Highly selective probe detects Cu2+ and endogenous NO gas in living cell

ACS Applied Materials and Interfaces

Volumn 6, Issue 9, 2014, Pages 6562-6569

  Muthuraj, Balakrishnan ^a   Deshmukh, Rohitas ^a   Trivedi, Vishal ^a   Iyer, Parameswar Krishnan ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

colorimetric; copper; fluorescein; fluorometric; NO gas; sensor

Indexed keywords

AMINO ACIDS; CADMIUM; CELLULAR ARRAYS; CELLULAR TELEPHONE SYSTEMS; COPPER COMPOUNDS; FLUORESCENCE; IRON COMPOUNDS; MEDICAL APPLICATIONS; NITRIC OXIDE; SENSORS;

BIOMEDICAL APPLICATIONS; COLORIMETRIC; FLUORESCEIN; FLUOROMETRIC; HIGHLY SENSITIVE DETECTIONS; IN-VIVO EXPERIMENTS; LIPOPOLYSACCHARIDES; PARAMAGNETIC NATURE;

COPPER;

COPPER; GAS; MOLECULAR PROBE; NITRIC OXIDE;

ANIMAL; CELL LINE; CHEMISTRY; COLORIMETRY; FLUORESCENCE RESONANCE ENERGY TRANSFER; GAS; LIMIT OF DETECTION; MACROPHAGE; MOLECULAR PROBE; MOUSE; SPECTROFLUOROMETRY;

ANIMALS; CELL LINE; COLORIMETRY; COPPER; FLUORESCENCE RESONANCE ENERGY TRANSFER; GASES; LIMIT OF DETECTION; MACROPHAGES; MICE; MOLECULAR PROBES; NITRIC OXIDE; SPECTROMETRY, FLUORESCENCE;

EID: 84900851739     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am501476w     Document Type: Conference Paper

References (66)

1. Yang, Y.; Zhao, Q.; Feng, W.; Li, F. Luminescent Chemodosimeters for Bioimaging Chem. Rev. 2013, 113, 192-270
2. Gaggelli, E.; Kozłowski, H.; Valensin, D.; Valensin, G. Copper Homeostasis and Neurodegenerative Disorders (Alzheimer's, Prion, and Parkinson's Diseases and Amyotrophic Lateral Sclerosis) Chem. Rev. 2006, 106, 1995-2044
3. Calabrese, V.; Mancuso, C.; Calvani, M.; Rizzarelli, E.; Butterfield, D. A.; Giuffrida Stella, A. M. Nitric Oxide in the Central Nervous System: Neuroprotection Versus Neurotoxicity Nat. Rev. Neurosci. 2007, 8, 766-775
4. Shiue, T. W.; Chen, Y. H.; Wu, C. M.; Singh, G.; Chen, H. Y.; Hung, C. H.; Liaw, W. F.; Wang, Y. M. Nitric Oxide Turn-On Fluorescent Probe Based on Deamination of Aromatic Primary Monoamines Inorg. Chem. 2012, 51, 5400-5408
5. McQuade, L. E.; Pluth, M. D.; Lippard, S. J. Mechanism of Nitric Oxide Reactivity and Fluorescence Enhancement of the NO-Specific Probe CuFL1 Inorg. Chem. 2010, 49, 8025-8033
6. Ford, P. C.; Lorkovic, I. M. Mechanistic Aspects of the Reactions of Nitric Oxide with Transition-Metal Complexes Chem. Rev. 2002, 102, 993-1017
7. 2 Within the Hydrophobic Interior of Biological Membranes Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 2175-2179
8. 2 Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 355-360
9. Gladwin, M. T.; Schechter, A. N. NO Contest: Nitrite Versus S-Nitroso-Hemoglobin Circ. Res. 2004, 94, 851-855
10. Vanin, A. F. Dinitrosyl Iron Complexes and S-Nitrosothiols are Two Possible Forms for Stabilization and Transport of Nitric Oxide in Biological Systems Biochemistry 1998, 63, 782-793
11. Ford, P. C.; Fernandez, B. O.; Lim, M. D. Mechanisms of Reductive Nitrosylation in Iron and Copper Models Relevant to Biological Systems Chem. Rev. 2005, 105, 2439-2456
12. Lim, M. H.; Wong, B. A.; Pitcock, W. H., Jr.; Mokshagundam, D.; Baik, M. H.; Lippard, S. J. Direct Nitric Oxide Detection in Aqueous Solution by Copper(II) Fluorescein Complexes J. Am. Chem. Soc. 2006, 128, 14364-14373
13. Egawa, T.; Koide, Y.; Hanaoka, K.; Komatsu, T.; Teraia, T.; Nagano, T. Development of a Fluorescein Analogue, TokyoMagenta, as a Novel Scaffold for Fluorescence Probes in Red Region Chem. Commun. 2011, 47, 4162-4164
14. Okuda, T.; Kataoka, K.; Yabuuchi, T.; Yugami, H.; Kato, A. Fluorescence-Guided Surgery of Metastatic Brain Tumors Using Fluorescein Sodium J. Clin. Neurosci. 2010, 17, 118-121
15. Okuda, T.; Yoshioka, H.; Kato, A. Fluorescence-Guided Surgery for Glioblastoma Multiforme Using High-Dose Fluorescein Sodium with Excitation and Barrier Filters J. Clin. Neurosci. 2012, 19, 1719-1722
16. Schebesch, K. M.; Proescholdt, M.; Höhne, J.; Hohenberger, C.; Hansen, E.; Riemenschneider, M. J.; Ullrich, W.; Doenitz, C.; Schlaier, J.; Lange, M.; Brawanski, A. Sodium Fluorescein-Guided Resection Under the YELLOW 560 nm Surgical Microscope Filter in Malignant Brain Tumor Surgery-A Feasibility Study Acta Neurochir. 2013, 155, 693-699
17. Acerbi, F.; Broggi, M.; Eoli, M.; Anghileri, E.; Cuppini, L.; Pollo, B.; Schiariti, M.; Visintini, S.; Orsi, C.; Franzini, A.; Broggi, G.; Ferroli, P. Fluorescein-Guided Surgery for Grade IV Gliomas with a Dedicated Filter on the Surgical Microscope: Preliminary Results In 12 Cases Acta Neurochir. 2013, 155, 1277-1286
18. Pluth, M. D.; McQuade, L. E.; Lippard, S. J. Cell-Trappable Fluorescent Probes for Nitric Oxide Visualization in Living Cells Org. Lett. 2010, 12, 2318-2321
19. McQuade, L. E.; Lippard, S. J. Fluorescence Based Nitric Oxide Sensing by Cu(II) Complexes that can be Trapped in Living Cells Inorg. Chem. 2010, 49, 7464-7471
20. Pluth, M. D.; Chan, M. R.; McQuade, L. E.; Lippard, S. J. Seminaphthofluorescein Based Fluorescent Probes for Imaging Nitric Oxide in Live Cells Inorg. Chem. 2011, 50, 9385-9392
21. Tonzetich, Z. J.; McQuade, L. E.; Lippard, S. J. Detecting and Understanding the Roles of Nitric Oxide in Biology Inorg. Chem. 2010, 49, 6338-6348
22. Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. Highly Zinc-Selective Fluorescent Sensor Molecules Suitable for Biological Applications J. Am. Chem. Soc. 2000, 122, 12399-12400
23. Miles, A. M.; Wink, D. A.; Cook, J. C.; Grisham, M. B. Determination of Nitric Oxide Using Fluorescence Spectroscopy Methods Enzymol. 1996, 268, 105-120
24. Nagano, T.; Yoshimura, T. Bioimaging of Nitric Oxide Chem. Rev. 2002, 102, 1235-1270
25. Sasaki, E.; Kojima, H.; Nishimatsu, H.; Urano, Y.; Kikuchi, K.; Hirata, Y.; Nagano, T. Highly Sensitive Near-Infrared Fluorescent Probes for Nitric Oxide and Their Application to Isolated Organs J. Am. Chem. Soc. 2005, 127, 3684-3685
26. Terai, T.; Urano, Y.; Izumi, S.; Kojima, H.; Nagano, T. A Practical Strategy to Create Near-Infrared Luminescent Probes: Conversion from Fluorescein-Based Sensors Chem. Commun. 2012, 48, 2840-2842
27. Yang, Y.; Seidlits, S. K.; Adams, M. M.; Lynch, V. M.; Schmidt, C. E.; Anslyn, E. V.; Shear, J. B. A Highly Selective Low-Background Fluorescent Imaging Agent for Nitric Oxide J. Am. Chem. Soc. 2010, 132, 13114-13116
28. Lim, M. H.; Xu, D.; Lippard, S. J. Visualization of Nitric Oxide in Living Cells by a Copper-Based Fluorescent Probe Nat. Chem. Biol. 2006, 2, 375-380
29. Rosenthal, J.; Lippard, S. J. Direct Detection of Nitroxyl in Aqueous Solution Using a Tripodal Copper(II) BODIPY Complex J. Am. Chem. Soc. 2010, 132, 5536-5537
30. Royzen, M.; Wilson, J. J.; Lippard, S. J. Physical and Structural Properties of [Cu(BOT1)Cl]Cl, a Fluorescent Imaging Probe for HNO J. Inorg. Biochem. 2013, 118, 162-170
31. Tsuge, K.; DeRosa, F.; Lim, M. D.; Ford, P. C. Intramolecular Reductive Nitrosylation: Reaction of Nitric Oxide and a Copper(II) Complex of a Cyclam Derivative with Pendant Luminescent Chromophores J. Am. Chem. Soc. 2004, 126, 6564-6565
32. 2+ Inorg. Chem. 2007, 46, 9323-9331
33. Wasser, I. M.; Vries, S. D.; Loccoz, P. M.; Schröder, I.; Karlin, K. D. Nitric Oxide in Biological Denitrification: Fe/Cu Metalloenzyme and Metal Complex NO(x) Redox Chemistry Chem. Rev. 2002, 102, 1201-1234
34. Yuan, L.; Lin, W.; Xie, Y.; Chen, B.; Song, J. Development of a Ratiometric Fluorescent Sensor for Ratiometric Imaging of Endogenously Produced Nitric Oxide in Macrophage Cells Chem. Commun. 2011, 47, 9372-9374
35. Zhang, X.; Shiraishi, Y.; Hirai, T. Cu(II)-Selective Green Fluorescence of a Rhodamine-Diacetic Acid Conjugate Org. Lett. 2007, 9, 5039-5042
36. Zhang, X.; Sumiya, S.; Shiraishi, Y.; Hirai, T. Effects of Alkyl Chain Length on Cu(II)-Selective Green Fluorescence of Rhodamine-Diacetic Acid Conjugates J. Photochem. Photobiol., A 2009, 205, 215-220
37. 2+ in Aqueous Solution Talanta 2008, 74, 1148-1153
38. 2+ in Aqueous Solution and Living Cells Anal. Chem. 2009, 81, 7022-7030
39. Zhao, M. L.; Yang, X. F.; He, S. H.; Wang, L. P. A Rhodamine-Based Chromogenic and Fluorescent Chemosensor for Copper Ion in Aqueous Media Sens. Actuators, B 2009, 135, 625-631
40. Swamy, K.; Ko, S. K.; Kwon, S. K.; Lee, H. N.; Mao, C.; Kim, J. M.; Lee, K. H.; Kim, J. H.; Shin, I.; Yoon, J. Y. Boronic Acid-Linked Fluorescent and Colorimetric Probes for Copper Ions Chem. Commun. 2008, 44, 5915-5917
41. 2+ Selective Ratiometric and "Off-On" Sensor Based on the Rhodamine Derivative Bearing Pyrene Group Org. Lett. 2009, 11, 4442-4445
42. Tang, R. R.; Lei, K.; Chen, K.; Zhao, H.; Chen, J. W. A Rhodamine-Based Off-On Fluorescent Chemosensor for Selectively Sensing Cu(II) in Aqueous Solution J. Fluoresc. 2011, 21, 141-148
43. 2+ Based on Rhodamine Derivative Org. Biomol. Chem. 2010, 8, 5277-5279
44. 2+ Based on Rhodamine B Derivative Sens. Actuators, B 2011, 156, 546-552
45. 2+ Based on Two Different Approaches Org. Lett. 2010, 12, 3852-3855
46. Xi, P. X.; Dou, J. Y.; Huang, L.; Xu, M.; Chen, F. J.; Wu, Y. J.; Bai, D. C.; Li, W. G.; Zeng, Z. Z. A Selective Turn-On Fluorescent Sensor for Cu(II) and Its Application in Imaging in Living Cells Sens. Actuators, B 2010, 148, 337-341
47. 2+ in Aqueous Media and Its Application to Bioimaging Dyes Pigm. 2011, 90, 265-268
48. 2+ Ions and Its Application in Bio-Imaging Dyes Pigm. 2011, 91, 378-382
49. 2+ Specific Molecular Probe Org. Biomol. Chem. 2011, 9, 4802-4805
50. 2+ in Aqueous Media and Living Cells Talanta 2011, 85, 1627-1633
51. Xu, Z.; Han, S. J.; Lee, C.; Yoon, J.; Spring, D. R. Development of Off-On Fluorescent Probes for Heavy and Transition Metal Ions Chem. Commun. 2010, 46, 1679-1681
52. Kim, H. N.; Guo, Z.; Zhu, W.; Yoon, J.; Tian, H. Recent Progress on Polymer-Based Fluorescent and Colorimetric Chemosensors Chem. Soc. Rev. 2011, 40, 79-93
53. Saikia, G.; Iyer, P. K. A Remarkable Superquenching and Superdequenching Sensor for the Selective and Non-Invasive Detection of Inorganic Phosphates in Saliva Macromolecules 2011, 44, 3753-3758
54. 3+ and Inorganic Phosphate in Blood Serum J. Mater. Chem. 2011, 21, 2502-2507
55. Saikia, G.; Dwivedi, A. K.; Iyer, P. K. Development of Solution, Film and Membrane Based Fluorescent Sensor for the Detection of Fluoride Anions from Water Anal. Methods 2012, 4, 3180-3186
56. Dwivedi, A. K.; Prasad, K. M. N.; Trivedi, V.; Iyer, P. K. Interaction of Heme Proteins with Anionic Polyfluorene: Insights into Physiological Effects, Folding Events and Inhibition Activity ACS Appl. Mater. Interfaces 2012, 4, 6371-6377
57. Dwivedi, A. K.; Iyer, P. K. A Fluorescence Turn on Trypsin Assay Based on Aqueous Polyfluorene J. Mater. Chem. B 2013, 1, 4005-4010
58. Muthuraj, B.; Hussain, S.; Iyer, P. K. A Rapid and Sensitive Detection of Ferritin at a Nanomolar Level and Disruption of Amyloid β Fibrils Using Fluorescent Conjugated Polymer Polym. Chem. 2013, 4, 5096-5107
59. Deshmukh, R.; Trivedi, V. Methemoglobin Exposure Produces Toxicological Effects in Macrophages due to Multiple ROS Spike Induced Apoptosis Toxicol In Vitro 2013, 27, 16-23
60. Bose, P.; Ghosh, P. Visible and Near-Infrared Sensing of Fluoride by Indole Conjugated Urea/Thiourea Ligands Chem. Commun. 2010, 46, 2962-2964
61. Takakusa, H.; Kikuchi, K.; Urano, Y.; Kojima, H.; Nagano, T. A Novel Design Method of Ratiometric Fluorescent Probes Based on Fluorescence Resonance Energy Transfer Switching by Spectral Overlap Integral Chem.-Eur. J. 2003, 9, 1479-1485
62. 1-Antichymotrypsin Detection Based on Surface Plasmon Resonance Biosens. Bioelectron. 2006, 21, 2106-2113
63. World Health Organization, Guidelines for Drinking-water Quality, 4 th ed.; WHO Press: Geneva, 2011; p 340.
64. Huo, F. J.; Yin, C. X.; Yang, Y. T.; Su, J.; Chao, J. B.; Liu, D. S. Ultraviolet-Visible Light (UV-Vis)-Reversible but Fluorescence-Irreversible Chemosensor for Copper in Water and Its Application in Living Cells Anal. Chem. 2012, 84, 2219-2223
65. Gaetke, L. M.; Chow, C. K. Copper Toxicity, Oxidative Stress, and Antioxidant Nutrients Toxicology 2003, 189, 147-163
66. Bonnefous, C.; Payne, J. E.; Roppe, J.; Zhuang, H.; Chen, X.; Symons, K. T.; Nguyen, P. M.; Sablad, M.; Rozenkrants, N.; Zhang, Y.; Wang, L.; Severance, D.; Walsh, J. P.; Yazdani, N.; Shiau, A. K.; Noble, S. A.; Rix, P.; Rao, T. S.; Hassig, C. A.; Nicholas, D.; Smith, N. D. Discovery of Inducible Nitric Oxide Synthase (iNOS) Inhibitor Development Candidate KD7332, Part 1: Identification of a Novel, Potent, and Selective Series of Quinolinone iNOS Dimerization Inhibitors that are Orally Active in Rodent Pain Models J. Med. Chem. 2009, 52, 3047-3062