Differentially selective chemosensor with fluorescence off-on responses on Cu2+ and Zn2+ ions in aqueous media and applications in pyrophosphate sensing, live cell imaging, and cytotoxicity

Inorganic Chemistry

Volumn 53, Issue 13, 2014, Pages 6655-6664

  Anbu, Sellamuthu ^a   Ravishankaran, Rajendran ^b   Guedes Da Silva, M Fátima C ^a   Karande, Anjali A ^b   Pombeiro, Armando J L ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATE; COPPER; METAL; PYROPHOSPHORIC ACID DERIVATIVE; SOLUTION AND SOLUBILITY; WATER; ZINC;

CELL SURVIVAL; CELLS; CHEMISTRY; DRUG EFFECTS; FLUORESCENCE; HELA CELL LINE; HUMAN; SOLUTION AND SOLUBILITY; TUMOR CELL LINE; ULTRASTRUCTURE;

ADENOSINE TRIPHOSPHATE; CELL LINE, TUMOR; CELL SURVIVAL; CELLS; COPPER; DIPHOSPHATES; FLUORESCENCE; HELA CELLS; HUMANS; METALS; SOLUTIONS; WATER; ZINC;

EID: 84903965386     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/ic500313m     Document Type: Article

References (67)

1. Que, E. L.; Domailli, D. W.; Chang, C. J. Chem. Rev. 2008, 108, 1517
2. Manez, R. M.; Sancenon, F. Chem. Rev. 2003, 103, 4419
3. Kim, J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780
4. Da silva, J. J. R. F.; Williams, R. J. P. The Biological Chemistry of the Elements; Clarendon Press: Gloucestershire, U.K., 1991.
5. Halliwell, B.; Gutteridge, J. M. Biochem. J. 1984, 219, 1
6. Sarkar, B. Chem. Rev. 1999, 99, 2535
7. Barnham, K. J.; Masters, C. L.; Bush, A. I. Nat. Rev. Drug Discovery 2004, 3, 205
8. Emami, S.; Hosseinimehr, S. J.; Taghdisi, S. M.; Akhlaghpoor, S. Bioorg. Med. Chem. Lett. 2007, 17, 45
9. Huang, Q.; Pan, Z.; Wang, P.; Chen, Z.; Zhang, X.; Xu, H. Bioorg. Med. Chem. Lett. 2006, 16, 3030
10. Nakayama, A.; Hiromura, M.; Adachi, Y.; Sakurai, H. J. Biol. Inorg. Chem. 2008, 13, 675
11. Sakurai, H.; Yoshikawa, Y.; Yasui, H. Chem. Soc. Rev. 2008, 7, 2383
12. Chohan, Z. H.; Arif, M.; Sarfraz, M. Appl. Organomet. Chem. 2007, 21, 294
13. Singh, V. P.; Katiyar, A. J. Coord. Chem. 2008, 61, 3200
14. Kaczmarek, M. T.; Jastrza, R.; Hołderna-Kedzia, E.; Radecka-Paryzek, W. Inorg. Chim. Acta 2009, 362, 3127
15. Anbu, S.; Kamalraj, S.; Varghese, B.; Muthumary, J.; Kandaswamy, M. Inorg. Chem. 2012, 51, 5580
16. Ali, M. M.; Frei, E.; Straubb, J.; Breuerb, A.; Wiesslerb, M. Toxicology 2002, 85, 179
17. Wang, J.; Lin, W.; Yuan, L.; Song, J.; Gao, W. Chem. Commun. 2011, 47, 12506
18. Huang, L.; Cheng, J.; Xie, K.; Xi, P.; Hou, F.; Li, Z.; Xie, G.; Shi, Y.; Liu, H.; Bai, D.; Zeng, Z. Dalton Trans. 2011, 40, 10815
19. Simmons, J. T.; Allen, J. R.; Morris, D. R.; Clark, R. J.; Levenson, C. W.; Davidson, M. W.; Zhu, L. Inorg. Chem. 2013, 52, 5338
20. Nowakowski, A. B.; Petering, D. H. Inorg. Chem. 2011, 50, 10124
21. Ahamed, B. N.; Ravikumar, I.; Ghosh, P. New J. Chem. 2009, 33, 1825
22. Tan, Y.; Gao, J.; Yu, J.; Wang, Z.; Cui, Y.; Yang, Y.; Qian, G. Dalton Trans. 2013, 42, 11465
23. APEX2 and SAINT; Bruker AXS Inc.: Madison, WI, 2004.
24. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112
25. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837
26. Spek, A. L. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990, 46, C34
27. Gatehouse, B. M.; Livingstone, S. E.; Nyholm, R. S. J. Inorg. Nucl. Chem. 1958, 8, 75
28. Okawa, H.; Tadocara, M.; Aratake, T. K.; Ohba, M.; Shindom, K.; Mitsumi, M.; Koikawa, M.; Tomono, M.; Fenton, D. E. J. Chem. Soc., Dalton Trans. 1993, 253
29. Klabunde, T.; Eicken, C.; Sacchettini, J. C.; Krebs, B. Nat. Struct. Biol. 1998, 5, 1084
30. Fernandes, C.; Neves, A.; Bortoluzzi, A. J.; Mangrich, A. S.; Rentschler, E.; Szpoganicz, B.; Schwingel, E. Inorg. Chim. Acta 2001, 320, 12
31. Murthy, N. N.; Karlin, K. D.; Berini, C.; Luchinat, J. J. Am. Chem. Soc. 1997, 119, 2156
32. Drew, M. G. B.; Yates, P. C.; Esho, F. S.; Grimshaw, J. T.; Lavery, A.; McKillop, K. P.; Nelson, S. M.; Nelson, J. J. Chem. Soc., Dalton Trans. 1988, 2995
33. Landers, A. E.; Philips, D. J. Inorg. Chim. Acta 1979, 32, 53
34. Kumar, M.; Kumar, R.; Bhalla, V.; Sharma, P. R.; Kaur, T.; Qurishi, Y. Dalton Trans. 2012, 41, 408
35. Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecule Recognition; American Chemical Society: Washington, DC, 1992.
36. Sinkeldam, R. W.; Greco, N. J.; Tor, Y. Chem. Rev. 2010, 110, 2579
37. 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
38. Li, Z.; Zhang, L.; Wang, L.; Guo, Y.; Cai, L.; Yu, M.; Wei, L. Chem. Commun. 2011, 47, 5798
39. Qin, H.; Ren, J.; Wang, J.; Wang, E. Chem. Commun. 2010, 46, 7385
40. Zhao, X. Y.; Liu, Y.; Schanze, K. S. Chem. Commun. 2007, 2914
41. Beltramello, M.; Gatos, M.; Mancin, F.; Tecillab, P.; Tonellatoa, U. Tetrahedron Lett. 2001, 42, 9143
42. Huang, L.; Chen, F.; Xi, P.; Xie, G.; Li, Z.; Shi, Y.; Xu, M.; Liu, H.; Maa, Z.; Bai, D.; Zeng, Z. Dyes Pigm. 2011, 90, 265
43. Midya, G. C.; Paladhi, S.; Bhowmik, S.; Sahaa, S.; Dash, J. Org. Biomol. Chem. 2013, 11, 3057
44. Simmons, J. T.; Allen, J. R.; Morris, D. R.; Clark, R. J.; Levenson, C. W.; Davidson, M. W.; Zhu, L. Inorg. Chem. 2013, 52, 5838
45. Tak, W. T.; Yoon, S. C. Korean. J. Nephrol. 2001, 20, 863
46. Eide, D. J. Biochim. Biophys. Acta 2006, 1763, 711
47. Maret, W.; Krezel, A. Mol. Med. 2007, 13, 371
48. Lin, W.; Buccella, D.; Lippard, S. J. J. Am. Chem. Soc. 2013, 135, 13512
49. Tak, W. T.; Yoon, S. C. Korean J. Nephrol. 2001, 20, 863
50. Eide, D. J. Biochim. Biophys. Acta 2006, 1763, 711
51. Maret, W.; Krezel, A. Mol. Med. 2007, 13, 371
52. Lin, W.; Buccella, D.; Lippard, S. J. J. Am. Chem. Soc. 2013, 135, 13512
53. Gunnlaugsson, T.; Davis, A. P.; O'Brien, J. E.; Glynn, M. Org. Lett. 2002, 4, 2449
54. Pathak, R. K.; Hinge, V. K.; Rai, A.; Panda, D.; Rao, C. P. Inorg. Chem. 2011, 17, 13999
55. Rurack, K. Spectrochim. Acta, Part A 2001, 57, 2161
56. Amendola, V.; Fabbrizzi, L.; Mangano, C.; Pallavicini, P. Acc. Chem. Res. 2001, 34, 488
57. deSilva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515
58. Linton, B. R.; Goodman, M. S.; Fan, E.; van Arman, S. A.; Hamilton, A. D. J. Org. Chem. 2001, 66, 7313
59. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647
60. Kelly, R. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072
61. Fan, E.; van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369
62. Dixon, R. P.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1992, 114, 365
63. Garcia-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393
64. Peng, X.; Wu, Y.; Fan, J.; Tian, M.; Han, K. J. Org. Chem. 2005, 70, 10524
65. Martinez-Manez, R.; Sancanon, F. Chem. Rev. 2003, 103, 4419
66. Liao, J.-H.; Chen, C.-T.; Fang, J.-M. Org. Lett. 2002, 4, 561
67. Anbu, S.; Kamalraj, S.; Jayabaskaran, C.; Mukherjee, P. S. Inorg. Chem. 2013, 52, 8294 a Tecnologia