Synthesis, labeling and bioanalytical applications of a tris(2,2'-bipyridyl)ruthenium(II)-based electrochemiluminescence probe

Nature Protocols

Volumn 9, Issue 5, 2014, Pages 1146-1159

  Zhou, Xiaoming ^a   Zhu, Debin ^a   Liao, Yuhui ^a   Liu, Weipeng ^a   Liu, Hongxing ^a   Ma, Zhaokui ^a   Xing, Da ^a  

^a SOUTH CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARCINOEMBRYONIC ANTIGEN; HEPATITIS B SURFACE ANTIGEN; MAGNETIC BEAD; NANOBEAD; PROPYLAMINE; RUTHENIUM COMPLEX; TRIPROPYLAMINE; TRIS(2,2' BIPYRIDINE)RUTHENIUM; TRIS(2,2' BIPYRIDYL)RUTHENIUM (2,2' BIPYRIDINE 4,4' DICARBOXYLIC ACID) BIS(HEXAFLUOROPHOSPHATE); TRIS(2,2' BIPYRIDYL)RUTHENIUM N HYDROXYSUCCINIMIDE ESTER; UNCLASSIFIED DRUG; ANTIBODY; DNA PROBE; MICROSPHERE; ORGANOMETALLIC COMPOUND; TRIS(2,2'-BIPYRIDYL)RUTHENIUM(II);

ABSORPTION SPECTROSCOPY; ALKALINITY; ANALYTIC METHOD; ANTIGEN DETECTION; ARTICLE; CHEMICAL LABELING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMOLUMINESCENCE; CLINICAL PROTOCOL; COVALENT BOND; ELECTROCHEMILUMINESCENCE PROBE; ELECTRODE; EXPERIMENTAL DESIGN; FLAME PHOTOMETRY; HBSAG GENE; LIMIT OF DETECTION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; SYNTHESIS; CHEMISTRY; DIAGNOSTIC USE; DNA PROBE; ELECTROCHEMISTRY; LUMINESCENCE; METABOLISM; MICROFLUIDIC ANALYSIS; PROCEDURES;

ANTIBODIES; DNA PROBES; ELECTROCHEMISTRY; LUMINESCENT MEASUREMENTS; MICROFLUIDIC ANALYTICAL TECHNIQUES; MICROSPHERES; ORGANOMETALLIC COMPOUNDS; PROPYLAMINES;

EID: 84899578199     PISSN: 17542189     EISSN: 17502799     Source Type: Journal    
DOI: 10.1038/nprot.2014.060     Document Type: Article

References (60)

1. Richter, M.M. Electrochemiluminescence (ECL). Chem. Rev. 104, 3003-3036 (2004).
2. Miao, W.J. Electrogenerated chemiluminescence and its biorelated applications. Chem. Rev. 108, 2506-2553 (2008).
3. Ma, D.L. et al. Label-free luminescent oligonucleotide-based probes. Chem. Soc. Rev. 42, 3427-3440 (2013).
4. Dodeigne, C., Thunus, L. & Lejeune, R. Chemiluminescence as diagnostic tool. A review. Talanta 51, 415-439 (2000).
5. Leung, K.H. et al. Detection of base excision repair enzyme activity using a luminescent G-quadruplex selective switch-on probe. Chem. Commun. 49, 5630-5632 (2013).
6. Pfleger, K.D. & Eidne, K.A. Illuminating insights into protein-protein interactions using bioluminescence resonance energy transfer (BRET). Nat. Methods 3, 165-174 (2006).
7. Leung, C.H. et al. Luminescent detection of DNA-binding proteins. Nucleic Acids Res. 40, 941-955 (2012).
8. Bard, A.J. & Faulkner, L.R. Electrochem. Methods (Wiley, 1980).
9. Bard, A.J. (ed.) Electrogenerated chemiluminescence (Marcel Dekker, 2004).
10. Knight, A.W. Electrogenerated chemiluminescence. in Chemiluminescence in Analytical Chemistry 211-247 (Marcel Dekker, 2001).
11. Chang, M.M., Saji, T. & Bard, A.J. Electrogenerated chemiluminescence. 30. Electrochemical oxidation of oxalate ion in the presence of luminescers in acetonitrile solutions. J. Am. Chem. Soc. 99, 5399-5403 (1977).
12. Rubinstein, I. & Bard, A.J. Electrogenerated chemiluminescence. 37. Aqueous ECL systems based on tris(2,2′-bipyridine)ruthenium2+ and oxalate or organic acids. J. Am. Chem. Soc. 103, 512-516 (1981).
13. Leland, J.K. & Powell, M.J. Electrogenerated chemiluminescence: An oxidative-reduction type ECL reaction sequence using tripropylamine. J. Electrochem. Soc. 137, 3127-3131 (1990).
14. Miao, W., Choi, J.-P. & Bard, A.J. Electrogenerated chemiluminescence 69: The tris(2,2′-bipyridine)ruthenium(II), (Ru(bpy)3 2+)/tri-n-propylamine (TPrA) system revisited-A new route involving TPrA+ cation radicals. J. Am. Chem. Soc. 124, 14478-14485 (2002).
15. Ge, L. et al. Three-dimensional paper-based electrochemiluminescence immunodevice for multiplexed measurement of biomarkers and point-of-care testing. Biomaterials 33, 1024-1031 (2012).
16. Wang, X. et al. A solid-state electrochemiluminescence biosensing switch for detection of thrombin based on ferrocene-labeled molecular beacon aptamer. Biosens. Bioelectron. 24, 3288-3292 (2009).
17. Yuan, T., Liu, Z., Hu, L., Zhang, L. & Xu, G. Label-free supersandwich electrochemiluminescence assay for detection of sub-nanomolar Hg2+. Chem. Commun. 47, 11951-11953 (2011).
18. Lin, Z., Chen, L., Zhu, X., Qiu, B. & Chen, G. Signal-on electrochemiluminescence biosensor for thrombin based on target-induced conjunction of split aptamer fragments. Chem. Commun. 46, 5563-5565 (2010).
19. Sun, B. et al. Double covalent coupling method for the fabrication of highly sensitive and reusable electrogenerated chemiluminescence sensors. Anal. Chem. 82, 5046-5052 (2010).
20. Tang, X. et al. Quenching of the electrochemiluminescence of tris(2,2′-bipyridine)ruthenium (II)/tri-n-propylamine by pristine carbon nanotube and its application to quantitative detection of DNA. Anal. Chem. 85, 1711-1718 (2013).
21. Wu, Y., Shi, H., Yuan, L. & Liu, S. A novel electrochemiluminescence immunosensor via polymerization-Assisted amplification. Chem. Commun. 46, 7763-7765 (2010).
22. Xu, L., Li, Y., Wu, S., Liu, X. & Su, B. Imaging latent fingerprints by electrochemiluminescence. Angew. Chem. Int. Ed. 124, 8192-8196 (2012).
23. Xu, X.H. & Bard, A.J. Electrogenerated chemiluminescence. 55. emission from adsorbed Ru(bpy)3 2+ on graphite, platinum, and gold. Langmuir 10, 2409-2414 (1994).
24. Blackburn, G.F. et al. Electrochemiluminescence detection for development of immunoassays and DNA probe assays for clinical diagnostics. Clin. Chem. 37, 91534-91539 (1991).
25. Yan, G.H., Xing, D., Tan, S.C. & Chen, Q. Rapid and sensitive immunomagnetic-electrochemiluminescent detection of p53 antibodies in human serum. J. Immunol. Methods 288, 47-54 (2004).
26. Kenten, J.H. et al. Rapid electrochemiluminescence assays of polymerase chain reaction products. Clin. Chem. 37, 1626-1632 (1991).
27. Zhu, D.B., Xing, D., Shen, X.Y. & Liu, J.F. A method to quantitatively detect H-ras point mutation based on electrochemiluminescence. Biochem. Biophys. Res. Commun. 324, 964-969 (2004).
28. Yin, X.B., Dong, S. & Wang, E. Analytical applications of the electrochemiluminescence of tris(2,2′-bipyridyl)ruthenium and its derivatives. Trends Anal. Chem. 23, 432-441 (2004).
29. Forster, R.J., Bertoncello, P. & Keyes, T.E. Electrogenerated chemiluminescence. Annu. Rev. Anal. Chem. 2, 359-385 (2009).
30. Lee, W.-Y. Tris(2,2′-bipyridyl)ruthenium(II) electrogenerated chemiluminescence in analytical science. Microchimica. Acta 127, 19-39 (1997).
31. Wei, H. & Wang, E.K. Solid-state electrochemiluminescence of tris(2,2′-bipyridyl) ruthenium. Trends Anal. Chem. 27, 447-459 (2008).
32. Hu, L.Z. & Xu, G.B. Applications and trends in electrochemiluminescence. Chem. Soc. Rev. 39, 3275-3304 (2010).
33. Bertoncello, P. & Forster, R.J. Nanostructured materials for electrochemiluminescence (ECL)-based detection methods: Recent advances and future perspectives. Biosens. Bioelectron. 24, 3191-3200 (2009).
34. Kijek, T.M., Rossi, C.A., Moss, D., Parker, R.W. & Henchal, E.A. Rapid and sensitive immunomagnetic-electrochemiluminescent detection of staphyloccocal enterotoxin B. J. Immunol. Methods 236, 9-17 (2000).
35. Gemen, B.V. et al. A one-Tube quantitative HIV-1 RNA NASBA nucleic acid amplification assay using electrochemiluminescent (ECL) labelled probes. J. Virol. Methods 49, 157-167 (1994).
36. Zhou, X.M., Xing, D., Zhu, D.B. & Jia, L. Magnetic bead and nanoparticle based electrochemiluminescence amplification assay for direct and sensitive measuring of telomerase activity. Anal. Chem. 81, 255-261 (2009).
37. Boom, R. et al. A highly sensitive assay for detection and quantitation of human cytomegalovirus DNA in serum and plasma by PCR and electrochemiluminescence. J. Clin. Microbiol. 37, 1489-1497 (1999).
38. Zhang, Y. et al. Magnetic beads-based electrochemiluminescence immunosensor for determination of cancer markers using quantum dot functionalized PtRu alloys as labels. Analyst 137, 2176-2182 (2012).
39. Zhu, X., Zhou, X.M. & Xing, D. Nano-magnetic primer based electrochemiluminescence-polymerase chain reaction (NMPE-PCR) assay. Biosens. Bioelectron. 31, 463-468 (2012).
40. Duan, R.X., Zhou, X.M. & Xing, D. Electrochemiluminescence biobarcode method based on cysteamine-gold nanoparticle conjugates. Anal. Chem. 82, 3099-3103 (2010).
41. Guglielmo-Viret, V. & Thullier, P. Comparison of an electrochemiluminescence assay in plate format over a colorimetric ELISA, for the detection of ricin B chain (RCA-B). J. Immunol. Methods 328, 70-78 (2007).
42. Guglielmo-Viret, V., Attrée, O., Blanco-Gros, V. & Thullier, P. Comparison of electrochemiluminescence assay and ELISA for the detection of Clostridium botulinum type B neurotoxin,. J. Immunol. Methods 301, 164-172 (2005).
43. Bruno, J.G. & Kiel, J.L. In vitro selection of DNA aptamers to anthrax spores with electrochemiluminescence detection. Biosens. Bioelectron. 14, 457-464 (1999).
44. Zhu, D.B., Tang, Y.B., Xing, D. & Chen, W.R. PCR-free quantitative detection of genetically modified organism from raw materials. An electrochemiluminescence-based bio bar code method. Anal. Chem. 80, 3566-3571 (2008).
45. Wu, S.L. et al. Detection of dengue viral RNA using a nucleic acid sequence-based amplification assay. J. Clin. Microbiol. 39, 2794-2798 (2001).
46. Antony, S. et al. Novel high-Throughput electrochemiluminescent assay for identification of human tyrosyl-DNA phosphodiesterase (Tdp1) inhibitors and characterization of furamidine (NSC 305831) as an inhibitor of Tdp1. Nucleic Acids Res. 35, 4474-4484 (2007).
47. Li, Q., Zhou, X.M. & Xing, D. Rapid and highly sensitive detection of mercury ion (Hg2+) by magnetic beads-based electrochemiluminescence assay. Biosens. Bioelectron. 26, 859-862 (2010).
48. Yu, H., Raymonda, J.W., McMahon, T.M. & Campagnari, A.A. Detection of biological threat agents by immunomagnetic microsphere-based solid-phase fluorogenic-And electro-chemiluminescence. Biosens. Bioelectron. 14, 829-840 (2000).
49. Deiss, F. et al. Multiplexed sandwich immunoassays using electrochemiluminescence imaging resolved at the single bead level. J. Am. Chem. Soc. 131, 6088-6089 (2009).
50. Liu, X., Shi, L., Niu, W., Li, H. & Xu, G. Environmentally friendly and highly sensitive ruthenium(II)tris(2,2′-bipyridyl) electrochemiluminescent system using 2-(dibutylamino) ethanol as co-reactant. Angew. Chem. Int. Ed. 119, 425-428 (2007).
51. Cao, W., Ferrance, J.P., Demas, J. & Landers, J.P. Quenching of the electrochemiluminescence of tris(2,2′-bipyridine)ruthenium(II) by ferrocene and its potential application to quantitative DNA detection. J. Am. Chem. Soc. 128, 7572-7578 (2006).
52. Zhou, M., Roovers, J., Robertson, G.P. & Grover, C.P. Multilabeling biomolecules at a single site. 1. Synthesis and characterization of a dendritic label for electrochemiluminescence assays. Anal. Chem. 75, 6708-6717 (2003).
53. Terpetschnig, E., Szmacinski, H., Malak, H. & Lakowicz, J.R. Metal-ligand complexes as a new class of long-lived fluorophores for protein hydrodynamics. Biophys. J. 68, 342-350 (1995).
54. Terpetschnig, E., Szmacinski, H. & Lakowicz, J.R. Fluorescence polarization immunoassay of a high-molecular-weight antigen based on a long-lifetime Ru-ligand complex. Anal. Biochem. 227, 140-147 (1995).
55. Gudibande, S.R., Kenten, J.H., Link, J., Friedman, K. & Massey, R.J. Rapid, non-separation electrochemiluminescent DNA hybridization assays for PCR products, using 3′-labelled oligonucleotide probes. Mol. Cell. Probes 6, 495-503 (1992).
56. Su, Q., Xing, D. & Zhou, X.M. Magnetic beads-based rolling-circle amplification-electrochemiluminescence assay for highly sensitive detection of point mutation. Biosens. Bioelectron. 25, 1615-1621 (2010).
57. Workman, S. & Richter, M.M. The effects of nonionic surfactants on the tris(2,2′-bipyridyl)ruthenium(II)-Tripropylamine electrochemiluminescence system. Anal. Chem. 72, 5556-5561 (2000).
58. Zu, Y. & Bard, A.J. Electrogenerated chemiluminescence. 67. dependence of light emission of the tris(2,2′)bipyridylruthenium(II)/ tripropylamine system on electrode surface hydrophobicity. Anal. Chem. 73, 3960-3964 (2001).
59. Komori, K., Takada, K., Hatozaki, O. & Oyama, N. Electrochemiluminescence of Ru(II) complexes immobilized on a magnetic microbead surface: Distribution of magnetic microbeads on the electrode surface and effect of azideion. Langmuir 23, 6446-6452 (2007).
60. Wang, J. et al. Amplified voltammetric detection of DNA hybridization via oxidation of ferrocene caps on gold nanoparticle/streptavidin conjugates. Anal. Chem. 75, 3941-3945 (2003).