Skip to main content

Lanthanide Complex-Based Fluorescence Label for Time-Resolved Fluorescence Bioassay

Abstract

Different from organic fluorescence dyes, fluorescent lanthanide complexes have the fluorescence properties of long fluorescence lifetime, large Stokes shift and sharp emission profile, which makes them favorable be used as the fluorescent labeling reagents for microsecond time-resolved fluorescence bioassay. Lanthanide complex-based fluorescence labels have been successfully used for highly sensitive time-resolved fluorescence immunoassay, DNA hybridization assay, cell activity assay, and bioimaging microscopy assay. Since the technique allows easy distinction of the specific fluorescence signal of the long-lived label from short-lived background noises associated with biological samples, scattering lights (Tyndall, Rayleigh and Raman scatterings) and the optical components (cuvettes, filters and lenses), the sensitivity of fluorescence bioassay has been remarkably improved. This paper summarized the recent developments of lanthanide complex-based fluorescence labels and their applications in time-resolved fluorescence bioassays mainly based on the authors’ researches and relative publications.

This is a preview of subscription content, access via your institution.

References

  1. H. G. Eckert (1976). Radioimmunoassay technique. Angew. Chem. 88, 565–574.

    Google Scholar 

  2. P. Tijssen (1985). Practice and Theory of Enzyme Immunoassay, Elsevier, Amsterdam.

    Google Scholar 

  3. B. J. Gould and V. Marks (1988). in T. T. Ngo (Ed.), Nonisotopic Immunoassay, Plenum, New York, pp. 3–26.

    Google Scholar 

  4. E. Koller (1989). Fluorescent labels for use in biology and biomedicine. Appl. Fluoresc. Technol. 1, 1–8.

    Google Scholar 

  5. L. M. Smith, J. Z. Sanders, R. J. Kaiser, P. Hughes, C. Dodd, C. R. Connell, C. Heiner, S. B. H. Kent, and L. E. Hodd (1986). Fluorescence detection in automated DNA sequence analysis. Nature 321, 674–679.

    Article  PubMed  Google Scholar 

  6. S. Beck and H. Koster (1990). Applications of dioxetane chemiluminescent probes to molecular biology. Anal. Chem. 62, 2258–2270.

    Article  PubMed  Google Scholar 

  7. A. Mayer and S. Neuenhofer (1994). Luminescent labels-more than just an alternative to radioisotopes. Angew. Chem. Int. Ed. Engl. 33, 1044–1072.

    Article  Google Scholar 

  8. J. M. Prober, G. L. Trainor, R. J. Dam, F. W. Hobbs, C. W. Robertson, R. J. Zagursky, A. J. Cocuzza, M. A. Jensen, and K. Baumeister (1987). A system for rapid DNA sequencing with fluorescent chain-terminating dideoxynucleotides. Science 238, 336–341.

    PubMed  Google Scholar 

  9. M. Schena, D. Shalon, R. W. Davis, and P. O. Brown (1995). Quantitative monitoring of gene expression patterns with a complementary DNA microarray. Science 270, 467–470.

    PubMed  Google Scholar 

  10. M. Schena, D. Shalon, R. Heller, A. Chai, P. O. Brown, and R. W. Davis (1996). Parallel human genome analysis: microarray-based expression monitoring of 1000 genes. Proc. Natl. Acad. Sci. USA 93, 10614–10619.

    Article  PubMed  Google Scholar 

  11. E. Soini and I. Hemmilä (1979). Fluoroimmunoassay: present status and key problems. Clin. Chem. 25, 353–361.

    PubMed  Google Scholar 

  12. A. P. Sinha (1971). Fluorescence and laser action in rare earth chelates. Spectrosc. Inorg. Chem. 2, 255–265.

    Google Scholar 

  13. F. Halverson, J. S. Brinen, and J. R. Leto (1964). Photoluminescence of lanthanide complexes. III. Synergic agent complexes involving extended chromophores. J. Chem. Phys. 41, 2752–2760.

    Article  Google Scholar 

  14. Y.-Y. Xu and I. Hemmilä (1992). Co-fluorescence enhancement system based on pivaloyltrifluoroacetone and yttrium for the simultaneous detection of europium, terbium, samarium and dysprosium. Anal. Chim. Acta 256, 9–16.

    Article  Google Scholar 

  15. J. Yuan and K. Matsumoto (1996). Fluorescence enhancement by electron-withdrawing groups on β-diketonates in Eu(III)-β-diketonato-topo ternary complexes. Anal. Sci. 12, 31–36.

    Google Scholar 

  16. H. Siitari, I. Hemmilä, E. Soini, T. Lövgren, and V. Koistinen (1983). Detection of hepatitis B surface antigen using time-resolved fluoroimmunoassay. Nature 301, 258–260.

    Article  PubMed  Google Scholar 

  17. I. Hemmilä (1985). Fluoroimmunoassays and immunofluorometric assays. Clin. Chem. 31, 359–370.

    PubMed  Google Scholar 

  18. E. Soini and T. Lövgren (1987). Time-resolved fluorescence of lanthanide probes and applications in biotechnology. CRC Crit. Rev. Anal. Chem. 18, 105–154.

    Google Scholar 

  19. E. P. Diamandis (1988). Immunoassay with time-resolved fluorescence spectroscopy: principle and applications. Clin. Biochem. 21, 139–150.

    PubMed  Google Scholar 

  20. I. Hemmilä (1988). Lanthanides as probes for time-resolved fluorometric immunoassays. Scand. J. Clin. Lab. Invest. 48, 389–400.

    PubMed  Google Scholar 

  21. E. P. Diamandis and T. K. Christopoulos (1990). Europium chelate labels in time-resolved fluorescence immunoassays and DNA hybridization assays. Anal. Chem. 62, 1149A–1157A.

    PubMed  Google Scholar 

  22. E. F. G. Dickson, A. Pollak, and E. P. Diamandis (1995). Ultrasensitive bioanalytical assays using time-resolved fluorescence detection. Pharmac. Ther. 66, 207–235.

    Article  Google Scholar 

  23. J. Yuan and K. Matsumoto (1999). Functionalization of fluorescent lanthanide complexes and their applications to biotechnology. Bunseki Kagaku 48, 1077–1083.

    Google Scholar 

  24. I. Hemmilä, V.-M. Mukkala (2001). Time-resolution in fluorometry: technologies, labels, and applications in bioanalytical assays. Crit. Rev. Clin. Lab. Sci. 38, 441–519.

    Article  Google Scholar 

  25. K. Matsumoto and J. Yuan, Metal Ions in Biological Systems, In A. Sigel and H. Sigel (Eds.), Marcel Dekker, Inc., New York and Basel, Vol. 40, 2003, pp. 191–232.

  26. W. D. Horrocks and D. R. Sudnick (1979). Lanthanide ion probes of structure in biology. Laser-induced luminescence decay constants provide a direct measure of the number of metal-coordinated water molecules. J. Am. Chem. Soc. 101, 334–340.

    Article  Google Scholar 

  27. A. G. Goryushko and N. K. Davidenko (1980). Stability of complexes of europium(III) with new fluorinated β-diketones. Zh. Neorg. Khim. 25, 2666–2668.

    Google Scholar 

  28. J. Yuan and K. Matsumoto (1996). Synthesis of a new tetradentate β-diketonate-europium chelate that can be covalently bound to protein in time-resolved fluorometry. Anal. Sci. 12, 695–699.

    Google Scholar 

  29. J. Yuan and K. Matsumoto (1997). Synthesis of a new tetradentate β-diketonate-europium chelate and its application for time-resolved fluorimetry of albumin. J. Pharm. Biomed. Anal. 15, 1397–1403.

    Article  PubMed  Google Scholar 

  30. J. Yuan, K. Matsumoto, and H. Kimura (1998). A new tetradentate β-diketonate-europium chelate that can be covalently bound to proteins for time-resolved fluoroimmunoassay. Anal. Chem. 70, 596–601.

    Article  PubMed  Google Scholar 

  31. R. Connally, D. Veal, and J. Piper (2002). High resolution detection of fluorescently labeled microorganisms in environmental samples using time-resolved fluorescence microscopy. FEMS Microbiol. Ecol. 41, 239–245.

    Article  Google Scholar 

  32. F.-B. Wu, S.-Q. Han, C. Zhang, and Y.-F. He (2002). Synthesis of a highly fluorescent β-diketone-europium chelate and its utility in time-resolved fluoroimmunoassay of serum total thyroxine. Anal. Chem. 74, 5882–5889.

    Article  PubMed  Google Scholar 

  33. F.-B. Wu and C. Zhang (2002). A new europium b-diketone chelate for ultrasensitive time-resolved fluorescence immunoassays. Anal. Biochem. 311, 57–67.

    Article  PubMed  Google Scholar 

  34. J. Yuan, S. Sueda, R. Somazawa, K. Matsumoto, and K. Matsumoto (2003). Structure and luminescence properties of the tetradentate b-diketonate-europium(III) complexes. Chem. Lett. 32, 492–493.

    Article  Google Scholar 

  35. R. A. Evangelista, A. pollak, B. Allore, E. F. Templeton, R. C. Morton, and E. P. Diamandis (1988). A new europium chelate for protein labelling and time-resolved fluorometric applications. Clin. Biochem. 21, 173–177.

    Article  PubMed  Google Scholar 

  36. G. Mathis (1993). Rare earth cryptates and homogeneous fluoroimmunoassays with human sera. Clin. Chem. 39, 1953–1959.

    PubMed  Google Scholar 

  37. A. K. Saha, K. Kross, E. D. Kloszewski, D. A. Upson, J. L. Toner, R. A. Snow, C. D. V. Black, and V. C. Desai (1993). Time-resolved fluorescence of a new europium-chelate complex: demonstration of highly sensitive detection of protein and DNA samples. J. Am. Chem. Soc. 115, 11032–11033.

    Article  Google Scholar 

  38. V.-M. Mukkala, M. Helenius, I. Hemmilä, J. Kankare, and H. Takalo (1993). Development of luminescent europium(III) and terbium(III) chelates of 2, 2′:6′,2″-terpyridine derivatives for protein labeling. Helv. Chim. Acta 76, 1361–1378.

    Article  Google Scholar 

  39. D. Horiguchi, K. Sasamoto, H. Terasawa, H. Mochizuki, and Y. Ohkura (1994). A novel time-resolved fluoroimmunoassay using a macrocyclic europium ligand as a label. Chem. Pharm. Bull. 42, 972–975.

    Google Scholar 

  40. H. Takalo, V.-M. Mukkala, H. Mikola, P. Liitti, and I. Hemmilä (1994). Synthesis of europium(III) chelates suitable for labeling of bioactive molecules. Bioconjugate Chem. 5, 278–282.

    Article  Google Scholar 

  41. M. Latva, H. Takalo, V.-M. Mukkala, C. Matachescu, J. C. Rodríguez-Ubis, and J. Kankare (1997). Correlation between the lowest triplet state energy level of the ligand and lanthanide(III) luminescence quantum yield. J. Lumin. 75, 149–169.

    Article  Google Scholar 

  42. H. Takalo, V.-M. Mukkala, L. Meriö, J. C. Rodríguez-Ubis, R. Sedano, O. Juanes, and E. Brunet (1997). Development of luminescent terbium(III) chelates for protein labeling: effect of triplet-state energy level. Helv. Chim. Acta 80, 372–387.

    Article  Google Scholar 

  43. H. Karsilayan, I. Hemmilä, H. Takalo, A. Toivonen, K. Pettersson, T. Lövgren, and V.-M. Mukkala (1997). Influence of coupling method on the luminescence properties, coupling efficiency, and binding affinity of antibodies labeled with europium(III) chelates. Bioconjugate Chem. 8, 71–75.

    Article  Google Scholar 

  44. J. Yuan, M. Tan, and G. Wang (2004). Synthesis and luminescence properties of lanthanide(III) chelates with polyacid derivatives of thienyl-substituted terpyridine analogues. J. Lumin. 106, 91–101.

    Article  Google Scholar 

  45. N. Weibel, L. J. Charbonniere, M. Guardigli, A. Roda, and R. Ziessel (2004). Engineering of highly luminescent lanthanide tags suitable for protein labeling and time-resolved luminescence imaging. J. Am. Chem. Soc. 126, 4888–4896.

    Article  PubMed  Google Scholar 

  46. M. Li and P. R. Selvin (1995). Luminescent polyaminocarboxylate chelates of terbium and europium: the effect of chelate structure. J. Am. Chem. Soc. 117, 8132–8138.

    Article  Google Scholar 

  47. M. Li and P. R. Selvin (1997). Amine-reactive forms of a luminescent diethylenetriaminepentaacetic acid chelate of terbium and europium: attachment to DNA and energy transfer measurements. Bioconjugate Chem. 8, 127–132.

    Article  Google Scholar 

  48. J. Chen and P. R. Selvin (1999). Thiol-reactive luminescent chelates of terbium and europium. Bioconjugate Chem. 10, 311–315.

    Article  Google Scholar 

  49. A. Scorilas and E. P. Diamandis (2000). Polyvinylamine-streptavidin complexes labeled with a europium chelator: a universal detection reagent for solid-phase time resolved fluorometric applications. Clin. Biochem. 33, 345–350.

    Article  PubMed  Google Scholar 

  50. A. Scorilas, A. Bjartell, H. Lilja, C. Moller, and E. P. Diamandis (2000). Streptavidin-polyvinylamine conjugates labeled with a europium chelate: applications in immunoassay, immunohistochemistry, and microarrays. Clin. Chem. 46, 1450–1455.

    PubMed  Google Scholar 

  51. L.-Y. Luo and E. P. Diamandis (2000). Preliminary examination of time-resolved fluorometry for protein array applications. Luminescence 15, 409–413.

    Article  PubMed  Google Scholar 

  52. Q.-P. Qin, T. Lövgren, and K. Pettersson (2001). Development of highly fluorescent detection reagents for the construction of ultrasensitive immunoassays. Anal. Chem. 73, 1521–1529.

    Article  PubMed  Google Scholar 

  53. H. Härmä, T. Soukka, and T. Lövgren (2001). Europium nanoparticles and time-resolved fluorescence for ultrasensitive detection of prostate-specific antigen. Clin. Chem. 47, 561–568.

    PubMed  Google Scholar 

  54. T. Soukka, H. Härmä, J. Paukkunen, and T. Lövgren (2001). Utilization of kinetically enhanced monovalent binding affinity by immunoassays based on multivalent nanoparticle-antibody bioconjugates. Anal. Chem. 73, 2254–2260.

    Article  PubMed  Google Scholar 

  55. T. Soukka, J. Paukkunen, H. Härmä, S. Lönnberg, H. Lindroos, and T. Lövgren (2001). Supersensitive time-resolved immunofluorometric assay of free prostate-specific antigen with nanoparticle label technology. Clin. Chem. 47, 1269–1278.

    PubMed  Google Scholar 

  56. T. Soukka, K. Antonen, H. Härmä, A.-M. Pelkkikangas, P. Huhtinen, and T. Lövgren (2003). Highly sensitive immunoassay of free prostate-specific antigen in serum using europium(III) nanoparticle label technology. Clin. Chim. Acta 328, 45–58.

    Google Scholar 

  57. T. Matsuya, S. Tashiro, N. Hoshino, N. Shibata, Y. Nagasaki, and K. Kataoka (2003). A core-shell-type fluorescent nanosphere possessing reactive poly(ethylene glycol) tethered chains on the surface for zeptomole detection of protein in time-resolved fluorometric immunoassay. Anal. Chem. 75, 6124–6132.

    Article  PubMed  Google Scholar 

  58. Z. Ye, M. Tan, G. Wang, and J. Yuan (2004). Preapration, characterization, and time-resolved fluorometric application of silica-coated terbium(III) fluorescent nanoparticles. Anal. Chem. 76, 513–518.

    Article  PubMed  Google Scholar 

  59. Z. Ye, M. Tan, G. Wang, and J. Yuan (2004). Novel fluorescent europium chelate-doped silica nanoparticles: preparation, characterization and time-resolved fluorometric application. J. Mater. Chem. 14, 851–856.

    Article  Google Scholar 

  60. M. Tan, Z. Ye, G. Wang, and J. Yuan (2004). Preparation and time-resolved fluorometric application of luminescent europium nanoparticles. Chem. Mater. 16, 2494–2498.

    Article  Google Scholar 

  61. Z. Ye, M. Tan, G. Wang, and J. Yuan (2005). Development of functionalized terbium fluorescent nanoparticles for antibody labeling and time-resolved fluoroimmunoassay application. Talanta 65, 206–210.

    Google Scholar 

  62. M. Tan, Z. Ye, G. Wang, and J. Yuan (2004). Development of functionalized fluorescent europium nanoparticles for biolabeling and time-resolved fluorometric applications. J. Mater. Chem. 14, 2896–2901.

    Article  Google Scholar 

  63. J. Yuan, G. Wang, H. Kimura, and K. Matsumoto (1997). Highly sensitive time-resolved fluoroimmunoassay of human immunoglobulin E by using a new europium fluorescent chelate as a label. Anal. Biochem. 254, 283–287.

    Article  PubMed  Google Scholar 

  64. J. Yuan, G. Wang, H. Kimura, and K. Matsumoto (1998). Sensitive time-resolved fluoroimmunoassay of human thyroid-stimulating hormone by using a new europium fluorescent chelate as a label. Anal. Sci. 14, 421–423.

    Article  Google Scholar 

  65. M. Ikegawa, J. Yuan, K. Matsumoto, S. Herrmann, A. Iwamoto, T. Nakamura, S. Matsushita, T. Kimura, T. Honjo, and K. Tashiro (2001). Elevated plasma stromal cell-derived factor 1 protein level in the progression of HIV type 1 infection/AIDS. AIDS Res. Hum. Retrov. 17, 587–595.

    Article  Google Scholar 

  66. H. Kimura, M. Suzui, F. Nagao, and K. Matsumoto (2001). Highly sensitive determination of plasma cytokines by time-resolved fluoroimmunoassay: effect of bicycle exercise on plasma level of interleukin-1a (IL-1α), tumor necrosis factor α (TNFα), and interferon λ (IFNλ). Anal. Sci. 17, 593–597.

    Article  PubMed  Google Scholar 

  67. M. Kobayashi, H. Kimura, J. Liao, M. Abe, S. Hirose, and Y. Tomino (2003). Measurement of mouse urinary type IV collagen using time-resolved fluoroimmunoassay. Anal. Sci. 19, 205–210.

    Article  PubMed  Google Scholar 

  68. H. Kimura, J. Yuan, G. Wang, K. Matsumoto, and M. Mukaida (1999). Highly sensitive quantitation of methamphetamine by time-resolved fluoroimmunoassay using a new europium chelate as a label. J. Anal. Toxicol. 23, 11–16.

    PubMed  Google Scholar 

  69. G. Wang, J. Yuan, K. Matsumoto, and H. Kimura (2001). Quantitative measurement of p21 protein in human serum by time-resolved fluoroimmunoassay. Anal. Sci. 17, 881–883.

    Article  PubMed  Google Scholar 

  70. J. Yuan, G. Wang, H. Kimura, and K. Matsumoto (1999). Highly sensitive detection of bensulfuron-methyl by time-resolved fluoroimmunoassay using a tetradentate β-diketonate europium chelate as a label. Anal. Sci. 15, 125–128.

    Article  Google Scholar 

  71. K. Majima, T. Fukui, J. Yuan, G. Wang, and K. Matsumoto (2002). Quantitative measurement of 17β-estradiol and estriol in river water by time-resolved fluoroimmunoassay. Anal. Sci. 18, 869–874.

    Article  PubMed  Google Scholar 

  72. K. Matsumoto, J. Yuan, G. Wang, and H. Kimura (1999). Simultaneous determination of α-fetoprotein and carcinoembryonic antigen in human serum by time-resolved fluoroimmunoassay. Anal. Biochem. 276, 81–87.

    Article  PubMed  Google Scholar 

  73. H. Kimura, M. Mukaida, G. Wang, J. Yuan, and K. Matsumoto (2000). Dual-label time-resolved fluoroimmunoassay of psychopharmaceuticals and stimulants in serum. Forensic Sci. Int. 113, 345–351.

    Article  PubMed  Google Scholar 

  74. J. Yuan, G. Wang, K. Majima, and K. Matsumoto (2001). Synthesis of a terbium fluorescent chelate and its application to time-resolved fluoroimmunoassay. Anal. Chem. 73, 1869–1876.

    Article  PubMed  Google Scholar 

  75. S. Inoue and R. Honda (1990). Microplate hybridization of amplified viral DNA segment. J. Clin. Microbiol. 28, 1469–1472.

    PubMed  Google Scholar 

  76. T. Sekiya, M. Fushimi, H. Hori, S. Hirohashi, S. Nishimura, and T. Sugimura (1984). Molecular cloning and the total nucleotide sequence of the human c-Ha-ras-1 gene activated in a melanoma from a Japanese patient. Proc. Natl. Acad. Sci. USA 81, 4771–4775.

    PubMed  Google Scholar 

  77. I. C. Hsu, R. A. Metcalf, T. Sun, J. A. Welsh, N. J. Wang, and C. C. Harris (1991). Mutational hot spot in the p53 gene in human hepatocellular carcinomas. Nature 350, 427–429.

    Article  PubMed  Google Scholar 

  78. R. A. Cardullo, S. Agrawal, C. Flores, P. C. Zamecnik, and D. E. Wolf (1988). Detection of nucleic acid hybridization by nonradiative fluorescence resonance energy transfer. Proc. Natl. Acad. Sci. USA 85, 8790–8794.

    PubMed  Google Scholar 

  79. J.-L. Mergny, A. S. Boutorine, T. Garestier, F. Belloc, M. Rougèe, N. V. Bulychev, A. A. Koshikin, J. Bourson, A. V. Lebedev, B. Valeur, N. T. Thuong, and C. Hèlène (1994). Fluorescence energy transfer as a probe for nucleic acid structures and sequences. Nucleic Acids Res. 22, 920–928.

    PubMed  Google Scholar 

  80. S. Sueda, J. Yuan, and K. Matsumoto (2000). Homogeneous DNA hybridization assay by using europium luminescence energy transfer. Bioconjugate Chem. 11, 827–831.

    Article  Google Scholar 

  81. S. Sueda, J. Yuan, and K. Matsumoto (2002). A homogeneous DNA hybridization system by using a new luminescence terbium chelate. Bioconjugate Chem. 13, 200–205.

    Article  Google Scholar 

  82. G. Wang, J. Yuan, K. Matsumoto, and Z. Hu (2001). Homogeneous time-resolved fluorescence DNA hybridization assay by DNA-mediated formation of an EDTA-Eu(III)-β-diketonate ternary complex. Anal. Biochem. 299, 169–172.

    Article  PubMed  Google Scholar 

  83. L. Seveus, M. Väisälä, S. Syrjänen, M. Sandberg, A. Kuusisto, R. Harju, J. Salo, I. Hemmilä, H. Kojola, and E. Soini (1992). Time-resolved fluorescence imaging of europium chelate label in immunohistochemistry and in situ hybridization. Cytometry 13, 329–338.

    Article  PubMed  Google Scholar 

  84. G. Marriott, M. Heidecker, E. P. Diamandis, and Y. Yan-Marriott (1994). Time-resolved delayed luminescence image microscopy using an europium ion chelate complex. Biophys. J. 67, 957–965.

    PubMed  Google Scholar 

  85. R. Connally, D. Veal, and J. A. Piper, Proceedings of SPIE, In J.-A. Conchello, C. J. Cogswell, T. Wilson (Eds.), The International Society for Optical Engineering, Vol. 4964, 2003, pp. 14–23.

  86. R. Connally, D. Veal, and J. A. Piper in Proceedings of SPIE, In A. P. Savitsky, D. J. Bornhop, R. Raghavachari, and S. I. Achilefu (Eds.), The International Society for Optical Engineering, Vol. 4967, 2003, pp. 146–155.

  87. R. Connally, D. Veal, and J. A. Piper (2004). Flash lamp-excited time-resolved fluorescence microscope suppresses autofluorescence in water concentrates to deliver an 11-fold increase in signal-to-noise ratio. J. Biomed. Opt. 9, 725–734.

    Article  PubMed  Google Scholar 

  88. X. Gao, Y. Cui, R. M. Levenson, L. W. K. Chung, and S. Nie (2004). In vivo cancer targeting and imaging with semiconductor quantum dots. Nat. Biotech. 22, 969–976.

    Article  Google Scholar 

  89. E. B. Voura, J. K. Jaiswal, H. Mattoussi, and S. Simon (2004). Tracking metastatic tumor cell extravasation with quantum dot nanocrystals and fluorescence emission-scanning microscopy. Nat. Med. 10, 993–998.

    Article  PubMed  Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to Jingli Yuan.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Yuan, J., Wang, G. Lanthanide Complex-Based Fluorescence Label for Time-Resolved Fluorescence Bioassay. J Fluoresc 15, 559–568 (2005). https://doi.org/10.1007/s10895-005-2829-3

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-005-2829-3

Keywords

  • lanthanide complex
  • fluorescence label
  • time-resolved fluorescence bioassay