Ratiometric two-photon fluorescent probes for mitochondrial hydrogen sulfide in living cells

Journal of Organic Chemistry

Volumn 79, Issue 20, 2014, Pages 9481-9489

  Liu, Xiu Ling ^a   Du, Xiao Jiao ^a   Dai, Chun Guang ^a   Song, Qin Hua ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOLOGY; FLUORESCENCE; HYDROGEN; MITOCHONDRIA; PHOTONS; PROBES; SULFUR DETERMINATION;

4-AMINO-1 ,8-NAPHTHALIMIDE; BIOLOGICAL APPLICATIONS; BIOLOGICAL RESEARCH; BIOLOGICAL SPECIMENS; LOW DETECTION LIMIT; PHYSIOLOGICAL CONDITION; RATIOMETRIC IMAGING; TWO PHOTON MICROSCOPY;

HYDROGEN SULFIDE;

4 AMINO 1,8 NAPHTHALIMIDE; FLUORESCENT DYE; HYDROGEN SULFIDE; NAPHTHALIMIDE DERIVATIVE; TWO PHOTON FLUORESCENT PROBE; UNCLASSIFIED DRUG; 1 NAPHTHYLAMINE; 4-AMINO-1,8-NAPHTHALIMIDE; 4-AZIDOBENZYL CARBAMATE; BENZYL DERIVATIVE; CARBAMIC ACID DERIVATIVE; QUINOLONE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CELL VIABILITY; CYTOTOXICITY; FLUORESCENCE IMAGING; LIMIT OF DETECTION; MCF 7 CELL LINE; MITOCHONDRION; MOLECULAR IMAGING; SYNTHESIS; ANALOGS AND DERIVATIVES; CHEMISTRY; HUMAN; PHOTON; PROCEDURES;

1-NAPHTHYLAMINE; BENZYL COMPOUNDS; CARBAMATES; FLUORESCENT DYES; HUMANS; HYDROGEN SULFIDE; MITOCHONDRIA; NAPHTHALIMIDES; OPTICAL IMAGING; PHOTONS; QUINOLONES;

EID: 84908251344     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5014838     Document Type: Article

References (80)

1. (a) Li, L.; Rose, P.; Moore, P. K. Annu. Rev. Pharmacol. Toxicol. 2011, 51, 169-187.
2. (b) Krishnan, N.; Fu, C.; Pappin, D. J.; Tonks, N. K. Sci. Signal. 2011, 4, ra86.
3. (a) Ishigami, M.; Hiraki, K.; Umemura, K. Y.; Ishii, O. K.; Kimura, H. Antioxid Redox Signal. 2009, 11, 205-214.
4. (b) Benavides, G. A.; Squadrito, G. L.; Mills, R. W.; Patel, H. D.; Isbell, T. S.; Patel, R. P.; Darley-Usmar, V. M.; Doeller, J. E.; Kraus, D. W. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 17977-17982.
5. (c) Singh, S.; Banerjee, R. Biochim. Biophys. Acta 2011, 1814, 1518-1527.
6. Kamoun, P. Amino Acids. 2004, 26, 243-254.
7. Szabó, C. Nat. Rev. Drug. Discovery 2007, 6, 917-935.
8. Kabil, O.; Banerjee, R. J. Biol. Chem. 2010, 285, 21903-21907.
9. (a) Shibuya, N.; Tanaka, M.; Yoshida, M.; Ogasawara, Y.; Togawa, T.; Ishii, K.; Kimura, H. Antioxid. Redox Signaling 2009, 11, 703-714.
10. (b) Kimura, Y.; Goto, Y.; Kimura, H. Antioxid. Redox Signaling 2010, 12, 1-13.
11. (a) Mari, M.; Morales, A.; Colell, A.; Garcia-Ruiz, C.; Fernandez-Checa, J. C. Antioxid. Redox Signaling 2009, 11, 2685-2700.
12. (b) Cheng, W. Y.; Tong, H.; Miller, E. W.; Chang, C. J.; Remington, J.; Zucker, R. M.; Bromberg, P. A.; Samet, J. M.; Hofer, T. P. Environ. Health Perspect. 2010, 118, 902-908.
13. (a) Pun, P. B. L.; Lu, J.; Kan, E. M.; Moochhala, S. Mitochondrion 2010, 10, 83-93.
14. (b) Fu, M.; Zhang, W.; Wu, L.; Yang, G.; Li, H.; Wang, R. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 2943-2948.
15. (a) Zhao, W.; Zhang, J.; Lu, Y.; Wang, R. EMBO J. 2001, 20, 6008-6016.
16. (b) Wang, R. FASEB J. 2002, 16, 1792-1798.
17. (c) Kabil, O.; Banerjee, R. J. Biol.chem. 2010, 285, 21903-21907.
18. (d) Lavu, M.; Bhushan, S.; Lefer, D. J. Clin. Sci. (London) 2011, 120, 219-229.
19. (e) Olson, K. R. Am. J. Physiol. 2011, 301, R297-R312.
20. (a) Peng, H.; Chen, W.; Burroughs, S.; Wang, B. Curr. Org. Chem. 2013, 17, 641-653.
21. (b) Kumar, N.; Bhalla, V.; Kumar, M. Coord. Chem. Rev. 2013, 257, 2335-2341.
22. (c) Lin, V. S.; Chang, C. J. Curr. Opin. Chem. Biol. 2012, 16, 595-601.
23. (d) Chan, J. S.; Dodani, C.; Chang, C. J. Nat. Chem. 2012, 4, 973-984.
24. (a) Lippert, A. R.; New, E. J.; Chang, C. J. J. Am. Chem. Soc. 2011, 133, 10078-10080.
25. (b) Peng, H.; Cheng, Y.; Dai, C.; King, A. L.; Predemore, B. L.; Lefer, D. J.; Wang, B. Angew. Chem., Int. Ed. 2011, 50, 9672-9675.
26. (c) Chen, S.; Chen, Z. J.; Ren, W.; Ai, H.-W. J. Am. Chem. Soc. 2012, 134, 9589-9592.
27. (d) Yu, F.; Li, P.; Song, P.; Wang, B.; Zhao, J.; Han, K. Chem. Commun. 2012, 48, 2852-2854.
28. (e) Montoya, L. A.; Pluth, M. D. Chem. Commun. 2012, 48, 4767-4769.
29. (f) Das, S. K.; Lim, C. S.; Yang, S. Y.; Han, J. H.; Cho, B. R. Chem. Commun. 2012, 48, 8395-8397.
30. (g) Xuan, W.; Pan, R.; Cao, Y.; Liu, K.; Wang, W. Chem. Commun. 2012, 48, 10669-10671.
31. (h) Wu, Z.; Li, Z.; Yang, L.; Han, J.; Han, S. Chem. Commun. 2012, 48, 10120-10122.
32. (i) Wu, M.; Li, K.; Hou, J.; Huang, Z.; Yu, X. Org. Biomol. Chem. 2012, 10, 8342-8347.
33. (j) Wan, Q.; Song, Y.; Li, Z.; Gao, X.; Ma, H. Chem. Commun. 2013, 49, 502-504.
34. (k) Sun, W.; Fan, J.; Hu, C.; Zhang, H.; Xiong, X.; Wang, J.; Cui, S.; Sun, S.; Peng, X. Chem. Commun. 2013, 49, 3890-3892.
35. (l) Bae, S. K.; Heo, C. H.; Choi, D. J.; Sen, D. E.; Joe, H.; Cho, B. R.; Kim, H. M. J. Am. Chem. Soc. 2013, 135, 9915-9923.
36. (m) Bailey, T. S.; D. Pluth, M. J. Am. Chem. Soc. 2013, 135, 16697-16704.
37. (n) Zhu, D.; Li, G.; Xue, L.; Jiang, H. Org. Biomol. Chem. 2013, 11, 4577-4580.
38. (o) Chen, B.; Li, W.; Lv, C.; Zhao, M.; Jin, H.; Jin, H.; Du, J.; Zhang, L.; Tang, X. Analyst 2013, 138, 946-951.
39. (p) Mao, G.; Wei, T.; Wang, X.; Huan, S.; Lu, D.; Zhang, J.; Zhang, X.; Tan, W.; Shen, G.; Yu, R. Anal. Chem. 2013, 85, 7875-7881.
40. (q) Li, W.; Sun, W.; Yu, X.; Du, L.; Li, M. J. Fluoresc. 2013, 23, 181-186.
41. (r) Zhang, H. T.; Wang, P.; Chen, G. C.; Cheung, H.-Y.; Sun, H. Y. Tetrahedron Lett. 2013, 54, 4826-4829.
42. (s) Zheng, Y.; Zhao, M.; Qiao, Q. L.; Liu, H. Y.; Lang, H. J.; Xu, Z. C. Dyes Pigments 2013, 98, 367-371.
43. (t) Chen, T.; Zheng, Y.; Xu, Z. C.; Zhao, M.; Xu, Y. G.; Cui, J. N. Tetrahedron Lett. 2013, 54, 2980-2892.
44. (u) Reja, S. I.; Kumar, N.; Sachdeva, R.; Bhalla, V.; Kumar, M. RSC Adv. 2013, 3, 17770-17774.
45. (a) Wang, X.; Sun, J.; Zhang, W.; Ma, X.; Lv, J.; Tang, B. Chem. Sci. 2013, 4, 2551-2556.
46. (b) Chen, Y.; Zhu, C.; Yang, Z.; Chen, J.; He, Y.; Jiao, Y.; He, W.; Qiu, L.; Cen, J.; Guo, Z. Angew. Chem., Int. Ed. 2013, 52, 1688-1691.
47. (c) Liu, J.; Sun, Y.; Zhang, J.; Yang, T.; Cao, J.; Zhang, L.; Guo, W. Chem. - Eur. J. 2013, 19, 4717-4722.
48. (d) Li, X.; Zhang, S.; Cao, J.; Xie, N.; Liu, T.; Yang, B.; He, Q.; Hu, Y. Chem. Commun. 2013, 49, 8656-6558.
49. (e) Liu, T.; Xu, Z.; Spring, D. R.; Cui, J. Org. Lett. 2013, 15, 2310-2313.
50. (f) Montoya, L. A.; Pearce, T. F.; Hansen, R. J.; Zakharov, L. N.; Plut, M. D. J. Org. Chem. 2013, 78, 6050-6064.
51. (g) Chen, X.; Wu, S.; Han, J.; Han, S. Biol. Med. Chem. Lett. 2013, 23, 5295-5299.
52. (h) Qian, Y.; Yang, B.; Shen, Y.; Du, Q.; Lin, L.; Lin, J.; Zhu, H. Sens. Actuators B 2013, 182, 498-503.
53. (i) Wang, J. L.; Lin, W. Y.; Li, W. L. Biomaterials 2013, 34, 7429-7436.
54. (j) Zhang, J. Y.; Sun, Y. Q.; Liu, J.; Shi, Y. W.; Guo, W. Chem. Commun. 2013, 49, 11305-11307.
55. (k) Liu, T. Y.; Zhang, X. F.; Qiao, Q. L.; Zou, C. Y.; Feng, L.; Cui, J. N.; Xu, Z. C. Dyes Pigments 2013, 99, 537-542.
56. (a) Sasakura, K.; Hanaoka, K.; Shibuya, N.; Mikami, Y.; Kimura, Y.; Komatsu, T.; Ueno, T.; Terai, T.; Kimura, H.; Nagano, T. J. Am. Chem. Soc. 2011, 133, 18003-180035.
57. (b) Qu, X.; Li, C.; Chen, H.; Mack, J.; Guo, Z.; Shen, Z. Chem. Commun. 2013, 49, 7510-7512.
58. (a) Wang, B. S.; Li, P.; Yu, F. B.; Song, P.; Sun, X. F.; Yang, S. Q.; Lou, Z. R.; Han, K. L. Chem. Commun. 2013, 49, 1014-1016.
59. (b) Wang, B. S.; Li, P.; Yu, F. B.; Chen, J. S.; Qu, Z. J.; Han, K. L. Chem. Commun. 2013, 49, 5790-5792.
60. (c) Lina, V. S.; Lippert, A. R.; Chang, C. J. PNAS USA 2013, 110, 7131-7135.
61. (d) Wei, L.; Yi, L.; Song, F. B.; Wei, C.; Wang, B. F.; Xi, Z. Sci. Rep. 2014, 4, 4521.
62. (e) Yuan, L.; Zuo, Q.-P. Chem. - Asian J. 2014, 9, 1544-1549.
63. Qian, X.; Xiao, Y.; Xu, Y.; Guo, X.; Qian, J.; Zhu, W. Chem. Commun. 2010, 46, 6418-6436.
64. Zhang, J. F.; Lim, C. S.; Bhuniya, S.; Cho, B. R.; Kim, J. S. Org. Lett. 2011, 13, 1190-1193.
65. Srikun, D.; Miller, E. W.; Domaille, D. W.; Chang, C. J. J. Am. Chem. Soc. 2008, 130, 4596-4597.
66. Robinson, A.-M.; Evers, E. L.; Griffin, R. J.; Irwin, W. J. J. Pharm. Pharmacol. 1988, 40, 61P.
67. (a) Cava, M. P.; Merkel, K. E.; Schlessinger, R. H. Tetrabedron 1965, 21, 3059-3064.
68. (b) Dong, M.; Wang, Y. W.; Peng, Y. Org. Lett. 2010, 12, 5310-5313.
69. Wu, J.; Huang, R.; Wang, C. C.; Liu, W. T.; Wang, J. Q.; Weng, X. C.; Tian, T.; Zhou, X. Org. Biomol. Chem. 2013, 11, 580-585.
70. Zhang, J. F.; Kim, S.; Han, J. H.; Lee, S.-J.; Pradhan, T.; Cao, Q. Y.; Lee, S. J.; Kang, C.; Kim, J. S. Org. Lett. 2011, 13, 5294-5297 and references therein.
71. Perrin, D. D. Ionization Constants of Inorganic Acids and Bases in Aqueous Solution, 2nd ed.; Pergamon: Oxford, 1982.
72. (a) Dombkowski, R. A.; Russell, M. J.; Olson, K. R. Am. J. Physiol. 2004, 286, R678-R685.
73. (b) Hughes, M. N.; Centelles, M. N.; Moore, K. P. Free Radical Biol. Med. 2009, 47, 1346-1353.
74. A Guide to Fluorescent Probes and Labeling Technologies, 11th ed.; Johnson, I., Spence, M. T. Z., Eds.; The Molecular Probes: Eugene, OR, 2010.
75. Demas, J. N.; Crosby, J. A. J. Phys. Chem. 1971, 73, 991-1024.
76. Dawson, W. R.; Windsor, M. W. J. Phys. Chem. 1968, 72, 3251-3260.
77. Ji, Z.; Li, Y.; Pritchett, T. M.; Makarov, N. S.; Haley, J. E.; Li, Z.; Drobizhev, M.; Rebane, A.; Sun, W. Chem. - Eur. J. 2011, 17, 2479-2491.
78. Zheng, Q.; He, G. S.; Prasad, P. N. J. Mater. Chem. 2005, 15, 579-587.
79. Li, D. M.; Zhang, Q.; Wang, P.; Wu, J. Y.; Kan, Y. H.; Tian, Y. P.; Zhou, H. P.; Yang, J. X.; Tao, X. T.; Jiang, M. H. Dalton Trans. 2011, 40, 8170-8178.
80. Fan, J.; Sun, W.; Hu, M.; Cao, J.; Cheng, G.; Dong, H.; Song, K.; Liu, Y.; Sun, S.; Peng, X. Chem. Commun. 2012, 48, 8117-8119.