Lanthanide complexes for luminescence imaging applications

Applied Spectroscopy Reviews

Volumn 40, Issue 1, 2005, Pages 1-31

  Faulkner, Stephen ^a   Pope, Simon J A ^a   Burton Pye, Benjamin P ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Europium(III) and terbium(III); Lanthanide complexes; Luminescence imaging; Near IR luminescence; Photosensitisers

Indexed keywords

CHARGE TRANSFER; EUROPIUM; IONS; LIGHT ABSORPTION; LIGHT EMISSION; LUMINESCENCE; OPTICAL MICROSCOPY; PHOTONS; PHOTOSENSITIZERS; SELF ASSEMBLY; TERBIUM; TRANSITION METALS;

ACYCLIC LIGAND; LANTHANIDE COMPLEXES; LUMINESCENCE IMAGING; LUMINESCENCE MICROSCOPY; MACROCYCLIC COMPLEXES; NEAR INFRARED LUMINESCENCE;

IMAGING TECHNIQUES;

EID: 12844252601     PISSN: 05704928     EISSN: None     Source Type: Journal    
DOI: 10.1081/ASR-200038308     Document Type: Article

References (91)

1. Piguet, C. and Bunzli, J.-C.G. (1999) Mono- and polymetallic lanthanide-containing functional assemblies: a field between tradition and novelty. Chem. Soc. Rev., 28 (6): 347-358.
2. Soini, E.Lovgren, T. (1987) Time-resolved fluorescence of lanthanide probes and applications in biotechnology. Crit. Rev. Anal. Chem., 18 (2): 105-154;
3. Hemmila, I.Mukkala, V.M. (2001) Time-resolution in fluorimetry technologies, labels, and applications in bio analytical assays. Crit. Rev. Clin. Lab. Sci., 38 (6): 441-519;
4. European Patent, EP0064484, Wallac Laboratories: Turku, Finland, 1982;
5. Lee, Y.C. (2001) Application of time-resolved fluorometry of lanthanide in glycobiology. Anal. Biochem., 297 (2): 123-200.
6. Peuralahti, J., Hakala, H., Mukkala, V.M., Loman, K., Hurskainen, p., Mulari, O., and Hovinen, J. (2002) Introduction of lanthanide(III) chelates to oligopeptides on solid phase. Bioconjugate Chem., 13: 870-875.
7. Thuren, T., Vitaren, J.A., Lalla, M., and Kinnuren, P.K. (1985) Fluorometric assay for phospholibase A2 in serum. Clin. Chem., 31 (5): 714-717.
8. Freed, S., Weissman, S.I., Fortress, F.E., and Jacobson, H.F. (1939) Ions of europium distributed between different configurations in homogeneous solutions. J. Chem. Phys., 7: 824-828.
9. Weissman, S.I. (1942) Intramolecular energy transfer. The fluorescence of complexes of europium, J. Chem. Phys., 10: 214-217.
10. Crosby, G.A., Whan, R.E., and Alire, R.M. (1961) Intramolecular energy transfer in rare earth metal chelates. Role of the triplet state. J. Chem. Phys., 34: 743-774.
11. Crosby, G.A., Whan, R.E., and Freeman, J.J. (1962) Spectroscopic studies of rare earth chelates. J. Phys. Chem., 66: 2493-2499.
12. Parker, D. and Williams, J.A.G. (1996) Getting excited about lanthanide complexation chemistry. J. Chem. Soc. Dalton Trans., 18: 3613-3629.
13. Evangalista, R.A., Pollack, A., Allore, B., Templeton, E.F., Morton, R.C., and Diamandis, E.P. (1988) A new europium chelate for protein labelling and time-resolved fluorometric applications. Clin. Biochem. 21: 173-178.
14. Mathis, G. (1995) Probing molecular interactions with homogeneous techniques based on rare earth cryptates and fluorescence energy transfer. Clin. Chem., 41 (9): 1391-1397.
15. Lopez, E., Chypre, C., Alpha, B., and Mathis, G. (1993) Europium(III) trisbipyr-idine cryptate for time-resolved fluorescence detection of polymerase chain reaction products fixed on a solid support. Clin. Chem., 39 (2): 196-201.
16. Horrocks, W.D., Jr. and Sudnick, D.R. (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 (2): 334-340.
17. Elbanowski, M. and Makowska, B. (1996) The lanthanides as luminescent probes in investigations of biochemical systems. J. Photochem. Photobiol. A: Chem., 99: 85-92.
18. Supkowski, R.M., Bolender, J.P., Smith, W.D., and Reynolds, L.E.L., Jr. (1999) Lanthanide ions as redox probes of long-range electron transfer in proteins. Coord. Chem. Rev., 185-186: 307-319.
19. Xu, Y.Y. and Hemmila, I.A. (1992) Co-fluorescence enhancement system based on pivaloyltrifluoroacetone and yttrium for the simultaneous detection of europium, terbium, samarium and dysprosium. Anal. Chim. Acta, 256 (1): 9-16.
20. Horrocks, W.D., Jr., Bolender, J.P., Smith, W.D., and Supkowski, R.M. (1997) Photosensitized near infrared luminescence of ytterbium(III) in proteins and complexes occurs via an internal redox process. J. Am. Chem. Soc., 119 (25): 5972-5973.
21. Eriksson, S., Vehniainen, M., Jansen, T., Meretoja, V., Saviranta, P., Pettersson, K., and Lovgren, T. (2000) Dual-label time-resolved immunofluorometric assay of free and total prostate-specific antigen based on recombinant Fab fragments. Clin. Chem., 46 (5): 658.
22. Harma, H., Aronkyoto, P., and Lovgren, T. (2000) Multiplex immunoassays on size-categorized individual beads using time-resolved fluorescence. Anal. Chim. Acta., 410: 85-96.
23. Elliott, C.T., Francis, K.S., and McCaughey, W.J. (1994) Investigation of dissociation enhanced lanthanide fluoroimmunoassay as ah alternative screening test for veterinary drug residues. Analyst, 119: 2565-2569.
24. Davidson, R.S. (1996) Application of fluorescence microscopy to a study of chemical problems. Chem. Soc. Rev., 25 (4): 241-253.
25. Singh, A. and Gopinathan, K.P. (1998) Confocal microscopy: a powerful technique for imaging research. Curr. Sci., 74: 841.
26. Selvin, P.R. (1995) Fluorescence resonance energy transfer. Methods Enzymol., 246: 300-334.
27. Beeby, A., Botchway, S.W., Clarkson, I.M., Faulkner, S., Parker, A.W., Parker, D., and Williams, J.A.G. (2000) Luminescence imaging microscopy and lifetime mapping using kinetically stable lanthanide(III) complexes. J. Photochem. Photobiol. B: Biol., 57: 83-89.
28. Charbonniere, L., Ziessel, R., Guardigli, M., Roda, A., Sabbatini, N., and Cesario, M. (2001) Lanthanide tags for time-resolved luminescence microscopy displaying improved stability and optical properties. J. Am. Chem. Soc., 123: 2436-2437.
29. Seveus, L., Vaisala, M., Syrjanen, S., Sandberg, M., Kuusisto, A., Harju, R., Salo, J., Hemmila, I., Kojola, H., and Soini, E. (1992) Time-resolved fluorescence imaging of europium chelate label in immunohistochemistry and in situ hybridis ation. Cytometry, 13 (4): 329-338.
30. Vereb, G., Jares-Erijman, E., Selvin, P.R., and Jovin, T.M. (1998) Temporally and spacially resolved imaging microscopy of lanthanide chelates. Biophys. J., 74 (5) 2210-2222.
31. Soini, A.E., Seveus, L., Meltola, N.J., Papovsky, D.B., and Soini, E. (2002) Phosphorescent metalloporphyrins as labels in time-resolved luminescence microscopy: effect of mounting on emission intensity. Microsci. Res. Tech., 58 (2): 125-131.
32. Connally, R., Veal, D., and Piper, J. (2002) High resolution detection of fluorescently labelled microorganisms in environmental samples using time-resolved fluorescence microscopy. FEMS Microbiol. Ecol., 41 (3): 239-245.
33. Lacowicz, J.R., Pisczek, G., Maliwal, B.P., and Gryczynski, I. (2001) Multiphoton excitation of lanthanides. Chem. Phys. Chem. 2, 2 (4): 247-252.
34. Phimphivong, S., Kolchens, S., Edmison, P.L., and Saavedra, S. (1995) Time-resolved, total internal reflection fluorescence microscopy of cultured cells using a Tb chelate label. Anal. Chim. Acta, 307 (2-3): 403-417.
35. Marriott, G., Heidecker, M., Diamandis, E.P., and Yan-Marriott, Y. (1994) Time-resolved luminescence image microscopy using an europium ion chelate complex. Biophys. J.,67 (3): 957-965.
36. Beverloo, H.B., Schadewijk, A.V., Bonnet, J., Geest, R.V.D., Runia, R., Verwoerd, N.P., Vrolijk, J., Ploem, J.S., and Tanke, H.J. (1992) Preparation and microscopic visualisation of multicolour luminescent immunophosphorous. Cytometry, 13 (6): 561-570.
37. Aarons, R.J., Burton-Pye, B.P., Faulkner, S., Botchway, S.W., Parker, A.W., Topley, S., Beeby, A., Snaith, J.S., Ashraf, A., and Notta, J. (2001/2002) Time- resolved imaging with lanthanide complexes. LSF Ann. Rep., 130.
38. Alpha, B., Lehn, J-M., and Mathis, G. (1987) Energy transfer of europium(III) and terbium(III) with macrobicyclic polypyridine ligands. Angew. Chemie., 99 (3): 259-261.
39. Vleck, J.H.V. (1937) The puzzle of rare-earth spectra in solids. J. Chem. Phys., 41 (1): 67-80.
40. Desreux, J.F. (1980) Nuclear magnetic resonance spectroscopy of lanthanide complexes with a tetraacetic tetraaza macrocycle. Unusual conformation properties. Inorg. Chem., 19 (5): 1319-1324.
41. Lauffer, R.B. (1987) Paramagnetic metal complexes as water proton relaxation agents for NMR imaging: theory and design. Chem. Rev., 87 (5): 901-927.
42. Aime, S., Batsanov, A.S., Botta, M., Dickins, R.S., Faulkner, S., Foster, C.E., Harrison, A., Howard, J.A.K., Moloney, J.M., Norman, T.J., Parker, D., Royale, L., and Williams, J.A.G. (1997) Nuclear magnetic resonance, luminescence and structural studies of lanthanide complexes with octadentate macrocyclic ligands bearing benzylphosphinate groups. J. Chem. Soc. Dalton Trans., 19: 3626-3636.
43. Desurvire, E. (1994) The golden age of optical fibre amplifiers. Phys. Today, 94 (1): 20-27.
44. An, D., Yue, Z., and Chen, R.T. (1998) Dual-functional polymeric waveguide with optical amplification and electro~optic modulation. Appl. Phys. Lett., 72 (22): 2806-2807.
45. Beeby, A., Parker, D., and Williams, J.A.G. (1996) Photochemical investigations of functionalised 1,4,7,10-tetraazacyclododecane ligands encorporating napthyl chromophores. J. Chem. Soc. Perkin Trans. 2, 8: 1565-1580.
46. Faulkner, S., Beeby, A., Dickins, R.S., Parker, D., and Williams, J.A.G. (1999) Generating a warm glow: lanthanide complexes which luminenscence in the near-IR. J. Flouresc., 9: 45-49.
47. Beeby, A. and Faulkner, S. (1997) Luminescence from neodymium(III) in solution. Chem. Phys. Lett., 266 (1-2): 116-122.
48. Beeby, A., Clarkson, I.M., Dickins, R.S., Faulkner, S., Parker, D., Royale, L., Sousa, A.S., Williams, J.A.G., and Woods, M. (1999) Non-radiative deactivation of the excited states of europium, terbium and ytterbium complexes by proximate energy-matched OH, NH and CH oscillators: an improved luminescence method for establishing solution hydration states. J. Chem. Soc. Perkin Trans 2, 3: 493-504.
49. Kropp, J.L. and Windsor, M.W. (1963) Enhancement of fluorescence yield of rare earth ions by heavy water. J. Chem. Phys., 39 (10): 2769-2770.
50. Kropp, J.L. and Windsor, M.W. (1965) Luminescence and energy transfer in solutions of rare-earth complexes. I. Enhancement of fluorescence by deuterium substitution. J. Chem. Phys., 42 (5): 1599-1609.
51. 2O mixtures. J. Chem. Phys., 45: 761.
52. Haas, Y. and Stein, G. (1971) Pathways of radiative and radiationless transitions in europium(HI) solutions. Role of solvents and anions. J. Phys. Chem., 75 (24): 3668-3677.
53. Stein, G. and Wurzberg, E. (1975) Energy gap law in the solvent isotope effect on radiationless transition of rare earth anions. J. Chem. Phys., 62 (1): 208-213.
54. Haas, Y. and Stein, G. (1972) Radiative and non-radiative pathways in solutions. Excited state of the europium(III) ion. J. Phys. Chem., 76 (8): 1093-1104.
55. Hole, R.C. and Horrocks, W.D. (1990) Spectroscopic characterization of some rare earth complexes of triethylenetetraaminehexaacetic acid. Inorg. Chim. Acta, 171 (2): 193-198.
56. 3+ luminescence spectroscopy and molecular mechanics. Inorg. Chem., 33 (13): 2882-2889.
57. Horrocks, W.D., Jr. and Sudnick, D.R. (1979) Time-resolved europium(III) excitation spectroscopy: a luminescence probe of metal ion binding. Science, 206 (4423): 1194-1196.
58. Horrocks, W.D., Jr., Schmidt, G.R., Sudnick, D.R., Kittrell, C., and Bernheim, R.A. (1977) Laser-induced lanthanide ion luminescence lifetime measurements by direct excitation of metal ion levels. A new class of structural probe for calcium-binding proteins and nucleic acids. J. Am. Chem. Soc., 99 (7): 2378-2380.
59. Horrocks, W.D., Jr. and Sudnick, D.R. (1979) Lanthanide ion probes of structure in biology. Environmentally sensitive fine structure in laser-induced terbium(III) luminescence. J. Am. Chem. Soc., 101 (2): 334-340.
60. 3+ complexes. J. Appl. Phys., 86: 1181-1185.
61. Klink, S.I., Hebbink, G.A., Grave, L., Peters, F.G.A., van Veggel, F.C.J. Reinhoudt, D.N., and Hofstraat, J.W. (2000) Near-infrared and visible luminescence from terphenyl-based lanthanide (III) complexes bearing amido and sulfonamido pendant arms. Eur. J. Org. Chem. 1923-1931.
62. Werts, M.H.V., Hofstraat, J.W., Geurts, F.A.J., and Verhoeven, J.W. (1997) Fluorescein and eosin as sensitizing chromophores in near-infrared luminescent ytterbium(III), neodymium(III) and erbium(III) chelates. Chem. Phys. Lett., 276: 196-201.
63. Murov, S.L., Carmichael, I., and Hug, G.L. (1993) Handbook of Photochemistry 2nd Ed.; Marcel Dekker: New York.
64. Werts, M.H.V., Verhoeven, J.W., and Hofstraat, J.W. (2000) Efficient visible light sensitisation of water soluble near infrared luminescent lanthanide complexes. J. Chem. Soc. Perkin Trans. 2433.
65. Werts, M.H.V., Woudenberg, R.H., Emmerink, P.G., van Gassel, R., Hofstraat, J.W., and Verhoeven, J.W. (2000) A near-infrared luminescent label based on Yb-III ions and its application in a fluoroimmunoassay. Angew Chem. Int. Ed., 39: 4542.
66. 3+ azatriphenylene complexes. Tetrahedron Lett., 39: 7583-7586.
67. Shavaleev, N.M., Pope, S.J.A., Bell, Z.R., Faulkner, S., and Ward, M.D. (2003) Efficient visible-light sensitisation of near-infrared luminescence from Yb(III), Nd(III) and Er(III) complexes of 3,6-bis 2-pyridyl)tetrazine. J. Chem. Soc. Dalton Trans. 808 - 814.
68. Beeby, A., Burton-Pye, B.P., Faulkner, S., Motson, G.R., Jeffery, J.C., McCleverty, J.A., and Ward, M.D. (2002) Synthesis and near-IR luminescence properties of neodymium(III) and ytterbium(III) complexes with poly(pyrazolyl) borate ligands. J. Chem. Soc. Dalton Trans. 1923-1928.
69. Hasegawa, Y., Ohkubo, T., Sogabe, K., Kawamura, Y., Wada, Y., Nakashima, N., and Yanagida, S. (2000) Luminescence of novel neodymium sulfonylaminate complexes in organic media. Angew. Chem. Int. Ed., 39 (2): 357-360.
70. Elhabiri, M., Scopelliti, R., Bünzli, J.-C.G., and Piguet, C. (1999) Lanthanide helicates self-assembled in water: a new class of highly stable and luminescent dimetallic carboxylates. J. Am. Chem. Soc., 121: 10747-10762.
71. Goncalves e Silva, F.R., Malta, O.L., Reinhard, C., Güdel, H.-U., Piguet, C., Moser, J.E., and Bünzli, J.-C.G. (2002) Visible and near-infrared luminescence of lanthanide-containing dimetallic triple-stranded helicates: energy transfer mechanisms in the Sm-III and Yb-III molecular edifices. J. Phys. Chem. A, 106: 1670-1677.
72. Horrocks, W.D., Jr., Bolender, J.P., Smith, W.D., and Supkowski, R.M. (1997) Photosensitized near infrared luminescence of ytterbium(III) in proteins and complexes occurs via an internal redox process. J. Am. Chem. Soc., 119: 5972-5973.
73. Faulkner, S., Beeby, A., Carrie, M.-C., Dadabhoy, A., Kenwright, A.M., and Sammes, P.G. (2001) Time-resolved near-IR luminescence from ytterbium and neodymium complexes of the Lehn cryptand. Inorg. Chem. Comm., 4: 187-190.
74. Beeby, A., Clarkson, I.M., Dickins, R.S., Faulkner, S., Parker, D., de Sousa, A.S., and Williams, J.A.G. (1999) Non-radiative deactivation of the excited states of europium, terbium and ytterbium complexes by proximate energy-matched OH, NH and CH oscillators: an improved luminescence method for establishing solution hydration states. J. Chem. Soc. Perkin Trans. 2493-503.
75. 3+. Inorg. Chem., 41: 1048-1055.
76. Shavaleev, N.M., Moorcraft, L.P., Pope, S.J.A., Bell, Z.R., Faulkner, S., and Ward, M.D. (2003) Sensitised near-infrared emission from lanthanides using a covalently-attached Pt(II) fragment as an antenna group. Chem. Commun. 1134-1135.
77. Destri, S., Porzio, W., Meinardi, F., Tubino, R., and Salemo, G. (2003) Novel erbium-substituted oligothiophene chelates for infrared emission. Macromolecules, 36 (2): 273-275.
78. Vicinelli, V., Ceroni, P., Maestri, M., Balzani, V., Gorka, M., and Vögtle, F. (2002) Luminescent lanthanide ions hosted in a fluorescent polylysin dendrimer. Antenna-like sensitization of visible and near-infrared emission. J. Am. Chem. Soc., 124: 6461-6468.
79. Parker, D., Senanayake, P.K., and Williams, J.A.G. (1998) Luminescent sensors for pH, pO(2), halide and hydroxide ions using phenanthridine as a photosensitiser in macrocyclic europium and terbium complexes. J. Chem. Soc. Perkin Trans. 22129-2139.
80. Beeby, A., Faulkner, S., and Williams, J.A.G. (2002) pH dependence of the energy transfer mechanism in a phenanthridine-appended ytterbium complex. J. Chem. Soc. Dalton Trans. 1918-1922.
81. Sato, S. and Wada, M. (1970) Relations between intramolecular energy transfer efficiencies and triplet state energies in rare earth beta-diketone chelates. Bull. Chem. Soc. Japan, 43: 1955.
82. Klink, S.I.Keizer, H.van Veggel, F.C.J.M. (2000) Transition metal complexes as photosensitizers for near-infrared lanthanide luminescence. Angew. Chem. Int. Ed. Engl., 39: 4319-4321;
83. Klink, S.I., Keizer, H., Hofstraat, H.W., and van Veggel, F.C.J.M. (2002) Transition metal complexes as a new class of photosensitizers for near-infrared lanthanide luminescence. Synth. Met., 127: 213-216.
84. Beeby, A., Dickins, R.S., Fitzgerald, S., Govenlock, L.J., Maupin, C.L., Parker, D., Riehl, J.P., Siligardi, G., and Williams, J.A.G. (2000) Porphyrin sensitization of circularly polarised near-IR lanthanide luminescence: enhanced emission with nucleic acid binding. Chem. Comm. 1183-1184.
85. Shavaleev, N.M., Moorcraft, L.P., Pope, S.J.A., Bell, Z.R., Faulkner, S., and Ward, M.D. (2003) Sensitized near-infrared emission from complexes of Yb-III, Nd-III and Er-III by energy-transfer from covalently attached Pt-II-based antenna units. Chem. Eur. J., 9 (21): 5283-5291.
86. Riesen, A.Kaden, T.A.Ritter, W.Maecke, H.R. (1989) Synthesis and x-ray structural characterization of seven-coordinate macrocyclic indium(3+) complexes with relevance to radiopharmaceutical applications. J. Chem. Soc. Chem. Comm.460-462;
87. Dischino, D.D., Delaney, E.J., Emswiler, J.E., Gaughan, G.T., and Prasad, J.S. (1991) Synthesis of nonionic gadolinium chelates useful as contrast agents for magnetic resonance imaging: 1,4,7-tris (carboxymethyl)-10-substituted-1,4,7,10-tetraazacyclododecanes and their corresponding gadolinium chelates. Inorg. Chem., 30: 1265-1269.
88. Faulkner, S., Burton-Pye, B.P., Khan, T., Martin, L.R., Wray, S.D., and Skabara, P.J. (2002) Interaction between tetrathiafulvalene carboxylic acid and ytterbium DO3A-solution state self-assembly of a ternary complex which is luminescent in the near IR. Chem. Comm. 1668-1669.
89. Pope, S.J.A., Kenwright, A.M., Heath, S.L., and Faulkner, S. (2003) Synthesis and luminescence properties of a kinetically stable dinuclear ytterbium complex with differentiated binding sites. Chem. Comm. 1550-1551.
90. Pope, S.J.A., Boote, V.A., Kenwright, A.M., and Faulkner, S. (2003) Synthesis and luminescence properties of dinuclear lanthanide complexes derived from covalently linked macrocyclic ligands. J. Chem. Soc. Dalton Trans.3780-3784.
91. Faulkner, S. and Pope, S.J.A. (2003) Lanthanide sensitized lanthanide luminescence: terbium sensitized ytterbium luminescence in a trinuclear complex. J. Am. Chem. Soc., 125: 10526-10527.