Emerging applications of phosphorescent metalloporphyrins

Journal of Fluorescence

Volumn 15, Issue 4, 2005, Pages 569-584

  Papkovsky, Dmitri B ^a,b   O'Riordan, Tomás C ^a  

^a UNIVERSITY COLLEGE CORK   (Ireland)

^b Luxcel Biosciences Ltd G17   (Ireland)

Author keywords

Bioanalytical applications; Labels; Metalloporphyrins; Phosphorescence; Probes; Time resolved fluorescence

Indexed keywords

ORGANOMETALLICS; PHOSPHORESCENCE; PROBES;

BIOANALYTICAL APPLICATIONS; METALLOPORPHYRINS; TIME-RESOLVED FLUORESCENCE;

PORPHYRINS;

LUMINESCENT AGENT; METALLOPORPHYRIN;

ARTICLE; BIOASSAY; CHEMISTRY; LUMINESCENCE;

BIOLOGICAL ASSAY; LUMINESCENCE; LUMINESCENT AGENTS; LUMINESCENT MEASUREMENTS; METALLOPORPHYRINS;

EID: 25444522193     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-005-2830-x     Document Type: Article

References (91)

1. J. E. Falk (1964). Porphyrins and Metalloporphyrins, Elsevier, Amsterdam.
2. M. Gouterman (1961). Spectra of porphyrins J. Mol. Spectrosc. 6, 138-163.
3. M. Gouterman (1959). Study of the effects of substitution on the absorption spectra of porphin. J. Chem. Phys. 30(5), 1139-1161.
4. M. Gouterman and G. Khalil (1974). Porphyrin free base phosphorescence. J. Mol. Spectrosc. 53(1), 88-100.
5. M. Gouterman (1978). In D. Dolphin (Ed.), The Porphyrins, Academic Press, New York.
6. J. B. Callis, J. M. Knowles, and M. Gouterman (1973). Porphyrins. XXVI. Triplet excimer quenching of free base, zinc, palladium, and platinum complexes. J. Phys. Chem. 77(2), 154-157.
7. D. Eastwood and M. Gouterman (1970). Porphyrins. XVIII. Luminescence of (Co), (Ni), Pd, Pt complexes J. Mol. Spectrosc. 35(3), 359-375.
8. P. G. Seybold and M. Gouterman (1969). Porphyrins. 13. Fluorescence spectra and quantum yields. J. Mol. Spectrosc. 31(1), 1.
9. J. B. Callis, M. Gouterman, Y. M. Jones, and B. H. Henderson (1971). Porphyrins. XXII. Fast fluorescence, delayed fluorescence, and quasiline structure in palladium and platinum complexes. J. Mol. Spectrosc. 39(3), 410-420.
10. M. Kaska (1952). Collisional perturbation of spin-orbit coupling and the mechanism of fluorescence quenching. A visual demonstration of the perturbation. J. Chem. Phys. 20, 71-74.
11. A. Harriman (1981). Luminescence of porphyrins and metalloporphyrins. 3. Heavy-atom effects. J. Chem. Soc. Faraday Trans. II 77(7), 1281-1291.
12. L. Bajema, M. Gouterman, and C. B. Rose (1971). Porphyrins. XXIII. Fluorescence of the second excited singlet and quasiline structure of zinc tetrabenzporphin. J. Mol. Spectrosc. 39(3), 421-431.
13. I. E. Zalesskii, V. N. Kotlo, A. N. Sevchenko, K. N. Solov'ev, and S. E. Shkirman (1973). Dokl. Akad. Nauk. Sssr. 210, 312.
14. I. E. Zalesskii, V. N. Kotlo, A. N. Sevchenko, K. N. Solov'ev, and S. F. Shkirman (1974). Dokl. Akad. Nauk. Sssr. 218, 324.
15. C. A. Parker (1968). Photoluminescence of Solutions, Elsevier, Amsterdam.
16. D. B. Papkovsky and G. V. Ponomarev (2001). Spectral-luminescent study of the porphyrin-diketones and their complexes. Spectrochim. Acta A 57(9), 1897-1905.
17. D. B. Papkovsky, G. V. Ponomarev, W. Trettnak, and P. O'Leary (1995). Phosphorescent complexes of porphyrin ketones: Optical properties and application to oxygen sensing. Anal. Chem. 67, 4112-4117.
18. S. B. Brown, M. Shillcock, and P. Jones (1976). Equilibrium and kinetic studies of the aggregation of porphyrins in aqueous solution. Biochem. J. 153(2), 279-285.
19. A. P. Savitski, E. V. Vorobyova, I. V. Berezin, and N. N. Ugarova (1981). Acid-base properties of protoporphyrin-Ix - Its dimethyl ester and heme solubilized on surfactant micelles - Spectrophotometric and fluorometric titration. J. Colloid Interface Sci. 84(1), 175-181.
20. C. R. Lambert, E. Reddi, J. D. Spikes, M. A. Rodgers, and G. Jori (1986). The effects of porphyrin structure and aggregation state on photosensitized processes in aqueous and micellar media. Photochem. Photobiol. 44(5), 595-601.
21. J. M. Vanderkooi, G. Maniara, T. J. Green, and D. F. Wilson (1987). An optical method for measurement of dioxygen concentration based upon quenching of phosphorescence. J Biol. Chem. 262(12), 5476-5482.
22. G. Khalil, M. Gouterman, and E. Green (1989). Method for measuring oxygen concentration, US Patent, 4,810,655.
23. A. Blum and L. I. Grossweiner (1985). Singlet oxygen generation by hematoporphyrin-IX, uroporphyrin-I and hematoporphyrin derivative at 546 nm in phosphate butler and in the presence of egg phosphatidylcholine liposomes. Photochem. Photobiol. 41(1), 27-32.
24. T. J. Dougherty and S. L. Marcus (1992). Photodynamic therapy. Eur. J. Cower 28A(10), 1734-1742.
25. M. Trinkel, W. Trettnak, and C. Kolle (2000). Oxygen trace analysis utilising a miniaturised luminescence lifetime-based sensor instrumentation. Quim. Anal. 19, 112-117.
26. O. Stern and M. Volmer (1919). Uber die ablingungszeit der fluoreszenz. Physik. Zeitschr 20, 183-188.
27. D. B. Papkovsky (2004). Methods in optical oxygen sensing: Protocols and critical analyses. Method Enzymol. 381, 715-735.
28. J. N. Demas, B. A. DeGraff, and P. B. Coleman (1999). Oxygen sensors based on luminescence quenching. Anal. Chem. 71(23), 793A-800A.
29. D. F. Wilson, J. M. Vanderkooi, T. J. Green, G. Maniara, S. P. DeFeo, and D. C. Bloomgarden (1987). A versatile and sensitive method for measuring oxygen. Adv. Exp. Med. Biol. 215, 71-77.
30. L. W. Lo, C. J. Koch, and D. F. Wilson (1996). Calibration of oxygen-dependent quenching of the phosphorescence of Pd-mesotetra (4-carboxyphenyl) porphine: A phosphor with general application for measuring oxygen concentration in biological systems. Anal. Biochem. 236(1), 153-160.
31. S. A. Vinogradov and D. F. Wilson (1995). Metallotetrabenzoporphyrins - New phosphorescent probes for oxygen measurements. J. Chem. Soc. Perkin Trans. 2(1), 103-111.
32. J. Hynes, S. Floyd, A. E. Soini, R. O'Connor, and D. B. Papkovsky (2003). Fluorescence-based cell viability screening assays using water-soluble oxygen probes. J. Biomol. Screen. 8(3), 264-272.
33. A. P. Savitskii, D. B. Papkovskii, G. V. Ponomarev, and I. V. Berezin (1989). Phosphorescence immunoassay - Metalloporphyrins as an alternative to rare-earth fluorescent labels. Dokl. Akad. Nauk. Sssr. 304(4), 1005-1008.
34. R. R. de Haas, R. P. van Gijlswijk, E. B. van der Tol, H. J. Zijlmans, T. Bakker-Schut, J. Bonnet, N. P. Verwoerd, and H. J. Tanke (1997). Platinum porphyrins as phosphorescent label for time-resolved microscopy. J. Histochem. Cytochem. 45(9), 1279-1292.
35. S. P. Martsev, V. Preygerzon, Y. I. Melnikova, Z. I. Kravchuk, G. V. Ponomarev, V. E. Lunev, and A. P. Savitsky (1995). Modification of monoclonal and polyclonal IgG with palladium(II) coproporphyrin-I - Stimulatory and inhibitory functional-effects induced by 2 different methods. J. Immunol. Methods 186(2), 293-304.
36. Y. I. Melnikova, Z. I. Kravchuk, V. A. Preygerzon, and S. P. Martsev (1997). Functional activation of antibodies on modification with Pd(II) coproporphyrin I N-hydroxysuccinimide ester. Biochem. Moscow 62(8), 924-927.
37. M. M. Koskelin, A. E. Soini, N. J. Meltola, and G. V. Ponomarev (2002). Phosphorescent labeling reagents of platinum(II) and palladium (II) coproporphyrin-II. Preparation and performance characteristics. J. Porphyr. Phthalocya 6(7-8), 533-543.
38. A. E. Soini, D. V. Yashunsky, N. J. Meltola, and G. V. Ponomarev (2001). Preparation of monofunctional and phosphorescent palladium(II) and platinum(II) coproporphyrin labeling reagents. J. Porphyr. Phthalocya 5(10), 735-741.
39. G. V. Ponomarev, D. V. Yashunsky, N. J. Meltola, and A. E. Soini (2001). Porphyrin compounds, their conjugates and assay methods based on the use of said conjugates, US Patent, 6,582,930.
40. A. E. Soini, D. V. Yashunsky, N. J. Meltola, and G. V. Ponomarev (2003). Influence of linker unit on performance of palladium(II) coproporphyrin labelling reagent and its bioconjugates. Luminescence 18(3), 182-192.
41. T. C. O'Riordan, A. E. Soini, J. T. Soini, and D. B. Papkovsky (2002). Performance evaluation of the phosphorescent porphyrin label: Solid-phase immunoassay of alpha-fetoprotein. Anal. Chem. 74(22), 5845-5850.
42. T. C. O'Riordan, A. E. Soini, and D. B. Papkovsky (2001). Mono-functional derivatives of coproporphyrins for phosphorescent labeling of proteins and binding assays. Anal. Biochem. 290(2), 366-375.
43. H. J. Tanke, R. R. De Haas, G. Sagner, M. Ganser, and R. P. van Gijlswijk (1998). Use of platinum coproporphyrin and delayed luminescence imaging to extend the number of targets FISH karyotyping. Cytometry 33(4), 453-459.
44. O. S. Fedorova, A. P. Savitskii, K. G. Shoikhet, and G. V. Ponomarev (1990). Palladium(II)-coproporphyrin-I as a photoactivable group in sequence-specific modification of nucleic-acids by oligonucleotide derivatives. FEBS Lett. 259(2), 335-337.
45. P. J. O'Sullivan, M. Burke, A. E. Soini, and D. B. Papkovsky (2002). Synthesis and evaluation of phosphorescent oligonucleotide probes for hybridisation assays. Nucleic Acids Res. 30(21), e114.
46. D. J. O'Shea, P. J. O'Sullivan, G. V. Ponomarev, and D. P. Papkovsky (2004). Post-PCR detection of nucleic acids using metalloporphyrin labels and time-resolved fluorescence. Anal. Chim. Acta. 537, 111-117.
47. I. Hemmila and V.-M. Mukkala (2001). Time-resolution in fluorometry technologies, labels, and applications in bioanalytical assays. Crit. Rev. Clin. Lab. Sci. 38(6), 441-519.
48. S. W. Englander, D. B. Calhoun, and J. J. Englander (1987). Biochemistry without oxygen. Anal. Biochem. 161(2), 300-306.
49. J. R. Lakowicz (1983). Principles of Fluorescence Spectroscopy, Plenum Press, New York.
50. A. P. Savitski, D. B. Papkovskii, and I. V. Berezin (1987). Fluorescent immunoassay. Porphyrins as a new type of label for immunoassay. Dokl. Akad. Nauk. Sssr. 293, 744.
51. A. P. Savitsky, K. N. Solovyov, and D. B. Papkovsky (1990). Time-resolved fluoroimmunoassay - Concepts, realization and prospects. Izv an Sssr Fiz 54(3), 518-523.
52. E. Puklin, B. Carlson, S. Gouin, C. Costin, E. Green, S. Ponomarev, H. Tanji, and M. Gouterman (2000). Ideality of pressure-sensitive paint. I. Platinum tetra(pentafluorophenyl)porphine in fluoroacrylic polymer. J. Appl. Polym. Sci. 77(13), 2795-2804.
53. S. A. Vinogradov, M. A. Fernandez-Seara, B. W. Dupan, and D. F. Wilson (2002). A method for measuring oxygen distributions in tissue using frequency domain phosphorometry. Comp. Biochem. Phys. A 132 (1), 147-152.
54. D. B. Papkovsky, M. A. Smiddy, N. Y. Papkovskaia, and J. P. Kerry (2002). Nondestructive measurement of oxygen in modified atmosphere packaged hams using a phase-fluorimetric sensor system. J. Food Sci. 67(8), 3164-3169.
55. F. C. O'Mahony, T. C. O'Riordan, N. Papkovskaia, V. I. Ogurtsov, J. P. Kerry, and D. B. Papkovsky (2004). Assessment of oxygen levels in convenience-style muscle-based Sous Vide products through optical means and impact on shelf-life stability. Packag. Technol. Sci. 17(4), 225-234.
56. C. Kolle, W. Gruber, W. Trettnak, K. Biebernik, C. Dolezal, F. Reininger, and P. OLeary (1997). Fast optochemical sensor for continuous monitoring of oxygen in breath-gas analysis. Sens. Actuators B Chem. 38(1-3), 141-149.
57. T. C. O'Riordan, D. Buckley, V. Ogurtsov, R. O'Connor, and D. B. Papkovsky (2000). A cell viability assay based on monitoring respiration by optical oxygen sensing. Anal. Biochem. 278(2), 221-227.
58. T. J. Green, D. F. Wilson, J. M. Vanderkooi, and S. P. DeFeo (1988). Phosphorimeters for analysis of decay profiles and real time monitoring of exponential decay and oxygen concentrations. Anal. Biochem. 174(1), 73-79.
59. J. M. Vanderkooi and J. W. Berger (1989). Excited triplet states used to study biological macromolecules at room temperature. Biochim. Biophys. Acta 976(1), 1-27.
60. J. M. Vanderkooi, W. W. Wright, and M. Erecinska (1990). Oxygen gradients in mitochondria examined with delayed luminescence from excited-state triplet probes. Biochemistry 29(22), 5332-5338.
61. W. L. Rumsey, J. M. Vanderkooi, and D. F. Wilson (1988). Imaging of phosphorescence: A novel method for measuring oxygen distribution in perfused tissue. Science 241(4873), 1649-1651.
62. D. F. Wilson, S. A. Vinogradov, B. W. Dugan, D. Biruski, L. Waldron, and S. A. Evans (2002). Measurement of tumor oxygenation using new frequency domain phosphorometers. Comp. Biochem. Phys. A 132(1), 153-159.
63. S. A. Vinogradov and D. F. Wilson (1997). Extended porphyrins - New IR phosphors for oxygen measurements. Oxygen Transport Tissue XVIII 411, 597-603.
64. S. A. Vinogradov, M. A. Fernandez-Searra, B. W. Dugan, and D. F. Wilson (2001). Frequency domain instrument for measuring phosphorescence lifetime distributions in heterogeneous samples. Rev. Sci. Instrum. 72(8), 3396-3406.
65. J. Alderman, J. Hynes, S. M. Floyd, J. Kruger, R. O'Connor, and D. B. Papkovsky (2004). A low-volume platform for cell-respirometric screening based on quenched-luminescence oxygen sensing. Biosens. Bioelectron. 19(11), 1529-1535.
66. J. Hynes, C. O'Donovan, F. C. O'Mahony, and D. P. Papkovsky (2004). Biological screening applications using optical oxygen sensing and soluble phosphorescent oxygen probes. In Presented at the Eight World Congress on Biosensors, Granada, Spain.
67. J. Hynes, T. C. O'Riordan, J. Curtin, T. G. Cotter, and D. B. Papkovsky (2005). Fluorescence based oxygen uptake analysis in the study of metabolic responses to apoptosis induction. J. Immunol. Methods, submitted for publication.
68. D. B. Papkovskii, A. P. Savitskii, A. I. Yaropolov, G. V. Ponomarev, V. D. Rumyantseva, and A. F. Mironov (1991). Flow-injection glucose determination with long-wave luminescent oxygen probes. Biomed. Sci. 2, 63-67.
69. D. B. Papkovsky, T. C. O'Riordan, and G. G. Guilbault (1999). An immunosensor based on the glucose oxidase label and optical oxygen detection. Anal. Chem. 71(8), 1568-1573.
70. E. Soini and I. Hemmila (1979). Fluoroimmunoassay: Present status and key problems. Clin. Chem. 25(3), 353-361.
71. I. I. Hemmila (1999). LANCEtrademark: Homogeneous assay platform for HTS. J. Biomol. Screen. 4(6), 303-308.
72. H. Bazin, M. Preaudat, E. Trinquet, and G. Mathis (2001). Homogeneous time resolved fluorescence resonance energy transfer using rare earth cryptates as a tool for probing molecular interactions in biology. Spectrochim. Acta A Mol. Biomol. Spectrosc. 57(11), 2197-2211.
73. M. V. Demcheva, E. Y. Mantrova, A. Savitsky, O. Behrsing, B. Micheel, and I. Hemmila (1995). Micelle stabilized phosphorescent immunoassay based on bispecific antibodies against label and antigen. Anal. Lett. 28(2), 249-258.
74. E. Y. Mantrova, M. V. Demcheva, and A. P. Savitsky (1994). Universal phosphorescence immunoassay. Anal. Biochem. 219(1), 109-114.
75. R. Huttunen, P. Harkonen, J. T. Soini, and A. E. Soini (2004). Application of phosphorescent metalloporphyrin labels in the study of cytokine induced expression of cell surface bound ICAM-1. Anal. Biochem., submitted for publication.
76. T. C. O'Riordan, J. Hynes, D. Yashunski, G. V. Ponomarev, and D. B. Papkovsky (2005). Homogeneous assays for cellular proteases employing the platinum(II)-coproporphyrin label and time-resolved phosphorescence. Anal. Biochem. 342(1), 111-119.
77. E. G. Matveeva, E. V. Gribkova, J. R. Sanborn, S. J. Gee, B. D. Hammock, and A. P. Savitsky (2001). Development of a homogeneous phosphorescent immunoassay for the detection of polychlorinated dibenzo-p-dioxins. Anal. Lett. 34(13), 2311-2320.
78. V. V. Didenko (2001). DNA probes using fluorescence resonance energy transfer (FRET): Designs and applications. Biotechniques 31, 1106-1121.
79. R. R. de Haas, R. P. M. van Gijlswijk, E. B. van der Toi, J. Veuskens, H. E. van Gijssel, R. B. Tijdens, J. Bonnet, N. P. Verwoerd, and H. J. Tanke (1999). Phosphorescent platinum/palladium coproporphyrins for time-resolved luminescence microscopy. J. Histochem. Cytochem. 47(2), 183-196.
80. M. Burke, P. J. O'Sullivan, A. E. Soini, H. Berney, and D. B. Papkovsky (2003). Evaluation of the phosphorescent palladium(II)-coproporphyrin labels in separation-free hybridization assays. Anal. Biochem. 320(2), 273-280.
81. E. J. Hennink, R. de Haas, N. P. Verwoerd, and H. J. Tanke (1996). Evaluation of a time-resolved fluorescence microscope using a phosphorescent Pt-porphine model system. Cytometry 24(4), 312-320.
82. D. B. Papkovsky, J. Olah, I. V. Troyanovsky, N. A. Sadovsky, V. D. Rumyantseva, A. F. Mironov, A. I. Yaropolov, and A. P. Savitsky (1992). Phosphorescent polymer films for optical oxygen sensors. Biosens. Bioelectron. 7(3), 199-206.
83. D. B. Papkovsky, G. V. Ponomarev, and O. S. Wolfbeis (1996). Long-wave luminescent porphyrin probes. Spectrochim. Acta A 52(12), 1629-1638.
84. B. T. Atwater (1992). Substituent effects of the excited-state properties of platinum meso-tetraphenylporphyrins. J. Fluoresc. 2(4), 237-246.
85. J. M. Vanderkooi, D. B. Calhoun, and S. W. Englander (1987). On the prevalence of room-temperature protein phosphorescence. Science 236(4801), 568-569.
86. D. F. Wilson, W. L. Rumsey, T. J. Green, and J. M. Vanderkooi (1988). The oxygen dependence of mitochondrial oxidative phosphorylation measured by a new optical method for measuring oxygen concentration. J. Biol. Chem. 263(6), 2712-2718.
87. D. F. Wilson, S. M. Evans, W. T. Jenkins, S. A. Vinogradov, E. Ong, and M. W. Dewhirst (1998). Oxygen distributions within R3230Ac tumors growing in dorsal flap window chambers in rats. Oxygen Transport Tissue XX 454, 603-609.
88. F. C. O'Mahony, C. O'Donovan, J. Hynes, T. Moore, J. Davenport, and D. B. Papkovsky (2005). Optical oxygen microrespirometry as a platform for environmental toxicology and animal model studies. Environ. Sci. Tech. 39, 5010-5014.
89. A. E. Soini, A. Kuusisto, N. J. Meltola, E. Soini, and L. Seveus (2003). A new technique for multiparameter imaging microscopy: Use of long decay time photoluminescent labels enables multiple color immunocytochemistry with low channel-to-channel crosstalk. Microsc. Res. Tech. 62(5), 396-407.
90. A. E. Soini, L. Seveus, N. J. Meltola, D. B. Papkovsky, and E. Soini (2002). Phosphorescent metalloporphyrins as labels in time-resolved luminescence microscopy: Effect of mounting on emission intensity. Microsc. Res. Tech. 58(2), 125-131.
91. P. Canty, L. Vare, M. Hakansson, A. M. Spehar, D. Papkovsky, T. Ala-Kleme, J. Kankare, and S. Kulmala (2002). Time-resolved electrochemiluminescence of platinum(II) coproporphyrin. Anal. Chim. Acta 453(2), 269-279.