Browse > Article
http://dx.doi.org/10.5012/bkcs.2010.31.12.3611

New 7-Hydroxycoumarin-Based Fluorescent Chemosensors for Zn(II) and Cd(II)  

Swamy, K.M.K. (Department of Chemistry and Nano Science (BK21) and Department of Bioinspired Science (WCU), Ewha Womans University)
Kim, Min-Jung (Department of Chemistry and Nano Science (BK21) and Department of Bioinspired Science (WCU), Ewha Womans University)
Jeon, Hye-Ryeong (Department of Chemistry and Nano Science (BK21) and Department of Bioinspired Science (WCU), Ewha Womans University)
Jung, Ji-Young (Department of Chemistry and Nano Science (BK21) and Department of Bioinspired Science (WCU), Ewha Womans University)
Yoon, Ju-Young (Department of Chemistry and Nano Science (BK21) and Department of Bioinspired Science (WCU), Ewha Womans University)
Publication Information
Abstract
Five new 4- or 8-substituted-7-hydroxycoumarin derivatives (1-5) were synthesized as fluorescent sensors for metal ions. Fluorescent changes and selectivity for metal ions were compared based on the introduction of different ligands and/or testing with different substitution positions of 7-hydroxycoumarin in aqueous solution. Especially, probes 2, 3 and 5 displayed large fluorescence enhancements with $Zn^{2+}$ and $Cd^{2+}$. Probes 2 and 3 showed moderate selectivity for $Zn^{2+}$ over $Cd^{2+}$. On the other hand, probe 4 showed large fluorescence quenching effects upon the addition of $Ag^+$ and $Hg^{2+}$.
Keywords
Fluorescent chemosensors; Coumarin; $Zn^{2+}$ sensor; $Cd^{2+}$ sensor; Fluorescence;
Citations & Related Records

Times Cited By Web Of Science : 7  (Related Records In Web of Science)
Times Cited By SCOPUS : 3
연도 인용수 순위
  • Reference
1 Swamy, K. M. K.; Kim, H. N.; Soh, J. H.; Kim, Y.; Kim, S.-J.; Yoon, J. Chem. Commun. 2009, 1234.
2 Chatterjee, A.; Santra, M.; Won, N.; Kim, S.; Kim, J. K.; Kim, S. B.; Ahn, K. H. J. Am. Chem. Soc. 2009, 131, 2040.   DOI   ScienceOn
3 Kang, J.; Choi, M.; Lee, E. Y.; Yoon, J. J. Org. Chem. 2002, 67, 4384.   DOI   ScienceOn
4 Samamoto, T.; Ojida, A.; Hamachi, I. Chem. Commun. 2009, 141.
5 Kim, S. K.; Lee, D. H.; Hong, J.-I.; Yoon, J. Acc. Chem. Res. 2009, 42, 23.   DOI   ScienceOn
6 Atilgan, S.; Ozdemir, T.; Akkaya, E. U. Org. Lett. 2008, 10, 4065.   DOI   ScienceOn
7 Chen, X.; Jou, M. J.; Yoon, J. Org. Lett. 2009, 11, 2181.   DOI   ScienceOn
8 Ojida, A.; Mito-oka, Y.; Sada, K.; Hamachi, I. J. Am. Chem. Soc. 2004, 126, 2454.   DOI   ScienceOn
9 Lee, D. H.; Kim, S. Y.; Hong, J.-I. Angew. Chem. Int. Ed. Engl. 2004, 43, 4777   DOI   ScienceOn
10 Lee, H. N.; Swamy, K. M. K.; Kim, S. K.; Kwon, J.-Y.; Kim, Y.; Kim, S.-J.; Yoon, Y. J.; Yoon, J. Org. Lett. 2007, 9, 243.   DOI   ScienceOn
11 Jang, Y. J.; Jun, E. J.; Lee, Y. J.; Kim, Y. S.; Kim, J. S.; Yoon, J. J. Org. Chem. 2005, 70, 9603.   DOI   ScienceOn
12 Peng, X.; Du, J.; Fan, J.; Wang, J.; Wu, Y.; Zhao, J.; Sun, S.; Xu, Tao J. Am. Chem. Soc. 2007, 129, 1500.   DOI   ScienceOn
13 Huang, X.; Guo, Z.; Zhu, W.; Xie, Y.; Tian, H. Chem. Commun. 2008, 5143.
14 Dakanali, M.; Roussakis, E.; Kay, A. R.; Katerinopoulos, H. E. Tetrahedron Lett. 2005, 45, 4193.
15 Jang, Y. J.; Moon, B.-S.; Park, M. S.; Kang, B.-G.; Kwon, J. Y.; Hong, J. S. J.; Yoon, Y. J.; Lee, K. D.; Yoon, J. Tetrahedron Lett. 2006, 47, 2707.   DOI   ScienceOn
16 Kulatilleke, C. P.; de Silva, S. A.; Eliav, Y. Polyhedron 2006, 25, 2593.   DOI   ScienceOn
17 Zhang, L.; Dong, S.; Zhu, L. Chem. Commun. 2007, 1891.
18 Kim, M. J.; Swamy, K. M. K.; Lee, K. M.; Jagdale, A. R.; Kim, Y.; Kim, S.-J.; Yoo, K. H.; Yoon, J. Chem. Commun. 2009, 7215.
19 Jung, H. S.; Kwon, P. S.; Lee, J. W.; Kim, J. I.; Hong, C. S.; Kim, J. W.; Yan, S.; Lee, J. Y.; Lee, J. H.; Joo, T.; Kim, J. S. J. Am. Chem. Soc. 2009, 131, 2008.   DOI   ScienceOn
20 Cho, Y. S.; Ahn, K. H. Tetrahedon Lett. 2010, 51, 3852.   DOI   ScienceOn
21 Chen, X.; Kang, S.; Kim, M. J.; Kim, J.; Kim, Y. S.; Kim, H.; Chi, B.; Kim, S.-J.; Lee, J. Y.; Yoon, J. Angew. Chem. Int. Ed. 2010, 49, 1422.   DOI   ScienceOn
22 Xu, Z.; Singh, N. J.; Lim, J.; Pan, J.; Kim, H. N.; Park, S.; Kim, K. S.; Yoon, J. J. Am. Chem. Soc. 2009, 131, 15528.   DOI   ScienceOn
23 Jou, M. J.; Chen, X.; Swamy, K. M. K.; Kim, H. N.; Kim, H.-J.; Lee, S.-g.; Yoon, J. Chem. Commun. 2009, 7218.
24 Chen, X.; Lee, J.; Jou, M. J.; Kim, J.-M.; Yoon, J. Chem. Commun. 2009, 3434.
25 Xu, Z.; Kim, S.; Lee, K.-H.; Yoon, J. Tetrahedron Lett. 2007, 48, 3797.   DOI   ScienceOn
26 Jun, E. J.; Won, H. N.; Kim, J. S.; Lee, K.-H.; Yoon, J. Tetrahedron Lett. 2006, 47, 4577.   DOI   ScienceOn
27 Parkesh, R.; Lee, T. C.; Gunnlaugsson, T. Org. Biomol. Chem. 2007, 310.
28 Choi, M.; Kim, M.; Lee, K. D.; Han, K.-N.; Yoon, I.-A.; Chung, H.-J.; Yoon, J. Org. Lett. 2001, 3, 3455.   DOI   ScienceOn
29 4-Methylumbelliferone (7-hydroxy-4-methyl coumarine) as a standard in 0.1 M NaOH solution. Chen, R. F. Anal. Lett. 1968, 1, 423.   DOI   ScienceOn
30 Wu, Y.; Peng, X.; Guo, B.; Fan, J.; Zhang, Z.; Wang, J.; Cui, A.; Gao, Y. Org. Biomol. Chem. 2005, 1387.
31 Joshi, B.; Cho, P. W.-M.; Kim, J. S.; Yoon, J.; Lee, K.-H. Bioorg. Med. Chem. Lett. 2007, 17, 6425.   DOI   ScienceOn
32 Park, M. S.; Swamy, K. M. K.; Lee, Y. J.; Lee, H. N.; Jang, Y. J.; Moon, Y. H.; Yoon, J. Tetrahedron Lett. 2006, 47, 8129.   DOI   ScienceOn
33 Lee, J. W.; Jung, H. S.; Kwon, P. S.; Kim, J. W.; Bartsch, R. A.; Kim, Y.; Kim, S.-J.; Kim, J. S. Org. Lett. 2008, 10, 3801.   DOI   ScienceOn
34 Xu, Z.; Kim, G.-H.; Han, S. J.; Jou, M. J.; Lee, C.; Shin, I.; Yoon, J. Tetrahedron 2009, 65, 2307.   DOI   ScienceOn
35 Du, J.; Fan, J.; Peng, X.; Li, H.; Sun, S. Sensors and Actuator B 2009, 144, 337.
36 Zhou, Y.; Kim, H. N.; Yoon, J. Bioorg. Med. Chem. Lett. 2010, 20, 125.   DOI   ScienceOn
37 Lu, X.; Zhu, W.; Xie, Y.; Li, X.; Gao, Y.; Li, F.; Tian, H. Chem. Eur J. 2010, 16, 8355.   DOI   ScienceOn
38 Goddard, J. P.; Raymond, J. L. Trends Biotechnol. 2004, 22, 363.
39 Katerinopoulos, H. E. Curr. Pharm. Des. 2004, 10, 3835.   DOI   ScienceOn
40 Mizukami, S.; Okada, S.; Kimura, S.; Kikuchi, K. Inorg. Chem. 2009, 48, 7630.   DOI   ScienceOn
41 Do, J. H.; Kim, H. N.; Yoon, J.; Kim, J. S.; Kim, H.-J. Org. Lett. 2010, 12, 932.   DOI   ScienceOn
42 Lim, N. C.; Schuster, J. V.; Porto, M. C.; Tanudra, M. A.; Yao, L.; Freake, H. C.; Bruckner, C. Inorg. Chem. 2005, 44, 2018.   DOI   ScienceOn
43 Kim, G.-J.; Kim, H.-J. Tetrahedron Lett. 2010, 51, 185.   DOI   ScienceOn
44 Komatsu, K.; Urano, Y.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2007, 129, 13447.   DOI   ScienceOn
45 Bush, A. I.; Pettingell, W. H.; Multhaup, G.; Paradis, M.; Vonsattel, J-P.; Gusella, J. F.; Beyreuther, K.; Masters, C. L.; Tanzi, R. E. Science 1994, 265, 1464.   DOI   ScienceOn
46 Koh, J. Y.; Suh, S. W.; Gwag, B. J.; He, Y. Y.; Hsu, C. Y.; Choi, D. W. Science 1996, 272, 1013.   DOI   ScienceOn
47 Frederickson, C. J.; Koh, J. Y.; Bush, A. I. Nat. Rev. Neurosci. 2005, 6, 449.   DOI   ScienceOn
48 Xu, Z.; Yoon, J.; Spring, D. R. Chem. Soc. Rev. 2010, 39, 1996.   DOI   ScienceOn
49 Que, E. L.; Domaille, D. W.; Chang, C. J. Chem. Rev. 2008, 108, 1517.   DOI   ScienceOn
50 Nolan, E. M.; Lippard, S. J. Acc. Chem. Res. 2009, 42, 193.   DOI   ScienceOn
51 Dai, Z.; Canary, J. W. New J. Chem. 2007, 31, 1708.   DOI   ScienceOn
52 Jiang, P.; Guo, J. Coord. Chem. Rev. 2004, 248, 205.   DOI   ScienceOn
53 Carol, P.; Sreejith, S.; Ajayaghosh, A. Chem. Asian J. 2007, 2, 338.   DOI
54 Lim, N. C.; Freake, H. C.; Brückner, C. Chem. Eur. J. 2005, 11, 38.   DOI   ScienceOn
55 Qian, F.; Zhang, C.; Zhang, Y.; He, W.; Gao, X.; Hu, P.; Guo, Z. J. Am. Chem. Soc. 2009, 131, 1460.   DOI   ScienceOn
56 Xu, Z.; Baek, K.-H.; Kim, H. N.; Cui, J.; Qian, X.; Spring, D. R.; Shin, I.; Yoon, J. J. Am. Chem. Soc. 2010, 132, 601.   DOI   ScienceOn
57 Wong, B. A.; Friedle, S.; Lippard, S. J. J. Am. Chem. Soc. 2009, 131, 7142.   DOI   ScienceOn
58 Kiyose, K.; Kojima, H.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2006, 128, 6548.   DOI   ScienceOn
59 Kim, H.M.; Seo, M. S.; An, M. J.; Hong, J. H.; Tian, Y. S.; Choi, J. H.; Kwon, O.; Lee, K. J.; Cho, B. R. Angew. Chem. Int. Ed. 2008, 47, 5167.   DOI   ScienceOn
60 Jiang, W.; Fu, Q.; Fan, H.; Wang, W. Chem. Commun. 2008, 259.
61 de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T. A.; Huxley, T. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.   DOI   ScienceOn
62 Xu, Z.; Chen, X.; Kim, H. N.; Yoon, J. Chem. Soc. Rev. 2010, 39, 127.   DOI   ScienceOn
63 Martinez-Manez, R.; Sancanon, F. Chem. Rev. 2003, 103, 4419.   DOI   ScienceOn
64 Gunnlaugsson, T.; Glynn, M.; Tocci, G. M.; Kruger, P. E.; Pfeffer, F. M. Coord. Chem. Rev. 2006, 250, 3094.   DOI   ScienceOn
65 Kim, S. K.; Kim, H. N.; Xiaoru, Z.; Lee, H. N.; Lee, H. N.; Soh, J. H.; Swamy, K. M. K.; Yoon, J. Supramolecular Chem. 2007, 19, 221.   DOI   ScienceOn
66 Kim, S. K.; Singh, N. J.; Kwon, J.; Hwang, I.-C.; Park, S. J.; Kim, K. S.; Yoon, J. Tetrahedron 2006, 62, 6065.   DOI   ScienceOn
67 Kim, J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780.   DOI   ScienceOn
68 Xu, Z.; Kim, S. K.; Yoon, J. Chem. Soc. Rev. 2010, 39, 1457.   DOI   ScienceOn
69 Chen, X.; Zhou, Y.; Peng, X.; Yoon, J. Chem. Soc. Rev. 2010, 39, 2120.   DOI   ScienceOn
70 Callan, J. F.; de Silva, A. P.; Magri, D. C. Tetrahedron 2005, 61, 8551.   DOI   ScienceOn
71 Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3.   DOI   ScienceOn
72 Prodi, L.; Bolletta, F.; Montalti, M.; Zaccheroni, N. Coord. Chem. Rev. 2000, 205, 59.   DOI   ScienceOn
73 Kim, H.; Lee, M.; Kim, H.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2008, 37, 1465.   DOI   ScienceOn