A rhodamine-hydroxamic acid-based fluorescent probe for hypochlorous acid and its applications to Biological imagings

Organic Letters

Volumn 11, Issue 4, 2009, Pages 859-861

  Yang, Young Keun ^a   Cho, Hyungseoph Jason ^a   Lee, Jihyun ^a   Shin, Injae ^a   Tae, Jinsung ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

DIAGNOSTIC AGENT; FLUORESCENT DYE; HYDROXAMIC ACID; HYPOCHLOROUS ACID; REACTIVE OXYGEN METABOLITE; RHODAMINE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DIAGNOSTIC IMAGING; HUMAN; SYNTHESIS; ZEBRA FISH;

ANIMALS; DIAGNOSTIC IMAGING; FLUORESCENT DYES; HUMANS; HYDROXAMIC ACIDS; HYPOCHLOROUS ACID; MOLECULAR STRUCTURE; REACTIVE OXYGEN SPECIES; RHODAMINES; ZEBRAFISH;

EID: 62749100714     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802822t     Document Type: Article

References (31)

1. (a) Gomes, A.; Fernandes, E.; Lima, J. L. F. C. J. Biochem. Biophys. Methods 2005, 65, 45-80.
2. (b) Li, X. H.; Zhang, G. X.; Ma, H. M.; Zhang, D. Q.; Li, J.; Zhu, D. B. J. Am. Chem. Soc. 2004, 126, 11543-11548.
3. In the physiological pH solutions, HOCl rather than OCl-is the actual species. See refs 6a, c, and d for the discussion.
4. (a) Kettle, A. J.; Winterbourn, C. C. Redox Rep. 1997, 3, 3-15.
5. (b) Hidalgo, E.; Bartolome, R.; Dominguez, C. Chem. Biol. Interact. 2002, 139, 265-282.
6. (c) Pattison, D. I.; Davies, M. J. Chem. Res. Toxicol. 2001, 14, 1453-1464.
7. (d) O'Brien, P. J. Chem. Biol. Interact. 2000, 129, 113-139.
8. (a) Yap, Y. W.; Whiteman, M.; Cheung, N. S. Cell Signal 2007, 19, 219-228.
9. (b) Pattison, D. I.; Davies, M. J. Biochemistry 2006, 45, 8152-8162.
10. (c) Sugiyama, S.; Kugiyama, K.; Aikawa, M.; Nakamura, S.; Ogawa, H.; Libby, P. Atrerioscler Thromb. Vasc. Biol. 2004, 24, 1309-1314.
11. (d) Podrez, E. A.; Abu-Soud, H. M.; Hazen, S. L. Free Radical Biol. Med. 2000, 28, 1717-1725.
12. (a) Kawai, Y.; Kiyokawa, H.; Kimura, Y.; Kato, Y.; Tsuchiya, K.; Terao, J. Biochemistry 2006, 45, 14201-14211.
13. (b) Pattison, D. I.; Davies, M. J. Biochemistry 2005, 44, 7378-7387.
14. (a) Sun, Z. N.; Liu, F. Q.; Chen, Y.; Tam, P. K. H.; Yang, D. Org. Lett. 2008, 10, 2171-2174.
15. (b) Chen, X.; Wang, X.; Wang, S.; Shi, W.; Wang, K.; Ma, H. Chem.-Eur. J. 2008, 14, 4719-4724.
16. (c) Kenmoku, S.; Urano, Y.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2007, 129, 7313-7318.
17. (d) Shepherd, J.; Hilderbrand, S. A.; Waternan, P.; Heinecke, J. W.; Weissleder, R.; Libby, P. Chem. Biol. 2007, 14, 1221-1231.
18. (e) Bizyukin, A. V.; Korkina, L. G.; Velichkovskii, B. T. Bull. Exp. Biol. Med. 1995, 119, 347-351.
19. (a) Pereira, W. E.; Hoyano, Y.; Summons, R. E.; Bacon, V. A.; Duffield, A. M. Biochim. Biophys. Acta 1973, 313, 170-180.
20. (b) Davies, M. J.; Hawkins, C. L. Free Radical Res. 2000, 33, 719-729.
21. Slates, H. L.; Taub, D.; Kuo, C. H.; Wendler, N. L. J. Org. Chem. 1964, 29, 1424-1429.
22. Kim, H. N.; Lee, M. H.; Kim, H. J.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2008, 37, 1467-1472.
23. (a) Yang, Y. K.; Yook, K. J.; Tae, J. J. Am. Chem. Soc. 2005, 127, 16760-16761.
24. (b) Ko, S. K.; Yang, Y. K.; Tae, J.; Shin, I. J. Am. Chem. Soc. 2006, 128, 14150-14155.
25. (c) Yang, Y. K.; Ko, S. K.; Shin, I.; Tae, J. Nat. protocols. 2007, 2, 1740-1745.
26. For the synthesis and characterization of fluorescent probe 1, see Supporting Information.
27. 2 or OH at the xantene ring (see ref 10a).
28. Cohen, A. D.; Zeng, B.-B.; King, S. B.; Toscano, J. P. J. Am. Chem. Soc. 2003, 125, 1444-1445.
29. 1H NMR spectrum obtained from the reaction mixture run in an NMR tube. Furthermore, rhodamine 19 is isolated as the major product after flash column chromatography of the reaction mixture (see Supporting Information).
30. Additions of 5-100 equiv of ROS other than NaOCl showed no fluorescence intensity changes at all (see Supporting Information).
31. It is not easy to directly compare properties of 1 with those of the known probes for HOCl. But we believe that the readily available rhodamine amide derivative 1 could find broad biological applications.