A colorimetric and luminescent dual-modal assay for Cu(II) ion detection using an iridium(III) complex

PLoS ONE

Volumn 9, Issue 6, 2014, Pages

  Ma, Dik Lung ^a   He, Hong Zhang ^a   Chan, Daniel Shiu Hin ^a   Wong, Chun Yuen ^b   Leung, Chung Hang ^c  

^a HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

^b CITY UNIVERSITY OF HONG KONG   (Hong Kong)

^c China Macau University of Science and Technology Zhuhai MUST Science and Technology Research Institute   (Macao)

Author keywords

[No Author keywords available]

Indexed keywords

1,10 PHENANTHROLINE; 5,6 BIS(SALICYLIDENEIMINO) 1,10 PHENANTHROLINE; CUPRIC ION; IRIDIUM COMPLEX; UNCLASSIFIED DRUG; COPPER; IRIDIUM;

ABSORPTION SPECTROSCOPY; ARTICLE; COLORIMETRY; LUMINESCENCE; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SENSITIVITY ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TITRIMETRY; ULTRAVIOLET RADIATION; CHEMISTRY; PROCEDURES;

COLORIMETRY; COPPER; IRIDIUM; LUMINESCENT MEASUREMENTS;

EID: 84902770792     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0099930     Document Type: Article

References (65)

1. Kramer R (1998) Fluorescent chemosensors for Cu2+ ions: fast, selective, and highly sensitive. Angew Chem Int Ed 37: 772-773.
2. Barnham KJ, Masters CL, Bush AI (2004) Neurodegenerative diseases and oxidative stress. Nat Rev Drug Discov 3: 205-214.
3. Gray NF (2008) Drinking water quality: Cambridge University Press.
4. Jung JY, Kang M, Chun J, Lee J, Kim J, et al. (2013) A thiazolothiazole based Cu2+ selective colorimetric and fluorescent sensor via unique radical formation. Chem Commun 49: 176-178.
5. Kaur N, Kumar S (2007) Single molecular colorimetric probe for simultaneous estimation of Cu2+ and Ni2+. Chem Commun: 3069-3070. (Pubitemid 47087706)
6. Beija M, Afonso CAM, Martinho JMG (2009) Synthesis and applications of Rhodamine derivatives as fluorescent probes. Chem Soc Rev 38: 2410-2433.
7. Quang DT, Kim JS (2010) Fluoro- and Chromogenic Chemodosimeters for Heavy Metal Ion Detection in Solution and Biospecimens. Chem Rev 110: 6280-6301.
8. Chen X, Ma H (2006) A selective fluorescence-on reaction of spiro form fluorescein hydrazide with Cu(II). Anal Chim Acta 575: 217-222. (Pubitemid 44118192)
9. Chen X, Jia J, Ma H, Wang S, Wang X (2009) Characterization of rhodamine B hydroxylamide as a highly selective and sensitive fluorescence probe for copper(II). Anal Chim Acta 632: 9-14.
10. Zhou Y, Wang F, Kim Y, Kim S-J, Yoon J (2009) Cu2+-Selective Ratiometric and "Off-On" Sensor Based on the Rhodamine Derivative Bearing Pyrene Group. Org Lett 11: 4442-4445.
11. Chen X, Pradhan T, Wang F, Kim JS, Yoon J (2012) Fluorescent Chemosensors Based on Spiroring-Opening of Xanthenes and Related Derivatives. Chem Rev 112: 1910-1956.
12. Hirayama T, Van dBGC, Gray LW, Lutsenko S, Chang CJ (2012) Near-infrared fluorescent sensor for in vivo copper imaging in a murine Wilson disease model. Proc Natl Acad Sci U S A 109: 2228-2233.
13. Domaille DW, Zeng L, Chang CJ (2010) Visualizing Ascorbate-Triggered Release of Labile Copper within Living Cells using a Ratiometric Fluorescent Sensor. J Am Chem Soc 132: 1194-1195.
14. Miller EW, Zeng L, Domaille DW, Chang CJ (2006) Preparation and use of Coppersensor-1, a synthetic fluorophore for live-cell copper imaging. Nat Protoc 1: 824-827.
15. Li X, Gao X, Shi W, Ma H (2013) Design Strategies for Water-Soluble Small Molecular Chromogenic and Fluorogenic Probes. Chem Rev DOI: 10.1021/cr300508p
16. Singh AK, Mehtab S, Jain AK (2006) Selective electrochemical sensor for copper(II) ion based on chelating ionophores. Anal Chim Acta 575: 25-31. (Pubitemid 44092617)
17. Singh LP, Bhatnagar JM (2004) Copper(II) selective electrochemical sensor based on Schiff Base complexes. Talanta 64: 313-319.
18. Yang W, Gooding JJ, Hibbert DB (2001) Redox voltammetry of sub-parts per billion levels of Cu2+ at polyaspartate-modified gold electrodes. Analyst 126: 1573-1577. (Pubitemid 32897042)
19. Ma B, Wu S, Zeng F (2010) Reusable polymer film chemosensor for ratiometric fluorescence sensing in aqueous media. Sens Actuators B Chem 145: 451-456.
20. Chen X-Y, Shi J, Li Y-M, Wang F-L, Wu X, et al. (2009) Two-Photon Fluorescent Probes of Biological Zn(II) Derived from 7-Hydroxyquinoline. Org Lett 11: 4426-4429.
21. Xu Z, Baek K-H, Kim HN, Cui J, Qian X, et al. (2010) Zn2+-Triggered Amide Tautomerization Produces a Highly Zn2+-Selective, Cell-Permeable, and Ratiometric Fluorescent Sensor. J Am Chem Soc 132: 601-610.
22. Xue L, Liu C, Hua J (2009) Highly Sensitive and Selective Fluorescent Sensor for Distinguishing Cadmium from Zinc Ions in Aqueous Media. Org Lett 11: 1655-1658.
23. Araya JC, Gajardo J, Moya SA, Aguirre P, Toupet L, et al. (2010) Modulating the luminescence of an iridium(iii) complex incorporating a di(2-picolyl)anilino-appended bipyridine ligand with Zn2+ cations. New J Chem 34: 21-24.
24. Charbonniere LJ, Ziessel RF, Sams CA, Harriman A (2003) Coordination Properties of a Diarylaza Crown Ether Appended with a Luminescent [Ru(bipy)3]2+ Unit. Inorg Chem 42: 3466-3474.
25. Li C-K, Lu X-X, Wong KM-C, Chan C-L, Zhu N, et al. (2004) Molecular Design of Luminescence Ion Probes for Various Cations Based on Weak Gold(I)⋯Gold(I) Interactions in Dinuclear Gold(I) Complexes. Inorg Chem 43: 7421-7430.
26. Lin H, Cinar ME, Schmittel M (2010) Comparison of ruthenium(ii) and cyclometalated iridium(iii) azacrown ether phenanthroline hybrids for the detection of metal cations by electrochemiluminescence. Dalton Trans 39: 5130-5138.
27. Ho M-L, Hwang F-M, Chen P-N, Hu Y-H, Cheng Y-M, et al. (2006) Design and synthesis of iridium(III) azacrown complex: application as a highly sensitive metal cation phosphorescence sensor. Org Biomol Chem 4: 98-103.
28. Brandel J, Sairenji M, Ichikawa K, Nabeshima T (2010) Remarkable Mg2+-selective emission of an azacrown receptor based on Ir(III) complex. Chem Commun 46: 3958-3960.
29. Gill MR, Garcia-Lara J, Foster SJ, Smythe C, Battaglia G, et al. (2009) A ruthenium(II) polypyridyl complex for direct imaging of DNA structure in living cells. Nat Chem 1: 662-667.
30. Shi H-F, Liu S-J, Sun H-B, Xu W-J, An Z-F, et al. (2010) Simple Conjugated Polymers with On-Chain Phosphorescent Iridium(III) Complexes: Toward Ratiometric Chemodosimeters for Detecting Trace Amounts of Mercury(II). Chem - Eur J 16: 12158-12167.
31. Ma D-L, He H-Z, Leung K-H, Zhong H-J, Chan DS-H, et al. (2013) Label-free luminescent oligonucleotide-based probes. Chem Soc Rev 42: 3427-3440.
32. Leung K-H, He H-Z, Ma VP-Y, Zhong H-J, Chan DS-H, et al. (2013) Detection of base excision repair enzyme activity using a luminescent G-quadruplex selective switch-on probe. Chem Commun 49: 5630-5632.
33. Chan DS-H, Lee H-M, Che C-M, Leung C-H, Ma D-L (2009) A selective oligonucleotide-based luminescent switch-on probe for the detection of nanomolar mercury(ii) ion in aqueous solution. Chem Commun: 7479-7481.
34. Man BY-W, Chan DS-H, Yang H, Ang S-W, Yang F, et al. (2010) A selective G-quadruplex-based luminescent switch-on probe for the detection of nanomolar silver(i) ions in aqueous solution. Chem Commun 46: 8534-8536.
35. Ma D-L, Xu T, Chan DS-H, Man BY-W, Fong W-F, et al. (2011) A highly selective, label-free, homogenous luminescent switch-on probe for the detection of nanomolar transcription factor NF-kappaB. Nucleic Acids Res 39: e67.
36. He H-Z, Chan DS-H, Leung C-H, Ma D-L (2012) A highly selective G-quadruplex-based luminescent switch-on probe for the detection of gene deletion. Chem Commun 48: 9462-9464.
37. Leung K-H, He H-Z, Ma VP-Y, Chan DS-H, Leung C-H, et al. (2013) A luminescent G-quadruplex switch-on probe for the highly selective and tunable detection of cysteine and glutathione. Chem Commun 49: 771-773.
38. He H-Z, Leung K-H, Yang H, Shiu-Hin Chan D, Leung C-H, et al. (2013) Label-free detection of sub-nanomolar lead(II) ions in aqueous solution using a metal-based luminescent switch-on probe. Biosens Bioelectron 41: 871-874.
39. He H-Z, Wang M, Chan DS-H, Leung C-H, Qiu J-W, et al. (2013) A label-free G-quadruplex-based luminescent switch-on assay for the selective detection of histidine. Methods 64: 205-211.
40. He H-Z, Wang M, Chan DS-H, Leung C-H, Lin X, et al. (2013) A parallel G-quadruplex-selective luminescent probe for the detection of nanomolar calcium(II) ion. Methods 64: 212-217.
41. Leung K-H, He H-Z, Wang W, Zhong H-J, Chan DS-H, et al. (2013) Label-Free Luminescent Switch-on Detection of Endonuclease IV Activity Using a G-Quadruplex-Selective Iridium(III) Complex. ACS Appl Mater Interfaces 5: 12249-12253.
42. He H-Z, Leung K-H, Wang W, Chan DS-H, Leung C-H, et al. (2014) Label-free luminescence switch-on detection of T4 polynucleotide kinase activity using a G-quadruplex-selective probe. Chem Commun 50: 5313-5315.
43. Ma D-L, Lin S, Leung K-H, Zhong H-J, Liu L-J, et al. (2014) An oligonucleotide-based label-free luminescent switch-on probe for RNA detection utilizing a G-quadruplex-selective iridium(iii) complex. Nanoscale DOI: 10.1039/C4NR00541D
44. Man BY-W, Chan H-M, Leung C-H, Chan DS-H, Bai L-P, et al. (2011) Group 9 metal-based inhibitors of [small beta]-amyloid (1-40) fibrillation as potential therapeutic agents for Alzheimer's disease. Chem Sci 2: 917-921.
45. Ma D-L, Ma VP-Y, Chan DS-H, Leung K-H, He H-Z, et al. (2012) Recent advances in luminescent heavy metal complexes for sensing. Coord Chem Rev 256: 3087-3113.
46. He H-Z, Chan W-I, Mak T-Y, Liu L-J, Wang M, et al. (2013) Detection of 3′→5′ exonuclease activity using a metal-based luminescent switch-on probe. Methods 64: 218-223.
47. Zhao Q, Li F, Huang C (2010) Phosphorescent chemosensors based on heavy-metal complexes. Chem Soc Rev 39: 3007-3030.
48. Yang Y, Zhao Q, Feng W, Li F (2013) Luminescent Chemodosimeters for Bioimaging. Chem Rev 113: 192-270.
49. You Y (2013) Phosphorescence bioimaging using cyclometalated Ir(III) complexes. Curr Opin Chem Biol 17: 699-707.
50. Huang W-S, Lin JT, Chien C-H, Tao Y-T, Sun S-S, et al. (2004) Highly Phosphorescent Bis-Cyclometalated Iridium Complexes Containing Benzoimidazole-Based Ligands. Chem Mater 16: 2480-2488.
51. Lowry MS, Bernhard S (2006) Synthetically tailored excited states: phosphorescent, cyclometalated iridium(III) complexes and their applications. Chem - Eur J 12: 7970-7977.
52. You Y, Han Y, Lee Y-M, Park SY, Nam W, et al. (2011) Phosphorescent Sensor for Robust Quantification of Copper(II) Ion. J Am Chem Soc 133: 11488-11491.
53. Kim H-B, Li Y, Hyun MH (2013) Phosphorescent Chemosensor Based on Iridium (III) Complex for the Selective Detection of Cu (II) Ion in Aqueous Acetonitrile. Bull Korean Chem Soc 34: 653-656.
54. Pellegrin Y, Quaranta A, Dorlet P, Charlot MF, Leibl W, et al. (2005) Heteroditopic Ligand Accommodating a Fused Phenanthroline and a Schiff Base Cavity as Molecular Spacer in the Study of Electron and Energy Transfer. Chem - Eur J 11: 3698-3710. (Pubitemid 40819452)
55. Tamayo AB, Alleyne BD, Djurovich PI, Lamansky S, Tsyba I, et al. (2003) Synthesis and Characterization of Facial and Meridional Tris-cyclometalated Iridium(III) Complexes. J Am Chem Soc 125: 7377-7387. (Pubitemid 36798984)
56. Nonoyama M (1974) [Benzo[h]quinolin-10-yl-N]iridium(III) complexes. Bull Chem Soc Jap 47: 767-768.
57. Burdette SC, Walkup GK, Spingler B, Tsien RY, Lippard SJ (2001) Fluorescent Sensors for Zn2+ Based on a Fluorescein Platform: Synthesis, Properties and Intracellular Distribution. J Am Chem Soc 123: 7831-7841. (Pubitemid 32899347)
58. Sun Y, Lutterman DA, Turro C (2008) Role of Electronic Structure on DNA Light-Switch Behavior of Ru(II) Intercalators. Inorg Chem 47: 6427-6434.
59. Crosby GA, Demas JN (1971) Measurement of photoluminescence quantum yields. J Phys Chem 75: 991-1024.
60. Benesi HA, Hildebrand JH (1949) A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons. J Am Chem Soc 71: 2703-2707.
61. Lamansky S, Djurovich P, Murphy D, Abdel-Razzaq F, Kwong R, et al. (2001) Synthesis and Characterization of Phosphorescent Cyclometalated Iridium Complexes. Inorg Chem 40: 1704-1711. (Pubitemid 32879659)
62. Horrocks WD, Jr., Sudnick DR (1981) Lanthanide ion luminescence probes of the structure of biological macromolecules. Acc Chem Res 14: 384-392.
63. Liu Y, Li M-Y, Zhao Q, Wu H-Z, Huang K-W, et al. (2011) Phosphorescent Iridium(III) Complex with an NO Ligand as a Hg2+-Selective Chemodosimeter and Logic Gate. Inorg Chem 50: 5969-5977.
64. Cheng PPH, Silvester D, Wang G, Kalyuzhny G, Douglas A, et al. (2006) Dynamic and Static Quenching of Fluorescence by 1-4 nm Diameter Gold Monolayer-Protected Clusters. J Phys Chem B 110: 4637-4644.
65. Wang W, Wen Q, Zhang Y, Fei X, Li Y, et al. (2013) Simple naphthalimide-based fluorescent sensor for highly sensitive and selective detection of Cd2+ and Cu2+ in aqueous solution and living cells. Dalton Trans 42: 1827-1833.