DYES; HUMANS; MICROSCOPY, CONFOCAL; MOLECULAR STRUCTURE; NUCLEOTIDES; OXIDATION-REDUCTION; RHODAMINES; ROSANILINE DYES;

EID: 84870673782     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja310049d     Document Type: Article

References (31)

1. Wilson, W. R.; Hay, M. P. Nat. Rev. Cancer 2011, 11, 393
2. Garvey, J. F.; Taylor, C. T.; McNicholas, W. T. Eur. Respir. J. 2009, 33, 1195
3. Tang, Y.; Lu, A.; Aronow, B. J.; Wagner, K. R.; Sharp, F. R. Eur. J. Neurosci. 2002, 15, 1937
4. Varia, M. A.; Calkins-Adams, D. P.; Rinker, L. H.; Kennedy, A. S.; Novotny, D. B.; Fowler, W. C., Jr.; Raleigh, J. A. Gynecol. Oncol. 1998, 71, 270
5. Kaanders, J. H. A. M.; Wijffels, K. I. E. M.; Marres, H. A. M.; Ljungkvist, A. S. E.; Pop, L. A. M.; Van den Hoogen, F. J. A.; De Wilde, P. C. M.; Bussink, J.; Raleigh, J. A.; Van der Kogel, A. J. Cancer Res. 2002, 62, 7066
6. Yang, D. J.; Wallace, S.; Cherif, A.; Li, C.; Gretzer, M. B.; Kim, E. E.; Podoloff, D. A. Radiology 1995, 194, 795
7. Dearlin, J. L. J.; Lewis, J. S.; Mullen, G. E. D.; Welch, M. J.; Blower, P. J. J. Biol. Inorg. Chem. 2002, 7, 249
8. Zhang, S.; Hosaka, M.; Yoshihara, T.; Negishi, K.; Iida, Y.; Tobita, S.; Takeuchi, T. Cancer Res. 2010, 70, 4490
9. Sakadžić, S.; Roussakis, E.; Yaseen, M. A.; Mandeville, E. T.; Srinivasan, V. J.; Arai, K.; Ruvinskaya, S.; Devor, A.; Lo, E. H.; Vinogradov, S. A.; Boas, D. A. Nat. Methods 2010, 7, 755
10. Pacheco-Torres, J.; Lopeź-Larrubia, P.; Ballesteros, P.; Cerdán, S. NMR Biomed. 2011, 24, 1
11. Iwaki, S.; Hanaoka, K.; Piao, W.; Komatsu, T.; Ueno, T.; Terai, T.; Nagano, T. Bioorg. Med. Chem. Lett. 2012, 22, 2798
12. Nakata, E.; Yukimachi, Y.; Kariyazono, H.; Im, S.; Abe, C.; Uto, Y.; Maezawa, H.; Hashimoto, T.; Okamoto, Y.; Hori, H. Bioorg. Med. Chem. 2009, 17, 6952
13. Cui, L.; Zhong, Y.; Zhu, W.; Xu, Y.; Du, Q.; Wang, X.; Qian, X.; Xiao, Y. Org. Lett. 2011, 13, 928
14. Komatsu, H.; Harada, H.; Tanabe, K.; Hiraoka, M.; Nishimoto, S. Med. Chem. Commun. 2010, 1, 50
15. Kiyose, K.; Hanaoka, K.; Oushiki, D.; Nakamura, T.; Kajimura, M.; Suematsu, M.; Nishimatsu, H.; Yamane, T.; Terai, T.; Hirata, Y.; Nagano, T. J. Am. Chem. Soc. 2010, 132, 15846
16. Semenza, G. L. Nat. Rev. Cancer 2003, 3, 721
17. Brown, J. M.; Wilson, W. R. Nat. Rev. Cancer 2004, 4, 437
18. Dewhirst, M. W.; Cao, Y.; Moeller, B. Nat. Rev. Cancer 2008, 8, 425
19. Hilberbrand, S. A.; Lim, M. H.; Lippard, S. T. J. Am. Chem. Soc. 2004, 126, 4972
20. Miller, E. W.; Bian, S. X.; Chang, C. J. J. Am. Chem. Soc. 2007, 129, 3458
21. Koide, Y.; Kawaguchi, M.; Urano, Y.; Hanaoka, K.; Komatsu, T.; Abo, M.; Terai, T.; Nagano, T. Chem. Commun. 2012, 48, 3091
22. Yu, F.; Li, P.; Li., G.; Zhao, G.; Chu, T.; Han, K. J. Am. Chem. Soc. 2011, 133, 11030
23. Iyanagi, T.; Yamazaki, I. Biochim. Biophys. Acta 1970, 216, 282
24. Henderson, A. L.; Schmitt, T. C.; Heinze, T. M.; Cerniglia, C. E. Appl. Environ. Microbiol. 1997, 63, 4099
25. Richard, P. Eur. Pat. EP 1 090 073 B1, 2003.
26. Van de Linde, S.; Krstić, I.; Prisner, T.; Doose, S.; Heilemann, M.; Sauer, M. Photochem. Photobiol. Sci. 2011, 10, 499
27. Gomberg, M. J. Am. Chem. Soc. 1900, 22, 757
28. Acar, M. H.; Yagci, Y.; Schnabel, W. Polym. Int. 1998, 46, 331
29. Sinclair, J.; Kivelson, D. J. Am. Chem. Soc. 1968, 11, 5074
30. Sato, S.; Tsunoda, M.; Suzuki, M.; Kutsuna, M.; Takido-uchi, K.; Shindo, M.; Mizuguchi, H.; Obara, H.; Ohya, H. Spectrochim. Acta A 2009, 71, 2030
31. Takahashi, E.; Sato, M. Am. J. Physiol. Cell Physiol. 2010, 299, C1318