Photophysical properties of acene DCDHF fluorophores: Long-wavelength single-molecule emitters designed for cellular imaging

Journal of Physical Chemistry A

Volumn 111, Issue 37, 2007, Pages 8934-8941

  Lord, Samuel J ^a   Lu, Zhikuan ^b   Wang, Hui ^b   Willets, Katherine A ^a,c   Schuck, P James ^a,d   Lee, Hsiao Lu D ^a   Nishimura, Stefanie Y ^a   Twieg, Robert J ^b   Moerner, W E ^a  

^a STANFORD UNIVERSITY   (United States)

^b KENT STATE UNIVERSITY   (United States)

^c UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^d LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DICYANOMETHYLENEDIHYDROFURAN (DCDHF); PHOTOPHYSICAL PROPERTIES; SINGLE-MOLECULE EMITTERS;

ANTHRACENE; ELECTRON EMISSION; MOLECULAR DYNAMICS; PHYSICAL PROPERTIES; QUANTUM YIELD; SENSITIVITY ANALYSIS;

FLUOROPHORES;

ANTHRACENE DERIVATIVE; DCDHF A 6; DCDHF N 6; DCDHF-A-6; DCDHF-N-6; DICYANOMETHYLENEDIHYDROFURAN; FLUORESCENT DYE; FURAN DERIVATIVE; NAPHTHALENE DERIVATIVE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CELL MEMBRANE; CHEMICAL STRUCTURE; CHEMISTRY; PHOTOCHEMISTRY; PHYSICAL CHEMISTRY; SPECTROSCOPY; VISCOSITY;

ANTHRACENES; CELL MEMBRANE; CHEMISTRY, PHYSICAL; FLUORESCENT DYES; FURANS; MOLECULAR STRUCTURE; NAPHTHALENES; NITRILES; PHOTOCHEMISTRY; SPECTRUM ANALYSIS; VISCOSITY;

EID: 34948891112     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0712598     Document Type: Article

References (36)

1. Sako, Y.; Yanagida, T. Review: Single-Molecule Visualization in Cell Biology. Nat. Rev. Mol. Cell Biol. 2003, 4, SS1-SS5.
2. Moerner, W. E. Optical Measurements of Single Molecules in Cells. TrAC, Trends Anal. Chem. 2003, 22, 544-548.
3. Tinnefeld, P.; Sauer, M. Branching Out of Single-Molecule Fluorescence Spectroscopy: Challenges for Chemistry and Influence on Biology. Angew. Chem., Int. Ed. 2005, 44, 2642-2671.
4. Schutz, G. J.; Kada, G.; Pastushenko, V. P.; Schindler, H. Properties of Lipid Microdomains in a Muscle Cell Membrane Visualized by Single Molecule Microscopy. EMBO J. 2000, 19, 892-901.
5. Vrljic, M.; Nishimura, S. Y.; Brasselet, S.; Moerner, W. E.; McConnell, H. M. Translational Diffusion of Individual Class II MHC Membrane Proteins in Cells. Biophys. J. 2002, 83, 2681-2692.
6. Lakadamyali, M.; Rust, M. J.; Babcock, H. P.; Zhuang, X. Visualizing Infection of Individual Influenza Viruses. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 9280-9285.
7. Kim, S. Y.; Gitai, Z.; Kinkhabwala, A.; Shapiro, L.; Moerner, W. E. Single Molecules of the Bacterial Actin MreB Undergo Directed Treadmilling Motion in Caulobacter Crescentus. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 10929-10934.
8. Xie, X. S.; Yu, J.; Yang, W. Y. Living Cells as Test Tubes. Science 2006, 312, 228-230.
9. Jung, C.; Muller, B. K.; Lamb, D. C.; Nolde, F.; Mullen, K.; Brauchte, C. A New Photostable Terrylene Diimide Dye for Applications in Single Molecule Studies and Membrane Labeling. J. Am. Chem. Soc. 2006, 128, 5283-5291.
10. Toutchkine, A.; Kraynov, V.; Hahn, K. Solvent-Sensitive Dyes to Report Protein Conformational Changes in Living Cells. J. Am. Chem. Soc. 2003, 125, 4132-4145.
11. Jaiswal, J. K.; Simon, S. M. Potentials and Pitfalls of Fluorescent Quantum Dots for Biological Imaging. Trends Cell Biol. 2004, 14, 497.
12. Chudakov, D. M.; Lukyanov, S.; Lukyanov, K. A. Fluorescent Proteins as a Toolkit for in Vivo Imaging. Trends Biotechnol. 2005, 23, 605-613.
13. Lee, T.; Gonzales, J. I.; Zheng, J.; Dickson, R. Single-Molecule Optoelectronics. Acc Chem. Res. 2005, 38, 534-541.
14. 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.
15. 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.
16. Willets, K. A.; Callis, P. R.; Moerner, W. E. Experimental and Theoretical Investigations of Environmentally Sensitive Single-Molecule Fluorophores. J. Phys. Chem. B 2004, 108, 10465-10473.
17. Schuck, P. J.; Willets, K. A.; Fromm, D. P.; Twieg, R. J.; Moerner, W. E. A Novel Fluorophore for Two-Photon-Excited Single-Molecule Fluorescence. Chem. Phys. 2005, 318, 7-11.
18. Grabowski, Z. R.; Rotkiewicz, K.; Rettig, W. Structural Changes Accompanying Intramolecular Electron Transfer: Focus on Twisted Intramolecular Charge-Transfer States and Structures. Chem. Rev. 2003, 103, 3899-4031.
19. Jacobson, A.; Petric, A.; Hogenkamp, D.; Sinur, A.; Barrio, J. R. 1,1-Dicyano-2-[6-(dimethylamino)naphthalen-2-yl]propene (DDNP): A Solvent Polarity and Viscosity Sensitive Fluorophore for Fluorescence Microscopy. J. Am. Chem. Soc. 1996, 118, 5572-5579.
20. Harms, G. S.; Cognet, L.; Lommerse, P. H. M.; Blab, G. A.; Schmidt, T. Autofluorescent Proteins in Single-Molecule Research: Applications to Live Cell Imaging Microscopy. Biophys. J. 2001, 80, 2396-2408.
21. Lu, Z.; Lord, S. J.; Wang, H.; Moerner, W. E.; Twieg, R. J. Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor-Acceptor Anthracene Structure. J. Org. Chem. 2006, 71, 9651-9657.
22. Nishimura, S. Y.; Lord, S. J.; Klein, L. O.; Willets, K. A.; He, M.; Lu, Z. K.; Twieg, R. J.; Moerner, W. E. Diffusion of Lipid-Like Single-Molecule Fluorophores in the Cell Membrane. J. Phys. Chem. B 2006, 110, 8151-8157.
23. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Springer: New York, 2006.
24. Soper, S. A.; Nutter, H. L.; Keller, R. A.; Davis, L. M.; Shera, E. B. The Photophysical Constants of several Fluorescent Dyes Pertaining to Ultrasensitive Fluorescence Spectroscopy. Photochem. Photobiol. 1993, 57, 972-977.
25. Moerner, W. E.; Fromm, D. P. Methods of Single-Molecule Fluorescence Spectroscopy and Microscopy. Rev. Sci. Instrum. 2003, 74, 3597-3619.
26. Zander, C., Enderlein, J., Keller, R. A., Eds. Single-Molecule Detection in Solution: Methods and Applications; Wiley-VCH: Berlin, 2002.
27. Gubler, U.; He, M.; Wright, D.; Roh, Y.; Twieg, R. J.; Moerner, W. E. Monolithic Photorefractive Organic Glasses with Large Coupling Gain and Strong Beam Fanning. Adv. Mater. 2002, 14, 313-317.
28. He, M.; Twieg, R.; Ostroverkhova, O.; Gubler, U.; Wright, D.; Moerner, W. E. Dicyanomethylenedihydrofuran Photorefractive Materials. Proc. SPIE-Int. Soc. Opt. Eng. 2002, 4802, 9-20.
29. Wang, H.; Lu, Z.; Lord, S.; Willets, K.; Bertke, J.; Bunge, S.; Moerner, W.; Twieg, R. The Influence of Tetrahydroquinoline Rings in Dicyanomethylenedihydrofuran (DCDHF) Single-Molecule Fluorophores. Tetrahedron 2007, 63, 103-114.
30. Picard, J. P.; Elyusufi, A. A.; Calas, R.; Dunogues, J.; Duffaut, N. Enamines of Acylsilanes: An Easy Access from Alpha-Siloxynitriles. Organometallics 1984, 3, 1660-1665.
31. Weast, R. C., Ed. CRC Handbook of Chemistry and Physics; CRC Press: Boca Raton, FL, 1989.
32. Gordon, A. J.; Ford, R. A. The Chemist's Companion; Wiley: New York, 1972.
33. Hou, Y.; Bardo, A. M.; Martinez, C.; Higgins, D. A. Characterization of Molecular Scale Environments in Polymer Films by Single Molecule Spectroscopy. J. Phys. Chem. B 2000, 104, 212-219.
34. Siegel, J.; Elson, D. S.; Webb, S. E. D.; Lee, K. C. B.; Vlanclas, A.; Gambaruto, G. L.; Leveque-Fort, S.; Lever, M. J.; Tadrous, P. J.; Stamp, G. W. H.; Wallace, A. L.; Sandison, A.; Watson, T. F.; Alvarez, F.; French, P. M. W. Studying Biological Tissue with Fluorescence Lifetime Imaging: Microscopy, Endoscopy, and Complex Decay Profiles. Appl. Opt. 2003, 42, 2995-3004.
35. Peterman, E. J. G.; Brasselet, S.; Moerner, W. E. The Fluorescence Dynamics of Single Molecules of Green Fluorescent Protein. J. Phys. Chem. A 1999, 103, 10553-10560.
36. Wang, H.; Lu, Z.; Lord, S. J.; Moerner, W. E.; Twieg, R. J. Modifications of DCDHF Single Molecule Fluorophores to Impart Water Solubility. Tetrahedron Lett. 2007, 48, 3471-3474.