Exploitation and application of a highly sensitive Ru(II) complex-based phosphorescent chemodosimeter for Hg2+ in aqueous solutions and living cells

ACS Applied Materials and Interfaces

Volumn 7, Issue 7, 2015, Pages 4247-4256

  Ru, Jiaxi ^a   Tang, Xiaoliang ^a   Ju, Zhenghua ^a   Zhang, Guolin ^a   Dou, Wei ^a   Mi, Xiangquan ^b   Wang, Chunming ^b   Liu, Weisheng ^a  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

cell imaging; chemodosimeter; Hg2+ recognition; phosphorescence; Ru(II) complex; TRES

Indexed keywords

DOSIMETRY; ELECTROSPRAY IONIZATION; MASS SPECTROMETRY; MERCURY COMPOUNDS; PH; PHOSPHORESCENCE; PHYSIOLOGICAL MODELS; SIGNAL TO NOISE RATIO;

CELL IMAGING; CHEMODOSIMETERS; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; MEMBRANE PERMEABILITY; RU COMPLEXES; THEORETICAL CALCULATIONS; TIME-RESOLVED PHOTOLUMINESCENCE; TRES;

RUTHENIUM COMPOUNDS;

FLUORESCENT DYE; MERCURY; RUTHENIUM DERIVATIVE;

CELL LINE; CHEMISTRY; DEVICES; EVALUATION STUDY; HUMAN; LIVER CELL; LUMINESCENCE; MOLECULAR IMAGING; PROCEDURES; SIGNAL NOISE RATIO;

CELL LINE; FLUORESCENT DYES; HEPATOCYTES; HUMANS; LUMINESCENT MEASUREMENTS; MERCURY; MOLECULAR IMAGING; RUTHENIUM COMPOUNDS; SIGNAL-TO-NOISE RATIO;

EID: 84923778616     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am508484q     Document Type: Article

References (63)

1. Marin, V.; Holder, E.; Hoogenboom, R.; Schubert, U. S. Functional Ruthenium(II)- and Iridium(III)-Containing Polymers for Potential Electro-Optical Applications Chem. Soc. Rev. 2007, 36, 618-635
2. Zhao, Q.; Huang, C.; Li, F. Phosphorescent Heavy-Metal Complexes for Bioimaging Chem. Soc. Rev. 2011, 40, 2508-2524
3. You, Y. Phosphorescence Bioimaging Using Cyclometalated Ir(III) Complexes Curr. Opin. Chem. Biol. 2013, 17, 699-707
4. Lo, K. K.; Li, S. P. Utilization of the Photophysical and Photochemical Properties of Phosphorescent Transition Metal Complexes in the Development of Photofunctional Cellular Sensors, Imaging Reagents, and Cytotoxic Agents RSC Adv. 2014, 4, 10560-10585
5. Sun, H.; Liu, S.; Lin, W.; Zhang, K. Y.; Lv, W.; Huang, X.; Huo, F.; Yang, H.; Jenkins, G.; Zhao, Q.; Huang, W. Smart Responsive Phosphorescent Materials for Data Recording and Security Protection Nat. Commun. 2014, 5, 3601
6. Zhang, K. Y.; Zhang, J.; Liu, Y.; Liu, S.; Zhang, P.; Zhao, Q.; Tang, Y.; Huang, W. Core-Shell Structured Phosphorescent Nanoparticles for Detection of Exogenous and Endogenous Hypochlorite in Live Cells via Ratiometric Imaging and Photoluminescence Lifetime Imaging Microscopy Chem. Sci. 2015, 6, 301-307
7. Yam, V. W.; Cheng, E. C. Highlights on the Recent Advances in Gold Chemistry-a Photophysical Perspective Chem. Soc. Rev. 2008, 37, 1806-1813
8. 3IL Equilibrium: Efficient Triplet Sensitizers for Low-Power Upconversion Angew. Chem., Int. Ed. 2011, 50, 1626-1629
9. Ma, Y.; Liu, S.; Yang, H.; Wu, Y.; Sun, H.; Wang, J.; Zhao, Q.; Li, F.; Huang, W. A Water-Soluble Phosphorescent Polymer for Time-Resolved Assay and Bioimaging of Cysteine/Homocysteine J. Mater. Chem. B 2013, 1, 319-329
10. Ma, Y.; Liu, S.; Yang, H.; Wu, Y.; Yang, C.; Liu, X.; Zhao, Q.; Wu, H.; Liang, J.; Li, F.; Huang, W. Water-Soluble Phosphorescent Iridium(III) Complexes as Multicolor Probes for Imaging of Homocysteine and Cysteine in Living Cells J. Mater. Chem. 2011, 21, 18974-18982
11. Louie, M.; Choi, A. W.; Liu, H.; Chan, B. T.; Lo, K. K. Synthesis, Emission Characteristics, Cellular Studies, and Bioconjugation Properties of Luminescent Rhenium(I) Polypyridine Complexes with a Fluorous Pendant Organometallics 2012, 31, 5844-5855
12. Gill, M. R.; Garcia-Lara, J.; Foster, S. J.; Smythe, C.; Battaglia, G.; Thomas, J. A. A Ruthenium(II) Polypyridyl Complex for Direct Imaging of DNA Structure in Living Cells Nat. Chem. 2009, 1, 662-667
13. 3IL Excited State as Sensitizer for Triplet-Triplet Annihilation Based Upconversion Angew. Chem., Int. Ed. 2011, 50, 8283-8286
14. Funaki, T.; Funakoshi, H.; Kitao, O.; Onozawa-Komatsuzaki, N.; Kasuga, K.; Sayama, K.; Sugihara, H. Cyclometalated Ruthenium(II) Complexes as Near-IR Sensitizers for High Efficiency Dye-Sensitized Solar Cells Angew. Chem., Int. Ed. 2012, 51, 7528-7531
15. Niu, Y.; Han, F.; Zhang, Q.; Xie, T.; Lu, L.; Li, S.; Xia, H. Off/On Fluorescent Chemosensors for Organotin Halides Based on Binuclear Ruthenium Complexes Angew. Chem., Int. Ed. 2013, 52, 5599-5603
16. Gill, M. R.; Thomas, J. A. Ruthenium(II) Polypyridyl Complexes and DNA-from Structural Probes to Cellular Imaging and Therapeutics Chem. Soc. Rev. 2012, 41, 3179-3192
17. Foxon, S. P.; Green, C.; Walker, M. G.; Wragg, A.; Adams, H.; Weinstein, J. A.; Parker, S. C.; Meijer, A. J.; Thomas, J. A. Synthesis, Characterization, and DNA Binding Properties of Ruthenium(II) Complexes Containing the Redox Active Ligand Benzo[ i ]dipyrido[3,2- a:2′,3′- c ]phenazine-11,16-quinone Inorg. Chem. 2012, 51, 463-471
18. Baggaley, E.; Gill, M. R.; Green, N. H.; Turton, D.; Sazanovich, I. V.; Botchway, S. W.; Smythe, C.; Haycock, J. W.; Weinstein, J. A.; Thomas, J. A. Dinuclear Ruthenium(II) Complexes as Two-Photon, Time-Resolved Emission Microscopy Probes for Cellular DNA Angew. Chem., Int. Ed. 2014, 53, 3367-3371
19. Xu, W. C.; Zuo, J. R.; Wang, L. L.; Ji, L. N. A.; Chao, H. Dinuclear Ruthenium(II) Polypyridyl Complexes as Single and Two-Photon Luminescence Cellular Imaging Probes Chem. Commun. 2014, 50, 2123-2125
20. Steiner, M. S.; Duerkop, A. Luminescent Ruthenium Probe for the Determination of Acetyl Phosphate in Complex Biological Matrices Analyst 2011, 136, 148-154
21. Zhang, R.; Ye, Z.; Yin, Y.; Wang, G.; Jin, D.; Yuan, J.; Piper, J. A. Developing Red-Emissive Ruthenium(II) Complex-Based Luminescent Probes for Cellular Imaging Bioconjugate Chem. 2012, 23, 725-733
22. Chen, H.; Li, X.; Wu, Y.; Gao, W.; Bai, R. A Ruthenium(II) Complex with Environment-Responsive Dual Emission and Its Application in the Detection of Cysteine/Homocysteine Dalton Trans. 2012, 41, 13292-13297
23. Zhang, R.; Ye, Z.; Song, B.; Dai, Z.; An, X.; Yuan, J. Development of a Ruthenium(II) Complex-Based Luminescent Probe for Hypochlorous Acid in Living Cells Inorg. Chem. 2013, 52, 10325-10331
24. Zheng, Z. B.; Wu, Y. Q.; Wang, K. Z.; Li, F. pH Luminescence Switching, Dihydrogen Phosphate Sensing, and Cellular Uptake of a Heterobimetallic Ruthenium(II)-Rhenium(I) Complex Dalton Trans. 2014, 43, 3273-3284
25. Chowdhury, B.; Khatua, S.; Dutta, R.; Chakraborty, S.; Ghosh, P. Bis-Heteroleptic Ruthenium(II) Complex of a Triazole Ligand as a Selective Probe for Phosphates Inorg. Chem. 2014, 53, 8061-8070
26. Botchway, S. W.; Charnley, M.; Haycock, J. W.; Parker, A. W.; Rochester, D. L.; Weinstein, J. A.; Williams, J. A. G. Time-Resolved and Two-Photon Emission Imaging Microscopy of Live Cells with Inert Platinum Complexes Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 16071-16076
27. Jin, D. Y.; Piper, J. A. Time-Gated Luminescence Microscopy Allowing Direct Visual Inspection of Lanthanide-Stained Microorganisms in Background-Free Condition Anal. Chem. 2011, 83, 2294-2300
28. Weitz, E. A.; Chang, J. Y.; Rosenfield, A. H.; Pierre, V. C. A Selective Luminescent Probe for the Direct Time-Gated Detection of Adenosine Triphosphate J. Am. Chem. Soc. 2012, 134, 16099-16102
29. You, Y.; Lee, S.; Kim, T.; Ohkubo, K.; Chae, W. S.; Fukuzumi, S.; Jhon, G. J.; Nam, W.; Lippard, S. J. Phosphorescent Sensor for Biological Mobile Zinc J. Am. Chem. Soc. 2011, 133, 18328-18342
30. Huang, K.; Marti, A. A. Optimizing the Sensitivity of Photoluminescent Probes Using Time-Resolved Spectroscopy: A Molecular Beacon Case Study Anal. Chem. 2012, 84, 8075-8082
31. Shi, H. F.; Sun, H. B.; Yang, H. R.; Liu, S. J.; Jenkins, G.; Feng, W.; Li, F. Y.; Zhao, Q.; Liu, B.; Huang, W. Cationic Polyfluorenes with Phosphorescent Iridium(III) Complexes for Time-Resolved Luminescent Biosensing and Fluorescence Lifetime Imaging Adv. Funct. Mater. 2013, 23, 3268-3276
32. Tang, Y.; Yang, H.; Sun, H.; Liu, S.; Wang, J.; Zhao, Q.; Liu, X.; Xu, W.; Li, S.; Huang, W. Rational Design of an "OFF-ON" Phosphorescent Chemodosimeter Based on an Iridium(III) Complex and Its Application for Time-Resolved Luminescent Detection and Bioimaging of Cysteine and Homocysteine Chem.-Eur. J. 2013, 19, 1311-1319
33. Xu, W.; Zhao, X.; Lv, W.; Yang, H.; Liu, S.; Liang, H.; Tu, Z.; Xu, H.; Qiao, W.; Zhao, Q.; Huang, W. Rational Design of Phosphorescent Chemodosimeter for Reaction-Based One- and Two-Photon and Time-Resolved Luminescent Imaging of Biothiols in Living Cells Adv. Healthcare Mater. 2014, 3, 658-669
34. Hanaoka, K.; Kikuchi, K.; Kobayashi, S.; Nagano, T. Time-Resolved Long-Lived Luminescence Imaging Method Employing Luminescent Lanthanide Probes with a New Microscopy System J. Am. Chem. Soc. 2007, 129, 13502-13509
35. Zhang, L.; Tian, L.; Ye, Z.; Song, B.; Yuan, J. Preparation of Visible-Light-Excited Europium Biolabels for Time-Resolved Luminescence Cell Imaging Application Talanta 2013, 108, 143-149
36. McMahon, B. K.; Gunnlaugsson, T. Lanthanide Luminescence Sensing of Copper and Mercury Ions Using an Iminodiacetate-Based Tb(III)-Cyclen Chemosensor Tetrahedron Lett. 2010, 51, 5406-5410
37. Tan, H. L.; Zhang, Y. Q.; Chen, Y. Detection of Mercury Ions (Hg2+) in Urine Using a Terbium Chelate Fluorescent Probe Sens. Actuators, B 2011, 156, 120-125
38. Cui, G. F.; Ye, Z. Q.; Zhang, R.; Wang, G. L.; Yuan, J. L. Design and Synthesis of a Terbium(III) Complex-Based Luminescence Probe for Time-Gated Luminescence Detection of Mercury(II) Ions J. Fluoresc. 2012, 22, 261-267
39. McMahon, B. K.; Pal, R.; Parker, D. A Bright and Responsive Europium Probe for Determination of pH Change within the Endoplasmic Reticulum of Living Cells Chem. Commun. 2013, 49, 5363-5365
40. Duong, T. Q.; Kim, J. S. Fluoro- and Chromogenic Chemodosimeters for Heavy Metal Ion Detection in Solution and Biospecimens Chem. Rev. 2010, 110, 6280-6301
41. Chen, X.; Pradhan, T.; Wang, F.; Kim, J. S.; Yoon, J. Fluorescent Chemosensors Based on Spiroring-Opening of Xanthenes and Related Derivatives Chem. Rev. 2012, 112, 1910-1956
42. Yang, Y.; Zhao, Q.; Feng, W.; Li, F. Luminescent Chemodosimeters for Bioimaging Chem. Rev. 2013, 113, 192-270
43. Carter, K. P.; Young, A. M.; Palmer, A. E. Fluorescent Sensors for Measuring Metal Ions in Living Systems Chem. Rev. 2014, 114, 4564-4601
44. 2+ through an Efficient Turn-On Photoinduced Electron Transfer Fluorescent Probe and Its Real Applications Anal. Chem. 2014, 86, 8693-8699
45. 2+ in Semiaqueous Environment by Intramolecular Charge Transfer Mechanism Tetrahedron Lett. 2013, 54, 3688-3693
46. Tchounwou, P. B.; Ayensu, W. K.; Ninashvili, N.; Sutton, D. Environmental Exposure to Mercury and Its Toxicopathologic Implications for Public Health Environ. Toxicol. 2003, 18, 149-175
47. Lee, R.; Middleton, D.; Caldwell, K.; Dearwent, S.; Jones, S.; Lewis, B.; Monteilh, C.; Mortensen, M. E.; Nickle, R.; Orloff, K.; Reger, M.; Risher, J.; Rogers, H. S.; Watters, M. A Review of Events That Expose Children to Elemental Mercury in the United States Environ. Health Perspect. 2009, 117, 871-878
48. Tong, Y.; Zhang, W.; Chen, C.; Chen, L.; Wang, W.; Hu, X.; Wang, H.; Hu, D.; Ou, L.; Wang, X.; Wang, Q. Fate Modeling of Mercury Species and Fluxes Estimation in an Urban River Environ. Pollut. 2014, 184, 54-61
49. Nolan, E. M.; Lippard, S. J. Tools and Tactics for the Optical Detection of Mercuric Ion Chem. Rev. 2008, 108, 3443-3480
50. Liu, B.; Tian, H. A Selective Fluorescent Ratiometric Chemodosimeter for Mercury Ion Chem. Commun. 2005, 3156-3158
51. 2+-Selective Chemodosimeter in Aqueous Solution: Fluorescent OFF-ON Org. Lett. 2007, 9, 907-910
52. 2+ Selective Chemodosimeter Exhibiting Blue-Green Fluorescence in Aqueous-Ethanol Environment Sens. Actuators, B 2013, 181, 584-595
53. Nakamura, K. Synthesis, Luminescence Quantum Yields, and Lifetimes of Trischelated Ruthenium(II) Mixed-Ligand Complexes Including 3,3′-Dimethyl-2,2′-Bipyridyl Bull. Chem. Soc. Jpn. 1982, 55, 2697-2705
54. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.01; Gaussian, Inc.: Wallingford, CT, 2009.
55. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density Phys. Rev. B 1988, 37, 785-789
56. Hay, P. J.; Wadt, W. R. Ab Initio Effective Core Potentials for Molecular Calculations. Potentials for the Transition Metal Atoms Sc to Hg J. Chem. Phys. 1985, 82, 270-283
57. Hehre, W. J.; Ditchfield, R.; Pople, J. A. Self-Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian-Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules J. Chem. Phys. 1972, 56, 2257-2261
58. Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. An Efficient Implementation of Time-Dependent Density-Functional Theory for the Calculation of Excitation Energies of Large Molecules J. Chem. Phys. 1998, 109, 8218-8224
59. Cossi, M.; Barone, V. Time-Dependent Density Functional Theory for Molecules in Liquid Solutions J. Chem. Phys. 2001, 115, 4708-4717
60. Lu, T.; Chen, F. Calculation of Molecular Orbital Composition Acta Chim. Sin. 2011, 69, 2393-2406
61. Boens, N.; Qin, W.; Basarić, N.; Hofkens, J.; Ameloot, M.; Pouget, J.; Lefevre, J. P.; Valeur, B.; Gratton, E.; vandeVen, M.; Silva, N. D., Jr.; Engelborghs, Y.; Willaert, K.; Sillen, A.; Rumbles, G.; Phillips, D.; Visser, A. J.; van Hoek, A.; Lakowicz, J. R.; Malak, H.; Gryczynski, I.; Szabo, A. G.; Krajcarski, D. T.; Tamai, N.; Miura, A. Fluorescence Lifetime Standards for Time and Frequency Domain Fluorescence Spectroscopy Anal. Chem. 2007, 79, 2137-2149
62. Mosmann, T. J. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays Immunol. Methods 1983, 65, 55-63
63. Mercury Update: Impact on Fish Advisories. EPA Fact Sheet EPA-823-F-01-011; EPA, Office of Water: Washington, DC, 2001.