Coumarin-based chemosensors for zinc(II): Toward the determination of the design algorithm for CHEF-type and ratiometric probes

Inorganic Chemistry

Volumn 44, Issue 6, 2005, Pages 2018-2030

  Lim, Nathaniel C ^a   Schuster, Jolene V ^a   Porto, Maura C ^a   Tanudra, Maria A ^a   Yao, Lili ^a   Freake, Hedley C ^a   Brückner, Christian ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN; SOLVENT; ZINC;

ALGORITHM; ANIMAL CELL; ARTICLE; CELL CULTURE; CHELATION; CHEMOSENSORS; CHROMATOPHORE; FLUORESCENCE MICROSCOPY; HEPATOMA CELL; HYPOPHYSIS CELL; MECHANICAL PROBE; NONHUMAN; RAT; SENSOR; SYNTHESIS;

ALGORITHMS; ANIMALS; CHELATING AGENTS; COUMARINS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED; ZINC;

EID: 15944376525     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic048905r     Document Type: Article

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61. excitation = 450-490 nm).
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63. For a representative selection, see: (a) Ibrahim, R.; Tsuchiya, S.; Ogawa, S. J. Am. Chem. Soc. 2000, 122, 12174-12185. (b) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. Angew. Chem., Int. Ed. 2000, 39, 1052-1054. (c) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2000, 122, 12399-12400. (d) Klein, G.; Kaufmann, D.; Schürch, S.; Reymond, J.-L. Chem. Commun. 2001, 561-562. (e) Goodall, W.; Williams, J. A. G. Chem. Commun. 2001, 2514-2515. (f) Jiang, P.; Chen, L.; Lin, J.; Liu, Q.; Ding, J.; Gao, X.; Guo, Z. Chem. Commun. 2002, 1424-1425. (g) Gunnlaugsson, T.; Lee, T. C.; Parkesh, R. Org. Biomol. Chem. 2003, 1, 3265-3267. (h) Wu, Z.: Chen, Q.; Yang, G.; Xiao, C.; Liu, J.; Yang, S.; Ma, J. S. Sens. Actuators B 2004, 99, 511-515. (i) Bencini, A.; Berni, E.; Bianchi, A.; Fornasari, P.; Giorgi, C.; Lima, J. C.; Lodeiro, C.; Melo, M. J.; de Melo, J. S.; Parola, A. J.; Pina, F.; Pina, J.; Valtancoli, B. Dalton Trans. 2004, 2180-2187. (j) Chen, Y.; Zeng, D. X. ChemPhysChem 2004, 5, 564-566.
64. For a representative selection, see: (a) Ibrahim, R.; Tsuchiya, S.; Ogawa, S. J. Am. Chem. Soc. 2000, 122, 12174-12185. (b) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. Angew. Chem., Int. Ed. 2000, 39, 1052-1054. (c) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2000, 122, 12399-12400. (d) Klein, G.; Kaufmann, D.; Schürch, S.; Reymond, J.-L. Chem. Commun. 2001, 561-562. (e) Goodall, W.; Williams, J. A. G. Chem. Commun. 2001, 2514-2515. (f) Jiang, P.; Chen, L.; Lin, J.; Liu, Q.; Ding, J.; Gao, X.; Guo, Z. Chem. Commun. 2002, 1424-1425. (g) Gunnlaugsson, T.; Lee, T. C.; Parkesh, R. Org. Biomol. Chem. 2003, 1, 3265-3267. (h) Wu, Z.: Chen, Q.; Yang, G.; Xiao, C.; Liu, J.; Yang, S.; Ma, J. S. Sens. Actuators B 2004, 99, 511-515. (i) Bencini, A.; Berni, E.; Bianchi, A.; Fornasari, P.; Giorgi, C.; Lima, J. C.; Lodeiro, C.; Melo, M. J.; de Melo, J. S.; Parola, A. J.; Pina, F.; Pina, J.; Valtancoli, B. Dalton Trans. 2004, 2180-2187. (j) Chen, Y.; Zeng, D. X. ChemPhysChem 2004, 5, 564-566.
65. For a representative selection, see: (a) Ibrahim, R.; Tsuchiya, S.; Ogawa, S. J. Am. Chem. Soc. 2000, 122, 12174-12185. (b) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. Angew. Chem., Int. Ed. 2000, 39, 1052-1054. (c) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2000, 122, 12399-12400. (d) Klein, G.; Kaufmann, D.; Schürch, S.; Reymond, J.-L. Chem. Commun. 2001, 561-562. (e) Goodall, W.; Williams, J. A. G. Chem. Commun. 2001, 2514-2515. (f) Jiang, P.; Chen, L.; Lin, J.; Liu, Q.; Ding, J.; Gao, X.; Guo, Z. Chem. Commun. 2002, 1424-1425. (g) Gunnlaugsson, T.; Lee, T. C.; Parkesh, R. Org. Biomol. Chem. 2003, 1, 3265-3267. (h) Wu, Z.: Chen, Q.; Yang, G.; Xiao, C.; Liu, J.; Yang, S.; Ma, J. S. Sens. Actuators B 2004, 99, 511-515. (i) Bencini, A.; Berni, E.; Bianchi, A.; Fornasari, P.; Giorgi, C.; Lima, J. C.; Lodeiro, C.; Melo, M. J.; de Melo, J. S.; Parola, A. J.; Pina, F.; Pina, J.; Valtancoli, B. Dalton Trans. 2004, 2180-2187. (j) Chen, Y.; Zeng, D. X. ChemPhysChem 2004, 5, 564-566.
66. For a representative selection, see: (a) Ibrahim, R.; Tsuchiya, S.; Ogawa, S. J. Am. Chem. Soc. 2000, 122, 12174-12185. (b) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. Angew. Chem., Int. Ed. 2000, 39, 1052-1054. (c) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2000, 122, 12399-12400. (d) Klein, G.; Kaufmann, D.; Schürch, S.; Reymond, J.-L. Chem. Commun. 2001, 561-562. (e) Goodall, W.; Williams, J. A. G. Chem. Commun. 2001, 2514-2515. (f) Jiang, P.; Chen, L.; Lin, J.; Liu, Q.; Ding, J.; Gao, X.; Guo, Z. Chem. Commun. 2002, 1424-1425. (g) Gunnlaugsson, T.; Lee, T. C.; Parkesh, R. Org. Biomol. Chem. 2003, 1, 3265-3267. (h) Wu, Z.: Chen, Q.; Yang, G.; Xiao, C.; Liu, J.; Yang, S.; Ma, J. S. Sens. Actuators B 2004, 99, 511-515. (i) Bencini, A.; Berni, E.; Bianchi, A.; Fornasari, P.; Giorgi, C.; Lima, J. C.; Lodeiro, C.; Melo, M. J.; de Melo, J. S.; Parola, A. J.; Pina, F.; Pina, J.; Valtancoli, B. Dalton Trans. 2004, 2180-2187. (j) Chen, Y.; Zeng, D. X. ChemPhysChem 2004, 5, 564-566.
67. For a representative selection, see: (a) Ibrahim, R.; Tsuchiya, S.; Ogawa, S. J. Am. Chem. Soc. 2000, 122, 12174-12185. (b) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. Angew. Chem., Int. Ed. 2000, 39, 1052-1054. (c) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2000, 122, 12399-12400. (d) Klein, G.; Kaufmann, D.; Schürch, S.; Reymond, J.-L. Chem. Commun. 2001, 561-562. (e) Goodall, W.; Williams, J. A. G. Chem. Commun. 2001, 2514-2515. (f) Jiang, P.; Chen, L.; Lin, J.; Liu, Q.; Ding, J.; Gao, X.; Guo, Z. Chem. Commun. 2002, 1424-1425. (g) Gunnlaugsson, T.; Lee, T. C.; Parkesh, R. Org. Biomol. Chem. 2003, 1, 3265-3267. (h) Wu, Z.: Chen, Q.; Yang, G.; Xiao, C.; Liu, J.; Yang, S.; Ma, J. S. Sens. Actuators B 2004, 99, 511-515. (i) Bencini, A.; Berni, E.; Bianchi, A.; Fornasari, P.; Giorgi, C.; Lima, J. C.; Lodeiro, C.; Melo, M. J.; de Melo, J. S.; Parola, A. J.; Pina, F.; Pina, J.; Valtancoli, B. Dalton Trans. 2004, 2180-2187. (j) Chen, Y.; Zeng, D. X. ChemPhysChem 2004, 5, 564-566.
68. For a representative selection, see: (a) Ibrahim, R.; Tsuchiya, S.; Ogawa, S. J. Am. Chem. Soc. 2000, 122, 12174-12185. (b) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. Angew. Chem., Int. Ed. 2000, 39, 1052-1054. (c) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2000, 122, 12399-12400. (d) Klein, G.; Kaufmann, D.; Schürch, S.; Reymond, J.-L. Chem. Commun. 2001, 561-562. (e) Goodall, W.; Williams, J. A. G. Chem. Commun. 2001, 2514-2515. (f) Jiang, P.; Chen, L.; Lin, J.; Liu, Q.; Ding, J.; Gao, X.; Guo, Z. Chem. Commun. 2002, 1424-1425. (g) Gunnlaugsson, T.; Lee, T. C.; Parkesh, R. Org. Biomol. Chem. 2003, 1, 3265-3267. (h) Wu, Z.: Chen, Q.; Yang, G.; Xiao, C.; Liu, J.; Yang, S.; Ma, J. S. Sens. Actuators B 2004, 99, 511-515. (i) Bencini, A.; Berni, E.; Bianchi, A.; Fornasari, P.; Giorgi, C.; Lima, J. C.; Lodeiro, C.; Melo, M. J.; de Melo, J. S.; Parola, A. J.; Pina, F.; Pina, J.; Valtancoli, B. Dalton Trans. 2004, 2180-2187. (j) Chen, Y.; Zeng, D. X. ChemPhysChem 2004, 5, 564-566.
69. For a representative selection, see: (a) Ibrahim, R.; Tsuchiya, S.; Ogawa, S. J. Am. Chem. Soc. 2000, 122, 12174-12185. (b) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. Angew. Chem., Int. Ed. 2000, 39, 1052-1054. (c) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2000, 122, 12399-12400. (d) Klein, G.; Kaufmann, D.; Schürch, S.; Reymond, J.-L. Chem. Commun. 2001, 561-562. (e) Goodall, W.; Williams, J. A. G. Chem. Commun. 2001, 2514-2515. (f) Jiang, P.; Chen, L.; Lin, J.; Liu, Q.; Ding, J.; Gao, X.; Guo, Z. Chem. Commun. 2002, 1424-1425. (g) Gunnlaugsson, T.; Lee, T. C.; Parkesh, R. Org. Biomol. Chem. 2003, 1, 3265-3267. (h) Wu, Z.: Chen, Q.; Yang, G.; Xiao, C.; Liu, J.; Yang, S.; Ma, J. S. Sens. Actuators B 2004, 99, 511-515. (i) Bencini, A.; Berni, E.; Bianchi, A.; Fornasari, P.; Giorgi, C.; Lima, J. C.; Lodeiro, C.; Melo, M. J.; de Melo, J. S.; Parola, A. J.; Pina, F.; Pina, J.; Valtancoli, B. Dalton Trans. 2004, 2180-2187. (j) Chen, Y.; Zeng, D. X. ChemPhysChem 2004, 5, 564-566.
70. For a representative selection, see: (a) Ibrahim, R.; Tsuchiya, S.; Ogawa, S. J. Am. Chem. Soc. 2000, 122, 12174-12185. (b) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. Angew. Chem., Int. Ed. 2000, 39, 1052-1054. (c) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2000, 122, 12399-12400. (d) Klein, G.; Kaufmann, D.; Schürch, S.; Reymond, J.-L. Chem. Commun. 2001, 561-562. (e) Goodall, W.; Williams, J. A. G. Chem. Commun. 2001, 2514-2515. (f) Jiang, P.; Chen, L.; Lin, J.; Liu, Q.; Ding, J.; Gao, X.; Guo, Z. Chem. Commun. 2002, 1424-1425. (g) Gunnlaugsson, T.; Lee, T. C.; Parkesh, R. Org. Biomol. Chem. 2003, 1, 3265-3267. (h) Wu, Z.: Chen, Q.; Yang, G.; Xiao, C.; Liu, J.; Yang, S.; Ma, J. S. Sens. Actuators B 2004, 99, 511-515. (i) Bencini, A.; Berni, E.; Bianchi, A.; Fornasari, P.; Giorgi, C.; Lima, J. C.; Lodeiro, C.; Melo, M. J.; de Melo, J. S.; Parola, A. J.; Pina, F.; Pina, J.; Valtancoli, B. Dalton Trans. 2004, 2180-2187. (j) Chen, Y.; Zeng, D. X. ChemPhysChem 2004, 5, 564-566.
71. For a representative selection, see: (a) Ibrahim, R.; Tsuchiya, S.; Ogawa, S. J. Am. Chem. Soc. 2000, 122, 12174-12185. (b) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. Angew. Chem., Int. Ed. 2000, 39, 1052-1054. (c) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2000, 122, 12399-12400. (d) Klein, G.; Kaufmann, D.; Schürch, S.; Reymond, J.-L. Chem. Commun. 2001, 561-562. (e) Goodall, W.; Williams, J. A. G. Chem. Commun. 2001, 2514-2515. (f) Jiang, P.; Chen, L.; Lin, J.; Liu, Q.; Ding, J.; Gao, X.; Guo, Z. Chem. Commun. 2002, 1424-1425. (g) Gunnlaugsson, T.; Lee, T. C.; Parkesh, R. Org. Biomol. Chem. 2003, 1, 3265-3267. (h) Wu, Z.: Chen, Q.; Yang, G.; Xiao, C.; Liu, J.; Yang, S.; Ma, J. S. Sens. Actuators B 2004, 99, 511-515. (i) Bencini, A.; Berni, E.; Bianchi, A.; Fornasari, P.; Giorgi, C.; Lima, J. C.; Lodeiro, C.; Melo, M. J.; de Melo, J. S.; Parola, A. J.; Pina, F.; Pina, J.; Valtancoli, B. Dalton Trans. 2004, 2180-2187. (j) Chen, Y.; Zeng, D. X. ChemPhysChem 2004, 5, 564-566.
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