Rhodamine triazole-based fluorescent probe for the detection of Pt 2+

Organic Letters

Volumn 12, Issue 22, 2010, Pages 5342-5345

  Kim, Hyemi ^a   Lee, Sunho ^a   Lee, Jihyun ^a   Tae, Jinsung ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CISPLATIN; FLUORESCENT DYE; ION; PLATINUM; RHODAMINE; TRIAZOLE DERIVATIVE; WATER;

ARTICLE; CHEMISTRY; COLORIMETRY; SOLUTION AND SOLUBILITY; SYNTHESIS;

CISPLATIN; COLORIMETRY; FLUORESCENT DYES; IONS; PLATINUM; RHODAMINES; SOLUTIONS; TRIAZOLES; WATER;

EID: 78449284170     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102397n     Document Type: Article

References (62)

1. Reedijk, J. Pure Appl. Chem. 1987, 59, 181-192
2. Cepeda, V.; Fuertes, M. A.; Castilla, J.; Alonso, C.; Quevedo, C.; Pérez, J. M. Anticancer Agents Med. Chem. 2007, 7, 3-18
3. Platinum; World Health Organization: Geneva, 1991.
4. Hartmann, J. T.; Lipp, H.-P. Expert Opin. Pharmacother. 2003, 4, 889-901
5. Schiller, J. H.; Bittner, G. Clin. Cancer Res. 1999, 5, 4287-4294
6. Rudolph, E.; Hann, S.; Stingeder, G.; Reiter, C. Anal. Bioanal. Chem. 2005, 382, 1500-1506
7. Danford, A. J.; Wang, D.; Wang, Q.; Tullius, T. D.; Lippard, S. J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 12311-12316
8. Ahmad, S. Chem. Biol. 2010, 7, 543-566
9. Jakubowski, N.; Feldmann, I.; Stuewer, D. J. Anal. At. Spectrom. 1997, 12, 151-157
10. Welters, M. J. P.; Fichtinger-Schepman, A. M. J.; Baan, R. A.; Jacobs-Bergmans, A. J.; Kegel, A.; Van Der Vijgh, W. J. F.; Braakhuis, B. J. M. Br. J. Cancer 1999, 79, 82-88
11. Ghezzi, A. R.; Aceto, M.; Cassino, C.; Gabano, E.; Osella, D. J. Inorg. Biochem. 2004, 98, 73-78
12. Klein, A. V.; Hambley, T. W. Chem. Rev. 2009, 109, 4911-4920
13. Garner, A. L.; Koide, K. Chem. Commun. 2009, 83-85
14. Garner, A. L.; Koide, K. Chem. Commun. 2009, 86-88
15. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
16. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128-1137
17. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249-1262
18. Fournier, D.; Hoogenboom, R.; Schubert, U. S. Chem. Soc. Rev. 2007, 36, 1369-1380
19. Angell, Y. L.; Burgess, K. Chem. Soc. Rev. 2007, 36, 1674-1689
20. Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952-3015
21. Amblard, F.; Cho, J. H.; Schinazi, R. F. Chem. Rev. 2009, 109, 4207-4220
22. Iha, R. K.; Wooley, K. L.; Nyström, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620-5686
23. Holub, J. M.; Kirshenbaum, K. Chem. Soc. Rev. 2010, 39, 1325-1337
24. Chang, K.-C.; Su, I.-H.; Senthivelan, A.; Chung, W.-S. Org. Lett. 2007, 9, 3363-3366
25. Chang, K.-C.; Su, I.-H.; Lee, G.-H.; Chung, W.-S. Tetrahedron Lett. 2007, 48, 7274-7278
26. Park, S. Y.; Yoon, J. H.; Hong, C. S.; Souane, R.; Kim, J. S.; Matthews, S. E.; Vicens, J. J. Org. Chem. 2008, 73, 8212-8218
27. Pathak, R. K.; Ibrahim, S. M.; Rao, C. P. Tetrahedron Lett. 2009, 50, 2730-2734
28. Tamanini, E.; Katewa, A.; Sedger, L. M.; Todd, M. H.; Watkinson, M. Inorg. Chem. 2009, 48, 319-324
29. Ballesteros-Garrido, R.; Abarca, B.; Ballesteros, R.; Ramírez de Arellano, C.; Leroux, F. R.; Colobert, F.; García-España, G. New J. Chem. 2009, 33, 2102-2106
30. Tamanini, E.; Flavin, K.; Motevalli, M.; Piperno, S.; Gheber, L. A.; Todd, M. H.; Watkinson, M. Inorg. Chem. 2010, 49, 3789-3800
31. Pathak, R. K.; Dikundwar, A. G.; Row, T. N. G.; Rao, C. P. Chem. Commun. 2010, 46, 4345-4347
32. Hsieh, Y.-C.; Chir., J.-L.; Wu, H.-H.; Chang, P.-S.; Wu, A.-T. Carbohydr. Res. 2009, 344, 2236-2239
33. Chen, Y.-B.; Wang, Y.-J.; Lin, Y.-J.; Hu, C.-H.; Chen, S.-J.; Chir, J.-L.; Wu, A.-T. Carbohydr. Res. 2010, 345, 956-959
34. Hsieh, Y.-C.; Chir, J.-L.; Wu, H.-H.; Guo, C.-Q.; Wu, A.-T. Tetrahedron Lett. 2010, 51, 109-111
35. Hung, H.-C.; Cheng, C.-W.; Wang, Y,-Y.; Chen, Y.-J.; Chung, W.-S. Eur. J. Org. Chem. 2009, 6360-6366
36. Kumar, A.; Pandey, P. S. Tetrahedron Lett. 2009, 50, 5842-5845
37. Huang, X.; Meng, J.; Dong, Y.; Cheng, Y.; Zhu, C. Polymer 2010, 51, 3064-3067
38. Li, H.; Yao, Y.; Han, C.; Zhan, J. Chem. Commun. 2009, 4812-4814
39. Zhang, Y.-M.; Chen, Y.; Li., Z.-Q.; Li, N.; Liu, Y. Bioorg. Med. Chem. 2010, 18, 1415-1420
40. Zhan, J.; Tian, D.; Li, H. New J. Chem. 2009, 33, 725-728
41. Maity, D.; Govindaraju, T. Chem. Commun. 2010, 46, 4499-4501
42. Kim, S. H.; Choi, H. S.; Kim, J.; Lee, S. J.; Quang, D. T.; Kim, J. S. Org. Lett. 2010, 12, 560-563
43. For selective examples of rhodamine amide-based fluorescent chemosensors, see
44. Kim, H. N.; Lee, M. H.; Kim, H. J.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2008, 37, 1467-1472
45. Yang, Y.-K.; Yook, K.-J.; Tae, J. J. Am. Chem. Soc. 2005, 127, 16760-16761
46. Ko, S.-K.; Yang, Y.-K.; Tae, J.; Shin, I. J. Am. Chem. Soc. 2006, 128, 14150-14155
47. Yang, Y.-K.; Ko, S.-K.; Shin, I.; Tae, J. Nat. Protoc. 2007, 2, 1740-1745
48. Yang, Y.-K.; Cho., H. J.; Lee, J.; Shin, I.; Tae, J. Org. Lett. 2009, 11, 859-861
49. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021
50. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
51. Yang, Y.-K.; Lee, S.; Tae, J. Org. Lett. 2009, 11, 5610-5613
52. Kang, S.; Kim, S.; Yang, Y.-K.; Bae, S.; Tae, J. Tetrahedron Lett. 2009, 50, 2010-2012
53. Moon, K.-S.; Yang, Y.-K.; Ji, S.; Tae, J. Tetrahedron Lett. 2010, 51, 3290-3293
54. Connors, K. A. Binding Constants-The Measurement of Molecular Complex Stability; John Wiley & Sons: New York, 1987; Chapter 4.
55. 2+ induce strong absorptions at ∼541 nm (see Supporting Information).
56. Duan, L. P.; Xu, Y. F.; Qian, X. H. Chem. Commun. 2008, 6339-6341
57. Li, H.; Fan, J.; Du, J.; Guo, K.; Sun, S.; Liu, X.; Peng, X. Chem. Commun. 2010, 1079-1081
58. For the review of the analytical detection method of cisplatin, see ref 4d.
59. For the detection of cisplatin using a fluorescent probe, see ref 5a.
60. It seems that the ligand exchange reactions of the platinum complexes take place slowly. See
61. Reedijk, J. Platinum Met. Rev. 2008, 52, 2-11
62. The related hydroxamate binding platforms containing a simple binding unit, such as a pyridine and an amino group instead of a triazole, show nonselective binding properties.