Fluorescent probes for selective probing thiol-containing amino acids

Current Organic Synthesis

Volumn 11, Issue 3, 2014, Pages 377-402

  Yu, Jin Gang ^a,b   Zhao, Xiu Hui ^a   Yu, Lin Yan ^a   Yang, Hua ^a   Chen, Xiao Qing ^a   Jiang, Jian Hui ^b  

^a CENTRAL SOUTH UNIVERSITY   (China)

^b HUNAN UNIVERSITY   (China)

Author keywords

Application; Cysteine; Design; Fluorescent probe; Glutathione; Homocysteine

Indexed keywords

EID: 84904100732     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570179411999140304143053     Document Type: Review

References (116)

1. Edgington, L.E.; Verdoes, M.; Ortega, A.; Withana, N.P.; Lee, J.; Syed, S.; Bachmann, M.H.; Blum, G.; Bogyo, M. Functional imaging of legumain in cancer using a new quenched activity-based probe. J. Am. Chem. Soc., 2013, 135(1), 174-182.
2. Pastore, A.; Piemonte, F.; Locatelli, M.; Russo, A.L.; Gaeta, L.M.; Tozzi, G.; Federici, G. Determination of blood total, reduced, and oxidized glutathione in pediatric subjects. Clin. Chem., 2003, 47(8), 1467-1469.
3. Peng, H.J.; Chen, W.X.; Cheng, Y.F.; Hakuna, L.; Strongin, R.; Wang, B.H. Thiol reactive probes and chemosensors. Sensors, 2012, 12(11), 15907-15946.
4. Hong, R.; Han, G.; Fernández, J.M.; Kim, B.J.; Forbes, N.S.; Rotello, V.M. Glutathione-mediated delivery and release using monolayer protected nanoparticle carriers. J. Am. Chem. Soc., 2006, 128(4), 1078-1079.
5. Ueland, P.M.; Refsum, H.; Beresford, S.A.A.; Vollset, S.E. The controversy over homocysteine and cardiovascular risk. Am. J. Clin. Nutr., 2000, 72(2), 324-332.
6. Refsum, H.; Ueland, P.M.; Nygard, O.; Vollset, S.E. Homocysteine and cardiovascular disease. Annu. Rev. Med., 1998, 49, 31-62.
7. Hong, R.; Han, G.; Fernandez, J.M.; Kim, B.J.; Forbes, N.S.; Rotello, V.M. Glutathione-mediated delivery and release using monolayer protected nanoparticle carriers. J. Am. Chem. Soc., 2006, 128(4), 1078-1079.
8. Lee, J.-S.; Ulmann, P.A.; Han, M.S.; Mirkin, C.A. A DNA gold nanoparticle-based colorimetric competition assay for the detection of cysteine. Nano Lett., 2008, 8(2), 529-533.
9. Wang, Y.; Lu, J.; Tang, L.; Chang, H.; Li, J. Graphene oxide amplified electrogenerated chemiluminescence of quantum dots and its selective sensing for glutathione from thiol-containing compounds. Anal. Chem., 2009, 81(23), 9710-9715.
10. Soriano, B.D.; Tam, L.T.T.; Lu, H.S.; Valladares, V.G. A fluorescent-based HPLC assay for quantification of cysteine and cysteamine adducts in Escherichia coli-derived proteins. J. Chromatogr. B, 2012, 880, 27-33.
11. Li, H.; Liu, J.; Fang, Y.; Qin, Y.; Xu, S.; Liu, Y.; Wang, E. G-quadruplex- based ultrasensitive and selective detection of histidine and cysteine. Biosens. Bioelectron., 2013, 41, 563-568.
12. Bianga, J.; Govasmark, E.; Szpunar, J. Characterization of selenium incorporation into wheat proteins by two-dimensional gel electrophoresis- laser ablation ICP MS followed by capillary HPLC-ICP MS and electrospray linear trap quadrupole orbitrap MS. Anal. Chem., 2013, 85(4), 2037-43.
13. Yin, L.L.; Chen, Z.Z.; Tong, L.L.; Xu, K.H.; Tang, B. Progress on fluorescent probes for thiols. Chinese J. Anal. Chem., 2009, 37(7), 1073-1081.
14. Tang, B.; Yin, L.L.; Wang, X.; Chen, Z.Z.; Tong, L.L.; Xu, K.H. A fast- response, highly sensitive and specific organoselenium fluorescent probe for thiols and its application in bioimaging. Chem. Commun., 2009, (35), 5293-5295.
15. Zhou, Y.; Yoon, J. Recent progress in fluorescent and colorimetric chemosensors for detection of amino acids. Chem. Soc. Rev., 2012, 41(1), 52-67.
16. Eun Jun, M.; Roy, B.; Han Ahn, K. Turn-on fluorescent sensing with reactive probes. Chem. Commun., 2011, 47(27), 7583-7601.
17. Huang, C.B.; Yi, D.S.; Feng, C.H.; Ren, A.X.; Sun, S.G. Two-photon fluorescence sensors. Prog. Chem., 2010, 22(12), 2408-2419.
18. Chen, X.; Zhou, Y.; Peng, X.J.; Yoon, J. Fluorescent and colorimetric probes for detection of thiols. Chem. Soc. Rev., 2010, 39(6), 2120-2135.
19. Jiang, W.; Fu, Q.Q.; Fan, H.Y.; Ho, J.; Wang, W. A highly selective fluorescent probe for thiophenols. Angew. Chem. Int. Edit., 2007, 46(44), 8445-8448.
20. Mei, J.; Wang, Y.J.; Tong, J.Q.; Wang, J.; Qin, A.J.; Sun, J.Z.; Tang, B.Z. Discriminatory detection of cysteine and homocysteine based on dialdehyde- functionalized aggregation-induced emission fluorophores. Chem. Eur. J., 2013, 19(2), 612-619.
21. Zhang, X.; Ren, X.; Xu, Q.-H.; Loh, K.P.; Chen, Z.K. One- and two-photon turn-on fluorescent probe for cysteine and homocysteine with large emission shift. Org. Lett., 2009, 11(6), 1257-1260.
22. 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. Highly selective red- and green-emitting two-photon fluorescent probes for cysteine detection and their bio-imaging in living cells. Chem. Commun., 2012, 48(28), 3442-3444.
23. Zhang, M.; Li, M.; Zhao, Q.; Li, F.; Zhang, D.; Zhang, J.; Yi, T.; Huang, C. Novel Y-type two-photon active fluorophore: synthesis and application in fluorescent sensor for cysteine and homocysteine. Tetrahedron Lett., 2007, 48(13), 2329-2333.
24. Wang, Y.; Xiao, J.; Wang, S.; Yang, B.; Ba, X. Tunable fluorescent sensing of cysteine and homocysteine by intramolecular charge transfer. Supramol. Chem., 2010, 22(6), 380-386.
25. Li, H.L.; Fan, J.L.; Wang, J.Y.; Tian, M.Z.; Du, J.J.; Sun, S.G.; Sun, P.P.; Peng, X.J. A fluorescent chemodosimeter specific for cysteine: effective discrimination of cysteine from homocysteine. Chem. Commun., 2009, (39), 5904-5906.
26. Lin, W.; Long, L.; Yuan, L.; Cao, Z.; Chen, B.; Tan, W. A ratiometric fluorescent probe for cysteine and homocysteine displaying a large emission shift. Org. Lett., 2008, 10(24), 5577-5580.
27. Lee, K.S.; Kim, T.K.; Lee, J.H.; Kim, H.J.; Hong, J.I. Fluorescence turn-on probe for homocysteine and cysteine in water. Chem. Commun., 2008, (46), 6173-6175.
28. Kim, T.K.; Lee, D.N.; Kim, H.J. Highly selective fluorescent sensor for homocysteine and cysteine. Tetrahedron Lett., 2008, 49(33), 4879-4881.
29. Duan, L.; Xu, Y.; Qian, X.; Wang, F.; Liu, J.; Cheng, T. Highly selective fluorescent chemosensor with red shift for cysteine in buffer solution and its bioimage: symmetrical naphthalimide aldehyde. Tetrahedron Lett., 2008, 49(47), 6624-6627.
30. Mei, J.; Tong, J.Q.; Wang, J.; Qin, A.J.; Sun, J.Z.; Tang, B.Z. Discriminative fluorescence detection of cysteine, homocysteine and glutathione via reaction-dependent aggregation of fluorophore-analyte adducts. J. Mater. Chem., 2012, 22(33), 17063-17070.
31. Yue, Y.; Guo, Y.; Xu, J.; Shao, S. A Bodipy-based derivative for selective fluorescence sensing of homocysteine and cysteine. New J. Chem., 2011, 35(1), 61-64.
32. Hu, M.M.; Fan, J.L.; Li, H.L.; Song, K.D.; Wang, S.; Cheng, G.H.; Peng, X.J. Fluorescent chemodosimeter for Cys/Hcy with a large absorption shift and imaging in living cells. Org. Biomol. Chem., 2011, 9(4), 980-983.
33. Ren, H.J.; Xiao, F.; Zhan, K.; Kim, Y.P.; Xie, H.X.; Xia, Z.Y.; Rao, J.A Biocompatible condensation reaction for the labeling of terminal cysteine residues on proteins. Angew. Chem. Int. Edit., 2009, 48(51), 9658-9662.
34. Deng, L.; Wu, W.T.; Guo, H.M.; Zhao, J.Z.; Ji, S.M.; Zhang, X.; Yuan, X.L.; Zhang, C.L. Colorimetric and ratiometric fluorescent chemosensor based on diketopyrrolopyrrole for selective detection of thiols: An experimental and theoretical study. J. Org. Chem., 2011, 76(22), 9294-9304.
35. Wang, H.L.; Zhou, G.D.; Mao, C.; Chen, X.Q. A fluorescent sensor bearing nitroolefin moiety for the detection of thiols and its biological imaging. Dyes Pigments, 2013, 96(1), 232-236.
36. Zhou, X.; Jin, X.J.; Sun, G.Y.; Li, D.H.; Wu, X. A cysteine probe with high selectivity and sensitivity promoted by response-assisted electrostatic attraction. Chem. Commun., 2012, 48(70), 8793-8795.
37. Zhang, M.; Wu, Y.C.; Zhang, S.Z.; Zhu, H.N.; Wu, Q.; Jiao, L.J.; Hao, E.H. A nitroolefin functionalized BODIPY chemodosimeter for biothiols driven by an unexpected conjugated addition mechanism. Chem. Commun., 2012, 48(71), 8925-8927.
38. Lin, W.; Yuan, L.; Cao, Z.; Feng, Y.; Long, L. A Sensitive and selective fluorescent thiol probe in water based on the conjugate 1,4-addition of thiols to, -unsaturated ketones. Chem. Eur. J., 2009, 15(20), 5096-5103.
39. Zhang, H.T.; Wang, P.; Yang, Y.X.; Sun, H.Y. A selective fluorescent probe for thiols based on alpha,beta-unsaturated acyl sulfonamide. Chem. Commun., 2012, 48(86), 10672-10674.
40. Zhang, M.; Yu, M.; Li, F.; Zhu, M.; Li, M.; Gao, Y.; Li, L.; Liu, Z.; Zhang, J.; Zhang, D.; Yi, T.; Huang, C. A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging. J. Am. Chem. Soc., 2007, 129(34), 10322-10323.
41. Zeng, X.D.; Zhang, X.L.; Zhu, B.C.; Jia, H.Y.; Li, Y.M. A highly selective wavelength-ratiometric and colorimetric probe for cysteine. Dyes Pigments, 2012, 94(1), 10-15.
42. Long, L.L.; Lin, W.Y.; Chen, B.B.; Gao, W.S.; Yuan, L. Construction of a FRET-based ratiometric fluorescent thiol probe. Chem. Commun., 2011, 47(3), 893-895.
43. Wang, L.G.; Zhou, Q.; Zhu, B.C.; Yan, L.G.; Ma, Z.M.; Du, B.; Zhang, X.L. A colorimetric and fluorescent chemodosimeter for discriminative and simultaneous quantification of cysteine and homocysteine. Dyes Pigments, 2012, 95(2), 275-279.
44. Wang, H.L.; Zhou, G.D.; Gai, H.W.; Chen, X.Q. A fluorescein-based probe with high selectivity to cysteine over homocysteine and glutathione. Chem. Commun., 2012, 48(67), 8341-8343.
45. Niu, L.Y.; Guan, Y.S.; Chen, Y.Z.; Wu, L.Z.; Tung, C.H.; Yang, Q.Z. BODIPY-based ratiometric fluorescent sensor for highly selective detection of glutathione over cysteine and homocysteine. J. Am. Chem. Soc., 2012, 134(46), 18928-18931.
46. Li, X.F.; Zhang, X.Q.; Chi, Z.G.; Chao, X.J.; Zhou, X.; Zhang, Y.; Liu, S.W.; Xu, J.R. Simple fluorescent probe derived from tetraphenylethylene and benzoquinone for instantaneous biothiol detection. Anal. Methods-UK, 2012, 4(10), 3338-3343.
47. Wei, W.; Liang, X.J.; Hu, G.Z.; Guo, Y.; Shao, S.J. A highly selective colorimetric probe based on 2,2',2"-trisindolylmethene for cysteine/homocysteine. Tetrahedron Lett., 2011, 52(13), 1422-1425.
48. Jung, H.S.; Han, J.H.; Pradhan, T.; Kim, S.; Lee, S.W.; Sessler, J.L.; Kim, T.W.; Kang, C.; Kim, J.S. A cysteine-selective fluorescent probe for the cellular detection of cysteine. Biomaterials, 2012, 33(3), 945-953.
49. Kim, G.J.; Lee, K.; Kwon, H.; Kim, H.J. Ratiometric fluorescence imaging of cellular glutathione. Org. Lett., 2011, 13(11), 2799-2801.
50. Ha, H.J.; Yoon, D.H.; Park, S.; Kim, H.J. Fluorescence turn-on probe for biothiols: intramolecular hydrogen bonding effect on the Michael reaction. Tetrahedron, 2011, 67(40), 7759-7762.
51. Garcia-Beltran, O.; Mena, N.; Perez, E.G.; Cassels, B.K.; Nunez, M.T.; Werlinger, F.; Zavala, D.; Aliaga, M.E.; Pavez, P. The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study. Tetrahedron Lett., 2011, 52(49), 6606-6609.
52. Chen, X.; Ko, S.K.; Kim, M.J.; Shin, I.; Yoon, J. A thiol-specific fluorescent probe and its application for bioimaging. Chem. Commun., 2010, 46(16), 2751-2753.
53. Zeng, Y.; Zhang, G.X.; Zhang, D.Q.; Zhu, D.B. A dual-function colorimetric chemosensor for thiols and transition metal ions based on ICT mechanism. Tetrahedron Lett., 2008, 49(52), 7391-7394.
54. Zeng, Y.; Zhang, G.X.; Zhang, D.Q. A selective colorimetric chemosensor for thiols based on intramolecular charge transfer mechanism. Anal. Chim. Acta, 2008, 627(2), 254-257.
55. Wang, P.; Liu, J.; Lv, X.; Liu, Y.L.; Zhao, Y.; Guo, W. A Naphthalimide- based glyoxal hydrazone for selective fluorescence turn-on sensing of Cys and Hcy. Org. Lett., 2012, 14(2), 520-523.
56. Bouffard, J.; Kim, Y.; Swager, T.M.; Weissleder, R.; Hilderbrand, S.A. A highly selective fluorescent probe for thiol bioimaging. Org. Lett., 2008, 10(1), 37-40.
57. Lee, J.H.; Lim, C.S.; Tian, Y.S.; Han, J.H.; Cho, B.R. A Two-photon fluorescent probe for thiols in live cells and tissues. J. Am. Chem. Soc., 2010, 132(2), 1216-1217.
58. Sun, W.; Li, W.H.; Li, J.; Zhang, J.; Du, L.P.; Li, M.Y. Naphthalimide-based fluorescent off/on probes for the detection of thiols. Tetrahedron, 2012, 68(27-28), 5363-5367.
59. Guo, Y.X.; Yang, X.F.; Hakuna, L.; Barve, A.; Escobedo, J.O.; Lowry, M.; Strongin, R.M. A Fast response highly selective probe for the detection of glutathione in human blood plasma. Sensors, 2012, 12(5), 5940-5950.
60. Leonard, N.J.; Ning, R.Y. The synthesis and stereochemistry of substituted 1,4-thiazepines related to the penicillins. J. Org. Chem., 1966, 31(12), 3928-35.
61. Yang, X.F.; Guo, Y.X.; Strongin, R.M. Conjugate addition/cyclization sequence enables selective and simultaneous fluorescence detection of cysteine and homocysteine. Angew. Chem. Int. Edit., 2011, 50(45), 10690-10693.
62. Isik, M.; Ozdemir, T.; Turan, I.S.; Kolemen, S.; Akkaya, E.U. Chromogenic and fluorogenic sensing of biological thiols in aqueous solutions using BODIPY-based reagents. Org. Lett., 2013, 15(1), 216-219.
63. Matsumoto, T.; Urano, Y.; Shoda, T.; Kojima, H.; Nagano, T. A thiol- reactive fluorescence probe based on donor-excited photoinduced electron transfer: Key role of ortho substitution. Org. Lett., 2007, 9(17), 3375-3377.
64. Shao, J.; Sun, H.; Guo, H.; Ji, S.; Zhao, J.; Wu, W.; Yuan, X.; Zhang, C.; James, T.D. A highly selective red-emitting FRET fluorescent molecular probe derived from BODIPY for the detection of cysteine and homocysteine: an experimental and theoretical study. Chem. Sci., 2012, 3(4), 1049-1061.
65. Shao, J.; Guo, H.; Ji, S.; Zhao, J. Styryl-BODIPY based red-emitting fluorescent OFF-ON molecular probe for specific detection of cysteine. Biosens. Bioelectron., 2011, 26(6), 3012-3017.
66. Jiang, X.D.; Zhang, J.; Shao, X.; Zhao, W. A selective fluorescent turn-on NIR probe for cysteine. Org. Biomol. Chem., 2012, 10(10), 1966-1968.
67. Nielsen, J.W.; Jensen, K.S.; Hansen, R.E.; Gotfredsen, C.H.; Winther, J.R. A fluorescent probe which allows highly specific thiol labeling at low pH. Anal. Biochem., 2012, 421(1), 115-120.
68. Lu, J.; Sun, C.; Chen, W.; Ma, H.; Shi, W.; Li, X. Determination of non- protein cysteine in human serum by a designed BODIPY-based fluorescent probe. Talanta, 2011, 83(3), 1050-1056.
69. Ji, S.M.; Yang, J.; Yang, Q.; Liu, S.S.; Chen, M.D.; Zhao, J.Z. Tuning the intramolecular charge transfer of alkynylpyrenes: effect on photophysical properties and its application in design of off-on fluorescent thiol probes. J. Org. Chem., 2009, 74(13), 4855-4865.
70. Li, Y.H.; Duan, Y.; Li, J.S.; Zheng, J.; Yu, H.; Yang, R.H. Simultaneous nucleophilic-substituted and electrostatic interactions for thermal switching of spiropyran: A new approach for rapid and selective colorimetric detection of thiol-containing amino acids. Anal. Chem., 2012, 84(11), 4732-4738.
71. Ma, L.M.; Qian, J.H.; Tian, H.Y.; Lan, M.B.; Zhang, W.B. A colorimetric and fluorescent dual probe for specific detection of cysteine based on intramolecular nucleophilic aromatic substitution. Analyst, 2012, 137(24), 5046-5050.
72. Yuan, L.; Lin, W.; Yang, Y. A ratiometric fluorescent probe for specific detection of cysteine over homocysteine and glutathione based on the drastic distinction in the kinetic profiles. Chem. Commun., 2011, 47(22), 6275-6277.
73. Guo, Z.Q.; Nam, S.; Park, S.; Yoon, J. A highly selective ratiometric near- infrared fluorescent cyanine sensor for cysteine with remarkable shift and its application in bioimaging. Chem. Sci., 2012, 3(9), 2760-2765.
74. Shiu, H.Y.; Chan, T.C.; Ho, C.M.; Liu, Y.; Wong, M.K.; Che, C.M. Electron-deficient alkynes as cleavable reagents for the modification of cysteine-containing peptides in aqueous medium. Chem. Eur. J., 2009, 15(15), 3839-3850.
75. Shiu, H.Y.; Chong, H.C.; Leung, Y.C.; Wong, M.K.; Che, C.M. A highly selective FRET-based fluorescent probe for detection of cysteine and homocysteine. Chem-Eur J., 2010, 16(11), 3308-3313.
76. Shao, N.; Jin, J.Y.; Wang, H.; Zheng, J.; Yang, R.H.; Chan, W.H.; Abliz, Z. Design of bis-spiropyran ligands as dipolar molecule receptors and application to in vivo glutathione fluorescent probes. J. Am. Chem. Soc., 2010, 132(2), 725-736.
77. Zhang, Y.; Li, Y.; Yan, X.P. Photoactivated CdTe/CdSe quantum dots as a near infrared fluorescent probe for detecting biothiols in biological fluids. Anal. Chem., 2009, 81(12), 5001-5007.
78. Wang, G.L.; Dong, Y.M.; Yang, H.X.; Li, Z.J. Ultrasensitive cysteine sensing using citrate-capped CdS quantum dots. Talanta, 2011, 83(3), 943-947.
79. Liu, J.F.; Bao, C.Y.; Zhong, X.H.; Zhao, C.C.; Zhu, L.Y. Highly selective detection of glutathione using a quantum-dot-based OFF-ON fluorescent probe. Chem. Commun., 2010, 46(17), 2971-2973.
80. Zhang, W.Z.; Zhang, R.; Zhang, J.M.; Ye, Z.Q.; Jin, D.Y.; Yuan, J.L. Photoluminescent and electrochemiluminescent dual-signaling probe for biothiols based on a ruthenium(II) complex. Anal. Chim. Acta, 2012, 740, 80-87.
81. Tsay, O.G.; Lee, K.M.; Churchill, D.G. Selective and competitive cysteine chemosensing: resettable fluorescent turn on aqueous detection via Cu2+ displacement and salicylaldimine hydrolysis. New J. Chem., 2012, 36(10), 1949-1952.
82. Pathak, R.K.; Tabbasum, K.; Rai, A.; Panda, D.; Rao, C.P. A Zn2+ specific triazole based calix 4 arene conjugate (L) as a fluorescence sensor for histidine and cysteine in HEPES buffer milieu. Analyst, 2012, 137(17), 4069-4075.
83. Yan, H.; Su, H.; Tian, D.; Miao, F.; Li, H. Synthesis of triazolo-thiadiazole fluorescent organic nanoparticles as primary sensor toward Ag+ and the complex of Ag+ as secondary sensor toward cysteine. Sensors Actuat. B- Chem., 2011, 160(1), 656-661.
84. Li, Q.; Guo, Y.; Shao, S.J. A BODIPY based fluorescent chemosensor for Cu(II) ions and homocysteine/cysteine. Sensors Actuat. B. Chem., 2012, 171, 872-877.
85. Miao, F.; Zhan, J.; Zou, Z.; Tian, D.; Li, H. A new Hg2+ fluorescent sensors based on 1,3-alternate thiacalix 4 arene (L) and the complex of L+Hg2+ as turn-on sensor for cysteine. Tetrahedron, 2012, 68(10), 2409-2413.
86. Chen, H.L.; Li, X.K.; Wu, Y.B.; Gao, W.; Bai, R.C. A ruthenium(II) complex with environment-responsive dual emission and its application in the detection of cysteine/homocysteine. Dalton Trans., 2012, 41(43), 13292-13297.
87. Zhou, X.B.; Chan, W.H.; Lee, A.W.M.; Yeung, C.C. Ratiometric fluorescent probe for enantioselective detection of D-cysteine in aqueous solution. Beilstein J. Org. Chem., 2011, 7, 1508-1515.
88. Luo, C.; Zhou, Q.X.; Zhang, B.W.; Wang, X.S. A new squaraine and Hg2+- based chemosensor with tunable measuring range for thiol-containing amino acids. New J. Chem., 2011, 35(1), 45-48.
89. Xu, L.; Xu, Y.F.; Zhu, W.P.; Zeng, B.B.; Yang, C.M.; Wu, B.; Qian, X.H. Versatile trifunctional chemosensor of rhodamine derivative for Zn2+, Cu2+ and His/Cys in aqueous solution and living cells. Org. Biomol. Chem., 2011, 9(24), 8284-8287.
90. Pathak, R.K.; Tabbasum, K.; Hinge, V.K.; Rao, C.P. Selective recognition of cysteine in its free and protein-bound states by the Zn2+ complex of a triazole-based calix 4 arene conjugate. Chem. Eur. J., 2011, 17(50), 13999-14003.
91. Jung, H.S.; Han, J.H.; Habata, Y.; Kang, C.; Kim, J.S. An iminocoumarin- Cu(II) ensemble-based chemodosimeter toward thiols. Chem. Commun. 2011, 47(18), 5142-5144.
92. Zhang, R.; Yu, X.J.; Ye, Z.Q.; Wang, G.L.; Zhang, W.Z.; Yuan, J.L. Turn-on luminescent probe for cysteine/homocysteine based on a ruthenium(II) complex. Inorg. Chem., 2010, 49(17), 7898-7903.
93. Ruan, Y.B.; Li, A.F.; Zhao, J.S.; Shen, J.S.; Jiang, Y.B. Specific Hg2+- mediated perylene bisimide aggregation for highly sensitive detection of cysteine. Chem. Commun., 2010, 46(27), 4938-4940.
94. Yang, Y.K.; Shim, S.; Tae, J. Rhodamine-sugar based turn-on fluorescent probe for the detection of cysteine and homocysteine in water. Chem. Commun., 2010, 46(41), 7766-7768.
95. Xiong, L.Q.; Zhao, Q.; Chen, H.L.; Wu, Y.B.; Dong, Z.S.; Zhou, Z.G.; Li, F.Y. Phosphorescence imaging of homocysteine and cysteine in living cells based on a cationic iridium(III) complex. Inorg. Chem., 2010, 49(14), 6402-6408.
96. Yang, X.F.; Liu, P.; Wang, L.P.; Zhao, M.L. A chemosensing ensemble for the detection of cysteine based on the inner filter effect using a rhodamine B spirolactam. J. Fluoresc., 2008, 18(2), 453-459.
97. Tang, B.; Liu, F.; Xu, K.H.; Tong, L.L. A novel metallobridged bis(beta- cyclodextrin)s fluorescent probe for the determination of glutathione. FEBS J., 2008, 275(7), 1510-1517.
98. Vallejos, S.; Estevez, P.; Ibeas, S.; Garcia, F.C.; Serna, F.; Garcia, J.M. An organic/inorganic hybrid membrane as a solid turn-on fluorescent chemosensor for coenzyme A (CoA), cysteine (Cys), and glutathione (GSH) in aqueous media. Sensors, 2012, 12(3), 2969-2982.
99. Shang, L.; Dong, S. Sensitive detection of cysteine based on fluorescent silver clusters. Biosens. Bioelectron., 2009, 24(6), 1569-1573.
100. Yu, C.M.; Zeng, F.; Luo, M.; Wu, S.Z. A silica nanoparticle-based sensor for selective fluorescent detection of homocysteine via interaction differences between thiols and particle-surface-bound polymers. Nanotechnology, 2012, 23(30), 305503.
101. Liu, X.M.; Xi, N.; Liu, S.J.; Ma, Y.; Yang, H.R.; Li, H.R.; He, J.H.; Zhao, Q.; Li, F.Y.; Huang, W. Highly selective phosphorescent nanoprobes for sensing and bioimaging of homocysteine and cysteine. J. Mater. Chem., 2012, 22(16), 7894-7901.
102. Yang, P.; Xu, Q.Z.; Jin, S.Y.; Zhao, Y.; Lu, Y.; Xu, X.W.; Yu, S.H. Synthesis of Fe3O4@phenol formaldehyde resin core-shell nanospheres loaded with Au nanoparticles as magnetic FRET nanoprobes for detection of thiols in living cells. Chem. Eur. J., 2012, 18(4), 1154-1160.
103. Tu, W.W.; Lei, J.P.; Wang, P.; Ju, H.X. Photoelectrochemistry of free-base- porphyrin-functionalized zinc oxide nanoparticles and their applications in biosensing. Chem. Eur. J., 2011, 17(34), 9440-9447.
104. Li, H.B.; Xu, J.; Yan, H.J. Ratiometric fluorescent determination of cysteine based on organic nanoparticles of naphthalene-thiourea-thiadiazole-linked molecule. Sensors Actuat. B-Chem., 2009, 139(2), 483-487.
105. Lin, H.; Li, L.; Lei, C.; Xu, X.; Nie, Z.; Guo, M.; Huang, Y.; Yao, S. Immune-independent and label-free fluorescent assay for Cystatin C detection based on protein-stabilized Au nanoclusters. Biosens. Bioelectron., 2013, 41, 256-61.
106. Shang, L.; Qin, C.; Wang, T.; Wang, M.; Wang, L.; Dong, S. Fluorescent conjugated polymer-stabilized gold nanoparticles for sensitive and selective detection of cysteine. J. Phys. Chem. C., 2007, 111(36), 13414-13417.
107. Xiao, Q.Y.; Gao, H.L.; Lu, C.; Yuan, Q.P. Gold nanoparticle-based optical probes for sensing aminothiols. Trac-Trend. Anal. Chem., 2012, 40, 64-76.
108. Guan, Z.P.; Li, S.; Cheng, P.B.S.; Zhou, N.; Gao, N.Y.; Xu, Q.H. Band- selective coupling-induced enhancement of two-photon photoluminescence in gold nanocubes and its application as turn-on fluorescent probes for cysteine and glutathione. ACS Appl. Mater. Interfaces, 2012, 4(10), 5711-5716.
109. Yuan, X.; Tay, Y.; Dou, X.; Luo, Z.; Leong, D.T.; Xie, J. Glutathione- protected silver nanoclusters as cysteine-selective fluorometric and colorimetric probe. Anal. Chem., 2013, 85(3), 1913-9.
110. Xu, J.P.; Jia, L.; Fang, Y.A.; Lv, L.P.; Song, Z.G.; Ji, J.A. Highly soluble PEGylated pyrene-gold nanoparticles dyads for sensitive turn-on fluorescent detection of biothiols. Analyst, 2010, 135(9), 2323-2327.
111. Li, C.; Wu, C.L.; Zheng, J.S.; Lai, J.P.; Zhang, C.L.; Zhao, Y.B. LSPR sensing of molecular biothiols based on noncoupled gold nanorods. Langmuir, 2010, 26(11), 9130-9135.
112. Iijima, S. Helical microtubules of graphitic carbon. Nature, 1991, 354(6348), 56-58.
113. Zhao, C.; Qu, K.; Song, Y.; Xu, C.; Ren, J.; Qu, X. A reusable DNA single- walled carbon-nanotube-based fluorescent sensor for highly sensitive and selective detection of Ag+ and cysteine in aqueous solutions. Chem-Eur. J., 2010, 16(27), 8147-8154.
114. Negi, D.P.S.; Chanu, T.I. Surface-modified CdS nanoparticles as a fluorescent probe for the selective detection of cysteine. Nanotechnology, 2008, 19(46), 465503.
115. Yang, S.W.; Liao, F. Poly(p-phenylenediamine) nanofibers having conjugated structures, a novel, simple and highly selective fluorescent probe for L-cysteine. Synth. Met., 2012, 162(15-16), 1343-1347.
116. Fan, H.L.; Zhang, T.; Li, Z.H.; Wu, L.Y.; Jin, Q.H. Specific assay of amino acids based on a fluorescent conjugated polyelectrolyte with multi- carboxylates. Chem. J. Chinese U., 2012, 33(1), 54-58.