Browse > Article
http://dx.doi.org/10.5012/bkcs.2014.35.12.3437

A Carbazole Based Bimodal "Turn-On" Fluorescent Probe for Biothiols (Cysteine/Homocysteine) and Fluoride: Sensing, Imaging and its Applications  

Kaur, Matinder (Department of Chemistry, Research Institute for Natural Sciences, Korea University)
Yoon, Byungkwon (Department of Chemistry, Research Institute for Natural Sciences, Korea University)
Kumar, Rajesh (Department of Chemistry, Research Institute for Natural Sciences, Korea University)
Cho, Min Ju (Department of Chemistry, Research Institute for Natural Sciences, Korea University)
Kim, Hak Joong (Department of Chemistry, Research Institute for Natural Sciences, Korea University)
Kim, Jong Seung (Department of Chemistry, Research Institute for Natural Sciences, Korea University)
Choi, Dong Hoon (Department of Chemistry, Research Institute for Natural Sciences, Korea University)
Publication Information
Abstract
A well-known carbazole-based precursor (probe 1) was used for the detection of cysteine/homocysteine and fluoride. Probe 1 shows a "turn-on" response to cysteine/homocysteine and fluoride via enhancement in emission intensity at 442 nm and 462 nm respectively, in solutions and living cells. Furthermore, probe 1 behaves as a fluorescent molecular switch between cysteine/homocysteine and fluoride as the chemical inputs, which have been used for the development of a combinatorial logic circuit and a molecular keypad lock.
Keywords
Carbazole probe; Cysteine/homocysteine sensing; Fluoride recognition; Molecular keypad lock; Bioimaging;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Horowitz, H. S. J. Public Health Dent. 2003, 63, 3.
2 Lennon, M. A. Bull. World Health Organ. 2006, 84, 759.   DOI   ScienceOn
3 Schubert, M. P. J. Biol. Chem. 1936, 114, 341.
4 Schubert, M. P. J. Biol. Chem. 1937, 121, 539.
5 Folmer-Andersen, J. F.; Buhler, E.; Candau, S. J.; Joulie, S.; Schmutz, M.; Lehn, J. M. Polym. Int. 2010, 59, 1477.   DOI   ScienceOn
6 Son, S.-H.; Kim, Y.; Heoc, M. B.; Lim, Y. T.; Lee, T. S. Tetrahedron 2014, 70, 2034.   DOI   ScienceOn
7 Kong, F.; Liu, R.; Chu, R.; Wang, X.; Xu, K.; Tang, B. Chem. Commun. 2013, 9176.
8 Das, P.; Mandal, A. K.; Chandar, N. B.; Baidya, M.; Bhatt, H. B.; Ganguly, B.; Ghosh, S. K.; Das, A. Chem. Eur. J. 2012, 18, 15382.   DOI   ScienceOn
9 Yang, Z.; Zhao, N.; Sun, Y.; Miao, F.; Liu, Y.; Liu, X.; Zhang, Y.; Ai, W.; Song, G.; Shen, X.; Yu, X.; Sun, J.; Wong, W. Y. Chem. Commun. 2012, 3442.
10 Hildebrand, J. H.; Benesi, H. A. J. Am. Chem. Soc. 1949 71, 2703.
11 Bhalla, V.; Roopa, Kumar, M. Org. Lett. 2012, 14, 2802.   DOI   ScienceOn
12 Szacilowski, K. Chem. Rev. 2008, 108, 3481.   DOI   ScienceOn
13 Molecular Devices and Machines. A Journey into the Nano World; Balzini, V., Venturi, M., Credi, A., Eds.; Wiley-VCH: Wienheim, 2003.
14 Mitchell, R. J. Microprocessor Systems: An Introduction; Macmillan:London, 1995.
15 Prakash, M.; Shetty, M. S.; Tilak, P.; Anwar, N. OJHAS 2009, 8, 2.
16 Zhang, S.; Ong, C. N.; Shen, H. M. Cancer Lett. 2004, 208, 143.   DOI   ScienceOn
17 Ueno, T.; Nagano, T. Nat. Methods 2011, 8, 642.   DOI   ScienceOn
18 Kobayashi, H.; Ogawa, M.; Alford, R.; Choyke, P. L.; Urano, Y. Chem. Rev. 2010, 110, 2620.   DOI   ScienceOn
19 Rao, J.; Dragulescu-Andrasi, A.; Yao, H. Curr. Opin. Chem. Biol. 2007, 18, 17.
20 Shi, J.; Wang, Y.; Tang, X.; Liu, W.; Jiang, H.; Dou, W.; Liu, W. Dyes Pigm. 2014, 100, 255.   DOI   ScienceOn
21 Yuan, Y.; Kwok, R. T. K.; Feng, G.; Liang, J.; Geng, J.; Tang, B. Z.; Liu, B. Chem. Commun. 2014, 295.
22 Liu, Y.; Zhang, S.; Lv, X.; Sun, Y.-Q.; Liu, J.; Guo, W. Analyst 2014, 139, 4081.   DOI
23 Song, Q.-H.; Wu, Q. Q.; Liu, C.-H.; Du, X.-J.; Guo, Q.-X. J. Mater. Chem. B 2013, 1, 438.   DOI
24 Isik, M.; Ozdemir, T.; Turan, I. S.; Kolemen, S.; Akkaya, E. U. Org. Lett. 2013, 15, 216.   DOI   ScienceOn
25 Ashokkumar, P.; Weißhoff, H.; Kraus, W.; Rurack, K. Angew. Chem. Int. Ed. 2014, 53, 2225.   DOI   ScienceOn
26 Roy, A.; Datar, A.; Kand, D.; Saha, T.; Talukdar, P. Org. Biomol. Chem. 2014, 12, 2143.   DOI   ScienceOn
27 Yuan, M. S.; Wang, Q.; Wang, W.; Wang, D. E.; Wang, J.; Wang, J. Analyst 2014, 139, 1541.   DOI   ScienceOn
28 Saravanan, C.; Easwaramoorthi, S.; Hsiow, C. Y.; Wang, K.; Hayashi, M.; Wang, L. Org. Lett. 2014, 16, 354.   DOI   ScienceOn
29 Cametti, M.; Rissanen, K. Chem. Soc. Rev. 2013, 42, 2016.   DOI   ScienceOn
30 Farley, J. R.; Wergeda, J. E.; Baylink, D. J. Science 1983, 222, 330.   DOI
31 Berndt, C.; Lillig, C. H.; Holmgren, A. Am. J. Physiol. Heart Circ. Physiol. 2007, 292, H1227.
32 Brosnan, J. T.; Brosnan, M. E. J. Nutr. 2006, 136, 1636S.
33 Kovar, J.; Stybrova, H.; Truksa, J.; Spevakova, K.; Valenta, T. Folia Biol. 2002, 48, 58.
34 Goswami, S.; Manna, A.; Paul, S.; Das, A. K.; Nandi, P. K.; Maity, A. K.; Saha, P. Tetrahedron Lett. 2014, 55, 490.   DOI   ScienceOn
35 Masella, R.; Mazza, G. Glutathione and Sulfur Amino Acids in Human Health and Disease; 2008, ISBN: 9780470170854.
36 Kaur, M.; Cho, M. J.; Choi, D. H. Dyes Pigm. 2014, 103, 154.   DOI   ScienceOn
37 Moriarty-Craige, S. E.; Jones, D. P. Ann. Rev. Nutr. 2004, 24, 481.   DOI   ScienceOn