Azido push-pull fluorogens photoactivate to produce bright fluorescent labels

Journal of Physical Chemistry B

Volumn 114, Issue 45, 2010, Pages 14157-14167

  Lord, Samuel J ^a   Lee, Hsiao Lu D ^a   Samuel, Reichel ^b   Weber, Ryan ^b   Liu, Na ^b   Conley, Nicholas R ^a   Thompson, Michael A ^a   Twieg, Robert J ^b   Moerner, W E ^a  

^a STANFORD UNIVERSITY   (United States)

^b KENT STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; CHROMOPHORES; QUANTUM YIELD;

ARYL AMINES; ARYL AZIDES; CHARGE-TRANSFER ABSORPTION; FLUORESCENT LABELING; FLUORESCENT LABELS; FLUOROGENICS; PHOTO-ACTIVATED; PHOTO-STABILITY; PHOTOACTIVATABLE; PHOTOACTIVATION; PHOTOAFFINITY LABELING; PHOTOCHEMICAL CONVERSION; PHOTOCONVERSION; PHOTOPHYSICAL PARAMETERS; PUSH-PULL CHROMOPHORES; SINGLE-MOLECULE; SINGLE-MOLECULE IMAGING; SUPER-RESOLUTION MICROSCOPY;

FLUORESCENCE;

EID: 77954577994     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp907080r     Document Type: Article

References (58)

1. Betzig, E.; Patterson, G. H.; Sougrat, R.; Lindwasser, O. W.; Olenych, S.; Bonifacino, J. S.; Davidson, M. W.; Lippincott-Schwartz, J.; Hess, H. F. Imaging Intracellular Fluorescent Proteins at Nanometer Resolution. Science 2006, 313, 1642-1645.
2. Hess, S. T.; Girirajan, T. P. K.; Mason, M. D. Ultra-High Resolution Imaging by Fluorescence Photoactivation Localization Microscopy. Biophys. J. 2006, 91, 4258-4272.
3. Rust, M. J.; Bates, M.; Zhuang, X. Sub-Diffraction-Limit Imaging by Stochastic Optical Reconstruction Microscopy (STORM). Nat. Methods 2006, 5, 793-795.
4. Moerner, W. E. New Directions in Single-Molecule Imaging and Analysis. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 12596-12602.
5. Dickson, R. M.; Cubitt, A. B.; Tsien, R. Y.; Moerner, W. E. On/ Off Blinking and Switching Behavior of Single Green Fluorescent Protein Molecules. Nature 1997, 388, 355-358.
6. Lukyanov, K. A.; Chudakov, D. M.; Lukyanov, S.; Verkhusha, V. V. Photoactivatable Fluorescent Proteins. Nat. Rev. Mol. Cell Biol. 2005, 6, 885-891.
7. Lippincott-Schwartz, J.; Patterson, G. H. Fluorescent Proteins for Photoactivation Experiments. Methods Cell Biol. 2008, 85, 45-61.
8. Bates, M.; Blosser, T. R.; Zhuang, X. Short-Range Spectroscopic Ruler Based on a Single-Molecule Switch. Phys. Rev. Lett. 2005, 94, 108101-1-108101-4.
9. Zhu, M.; Zhu, L.; Han, J. J.; Wu, W.; Hurst, J. K.; Li, A. D. Q. Spiropyran-Based Photochromic Polymer Nanoparticles with. Optically Switchable Luminescence. J. Am. Chem. Soc. 2006, 128, 4303-4309.
10. Fukaminato, T.; Umemoto, T.; Iwata, Y.; Yokojima, S.; Yoneyama, M.; Nakamura, S.; Irie, M. Photochromism of Diarylethene Single Molecules in Polymer Matrices. J. Am. Chem. Soc. 2007, 129, 5932-5938.
11. Fölling, J.; Belov, V.; Kunetsky, R.; Medda, R.; Schönle, A.; Egner, A.; Eggeling, C.; Bossi, M.; Hell, S. W. Photochromic Rhodamines Provide Nanoscopy with Optical Sectioning. Angew. Chem., Int. Ed. 2007, 46, 62666270.
12. Conley, N. R.; Biteen, J. S.; Moerner, W. E. Cy3-Cy5 Covalent Heterodimers for Single-Molecule Photoswitching. J. Phys. Chem. B 2008, 112, 11878-11880.
13. Han, G.; Mokari, T.; Ajo-Franklin, C.; Cohen, B. E. Caged Quantum. Dots. J. Am. Chem. Soc. 2008, 130, 15811-15813.
14. Fernandez-Suarez, M.; Ting, A. Y. Fluorescent Probes for SuperResolution Imaging in Living Cells. Nat. Rev. Mol. Cell Biol. 2008, 9, 929943.
15. Lord, S. J.; Conley, N. R.; Lee, H. D.; Samuel, R.; Liu, N.; Twieg, R. J.; Moerner, W. E. A Photoactivatable Push-Pull Fluorophore for SingleMolecule Imaging in Live Cells. J. Am. Chem. Soc. 2008, 130, 9204-9205.
16. Nicoud, J. F.; Twieg, R. J. Nonlinear Optical Properties of Organic Molecules and Crystals. In Design and Synthesis of Organic Molecular Compounds for Efficient Second Harmonic Generation; Chemla, D. S., Zyss, J., Eds.; Academic Press: New York, 1987; Vol. 1, pp 227-296.
17. Debreczeny, M. P.; Svec, W. A.; Wasielewski, M. R. Optical. Control of Photogenerated Ion Pair Lifetimes: An. Approach to a Molecular Switch. Science 1996, 274, 584-587.
18. Ostroverkhova, O.; Moerner, W. E. Organic Photorefractives: Mechanisms, Materials, and Applications. Chem. Rev. 2004, 104, 32673314.
19. Willets, K. A.; Ostroverkhova, O.; He, M.; Twieg, R. J.; Moerner, W. E. New Fluorophores for Single-Molecule Spectroscopy. J. Am. Chem. Soc. 2003, 125, 1174-1175.
20. Willets, K. A.; Nishimura, S. Y.; Schuck, P. J.; Twieg, R. J.; Moerner, W. E. Nonlinear Optical Chromophores as Nanoscale Emitters for Single-Molecule Spectroscopy. Acc. Chem. Res. 2005, 38, 549-556.
21. Lord, S. J.; Lu, Z.; Wang, H.; Willets, K. A.; Schuck, P. J.; Lee, H. D.; Nishimura, S. Y.; Twieg, R. J.; Moerner, W. E. Photophysical Properties of Acene DCDHF Fluorophores: Long-Wavelength SingleMolecule Emitters Designed for Cellular Imaging. J. Phys. Chem. A 2007, 111, 8934-8941.
22. Lu, Z.; Liu, N.; Lord, S. J.; Bunge, S. D.; Moerner, W. E.; Twieg, R. J. Bright, Red Single-Molecule Emitters: Synthesis and Properties of Environmentally Sensitive Dicyanomethylenedihydrofuran. (DCDHF) Fluorophores with Bisaromatic Conjugation. Chem. Mater: 2009, 21, 797-810.
23. Lord, S. J.; Conley, N. R.; Lee, H. D.; Nishimura, S. Y.; Pomerantz, A. K.; Willets, K. A.; Lu, Z.; Wang, H.; Liu, N.; Samuel, R.; Weber, R.; Semyonov, A. N.; He, M.; Twieg, R. J.; Moerner, W. E. DCDHF Fluorophores for Single-Molecule Imaging in Cells. ChemPhysChem 2009, 10, 55-65.
24. Doub, L.; Vandenbelt, J. M. The Ultraviolet Absorption Spectra of Simple Unsaturated Compounds. I. Mono- and p-Disubstituted Benzene Derivatives. J. Am. Chem. Soc. 1947, 69, 2714-2723.
25. Stevenson, P. E. Effects of Chemical Substitution on the Electronic Spectra of Aromatic Compounds: Part I. the Effects of Strongly Perturbing Substituents on Benzene. J. Mol. Spectrosc. 1965, 15, 220-256.
26. Bouffard, J.; Kim, Y.; Swager, T. M.; Weissleder, R.; Hilderbrand, S. A. A Highly Selective Fluorescent Probe for Thiol Bioimaging. Org. Lett. 2008, 10, 37-40.
27. Budyka, M. F.; Biktimirova, N. V.; Gavrishova, T. N.; Kozlovskii, V. I. Azido Derivative of a Hemicyanine Dye with High Sensitivity to Visible Light. Mendeleev Commun. 2007, 17, 159-160.
28. Hansch, C.; Leo, A.; Taft, R. W. A Survey of Hammett Substituent Constants and Resonance and Field Parameters. Chem. Rev. 1991, 91, 165195.
29. Schriven, E. F. V., Ed. Azides and Nitrenes: Reactivity and Utility; Academic Press: Orlando, FL, 1984.
30. Soundararajan, N.; Platz, M. S. Descriptive Photochemistry of Polyfluorinated Azi.e Derivatives of Methyl Benzoate. J. Org. Chem. 1990, 55, 2034-2044.
31. Cline, M. R.; Mandel, S. M.; Platz, M. S. Identification of the Reactive Intermediates Produced upon Photolysis of p-Azidoacetophenone and its Tetrafluoro Analogue in Aqueous and Organic Solvents: Implications for Photoaffinity Labeling. Biochemistry 2007, 46, 1981-1987.
32. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Springer Science: New York, 2006.
33. Moerner, W. E.; Fromm, D. P. Methods of Single-Molecule Fluorescence Spectroscopy and Microscopy. Rev. Sci. Instrum. 2003, 74, 3597-3619.
34. Vrljic, M.; Nishimura, S. Y.; Moerner, W. E.; McConnell, H. M. Cholesterol Depletion Suppresses the Translational Diffusion of Class II Major Histocompatibility Complex Proteins in the Plasma Membrane. Biophys. J. 2005, 88, 334-347.
35. Bartoszewska, B.; Szczerek, I. Synthesis and use of 2,6-B. is(pAzidobenzylidene)Cyclohexanone. Organika 1979, 31-5.
36. Moerner, W. E.; Twieg, R. J.; Kline, D. W.; He, M. Fluorophore Compounds and Their Use in Biological Systems. US Patent Application 2005, Application number 10/604,282.
37. Pavani, S. R. P.; Thompson, M. A.; Biteen, J. S.; Lord, S. J.; Liu, N.; Twieg, R. J.; Piestun, R.; Moerner, W. E. Three-Dimensional, SingleMolecule Fluorescence Imaging Beyond the Diffraction Limit by using a Double-Helix Point Spread Function. Proc Nat. Acad. Sci. U.S.A. 2009, 106, 2995-2999.
38. Keana, J. F. W.; Cai, S. X. New Reagents for Photoaffinity Labeling: Synthesis and Photolysis of Functionalized Perfluorophenyl Azides. J. Org. Chem. 1990, 55, 3640-3647.
39. Keana, J. F. W.; Cai, S. X. Functionalized Perfluorophenyl Azides: New Reagents for Photoaffinity Labeling. J. Fluorine Chem. 1989, 43, 151154.
40. Stromgaard, K.; Saito, D. R.; Shindou, H.; Ishii, S.; Shimizu, T.; Nakanishi, K. Ginkgolide Derivatives for Photolabeling Studies: Preparation and Pharmacological Evaluation. J. Med. Chem. 2002, 45, 4038-4046.
41. Wiegand, M.; Lindhorst, T. K. Synthesis of Photoactive AlphaMannosides and Mannosyl Peptides and their Evaluation for Lectin Labeling. Eur: J. Org. Chem. 2006, 2006, 4841-4851.
42. Hassner, A.; Birnbaum, D.; Loew, L. M. Charge-Shift Probes of Membrane Potential. Synthesis. J. Org. Chem. 1984, 49, 2546-2551.
43. Thompson, R. E.; Larson, D. R.; Webb, W. W. Precise Nanometer Localization Analysis for Individual Fluorescent Probes. Biophys. J. 2002, 82, 2775-2783.
44. Ober, R. J.; Ram, S.; Ward, E. S. Localization Accuracy in SingleMolecule Microscopy. Biophys. J. 2004, 86, 1185-1200.
45. Nyquist, H. Certain Topics in Telegraph Transmission Theory. Tram. AIEE 1928, 47, 617-644.
46. Shannon, C. E. Communication in the Presence of Noise. Proc. IRE 1949, 37, 10-21.
47. Shroff, H.; Galbraith, C. G.; Galbraith, J. A.; Betzig, E. Live-Cell Photoactivated Localization Microscopy of Nanoscale Adhesion Dynamics. Nat. Methods 2008, 5, 417-423.
48. Shroff, H.; Galbraith, C. G.; Galbraith, J. A.; White, H.; Gillette, J.; Olenych, S.; Davidson, M. W.; Betzig, E. Dual-Color Superresolution Imaging of Genetically Expressed Probes within Individual Adhesion Complexes. Proc. Nat. Acad. Sci. U.S.A. 2007, 104, 20308-20313.
49. Biteen, J. S.; Thompson, M. A.; Tselentis, N. K.; Bowman, G. R.; Shapiro, L.; Moerner, W. E. Super-Resolution Imaging in Live Caulobacter Crescentus Cells using Photoswitchable EYFP. Nat. Methods 2008, 5, 947949.
50. Kotzyba-Hibert, F.; Kapfer, I.; Goeldner, M. Recent Trends in Photoaffinity Labeling. Angew. Chem., Int. Ed. 1995, 34, 1296-1312.
51. Vodovozova, E. Photoaffinity Labeling and its Application in Structural Biology. Biochemistry (Moscow) 2007, 72, 1-20.
52. Dormán, G.; Prestwich, G. D. Using Photolabile Ligands in Drug Discovery and Development. Trends Biotechnol. 2000, 18, 64-77.
53. Baruah, H.; Puthen veetil, S.; Choi, Y.; Shah, S.; Ting, A. Y. An Engineered Aryl Azide Ligase for Site-Specific Mapping of Protein-Protein Interactions through Photo-Cross-L.inking. Angew. Chem., Int. Ed. 2008, 47, 7018-7021.
54. Dockter, M. E. Fluorescent Photochemical Surface Labeling of Intact Human Erythrocytes. J. Biol. Chem. 1979, 254, 2161-2164.
55. Dreyfuss, G.; Schwartz, K.; Blout, E. R.; Barrio, J. R.; Liu, F.; Leonard, N. J. Fluorescent Photoaffinity Labeling: Adenosine 3',5'-Cyclic Monophosphate Receptor Sites. Proc Natl. Acad Sci. U.S.A. 1978, 75, 1199-1203.
56. Thevenin, B.; Shahrokh, Z.; Williard, R.; Fujimoto, E.; Kang, J.; Ikemoto, N.; Shohet, S. A Novel Photoactivatable Cross-Linker for the Functionally-Directed Region-Specific Fluorescent Labeling of Proteins. Eur. J. Biochem. 1992, 206, 471-7.
57. Moreland, R. B.; Dockter, M. E. Preparation and Characterization of 3-Azido-2,7-Naphthalene Disulfonate: A Photolabile Fluorescent Precursor Useful, as a Hydrophilic Surface Probe. Anal. Biochem. 1980, 103, 2632.
58. Angelides, K. J. Application of Photoactivatable Fluorescent ActiveSite Directed Probes to Serine-Containing Enzymes. Biochim. Biophys. Acta Protein Struct. 1981, 669, 149-156.