New regioisomeric naphthol-substituted thiazole based ratiometric fluorescence sensor for Zn2+ with a remarkable red shift in emission spectra

Tetrahedron

Volumn 68, Issue 2, 2012, Pages 647-653

  Helal, Aasif ^a   Rashid, Mohammad Harun Or ^a   Choi, Cheol Ho ^a   Kim, Hong Seok ^a  

^a Kyungpook National University   (South Korea)

Author keywords

Naphthol thiazole; Ratiometric fluorescence; Ring annulation; Zinc ion

Indexed keywords

1 NAPHTHOL DERIVATIVE; ALCOHOL; THIAZOLE; ZINC ION;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; FIELD EMISSION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; RATIOMETRIC FLUORESCENT CHEMOSENSOR; SENSOR; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 82955249286     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.10.106     Document Type: Article

References (77)

1. Z. Xu, J. Yoon, and D.R. Spring Chem. Soc. Rev. 39 2010 1996
2. J.M. Berg, Y. Shi, E.L. Que, D.W. Domaille, and C.J. Chang Chem. Rev. 108 2008 1517
3. P. Carol, S. Sreejith, and A. Ajayaghosh Chem. Asian J. 2 2007 338
4. J.W. Lichtman, and J.-A. Conchello Nat. Methods 2 2005 910
5. P.N. Prasad Introduction to Biophotonics 2003 Wiley Interscience New York, NY
6. F.J.J.R. de Silva, and R.J.P. Williams The Biological Chemistry of the Elements 2nd ed. 2001 Oxford University Press New York, NY
7. J.M. Berg, and Y. Shi Science 271 1996 1081
8. J.B. Pawley Handbook of Biological Confocal Microscopy 1995 Plenum New York, NY
9. S.Y. Assaf, and S.H. Chung Nature 308 1984 734
10. M. Rouffet, C.A.F. de Oliveira, Y. Udi, A. Agrawal, I. Sagi, J.A. McCammon, and S.M. Cohen J. Am. Chem. Soc. 132 2010 8232
11. L. Xue, C. Liu, and H. Jiang Chem. Commun. 2009 1061
12. A.V. Gyulkhandanyan, H.F. Lu, S.C. Lee, A. Bhattacharjee, N. Wijesekara, J.E.M. Fox, P.E. MacDonald, F. Chimienti, F.F. Dai, and M.B. Wheeler J. Biol. Chem. 283 2008 10184
13. A.M.L. Edstrom, J. Malm, B. Frohm, J.A. Martellini, A. Giwercman, M. Morgelin, A.M. Cole, and O.E. Sorensen J. Immunol. 181 2008 3413
14. K. Komatsu, K. Kikuchi, H. Kojima, Y. Urano, and T. Nagano J. Am. Chem. Soc. 127 2005 10197
15. C.J. Frederickson, J.Y. Koh, and A.I. Bush Nat. Rev. Neurosci. 6 2005 449
16. S.C. Burdette, and S.J. Lippard Proc. Natl. Acad. Sci. U.S.A. 100 2003 3605
17. M.P. Cuajungco, and K.Y. Faget Brain Res. Rev. 41 2003 44
18. D. Beyersmann, and H. Haase Biometals 14 2001 331
19. A. Takeda Biometals 14 2001 343
20. D. Srikun, E.W. Miller, D.W. Domaille, and C.J. Chang J. Am. Chem. Soc. 130 2008 4596
21. K. Komatsu, Y. Urano, H. Kojima, and T. Nagano J. Am. Chem. Soc. 129 2007 13447
22. Z. Zhou, M. Yu, H. Yang, K. Huang, F. Li, T. Yi, and C. Huang Chem. Commun. 2008 3387
23. Y. Zhang, X. Guo, W. Si, L. Jia, and X. Qian Org. Lett. 10 2008 473
24. M.M. Henary, and C.J. Fahrni J. Phys. Chem. A 106 2002 5210
25. P.T.C. So, C.Y. Dong, B.R. Masters, and K.M. Berland Annu. Rev. Biomed. Eng. 2 2000 399
26. K. Konig J. Microsc. 200 2000 83
27. K. Konig, U. Simon, and K.J. Halbhuber Cell. Mol. Biol. 42 1996 1181
28. T. Liu, and S. Liu Anal. Chem. 83 2011 2775
29. H. Xu, R. Miao, Z. Fang, and X. Zhong Anal. Chim. Acta 687 2011 82
30. M. Taki, Y. Watanabe, and Y. Yukio Tetrahedron Lett. 50 2009 1345
31. T. Hirano, K. Kikuchi, Y. Urano, and T. Nagano J. Am. Chem. Soc. 124 2002 6555
32. X. Zhou, B. Yu, Y. Guo, X. Tang, H. Zhang, and W. Liu Inorg. Chem. 49 2010 4002
33. F. Qian, C. Zhang, Y. Zhang, W. He, X. Gao, P. Hu, and Z. Guo J. Am. Chem. Soc. 131 2009 1460
34. J.L. Vinkenborg, T.J. Nicolson, E.A. Bellomo, M.S. Koay, G.A. Rutter, and M. Merkx Nat. Methods 6 2009 737
35. R.A. Bozym, R.B. Thompson, A.K. Stoddard, and C.A. Fierke ACS Chem. Biol. 1 2006 103
36. N.C. Lim, J.V. Schuster, M.C. Porto, M.A. Tanudra, L. Yao, and H.C. Freake Inorg. Chem. 44 2005 2018
37. K. Honda, S.-H. Fujishima, A. Ojida, and I. Hamachi ChemBioChem 8 2007 1370
38. Z. Li, M. Yu, L. Zhang, M. Yu, J. Liu, L. Wei, and H. Zhang Chem. Commun. 2010 7169
39. C.C. Woodroofe, and S.J. Lippard J. Am. Chem. Soc. 125 2003 11458
40. A. Ajayaghosh, P. Carol, and S. Sreejith J. Am. Chem. Soc. 127 2005 14962
41. Z. Wu, Y. Zhang, J.S. Ma, and G. Yang Inorg. Chem. 45 2006 3140
42. J. Wu, W. Liu, J. Ge, H. Zhang, and P. Wang Chem. Soc. Rev. 40 2011 3483
43. A. McCarthy, and A.A. Ruth Phys. Chem. Chem. Phys. 13 2011 7485
44. G. Krishnamoorthy, and F.A.S. Chipem J. Phys. Chem. A 113 2009 12063
45. M. Taki, J.L. Wolford, and T.V. O'Halloran J. Am. Chem. Soc. 126 2004 712
46. M.M. Henary, Y.G. Wu, and C.J. Fahrni Chem. - Eur. J. 10 2004 3015
47. S. Banthia, and A. Samanta J. Phys. Chem. B 110 2006 6437
48. A.P. de Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, and P.L.M. Lynch New J. Chem. 20 1996 871
49. J.R. Lakowicz Topics in Fluorescence Spectroscopy Vol. 4 1994 Plenum New York, NY
50. Y.-H. Kim, S.-G. Roh, S.-D. Jung, M.-A. Chung, H.-K. Kim, and D.-W. Cho Photochem. Photobiol. Sci. 9 2010 722
51. C.H. Kim, J. Park, J. Seo, S.Y. Park, and T. Joo J. Phys. Chem. A 114 2010 5618
52. M.M. Henary, Y. Wu, J. Cody, S. Sumalekshmy, J. Li, S. Mandal, and C.J. Fahrni J. Org. Chem. 72 2007 4784
53. J.B. Birks Organic Molecular Photophysics 1973 John Wiley New York, NY
54. T. Iijima, A. Momotake, Y. Shinohara, T. Sato, Y. Nishimura, and T. Arai J. Phys. Chem. A 114 2010 1603
55. S. Park, J.E. Kwon, S.H. Kim, J. Seo, K. Chung, S.-Y. Park, D.-J. Jang, B.M. Medina, J. Gierschner, and S.Y. Park J. Am. Chem. Soc. 131 2009 14043
56. S. Nagaoka, J. Kusunoki, T. Fujibuchi, S. Hatakenaka, K. Mukai, and U. Nagashima J. Photochem. Photobiol., A: Chem. 122 1999 151
57. A. Helal, S.-H. Kim, and H.-S. Kim Tetrahedron 66 2010 9925
58. A. Helal, S.H. Lee, S.H. Kim, and H.-S. Kim Tetrahedron Lett. 51 2010 3531
59. A. Helal, and H.-S. Kim Tetrahedron Lett. 50 2009 5510
60. E.M. Nolan, and S.J. Lippard Acc. Chem. Res. 42 2009 193
61. C.J. Chang, and S.J. Lippard Met. Ions Life Sci. 1 2006 281
62. Y. Huang, R.R. Luedtke, R.A. Freeman, L. Wu, and R.H. Mach J. Med. Chem. 44 2001 1815
63. J.M. Keith, L.A. Gomez, A.J. Barbier, S.J. Wilson, J.D. Boggs, B.L.C. Mazur, L. Aluisio, T.W. Lovenberg, and N.I. Carruthers Bioorg. Med. Chem. Lett. 17 2007 4374
64. X. Zhang, Y. Xiao, and X. Qian Angew. Chem., Int. Ed. 47 2008 8025
65. X. Peng, J. Du, J. Fan, J. Wang, Y. Wu, J. Zhao, S. Sun, and T. Xu J. Am. Chem. Soc. 129 2007 1500
66. Z. Zhang, D. Wu, X. Guo, X. Qian, Z. Lu, Q. Xu, Y. Yang, L. Duan, Y. He, and Z. Feng Chem. Res. Toxicol. 18 2005 1814
67. J. Keck, H.E.A. Kramer, H. Port, T. Hirsch, P. Fischer, and G. Rytz J. Phys. Chem. 100 1996 14468
68. P. Thordarson Chem. Soc. Rev. 40 2011 1305
69. S.F. Forgues, M.T. LeBris, J.P. Gutte, and B. Valuer J. Phys. Chem. 92 1988 6233
70. K.A. Connors Binding Constants: the Measurement of Molecular Complex Stability 1987 Wiley New York, NY pp 21-101, 339-343
71. B. Zhu, X. Zhang, Y. Li, P. Wang, H. Zhang, and X. Zhuang Chem. Commun. 2010 5710
72. P. Du, and S.J. Lippard Inorg. Chem. 49 2010 10753
73. M.W. Schmidt, K.K. Balbridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.H. Jensen, S. Koseki, N. Matsunaga, K.A. Nguyen, S. Su, T.L. Windus, M. Dupuis, and J.A.J. Montgomery J. Comput. Chem. 14 1993 1347
74. G.D. Fletcher, M.W. Schmidt, and M.S. Gordon Adv. Chem. Phys. 110 1999 267
75. A.D. Becke J. Chem. Phys. 98 1993 5648
76. A. Dreuw, and M. Head-Gordon Chem. Rev. 105 2005 4009
77. A. Helal, M.H.O. Rashid, C.-H. Choi, and H.-S. Kim Tetrahedron 67 2011 2794