Boronate-based fluorescent probes: Imaging hydrogen peroxide in living systems

Methods in Enzymology

Volumn 526, Issue , 2013, Pages 19-43

  Lin, Vivian S ^a   Dickinson, Bryan C ^c   Chang, Christopher J ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b HOWARD HUGHES MEDICAL INSTITUTE   (United States)

^c HARVARD UNIVERSITY   (United States)

Author keywords

Boronate oxidation; Fluorescence; Hydrogen peroxide; Imaging

Indexed keywords

ANILINE; BENZENE; BORON; FLUORESCEIN DERIVATIVE; FLUORESCENT DYE; GREEN FLUORESCENT PROTEIN; HYDROGEN PEROXIDE; OXYGEN; PEROXYNITRITE; XANTHENE;

AQUEOUS SOLUTION; ARTICLE; ATOM; BIOLOGY; BRIGHTNESS; CELL MEMBRANE; COLOR; FLOW CYTOMETRY; FLUORESCENCE; FLUORESCENCE MICROSCOPY; FLUOROMETRY; HALF LIFE TIME; HYDROPHILICITY; IMAGING; IN VITRO STUDY; MITOCHONDRION; NONHUMAN; OXIDATION; PERMEABILITY; PRIORITY JOURNAL; TAUTOMERIZATION;

EID: 84879744031     PISSN: 00766879     EISSN: 15577988     Source Type: Book Series    
DOI: 10.1016/B978-0-12-405883-5.00002-8     Document Type: Chapter

References (57)

1. A.E. Albers, V.S. Okreglak, and C.J. Chang A FRET-based approach to ratiometric fluorescence detection of hydrogen peroxide Journal of the American Chemical Society 128 2006 9640 9641
2. S.C. Albrecht, A.G. Barata, J. Grosshans, A.A. Teleman, and T.P. Dick In vivo mapping of hydrogen peroxide and oxidized glutathione reveals chemical and regional specificity of redox homeostasis Cell Metabolism 14 2011 819 829
3. K. Bedard, and K.-H. Krause The NOX family of ROS-generating NADPH oxidases: Physiology and pathophysiology Physiological Reviews 87 2007 245 313
4. V.V. Belousov, A.F. Fradkov, K.A. Lukyanov, D.B. Staroverov, K.S. Shakhbazov, and A.V. Terskikh Genetically encoded fluorescent indicator for intracellular hydrogen peroxide Nature Methods 3 2006 281 286
5. 2 probe with improved performance for ratiometric and fluorescence lifetime imaging ACS Chemical Biology 8 2013 535 542
6. J. Chan, S.C. Dodani, and C.J. Chang Reaction-based small-molecule fluorescent probes for chemoselective bioimaging Nature Chemistry 4 2012 973 984
7. M.C.Y. Chang, A. Pralle, E.Y. Isacoff, and C.J. Chang A selective, cell-permeable optical probe for hydrogen peroxide in living cells Journal of the American Chemical Society 126 2004 15392 15393
8. D.G. Cho, and J.L. Sessler Modern reaction-based indicator systems Chemical Society Reviews 38 2009 1647 1662
9. A.W. Czarnik Chemical communication in water using fluorescent chemosensors Accounts of Chemical Research 27 1994 302 308
10. B. D'Autréaux, and M.B. Toledano ROS as signaling molecules: Mechanisms that generate specificity in ROS homeostasis Nature Reviews Molecular Cell Biology 8 2007 813 824
11. B.C. Dickinson, and C.J. Chang A targetable fluorescent probe for imaging hydrogen peroxide in the mitochondria of living cells Journal of the American Chemical Society 130 2008 9638 9639
12. B.C. Dickinson, and C.J. Chang Chemistry and biology of reactive oxygen species in signaling or stress responses Nature Chemical Biology 7 2011 504 511
13. B.C. Dickinson, C. Huynh, and C.J. Chang A palette of fluorescent probes with varying emission colors for imaging hydrogen peroxide signaling in living cells Journal of the American Chemical Society 132 2010 5906 5915
14. Dickinson, B. C., Lin, V. S., & Chang, C. J. (in press). Preparation and use of MitoPY1, a synthetic fluorophore for imaging hydrogen peroxide in mitochondria of live biological specimens. Nature Protocols.
15. B.C. Dickinson, J. Peltier, D. Stone, D.V. Schaffer, and C.J. Chang Nox2 redox signaling maintains essential cell populations in the brain Nature Chemical Biology 7 2011 106 112
16. B.C. Dickinson, Y. Tang, Z. Chang, and C.J. Chang A nuclear-localized fluorescent hydrogen peroxide probe for monitoring sirtuin-mediated oxidative stress responses in vivo Chemical Biology 18 2011 943 948
17. J. Du, M. Hu, J. Fan, and X. Peng Fluorescent chemodosimeters using 'mild' chemical events for the detection of small anions and cations in biological and environmental media Chemical Society Reviews 41 2012 4511 4535
18. N. Exner, A.K. Lutz, C. Haass, and K.F. Winklhofer Mitochondrial dysfunction in Parkinson's disease: Molecular mechanisms and pathophysiological consequences EMBO Journal 31 2012 3038 3062
19. M. Frisard, and E. Ravussin Energy metabolism and oxidative stress: Impact on the metabolic syndrome and the ageing process Endocrine 29 2006 27 32
20. M. Giorgio, M. Trinei, E. Migliaccio, and P.G. Peliccil Hydrogen peroxide: A metabolic by-product or a common mediator of ageing signals? Nature Reviews Molecular Cell Biology 8 2007 722 728
21. J.M. Harris, V. Esain, G.M. Frechette, L.J. Harris, A.G. Cox, and M. Cortes Glucose Metabolism Impacts the Spatiotemporal Onset and Magnitude of HSC Induction in Vivo Blood 121 2013 2483 2493
22. Y. Huang, and L. Mucke Alzheimer mechanisms and therapeutic strategies Cell 148 2012 1204 1222
23. W.P. Jencks, and J.C. Carriulo Reactivity of nucleophilic reagents towards esters Journal of the American Chemical Society 82 1960 1778 1786
24. A. Juillerat, T. Gronemeyer, A. Keppler, S. Gendreizig, H. Pick, and H. Vogel Directed evolution of O6-alkylguanine-DNA alkyltransferase for efficient labeling of fusion proteins with small molecules in vivo Chemical Biology 10 2003 313 317
25. M.E. Jun, B. Roy, and K.H. Ahn 'Turn-on' fluorescent sensing with 'reactive' probes Chemical Communications 47 2011 7583 7601
26. A. Keppler, M. Kindermann, S. Gendreizig, H. Pick, H. Vogel, and K. Johnsson Labeling of fusion proteins of O6-alkylguanine-DNA alkyltransferase with small molecules in vivo and in vitro Methods 32 2004 437 444
27. H.G. Kuivila Electrophilic displacement reactions: Kinetics of the reaction between hydrogen peroxide and benzeneboronic acid Journal of the American Chemical Society 76 1954 870 874
28. H.G. Kuivila, and A.G. Armour Electrophilic displacement reactions: Effects of substituents on rates of reactions between hydrogen peroxide and benzeneboronic acid Journal of the American Chemical Society 79 1957 5659 5662
29. H.G. Kuivila, and R.A. Wiles Electrophilic displacement reactions: Catalysis by chelating agents in the reaction between hydrogen peroxide and benzeneboronic acid Journal of the American Chemical Society 77 1955 4830 4834
30. J.D. Lambeth NOX enzymes and the biology of reactive oxygen Nature Reviews Immunology 4 2004 181 189
31. M.T. Lin, and M.F. Beal Mitochondrial dysfunction and oxidative stress in neurodegenerative diseases Nature 443 2006 787 795
32. A.R. Lippert, G.C. Van de Bittner, and C.J. Chang Boronate oxidation as a bioorthogonal reaction approach for studying the chemistry of hydrogen peroxide in living systems Accounts of Chemical Research 44 2011 793 804
33. M.P. Mattson Pathways towards and away from Alzheimer's disease Nature 430 2004 631 639
34. E.W. Miller, A.E. Albers, A. Pralle, E.Y. Isacoff, and C.J. Chang Boronate-based fluorescent probes for imaging cellular hydrogen peroxide Journal of the American Chemical Society 127 2005 16652 16659
35. E.W. Miller, B.C. Dickinson, and C.J. Chang Aquaporin-3 mediates hydrogen peroxide uptake to regulate downstream intracellular signaling Proceedings of the National Academy of Sciences of the United States of America 107 2010 15681 15686
36. E.W. Miller, O. Tulyathan, E.Y. Isacoff, and C.J. Chang Molecular imaging of hydrogen peroxide produced for cell signaling Nature Chemical Biology 3 2007 263 267
37. M.P. Murphy, A. Holmgren, N.-G. Larsson, B. Halliwell, C.J. Chang, and B. Kalyanaraman Unraveling the biological roles of reactive oxygen species Cell Metabolism 13 2011 361 366
38. K.J. Nelson, C. Klomsiri, S.G. Codreanu, L. Soito, D.C. Liebler, and L.C. Rogers Use of dimedone-based chemical probes for sulfenic acid detection: Methods to visualize and identify labeled proteins Methods in Enzymology 473 2010 95 115
39. T.D. Palmer, E.A. Markakis, A.R. Willhoite, F. Safar, and F.H. Gage Fibroblast growth factor-2 activates a latent neurogenic program in neural stem cells from diverse regions of the adult CNS Journal of Neuroscience 19 1999 8487 8497
40. C.E. Paulsen, and K.S. Carroll Orchestrating redox signaling networks through regulatory cysteine switches ACS Chemical Biology 5 2010 47 62
41. D.T. Quang, and J.S. Kim Fluoro- and chromogenic chemodosimeters for heavy metal ion detection in solution and biospecimens Chemical Reviews 110 2010 6280 6301
42. N2 reactions: Existence and the origin of the effect Journal of Organic Chemistry 72 2007 5660 5667
43. 2, a necessary evil for cell signaling Science 312 2006 1882 1883
44. K. Setsukinai, Y. Urano, K. Kakinuma, H.J. Majima, and T. Nagano Development of novel fluorescence probes that can reliably detect reactive oxygen species and distinguish specific species Journal of Biological Chemistry 278 2003 3170 3175
45. A. Sikora, J. Zielonka, M. Lopez, J. Joseph, and B. Kalyanaraman Direct oxidation of boronates by peroxynitrite: Mechanism and implications in fluorescence imaging of peroxynitrite Free Radical Biology & Medicine 47 2009 1401 1407
46. D. Srikun, A.E. Albers, and C.J. Chang A dendrimer-based platform for simultaneous dual fluorescence imaging of hydrogen peroxide and pH gradients produced in living cells Chemical Science 2 2011 1156 1165
47. D. Srikun, A.E. Albers, C.I. Nam, A.T. Iavarone, and C.J. Chang Organelle-targetable fluorescent probes for imaging hydrogen peroxide in living cells via SNAP-tag protein labeling Journal of the American Chemical Society 132 2010 4455 4465
48. D. Srikun, E.W. Miller, D.W. Domaille, and C.J. Chang An ICT-Based approach to ratiometric fluorescence imaging of hydrogen peroxide produced in living cells Journal of the American Chemical Society 130 2008 4596 4597
49. J.R. Stone, and S. Yang Hydrogen peroxide: A signaling messenger Antioxid Redox Signaling 8 2006 243 270
50. R.Y. Tsien A non-disruptive technique for loading calcium buffers and indicators into cells Nature 290 1981 527 528
51. Y. Urano, M. Kamiya, K. Kanda, T. Ueno, K. Hirose, and T. Nagano Evolution of fluorescein as a platform for finely tunable fluorescence probes Journal of the American Chemical Society 127 2005 4888 4894
52. G.C. Van de Bittner, C.R. Bertozzi, and C.J. Chang A strategy for dual-analyte luciferin imaging: In vivo bioluminescence detection of hydrogen peroxide and caspase activity in a murine model of acute inflammation Journal of the American Chemical Society 135 2013 1783 1795
53. G.C. Van de Bittner, E.A. Dubikovskaya, C.R. Bertozzi, and C.J. Chang In vivo imaging of hydrogen peroxide production in a murine tumor model with a chemoselective bioluminescent reporter Proceedings of the National Academy of Sciences of the United States of America 107 2010 21316 21321
54. E.A. Veal, A.M. Day, and B.A. Morgan Hydrogen peroxide sensing and signaling Molecular Cell 26 2007 1 14
55. C.C. Winterbourn Reconciling the chemistry and biology of reactive oxygen species Nature Chemical Biology 4 2008 278 286
56. Z. Xun, S. Rivera-Sánchez, S. Ayala-Peña, J. Lim, H. Budworth, and E.M. Skoda Targeting of XJB-5-131 to mitochondria suppresses oxidative DNA damage and motor decline in a mouse model of Huntington's Disease Cell Reports 2 2012 1137 1142
57. I.N. Zelko, T.J. Mariani, and R.J. Folz Superoxide dismutase multigene family: A comparison of the CuZn-SOD (SOD1), Mn-SOD (SOD2), and EC-SOD (SOD3) gene structures, evolution, and expression Free Radical Biology & Medicine 33 2002 337 349