Enhancement of anion binding in lanthanide optical sensors

Accounts of Chemical Research

Volumn 46, Issue 11, 2013, Pages 2576-2584

  Cable, Morgan L ^a   Kirby, James P ^c   Gray, Harry B ^b   Ponce, Adrian ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^c PLANETARY SCIENCE INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; LANTHANIDE; LIGAND;

ARTICLE; CHEMISTRY; OPTICAL INSTRUMENTATION;

ANIONS; LANTHANOID SERIES ELEMENTS; LIGANDS; OPTICAL DEVICES;

EID: 84888617525     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar400050t     Document Type: Article

References (87)

1. Butler, S. J.; Parker, D. Anion binding in water at lanthanide centres: from structure and selectivity to signalling and sensing Chem. Soc. Rev. 2013, 42, 1652-1666
2. Selvin, P. R. Principles and biophysical applications of lanthanide-based probes Ann. Rev. Biophys. Biomol. Struct. 2002, 31, 275-302
3. Parker, D.; Dickins, R. S.; Puschmann, H.; Crossland, C.; Howard, J. A. K. Being excited by lanthanide coordination complexes: Aqua species, chirality, excited-state chemistry, and exchange dynamics Chem. Rev. 2002, 102, 1977-2010
4. Gunnlaugsson, T.; Glynn, M.; Tocci, G. M.; Kruger, P. E.; Pfeffer, F. M. Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors Coord. Chem. Rev. 2006, 250, 3094-3117
5. Hemmila, I.; Laitala, V. Progress in lanthanides as luminescent probes J. Fluoresc. 2005, 15, 529-542
6. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 3 rd ed.; Springer Science+Business Media, LLC: Singapore, 2006.
7. Cotton, S. Lanthanide and Actinide Chemistry; John Wiley & Sons Ltd.: West Sussex, England, 2006.
8. Gassner, A.-L.; Duhot, C.; Bünzli, J. C. G.; Chauvin, A. S. Remarkable tuning of the photophysical properties of bifunctional lanthanide tris(dipicolinates) and its consequence on the design of bioprobes Inorg. Chem. 2008, 47, 7802-7812
9. Bünzli, J. C. G.; Comby, S.; Chauvin, A. S.; Vandevyver, C. D. B. New opportunities for lanthanide luminescence J. Rare Earths 2007, 25, 257-274
10. Rao, S. S.; Mohan, K. V. K.; Atreya, C. D. Detection technologies for Bacillus anthracis: Prospects and challenges J. Microbiol. Methods 2010, 82, 1-10
11. Shafaat, H. S.; Ponce, A. Applications of a rapid endospore viability assay for monitoring UV inactivation and characterizing Arctic ice cores Appl. Environ. Microbiol. 2006, 72, 6808-6814
12. Nicholson, W. L. Using thermal inactivation kinetics to calculate the probability of extreme spore longevity: implications for paleomicrobiology and lithopanspermia Origins Life Evol. Biospheres 2003, 33, 621-631
13. Roberts, T. A.; Hitchins, A. D. Resistance of spores. In The Bacterial Spore; Gould, G. W.; Hurst, A., Eds.; Academic Press, 1969; Vol. 1, pp 611-670.
14. Byrne, A. F.; Burton, T. H.; Koch, R. B. Relation of dipicolinic acid content of anaerobic bacterial endospores to their heat resistance J. Bacteriol. 1960, 80, 139-140
15. Aronson, A. I.; Fitz-James, P. Structure and morphogenesis of the bacterial spore coat Bacteriol. Rev. 1976, 40, 360-402
16. Bisset, K. A. Evolution in bacteria and the significance of the bacterial spore Nature 1950, 166, 431-432
17. Driks, A. The dynamic spore Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3007-3009
18. Nicholson, W. L.; Munakata, N.; Horneck, G.; Melosh, H. J.; Setlow, P. Resistance of Bacillus endospores to extreme terrestrial and extraterrestrial environments Microbiol. Mol. Biol. Rev. 2000, 64, 548-572
19. Horneck, G.; Bucker, H.; Reitz, G. Long-term survival of bacterial spores in space Adv. Space Res. 1994, 14, 41-45
20. Novikova, N.; Gusev, O.; Polikarpov, N.; Deshevaya, E.; Levinskikh, M.; Alekseev, V.; Okuda, T.; Sugimoto, M.; Sychev, V.; Grigoriev, A. Survival of dormant organisms after long-term exposure to the space environment Acta Astronaut. 2011, 68, 1574-1580
21. Probst, A.; Facius, R.; Wirth, R.; Wolf, M.; Moissl-Eichinger, C. Recovery of Bacillus Spore Contaminants from Rough Surfaces: A Challenge to Space Mission Cleanliness Control Appl. Environ. Microbiol. 2011, 77, 1628-1637
22. Pflug, I. J.; Evans, K. D. Carrying out biological qualification, the control operation of moist-heat (steam sterilization) processes for producing sterile pharmaceuticals and medical devices PDA J. Pharm. Sci. Technol. 2000, 54, 117-135
23. Hindle, A. A.; Hall, E. A. H. Dipicolinic acid (DPA) assay revisited and appraised for spore detection Analyst 1999, 124, 1599-1604
24. Gerhardt, P.; Marquis, R. E.: Spore thermoresistance mechanisms. In Regulation of prokaryotic development; Smith, I.; Slepecky, R. A.; Setlow, P., Eds.; American Society for Microbiology:: Washington, D.C., 1989; pp 43-63.
25. Murrell, W. G. The Bacterial Spore; Academic Press: New York, 1969.
26. Gould, G. W.; Hurst, A. The Bacterial Spore; Academic Press, 1969.
27. Scott, I. R.; Ellar, D. J. Study of calcium dipicolinate release during bacterial spore germination by using a new, sensitive assay for dipicolinate J. Bacteriol. 1978, 135, 133-137
28. Kong, L.; Zhang, P.; Wang, G.; Yu, J.; Setlow, P.; Li, Y.-q. Characterization of bacterial spore germination using phase-contrast and fluorescence microscopy, Raman spectroscopy and optical tweezers Nat. Protoc. 2011, 6, 625-639
29. Ammann, A. B.; Kölle, L.; Brandl, H. Detection of bacterial endospores in soil by terbium fluorescence Int. J. Microbiol. 2011, 2011, 1-5
30. Rosen, D. L. Bacterial spore detection and determination by use of terbium dipicolinate photoluminescence Anal. Chem. 1997, 69, 1082-1085
31. Jones, G.; Vullev, V. I. Medium effects on the photophysical properties of terbium(III) complexes with pyridine-2,6-dicarboxylate Photochem. Photobiol. Sci. 2002, 1, 925-933
32. Yung, P. T.; Ponce, A. Fast Sterility Assessment by Germinable-Endospore Biodosimetry Appl. Environ. Microbiol. 2008, 74, 7669-7674
33. Yang, W.-W.; Ponce, A. Rapid endospore viability assay of Clostridium sporogenes spores Int. J. Food Microbiol. 2009, 133, 213-216
34. Sammes, P. G.; Yahioglu, G. Modern bioassays using metal chelates as luminescent probes Nat. Prod. Rep. 1996, 13, 1-28
35. Stryer, L.; Thomas, D. D.; Meares, C. F. Diffusion-enhanced fluorescence energy transfer Annu. Rev. Biophys. Bioeng. 1982, 11, 203-222
36. Sabbatini, N.; Guardigli, M.; Lehn, J. M. Luminescent Lanthanide Complexes As Photochemical Supramolecular Devices Coord. Chem. Rev. 1993, 123, 201-228
37. Cable, M. L.; Kirby, J. P.; Levine, D. J.; Manary, M. J.; Gray, H. B.; Ponce, A. Detection of bacterial spores with lanthanide-macrocycle binary complexes J. Am. Chem. Soc. 2009, 131, 9562-9570
38. Rosen, D. L.; Sharpless, C.; McGown, L. B. Bacterial endospore detection using photoluminescence from terbium dipicolinate Rev. Anal. Chem. 1999, 18, 1-21
39. Aebischer, A.; Gumy, F.; Bünzli, J.-C. G. Intrinsic quantum yields and radiative lifetimes of lanthanide tris(dipicolinates) Phys. Chem. Chem. Phys. 2009, 11, 1346-1353
40. Bünzli, J.-C. G. Lanthanide probes in life, chemical and earth sciences: Theory and practice; Elsevier: New York, 1989.
41. Ariga, K.; Ito, H.; Hill, J. P.; Tsukube, H. Molecular recognition: from solution science to nano/materials technology Chem. Soc. Rev. 2012, 41, 5800-5835
42. Shao, Y.-F.; Yan, B. Photofunctional hybrids of rare earth complexes covalently bonded to ZnO core-shell nanoparticle substrate through polymer linkage Dalton Trans. 2012, 41, 7423-7430
43. Lehn, J. M. Design of organic complexing agents: Strategies towards properties Struct. Bonding (Berlin, Ger.) 1973, 16, 1-69
44. Arnaudneu, F. Solution Chemistry Of Lanthanide Macrocyclic Complexes Chem. Soc. Rev. 1994, 23, 235-241
45. Lee, D. Metal Chelation Chemistry. In Chemosensors: Principles, Strategies, and Applications; Wang, B.; Anslyn, E. V., Eds.; John Wiley & Sons, 2011; pp 41-64.
46. Chang, C. A.; Chen, Y.-H.; Chen, H.-Y.; Shieh, F.-K. Capillary electrophoresis, potentiometric and laser excited luminescence studies of lanthanide(III) complexes of 1,7-dicarboxymethyl-1,4,7,10-tetraazacyclododecane (DO2A) J. Chem. Soc., Dalton Trans. 1998, 3243-3248
47. Haas, K. L.; Franz, K. J. Application of Metal Coordination Chemistry To Explore and Manipulate Cell Biology Chem. Rev. 2009, 109, 4921-4960
48. Mewis, R. E.; Archibald, S. J. Biomedical applications of macrocyclic ligand complexes Coord. Chem. Rev. 2010, 254, 1686-1712
49. 3+(macrocycle)(dipicolinate)] Luminescence J. Am. Chem. Soc. 2007, 129, 1474-1475
50. Kirby, J. P.; Cable, M. L.; Levine, D. J.; Gray, H. B.; Ponce, A. Spectroscopic analysis of ligand binding to lanthanide-macrocycle platforms Anal. Chem. 2008, 80, 5750-5754
51. Persson, I.; D'Angelo, P.; De Panfilis, S.; Sandström, M.; Eriksson, L. Hydration of Lanthanoid(III) Ions in Aqueous Solution and Crystalline Hydrates Studied by EXAFS Spectroscopy and Crystallography: The Myth of the "Gadolinium Break Chem.-Eur. J. 2008, 14, 3056-3066
52. Silber, H. B.; Paquette, S. J. Complexes of Lanthanide Ions with Amino Acids, Nucleotides, and Other Ligands of Biological Interest in Solution. In Metal Ions in Biological Systems: The Lanthanides and Their Interrelations with Biosystems; Sigel, A.; Sigel, H., Eds.; Marcel Dekker, Inc.: New York, 2003; Vol. 40, pp 69-104.
53. Yerly, F.; Dunand; Frank, A.; Tóth, é.; Figueirinha, A.; Kovács, Z.; Sherry, A. D.; Geraldes, C. F. G. C.; Merbach; André, E. Spectroscopic Study of the Hydration Equilibria and Water Exchange Dynamics of Lanthanide(III) Complexes of 1,7-Bis(carboxymethyl)-1,4,7,10- tetraazacyclododecane (DO2A) Eur. J. Inorg. Chem. 2000, 2000, 1001-1006
54. Sicre, J. E.; Dubois, J. T.; Eisentraut, K. J.; Sievers, R. E. Volatile lanthanide chelates. II. Vapor pressures, heats of vaporization, and heats of sublimation J. Am. Chem. Soc. 1969, 91, 3476-3481
55. Spedding, F. H.; Pikal, M. J. Relative Viscosities of Some Aqueous Rare Earth Chloride Solutions at 25 J. Phys. Chem. 1966, 70, 2430-2440
56. Spedding, F. H.; Jones, K. C. Heat Capacities of Aqueous Rare Earth Chloride Solutions at 25 J. Phys. Chem. 1966, 70, 2450-2455
57. Yang, Z.; Batra, R.; Floyd, D. L.; Hung, H.-C.; Chang, G.-G.; Tong, L. Potent and competitive inhibition of malic enzymes by lanthanide ions Biochem. Biophys. Res. Commun. 2000, 274, 440-444
58. Grenthe, I. Stability Relationships Among Rare Earth Dipicolinates J. Am. Chem. Soc. 1961, 83, 360-364
59. Powell, J. E.; Ingemanson, J. W. Lanthanide picolinate chelate stabilities Inorg. Chem. 1968, 7, 2459-2461
60. Elkström, C.-G.; Nilsson, L.; Duncan, I. A.; Grenthe, I. The rate and mechanism for the formation of mixed complexes between lanthanoid EDTA and pyridine-2-carboxylate or 8-hydroxyquinoline-5-sulfonate Inorg. Chim. Acta 1980, 40, 91-98
61. Moeller, T.; Martin, D. F.; Thompson, L. C.; Ferrus, R.; Feistel, G. R.; Randall, W. J. The coordination chemistry of yttrium and the rare earth metal ions Chem. Rev. 1965, 65, 1-50
62. Bruce, J. I.; Dickins, R. S.; Govenlock, L. J.; Gunnlaugsson, T.; Lopinski, S.; Lowe, M. P.; Parker, D.; Peacock, R. D.; B., P. J. J.; Aime, S.; Botta, M. The selectivity of reversible oxy-anion binding in aqueous solution at a chiral europium and terbium center: Signaling of carbonate chelation by changes in the form and circular polarization of luminescence emission J. Am. Chem. Soc. 2000, 122, 9674-9684
63. Kolat, R. S.; Powell, J. E. Acetate complexes of the rare earth and several transition metal ions Inorg. Chem. 1962, 1, 293-296
64. Cable, M. L.; Levine, D. J.; Kirby, J. P.; Gray, H. B.; Ponce, A. Luminescent Lanthanide Sensors. In Advances in Inorganic Chemistry: Inorganic Photochemistry; Van Eldik, R., Ed.; Elsevier: San Diego, 2011; Vol. 63, pp 1-45.
65. Jones, G.; Vullev, V. I. Medium effects on the stability of terbium(III) complexes with pyridine-2,6-dicarboxylate J. Phys. Chem. A 2002, 106, 8213-8222
66. Doyle, M.; Silber, H. B. Successive complexation steps in the coordination kinetics of the dysprosium(III)-acetate system J. Chem. Soc., Chem. Commun. 1972, 1067-1068
67. Bulman, R. A.: Mobilization of Lanthanides through the Terrestrial Biosphere. In Metal Ions in Biological Systems: The Lanthanides and Their Interrelations with Biosystems; Sigel, A.; Sigel, H., Eds.; Marcel Dekker, Inc.: New York, 2003; Vol. 40, pp 39-67.
68. Parker, D.; Williams, J. A. G. Luminescence behaviour of cadmium, lead, zinc, copper, nickel and lanthanide complexes of octadentate macrocyclic ligands bearing naphthyl chromophores J. Chem. Soc., Perkin Trans. 2 1995, 1305-1314
69. Beeby, A.; Clarkson, I. M.; Dickins, R. S.; Faulkner, S.; Parker, D.; Royle, L.; de Sousa, A. S.; Williams, J. A. G.; Woods, M. 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 1999, 493-503
70. Rinehart, J. D.; Long, J. R. Exploiting single-ion anisotropy in the design of f-element single-molecule magnets Chem. Sci. 2011, 2, 2078-2085
71. Bretonniere, Y.; Cann, M. J.; Parker, D.; Slater, R. Design, synthesis and evaluation of ratiometric probes for hydrogencarbonate based on europium emission Org. Biomol. Chem. 2004, 2, 1624-1632
72. Yu, J. H.; Parker, D.; Pal, R.; Poole, R. A.; Cann, M. J. A europium complex that selectively stains nucleoli of cells J. Am. Chem. Soc. 2006, 128, 2294-2299
73. Leonard, J. P.; Dos Santos, C. M. G.; Plush, S. E.; McCabe, T.; Gunnlaugsson, T. pH driven self-assembly of a ternary lanthanide luminescence complex: The sensing of anions using a beta-diketonate-Eu(III) displacement assay Chem. Commun. 2007, 129-131
74. Hsu, S.-H.; Yilmaz, M. D.; Blum, C.; Subramaniam, V.; Reinhoudt, D. N.; Velders, A. H.; Huskens, J. Expression of Sensitized Eu3+ Luminescence at a Multivalent Interface J. Am. Chem. Soc. 2009, 131, 12567-12569
75. Karhunen, U.; Jaakkola, L.; Wang, Q.; Lamminmäki, U.; Soukka, T. Luminescence Switching by Hybridization-Directed Mixed Lanthanide Complex Formation Anal. Chem. 2010, 82, 751-754
76. Zheng, Y.; Tan, C.; Drummen, G. P. C.; Wang, Q. A luminescent lanthanide complex-based anion sensor with electron-donating methoxy groups for monitoring multiple anions in environmental and biological processes Spectrochim. Acta, Part A 2012, 96, 387-394
77. Pal, R.; Parker, D.; Costello, L. C. A europium luminescence assay of lactate and citrate in biological fluids Org. Biomol. Chem. 2009, 7, 1525-1528
78. Dickins, R. S.; Parker, D.; Bruce, J. I.; Tozer, D. J. Correlation of optical and NMR spectral information with coordination variation for axially symmetric macrocyclic Eu(III) and Yb(III) complexes: axial donor polarisability determines ligand field and cation donor preference Dalton Trans. 2003, 1264-1271
79. Piguet, C.; Bünzli, J. C. G. Mono- and polymetallic lanthanide-containing functional assemblies: A field between tradition and novelty Chem. Soc. Rev. 1999, 28, 347-358
80. Hockenbury, D. H.; Hockenbury, S. E. Psychology; Fourth ed.; Worth Publishers: New York, 2006.
81. Raab, W. Key position of catecholamines in function and degenerative cardiovascular pathology Am. J. Cardiol. 1960, 5, 571-578
82. Greer, M.; Williams, C. M. Dopamine metabolism in Parkinson's disease Neurology 1963, 13, 73-76
83. Jameson, R. F.; Neillie, W. F. S. Complexes formed by adrenaline and related compounds with transition-metal ions. II. Complexes with copper(II) J. Inorg. Nucl. Chem. 1965, 27, 2623-2634
84. Jameson, R. F.; Neillie, W. F. S. Complexes formed by adrenaline and related compounds with transition-metal ions J. Inorg. Nucl. Chem. 1966, 28, 2667-2675
85. Zhu, R. H.; Kok, W. T. Determination of catecholamines and related compounds by capillary electrophoresis with postcolumn terbium complexation and sensitized luminescence detection Anal. Chem. 1997, 69, 4010-4016
86. Arnaud, N.; Georges, J. Improved detection of salicylic acids using terbium-sensitized luminescence in aqueous micellar solutions of cetyltrimethylammonium chloride Analyst 1999, 124, 1075-1078
87. Esplin, T. L.; Cable, M. L.; Gray, H. B.; Ponce, A. Terbium-macrocycle complexes as chemical sensors: Detection of an aspirin metabolite in urine using a salicylurate-specific receptor site Inorg. Chem. 2010, 49, 4643-4647