Cysteamine-based cell-permeable Zn2+-specific molecular bioimaging materials: From animal to plant cells

ACS Applied Materials and Interfaces

Volumn 5, Issue 22, 2013, Pages 11730-11740

  Sinha, Sougata ^a   Dey, Gourab ^a   Kumar, Sunil ^a   Mathew, Jomon ^b   Mukherjee, Trinetra ^c   Mukherjee, Subhrakanti ^c   Ghosh, Subrata ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MANDI   (India)

^b TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^c UNIVERSITY OF BURDWAN   (India)

Author keywords

fluorescence bioimaging; intracellular zinc; live plant imaging; molecular marker; turn on

Indexed keywords

BIO-IMAGING; COMPUTATIONAL ANALYSIS; DETECTION AND LOCALIZATION; EMISSION PROPERTIES; FLUORESCENCE IMAGING; MOLECULAR MARKER; REAL TIME ANALYSIS; TURN-ON;

BIOLOGICAL MATERIALS; CROPS; FLUORESCENCE; IMAGING TECHNIQUES; PLANTS (BOTANY); PROBES;

ZINC;

FLUORESCENT DYE; MERCAPTAMINE; RADIOPROTECTIVE AGENT; ZINC;

ANIMAL; ARTICLE; BACILLUS THURINGIENSIS; CANDIDA ALBICANS; CHEMISTRY; CYTOLOGY; FISH; FLUORESCENCE MICROSCOPY; METABOLISM; METHODOLOGY; PEPEROMIA; PLANT CELL;

ANIMALS; BACILLUS THURINGIENSIS; CANDIDA ALBICANS; CYSTEAMINE; FISHES; FLUORESCENT DYES; MICROSCOPY, FLUORESCENCE; PEPEROMIA; PLANT CELLS; RADIATION-PROTECTIVE AGENTS; ZINC;

EID: 84889261527     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am403388g     Document Type: Article

References (82)

1. Nolan, E. M.; Lippard, S. J. Acc. Chem. Res. 2009, 42, 193-203
2. Yang, Y.; Zhao, Q.; Feng, W.; Li, F. Chem. Rev. 2013, 113, 192-270
3. Terai, T.; Nagano, T. Pflug Arch- Eur. J. Phy. 2013, 465, 347-359
4. Kikuchi, K.; Komatsu, K.; Nagano, T. Curr. Opin. Chem. Biol. 2004, 8, 182-191
5. Vallee, B. L. Physiol. Rev. 1959, 39, 443-490
6. Sun, F.; Zhang, G.; Zhang, D.; Xue, L.; Jiang, H. Org. Lett. 2011, 13, 6378-6381
7. Cuajungco, M. P.; Lees, G. J. Neurobiol. Dis. 1997, 4, 137-169
8. Choi, D. W.; Koh, J. Y. Annu. Rev. Neurosci. 1998, 21, 347-375
9. Maret, W.; Jacob, C.; Vallee, B. L.; Fischer, E. H. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 1936-1940
10. Zalewski, P. D.; Forbes, I. J.; Betts, W. H. Biochem. J. 1993, 296, 403-0
11. Falchuk, K. H. Mol. Cell. Biochem. 1998, 188, 41-48
12. Vallee, B. L.; Falchuk, K. H. Physiol. Rev. 1993, 73, 79-118
13. Kimura, E.; Koike, T. Chem. Soc. Rev. 1998, 27, 179-184
14. Lippard, S. J.; Berg, J. M. Principles of Bioinorganic Chemistry; University Science Books: Mill Valley, CA, 1994.
15. Walkup, G. K.; Burdette, S. C.; Lippard, S. J.; Tsien, R. Y. J. Am. Chem. Soc. 2000, 122, 5644-5645
16. Sensi, S. L.; Ton-That, D.; Sullivan, P. G.; Jonas, E. A.; Gee, K. R.; Kaczmarek, L. K.; Weiss, J. H. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 6157-6162
17. Burdette, S. C.; Walkup, G. K.; Spingler, B.; Tsien, R. Y.; Lippard, S. J. J. Am. Chem. Soc. 2001, 123, 7831-7841
18. Zalewski, P. D.; Forbes, I. J.; Seamark, R. F.; Borlinghaus, R.; Betts, W. H.; Lincoln, S. F.; Ward, A. D. Chem. Biol. 1994, 1, 153-161
19. Lim, N. C.; Yao, L.; Freake, H. C.; Bruckner, C. Bioorg. Med. Chem. Lett. 2003, 13, 2251-2254
20. Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. Angew. Chem., Int. Ed. Engl. 2000, 39, 1052-1054
21. Hirano, T.; Kikuchi, K.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2002, 124, 6555-6562
22. Gee, K. R.; Zhou, Z.-L.; Qian, W.-J.; Kennedy, R. J. Am. Chem. Soc. 2002, 124, 776-778
23. Burdette, S. C.; Frederickson, C. J.; Bu, W.; Lippard, S. J. J. Am. Chem. Soc. 2003, 125, 1778-1787
24. Maruyama, S.; Kikuchi, K.; Hirano, T.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2002, 124, 10650-10651
25. Qian, W.-J.; Gee, K. R.; Kennedy, R. T. Anal. Chem. 2003, 75, 3468-3475
26. Gee, K. R.; Zhou, Z. L.; Ton-That, D.; Sensi, S. L.; Weiss, J. H. Cell Calcium 2002, 31, 245-251
27. Sensi, S. L.; Ton-That, D.; Weiss, J. H.; Rothe, A.; Gee, K. R. Cell Calcium 2003, 34, 281-284
28. Nolan, E. M.; Jaworski, J.; Okamoto, K.-I.; Hayashi, Y.; Sheng, M.; Lippard, S. J. J. Am. Chem. Soc. 2005, 127, 16812-16823
29. Nolan, E. M.; Jaworski, J.; Racine, M. E.; Sheng, M.; Lippard, S. J. Inorg. Chem. 2006, 45, 9748-9757
30. Woodroofe, C. C.; Masalha, R.; Barnes, K. R.; Frederickson, C. J.; Lippard, S. J. Chem. Biol. 2004, 11, 1659-1666
31. Chang, C. J.; Nolan, E. M.; Jaworski, J.; Burdette, S. C.; Sheng, M.; Lippard, S. J. Chem. Biol. 2004, 11, 203-210
32. Lim, N. C.; Freake, H. C.; Bruckner, C. Chem.-Eur. J. 2005, 11, 38-49
33. Ueno, S.; Tsukamoto, M.; Hirano, T.; Kikuchi, K.; Yamada, M. K.; Nishiyama, M.; Nagano, T.; Matsuki, N.; Ikegaya, Y. J. Cell. Biol. 2002, 158, 215-220
34. Fang, X.; Li, H.; Zhao, G.; Fang, X.; Xu, J.; Yang, W. Biosens. Bioelectron. 2013, 42, 308-313
35. Lee, S.; Lee, J. H.; Pradhan, T.; Lim, C. S.; Cho, B. R.; Bhuniya, S.; Kim, S.; Kim, J. S. Sens. Actuators, B 2011, 160, 1489-1493
36. Ding, Y.; Xie, Y.; Li, X.; Hill, J. P.; Zhang, W.; Zhu, W. Chem. Commun. 2011, 47, 5431-5433
37. Xu, Z.; Liu, X.; Pan, J.; Spring, D. R. Chem. Commun. 2012, 48, 4764-4766
38. Liu, Z.; Zhang, C.; Chen, Y.; He, W.; Guo, Z. Chem. Commun. 2012, 48, 8365-8367
39. Kumar, M.; Kumar, N.; Bhalla, V. Chem. Commun. 2013, 49, 877-879
40. Kim, J. H.; Hwang, I. H.; Jang, S. P.; Kang, J.; Kim, S.; Noh, I.; Kim, Y.; Kim, C.; Harrison, R. G. Dalton Trans. 2013, 42, 5500-5507
41. Sarkar, S.; Khuda-Bukhsh, A. R.; Mukherjee, M.; Helliwell, M.; Chattopadhyay, P. Inorg. Chem. 2011, 50, 1213-1219
42. Iyoshi, S.; Taki, M.; Yamamoto, Y. Org. Lett. 2011, 13, 4558-4561
43. Chang, C. J.; Jaworski, J.; Nolan, E. M.; Sheng, M.; Lippard, S. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 1129-1134
44. Zhou, Y.; Li, Z.-X.; Zang, S.-Q.; Zhu, Y.-Y.; Zhang, H.-Y.; Hou, H.-W.; Mak, T. C. W. Org. Lett. 2012, 14, 1214-1217
45. Pisoni, R. L.; Park, G. Y.; Velilla, V. Q.; Thoene, J. G. J. Biol. Chem. 1995, 270, 1179-1184
46. Kim, M. J.; Kaur, K.; Singh, N.; Jang, D. O. Tetrahedron 2012, 68, 5429-5433
47. Wang, L.; Qin, W.; Tang, X.; Dou, W.; Liu, W. J. Phys. Chem. A 2011, 115, 1609-1616
48. Zhang, Y.; Guo, X.; Jia, L.; Xu, S.; Xu, Z.; Zheng, L.; Qian, X. Dalton Trans. 2012, 41, 11776-11782
49. Zhang, Y.; Guo, X.; Si, W.; Jia, L.; Qian, X. Org. Lett. 2008, 10, 473-476
50. Roy, P.; Dhara, K.; Manassero, M.; Ratha, J.; Banerjee, P. Inorg. Chem. 2007, 46, 6405-6412
51. Dayal, D.; Palanimuthu, D.; Shinde, S.; Somasundaram, K.; Samuelson, A. J. Biol. Inorg. Chem. 2011, 16, 621-632
52. Karak, D.; Das, S.; Lohar, S.; Banerjee, A.; Sahana, A.; Hauli, I.; Mukhopadhyay, S. K.; Safin, D. A.; Babashkina, M. G.; Bolte, M.; Garcia, Y.; Das, D. Dalton Trans. 2013, 42, 6708-6715
53. Zhou, Y.; Li, Z.-X.; Zang, S.-Q.; Zhu, Y.-Y.; Zhang, H.-Y.; Hou, H.-W.; Mak, T. C. W. Org. Lett. 2012, 14, 1214-1217
54. Tochtrop, G. P.; Sadhukhan, S.; Koner, R. R.; Ghosh, S. Tetrahedron 2009, 65, 10515-10534
55. Ghosh, S.; Tochtrop, G. P. Tetrahedron Lett. 2009, 50, 1723-1726
56. Brodin-Sartorius, A.; Tete, M.-J.; Niaudet, P.; Antignac, C.; Guest, G.; Ottolenghi, C.; Charbit, M.; Moyse, D.; Legendre, C.; Lesavre, P.; Cochat, P.; Servais, A. Kidney Int. 2012, 81, 179-189
57. Cherqui, S. Kidney Int. 2012, 81, 127-129
58. Chakrabarti, E.; Ghosh, S.; Sadhukhan, S.; Sayre, L.; Tochtrop, G. P.; Smith, J. D. J. Med. Chem. 2010, 53, 5302-5319
59. Brown, A. D.; PCT Int. Appl. 2004, WO 2004108675 A1 20041216.
60. Moss, R. D.; Hamilton, P. M. Sulfur-containing schiff's bases 1964. US 3147307 19640901.
61. V. Alfimov, M.; V. Churakov, A.; V. Fedorov, Y.; A. Fedorova, O.; P. Gromov, S.; E. Hester, R.; A. K. Howard, J.; G. Kuz'mina, L.; K. Lednev, I.; N. Moore, J. J. Chem. Soc., Perkin Trans. 2 1997, 2249-2256
62. Kubo, Y.; Kato, M.; Misawa, Y.; Tokita, S. Tetrahedron Lett. 2004, 45, 3769-3773
63. Bhalla, V.; Roopa; Kumar, M. Dalton Trans. 2013, 42, 975-980
64. Choi, J. Y.; Kim, D.; Yoon, J. Dyes Pigm. 2013, 96, 176-179
65. Caballero, A.; Martínez, R.; Lloveras, V.; Ratera, I.; Vidal-Gancedo, J.; Wurst, K.; Tárraga, A.; Molina, P.; Veciana, J. J. Am. Chem. Soc. 2005, 127, 15666-15667
66. Job, P. Ann. Chim. Appl. 1928, 9, 113-203
67. Foresman, J. B.; Head-Gordon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135-149
68. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
69. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
70. Frisch, M. J.; Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2010.
71. Martínez, R. F.; ávalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Light, M. E.; Palacios, J. C. Eur. J. Org. Chem. 2011, 3137-3145
72. Mennucci, B.; Cammi, R.; Tomasi, J. J. Chem. Phys. 1999, 110, 6858-6870
73. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43-54
74. Meerloo, J. Cell Sensitivity Assays: The MTT Assay. Cancer Cell Culture: Methods and Protocols, 2nd ed.; Methods in Molecular Biology; Springer: New York, 2011; DOI 10.1007/978-1-61779-080-5-20; vol. 731.
75. Tim, M. J. Immunol. Methods 1983, 65 (1-2) 55-63
76. Berridge, M. V.; Herst, P. M.; Tan, A. S. Biotechnol. Annu. Rev. 2005, 11, 127-152
77. Slater, T.F.; Sawyer, B.; Strauli, U. D. Biochim. Biophys. Acta 1963, 77, 383-393
78. Fard, S. R.; Khourgami, A.; Rafee, M.; Nasrollahi, H. Ann. Biol. Res. 2012, 3, 4166-4171
79. Cakmak, I. Plant Soil 2008, 302, 1-17
80. Ozturk, L.; Yazici, M. A.; Yucel, C.; Torun, A.; Cekic, C.; Bagci, A.; Ozkan, H.; Braun, H. -J.; Sayers, Z.; Cakmak, I. Physiol. Plant. 2008, 128, 144-152
81. Steponěnieně, L.; Tautkus, S.; Kazlauskas, R. Chemija (Vilnius) 2003, 14, 99-102
82. Paltridge, N. G.; Palmer, L. J.; Milham, P. J.; Guild, G. E.; Stangoulis, J. C. R. Plant Soil 2012, 361, 251-260