Designing reaction-based fluorescent probes for selective hydrogen sulfide detection

Journal of Inorganic Biochemistry

Volumn 133, Issue , 2014, Pages 136-142

  Lippert, Alexander R ^a  

^a SOUTHERN METHODIST UNIVERSITY   (United States)

Author keywords

Fluorescent probes; Hydrogen sulfide; Near infrared; Ratiometric; Two photon

Indexed keywords

FLUORESCENT DYE; HYDROGEN SULFIDE; METAL; MOLECULAR SCAFFOLD;

ARTICLE; CHEMICAL REACTION; HUMAN; IMAGING; IN VIVO STUDY; NONHUMAN; NUCLEOPHILICITY; PRACTICE GUIDELINE; PRECIPITATION; REDUCTION; SENSITIVITY ANALYSIS; SENSOR;

FLUORESCENT PROBES; HYDROGEN SULFIDE; NEAR-INFRARED; RATIOMETRIC; TWO-PHOTON;

BIOSENSING TECHNIQUES; FLUORESCENT DYES; HUMANS; HYDROGEN SULFIDE; PHOTONS;

EID: 84897111390     PISSN: 01620134     EISSN: 18733344     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2013.10.010     Document Type: Short Survey

References (107)

1. S.F. Watts Atmos. Environ. 34 2000 761 779
2. T.L. Guidotti Int. J. Toxicol. 29 2010 569 581
3. K. Abe, and H. Kimura J. Neurosci. 16 1996 1066 1071
4. A.K. Mustafa, G. Sikka, S.K. Gazi, J. Steppan, S.M. Jung, A.K. Bhunia, V.M. Barodka, F.K. Gazi, R.K. Barrow, R. Wang, L.M. Amzel, D.E. Berkowitz, and S.H. Snyder Circ. Res. 109 2011 1259 1268
5. A. Papapetropoulos, A. Pyriochou, Z. Altaany, G. Yang, A. Marazioti, Z. Zhou, M.G. Jeschke, L.K. Branski, D.N. Herndon, R. Wang, and C. Szabó Proc. Natl. Acad. Sci. U. S. A. 106 2009 21972 21977
6. C. Szabó, and A. Papapetropoulos Br. J. Pharmacol. 164 2011 853 865
7. K.R. Olson, R.A. Dombkowski, M.J. Russel, M.M. Doellman, S.K. Head, N.L. Whitfield, and J.A. Madden J. Exp. Biol. 209 2006 4011 4023
8. Y.J. Peng, J. Nanduri, G. Raghuraman, D. Souvannakitti, M.M. Gadalla, G.K. Kumar, S.H. Snyder, and N.R. Prabhakar Proc. Natl. Acad. Sci. U. S. A. 107 2010 10719 10724
9. M. Lee, C. Schwab, S. Yu, E. McGeer, and P.L. McGeer Neurobiol. Aging 30 2009 1523 1534
10. M. Fu, W. Zhang, L. Wu, G. Yang, H. Li, and R. Wang Proc. Natl. Acad. Sci. U. S. A. 109 2012 2934 2948
11. M.S. Vandiver, and S.H. Snyder J. Mol. Med. 90 2012 255 263
12. P. Kamoun Amino Acids 26 2004 243 254
13. W. Zhao, and R. Wang Am. J. Physiol. Heart Circ. Physiol. 283 2002 H474 H480
14. S. Singh, D. Padovani, R.A. Leslie, T. Chiku, and R. Banerjee J. Biol. Chem. 284 2009 22457 22466
15. N. Shibuya, M. Tanaka, M. Yoshida, Y. Ogasawara, T. Togawa, K. Ishii, and H. Kimura Antioxid. Redox Signal. 11 2009 703 714
16. O. Kabil, and R. Banerjee J. Biol. Chem. 285 2010 21903 21907
17. R. Pietri, E. Román-Morales, and J. López-Garriga Antioxid. Redox Signal. 15 2011 393 404
18. M. Kajimura, R. Fukuda, R.M. Bateman, T. Yamamoto, and M. Suematsu Antioxid. Redox Signal. 13 2010 157 192
19. A.K. Mustafa, M.M. Gadalla, N. Sen, S. Kim, W. Mu, S.K. Gazi, R.K. Barrow, G. Yang, R. Wang, and S.H. Snyder Sci. Signal. 2 2009 ra72
20. G. Yang, L. Wu, B. Jiang, W. Yang, J. Qi, K. Cao, Q. Meng, A.K. Mustafa, W. Mu, S. Zhang, S.H. Snyder, and R. Wang Science 322 2008 587 590
21. Y.H. Liu, M. Lu, L.F. Hu, P.T.H. Wong, G.D. Webb, and J.S. Bian Antioxid. Redox Signal. 17 2012 141 185
22. K. Eto, T. Asada, K. Arima, T. Makifuchi, and H. Kimura Biochem. Biophys. Res. Commun. 293 2002 1485 1488
23. P. Kamoun, M.C. Belardinelli, A. Chabli, K. Lallouchi, and B. Chasefaux-Vekemans Am. J. Med. Genet. A 116A 2003 310 311
24. L. Wu, W. Yang, X. Jia, G. Yang, D. Duridanova, K. Cao, and R. Wang Lab. Invest. 89 2009 59 67
25. S. Fiorucci, E. Antonelli, A. Mencarelli, S. Orlandi, B. Renga, G. Rizzo, E. Distrutti, V. Shah, and A. Morelli Hepatology 42 2005 539 548
26. K. Kashfi, and K.R. Olson Biochem. Pharmacol. 85 2013 689 703
27. C. Szabó Nat. Rev. Drug Discov. 6 2007 917 935
28. H. Kimura Antioxid. Redox Signal. 12 2010 1111 1123
29. D.R. Linden, M.D. Levitt, G. Farrugia, and J.H. Szurszewski Antioxid. Redox Signal. 12 2010 1135 1146
30. L. Li, P. Rose, and P.K. Moore Annu. Rev. Pharmacol. Toxicol. 51 2011 169 187
31. E. Fisher Chem. Ber. 16 1883 2234 2236
32. J.K. Fogo, and M. Popowsky Anal. Chem. 21 1949 732 734
33. J. Furne, A. Saeed, and M.D. Levitt Am. J. Physiol. Regul. Integr. Comp. Physiol. 295 2008 R1479 R1485
34. A. Tangerman J. Chromatogr. B 877 2009 3366 3377
35. N.S. Lawrence, J. Davis, and R.G. Compton Talanta 52 2000 771 784
36. W.M. Xuan, C.Q. Sheng, Y.T. Cao, W.H. He, and W. Wang Angew. Chem. Int. Ed. 51 2012 2282 2284
37. V.S. Lin, and C.J. Chang Curr. Opin. Chem. Biol. 16 2012 595 601
38. C.X. Duan, and Y.G. Liu Curr. Med. Chem. 20 2013 2929 2937
39. N. Kumar, V. Bhalla, and M. Kumar Coord. Chem. Rev. 257 2013 2335 2347
40. J.J. Liu, C. Liu, and W. He Curr. Org. Chem. 17 2013 641 653
41. G.K. Kolluru, X. Shen, S.C. Bir, and C.G. Kevil Nitric Oxide 23 2013 5 20
42. E.F.V. Scriven, and K. Turnbull Chem. Rev. 88 1988 297 368
43. D.C. Dittmer Encyclopedia of Reagents for Organic Synthesis, Hydrogen Sulfide 2010 Wiley New York
44. S. Wu, Y. Fu, R. Yan, Y. Wu, X. Lei, and X.S. Ye Tetrahedron 66 2010 3433 3440
45. A.R. Lippert, E.J. New, and C.J. Chang J. Am. Chem. Soc. 133 2011 10078 10080
46. H.J. Peng, Y.F. Cheng, C.F. Dai, A.L. King, B.L. Predmore, D.J. Lefer, and B.H. Wang Angew. Chem. Int. Ed. 50 2011 9672 9675
47. F. Yu, P. Li, P. Song, B.S. Wang, J.Z. Zhao, and K.L. Han Chem. Commun. 48 2012 2852 2854
48. S.K. Das, C.S. Lim, S.Y. Yang, J.H. Han, and B.R. Cho Chem. Commun. 48 2012 8395 8397
49. Z. Wu, Z. Li, J. Han, and S. Han Chem. Commun. 48 2012 10120 10122
50. K. Zheng, W. Lin, and L. Tan Org. Biomol. Chem. 10 2012 9683 9688
51. B. Chen, C. Lv, and X. Tang Anal. Bioanal. Chem. 404 2012 1919 1923
52. C. Yu, X. Li, F. Zeng, F. Zheng, and S. Wu Chem. Commun. 49 2013 403 405
53. B. Chen, W. Li, C. Lv, M. Zhao, H. Jin, H. Jin, J. Du, L. Zhang, and X. Tang Analyst 138 2013 946 951
54. Q. Wan, Y. Song, Z. Li, X. Gao, and H. Ma Chem. Commun. 49 2013 502 504
55. W. Li, W. Sun, X. Yu, L. Du, and M. Li J. Fluoresc. 23 2013 181 186
56. W. Sun, J. Fan, C. Hu, J. Cao, H. Zhang, X. Xiong, J. Wang, S. Cui, S. Sun, and X. Peng Chem. Commun. 49 2013 3890 3892
57. G. Zhou, H. Wang, Y. Ma, and X. Chen Tetrahedron 69 2013 867 870
58. V.S. Lin, A.R. Lippert, and C.J. Chang Proc. Natl. Acad. Sci. U. S. A. 110 2013 7131 7135
59. T. Chen, Y. Zheng, Z. Xu, M. Zhai, Y. Xu, and J. Cui Tetrahedron Lett. 54 2013 2980 2982
60. S.K. Bae, C.H. Heo, D.J. Choi, D. Sen, E.H. Joe, B.R. Cho, and H.M. Kim J. Am. Chem. Soc. 135 2013 9915 9923
61. S. Chen, Z.J. Chen, W. Ren, and H.W. Ai J. Am. Chem. Soc. 134 2012 9589 9592
62. S.J. Lord, N.R. Conley, H.D. Lee, R. Samuel, N. Liu, R.J. Twieg, and W.E. Moerner J. Am. Chem. Soc. 130 2008 9204 9205
63. L.A. Montoya, and M.D. Pluth Chem. Commun. 48 2012 4767 4769
64. R. Wang, F. Yu, L. Chen, H. Chen, L. Wang, and W. Zhang Chem. Commun. 48 2012 11757 11759
65. W. Xuan, R. Pan, Y. Cao, K. Liu, and W. Wang Chem. Commun. 48 2012 10669 10671
66. X.F. Yang, L. Wang, H. Xu, and M. Zhao Anal. Chim. Acta. 631 2009 91 95
67. X. Cao, W. Lin, K. Zheng, and L. He Chem. Commun. 48 2012 10529 10531
68. T. Liu, Z. Xu, D.R. Spring, and J. Cui Org. Lett. 15 2013 2310 2313
69. L.A. Montoya, T.F. Pearce, R.J. Hansen, L.N. Zakharov, and M.D. Pluth J. Org. Chem. 78 2013 6550 6557
70. X. Shen, C.B. Pattillo, S. Pardue, S.C. Bir, R. Wang, and C.G. Kevil Free Radic. Biol. Med. 50 2011 1021 1031
71. C.R. Liu, J. Pan, S. Li, Y. Zhao, L.Y. Wu, C.E. Berkman, A.R. Whorton, and M. Xian Angew. Chem. Int. Ed. 50 2011 10327 10329
72. Z. Xu, L. Xu, J. Zhou, Y. Xu, W. Zhu, and X. Qian Chem. Commun. 48 2012 10871 10873
73. Y. Qian, J. Karpus, O. Kabil, S.Y. Zhang, H.L. Zhu, R. Banerjee, J. Zhao, and C. He Nat. Commun. 2 2011 495 501
74. Y. Qian, L. Zhang, S. Ding, X. Deng, C. He, X.E. Zheng, H.L. Zhu, and J. Zhao Chem. Sci. 3 2012 2920 2923
75. C. Liu, B. Peng, S. Li, C.M. Park, A.R. Whorton, and M. Xian Org. Lett. 14 2012 2184 2187
76. X. Wang, J. Sun, W. Zhang, X. Ma, J. Lv, and B. Tang Chem. Sci. 4 2013 2551 2556
77. Y. Chen, C. Zhu, Z. Yang, J. Chen, Y. He, Y. Jiao, W. He, L. Qiu, J. Cen, and Z. Guo Angew. Chem. Int. Ed. 52 2013 1688 1691
78. J. Liu, Y.Q. Sun, J. Zhang, T. Yang, J. Cao, L. Zhang, and W. Guo Chem. Eur. J. 19 2013 4717 4722
79. E. Galardon, A. Tomas, P. Roussel, and I. Artaud Dalton Trans. 2009 9126 9130
80. M.G. Choi, S. Cha, H. Lee, H.L. Jeon, and S.K. Chang Chem. Commun. 2009 7390 7392
81. K. Sasakura, K. Hanaoka, N. Shibuya, Y. Mikami, Y. Kimura, T. Komatsu, T. Ueno, T. Terai, H. Kimura, and T. Nagano J. Am. Chem. Soc. 133 2011 18003 18005
82. F. Hou, J. Cheng, P. Xi, F. Chen, L. Huang, G. Xie, Y. Shi, H. Liu, D. Bai, and Z. Zeng Dalton Trans. 41 2012 5799 5804
83. F. Hou, L. Huang, P. Xi, J. Cheng, X. Zhao, G. Xie, Y. Shi, F. Cheng, X. Yao, D. Bai, and Z. Zeng Inorg. Chem. 51 2012 2454 2460
84. M.Q. Wang, K. Li, J.T. Hou, M.Y. Wu, Z. Huang, and X.Q. Yu J. Org. Chem. 77 2012 8350 8354
85. J. Wang, L. Long, D. Xie, and Y. Zhan J. Lumin. 139 2013 40 46
86. M. Strianese, F. De Martino, C. Pellecchia, G. Ruggiero, and S. D'Auria Protein Pept. Lett. 18 2011 282 286
87. M. Strianese, G.J. Palm, S. Milione, O. Kühl, W. Hinrichs, and C. Pellecchia Inorg. Chem. 51 2012 11220 11222
88. B. Wang, P. Li, F. Yu, P. Song, X. Sun, S. Yang, Z. Lou, and K. Han Chem. Commun. 49 2013 1014 1016
89. Z. Lou, P. Li, Q. Pan, and K. Han Chem. Commun. 49 2013 2445 2447
90. B. Wang, P. Li, F. Yu, J. Chen, Z. Qu, and K. Han Chem. Commun. 49 2013 5790 5792
91. C. Hansch, A. Leo, and R.W. Taft Chem. Rev. 91 1991 165 195
92. J.P.Y. Kao, A.T. Harootunian, and R.Y. Tsien J. Biol. Chem. 264 1989 8179 8184
93. S. Izumi, Y. Urano, K. Hanaoka, T. Terai, and T. Nagano J. Am. Chem. Soc. 131 2009 10189 10200
94. A.R. Lippert, G.C. Van de Bittner, and C.J. Chang Acc. Chem. Res. 44 2011 793 804
95. J.A. Prescher, and C.R. Bertozzi Nat. Chem. Biol. 1 2005 13 21
96. P.V. Chang, J.A. Prescher, M.J. Hangauer, and C.R. Bertozzi J. Am. Chem. Soc. 129 2007 8400 8401
97. S.T. Laughlin, J.M. Baskin, S.L. Amacher, and C.R. Bertozzi Science 320 2008 664 667
98. P.V. Chang, X. Chen, C. Smyrniotis, A. Xenakis, T. Hu, C.R. Bertozzi, and P. Wu Angew. Chem. Int. Ed. 48 2009 4030 4033
99. R. Weissleder Nat. Biotechnol. 19 2001 316 317
100. M. Pawlicki, H.A. Collins, R.G. Denning, and H.L. Anderson Angew. Chem. Int. Ed. 48 2009 3244 3266
101. F. Helmchen, and W. Denk Nat. Methods 2 2005 932 940
102. G. Grynkiewicz, M. Poenie, and R.Y. Tsien J. Biol. Chem. 260 1985 3440 3450
103. R.Y. Tsien, and M. Poenie Trends Biochem. Sci. 11 1986 450 455
104. J.P.Y. Kao, and R.Y. Tsien Biophys. J. 53 1988 635 639
105. M. Naraghi Cell Calcium 22 1997 255 268
106. S.M. Namin, S. Nofallah, M.S. Joshi, K. Kavallieratos, and N.M. Tsoukias Nitric Oxide 28 2013 39 46
107. M.K. Thorson, T. Majtan, J.P. Kraus, and A.M. Barrios Angew. Chem. Int. Ed. 52 2013 4641 4644