Fluorene-based fluorescent probes with high two-photon action cross-sections for biological multiphoton imaging applications

Journal of Biomedical Optics

Volumn 10, Issue 5, 2005, Pages

  Schafer Hales, Katherine J ^a   Belfield, Kevin D ^a,b   Yao, Sheng ^a   Frederiksen, Peter K ^a,b   Hales, Joel M ^a,b   Kolattukudy, Pappachan E ^a  

^a UNIVERSITY OF CENTRAL FLORIDA COLLEGE OF MEDICINE   (United States)

^b UNIVERSITY OF CENTRAL FLORIDA   (United States)

Author keywords

Multiphoton bioimaging; Reactive dyes; Two photon fluorescence

Indexed keywords

DYES; LIGHT ABSORPTION; MEDICAL IMAGING; MICROSCOPIC EXAMINATION; MULTIPHOTON PROCESSES; PROBES;

MULTIPHOTON BIOIMAGING; REACTIVE DYES; TWO-PHOTON FLUORESCENCE;

FLUORESCENCE;

BOS TAURUS;

FLUORENE DERIVATIVE; FLUORESCENT DYE;

ANIMAL; ARTICLE; CELL LINE; CYTOLOGY; GENETIC PROCEDURES; HEART MUSCLE CELL; IMAGE ENHANCEMENT; METHODOLOGY; MULTIPHOTON MICROSCOPY; PHOTON; RAT; REPRODUCIBILITY; SENSITIVITY AND SPECIFICITY; STAINING;

ANIMALS; CELL LINE; FLUORENES; FLUORESCENT DYES; IMAGE ENHANCEMENT; MICROSCOPY, FLUORESCENCE, MULTIPHOTON; MOLECULAR PROBE TECHNIQUES; MYOCYTES, CARDIAC; PHOTONS; RATS; REPRODUCIBILITY OF RESULTS; SENSITIVITY AND SPECIFICITY; STAINING AND LABELING;

EID: 33645459275     PISSN: 10833668     EISSN: 15602281     Source Type: Journal    
DOI: 10.1117/1.2104528     Document Type: Article

References (49)

1. W. Denk, J. H. Strickler, and W. W. Webb, "Two-photon laser scanning fluorescence microscopy," Science 249, 73-76 (1990).
2. M. Goppert-Mayer, "Uber elementarakte mit zwei quantensprungen, " Ann. Phys. 9, 273-294 (1931).
3. J. R. Lakowicz, in Topics in Fluorescence Spectroscopy Vol. 5: Non- Linear and Two-Photon-Induced Fluorescence, Plenum Press, New York (1997).
4. W. Denk, D. W. Piston, and W. W. Webb, "Two-photon molecular excitation in laser scanning microscopy," Chap. 28 in Handbook of Biological Confocal Microscopy, J. B. Pawley, Ed., pp. 445-458, Plenum Press, New York (1995).
5. A. Periasamy and P. T. So, Eds., Multiphoton Microscopy in the Biomedical Sciences III, SPIE Press, Bellingham, WA (2003).
6. R. M. Williams, W. R. Zipfel, and W. W. Webb, "Multiphoton microscopy in biological research," Curr. Opin. Chem. Biol. 5, 603-608 (2001). (Pubitemid 32907614)
7. K. Konig, "Multiphoton microscopy in life sciences," J. Microsc. 200, 83-104 (2000).
8. D. W. Piston, "Imaging living cells and tissues by two-photon excitation microscopy," Trends Cell Biol. 9, 66-69 (1999). (Pubitemid 29151795)
9. F. Bestvater, E. Spiess, G. Stobrawa, M. Hacker, T. Feurer, T. Porwol, U. Berchner-Pfannschmidt, C. Wotzlaw, and H. Acker, "Twophoton fluorescence absorption and emission spectra of dyes relevant for cell imaging," J. Microsc. 208, 108-115 (2002). (Pubitemid 35356983)
10. T. R. Neu, U. Kuhlicke, and J. R. Lawrence, "Assessment of fluorochromes for two-photon laser scanning microscopy of biofilms," Appl. Environ. Microbiol. 68, 901-909 (2002). (Pubitemid 34113083)
11. M. A. Albota, C. Xu, and W. W. Webb, "Two-photon fluorescence excitation cross sections of biomolecular probes from 690 to 960," Appl. Opt. 37, 7352-7356 (1998). (Pubitemid 128659481)
12. C. Xu, W. Zipfel, J. B. Shear, R. Williams, and W. W. Webb, "Multiphoton fluorescence excitation: new spectral windows for biological nonlinear microscopy," Proc. Natl. Acad. Sci. U.S.A. 93, 10763-10768 (1996). (Pubitemid 26333063)
13. C. Xu, and W. W. Webb, "Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm," J. Opt. Soc. Am. B 13, 481-491 (1996).
14. K. D. Belfield, A. R. Morales, B.-S. Kang, J. M. Hales, D. J. Hagan, E. W. Van Stryland, V. M. Chapela, and J. Percino, "Synthesis, characterization and optical properties of two-photon absorbing fluorene derivatives," Chem. Mater. 16, 4634-4641 (2004)
15. K. D. Belfield, A. R. Morales, J. M. Hales, D. J. Hagan, E. W. Van Stryland, V. M. Chapela, and J. Percino, "Linear and two-photon photophysical properties of a series of symmetrical diphenylaminofluorenes, " Chem. Mater. 16, 2267-2273 (2004)
16. K. D. Belfield, M. V. Bondar, O. V. Przhonska, and K. J. Schafer, "Photostability of a series of twophoton absorbing fluorene derivatives," J. Photochem. Photobiol., A, 162, 489-496 (2004)
17. K. D. Belfield, M. V. Bondar, O. V. Przhonska, and K. J. Schafer, "Photochemical properties of 7-benzothiazol-2-yl- 9,9-didecylfluoren-2- yldiphenylamine under one- and two-photon excitation," J. Photochem. Photobiol., A, 162 569-574 (2004)
18. K. D. Belfield, M. V. Bondar, O. V. Przhonska, and K. J. Schafer, "Steadystate spectroscopic and fluorescence lifetime measurements of new two-photon absorbing fluorene derivatives," J. Fluoresc. 12, 449-454 (2002)
19. K. D. Belfield, M. V. Bondar, O. V. Przhonska, K. J. Schafer, and W. Mourad, "Spectral properties of several fluorene derivatives with potential as two-photon fluorescent dyes," J. Lumin. 97, 141-146 (2002) (Pubitemid 34524878)
20. K. D. Belfield, K. J. Schafer, W. Mourad, and B. A. Reinhardt, "Synthesis of new two-photon absorbing fluorene derivatives via Cu-mediated Ullmann condensation," J. Org. Chem. 65, 4475-4481 (2000) (Pubitemid 30620552)
21. K. D. Belfield, D. J. Hagan, E. W. Van Stryland, K. J. Schafer, and R. A. Negres, "New two-photon absorbing fluorene derivatives: synthesis and nonlinear optical characterization," Org. Lett. 1, 1575-1578 (1999)
22. K. D. Belfield and K. J. Schafer, "A new photosensitive polymeric material for WORM optical data storage using multichannel two-photon fluorescence readout," Chem. Mater. 14, 3656-3662 (2002).
23. O. Mongin, L. Porres, L. Moreaux, J. Mertz, and M. Blanchard- Desce, "Synthesis and photophysical properties of new conjugated fluorophores designed for two-photon-excited fluorescence," Org. Lett. 4, 719-722 (2002).
24. A. Abbotto, L. Beverina, R. Bozio, A. Facchetti, C. Ferrante, G. A. Panani, D. Pedron, and R. Signorini, "Novel heterocycle-based twophoton absorbing dyes," Org. Lett. 4, 1495-1498 (2002).
25. M. Rumi, J. E. Ehrlich, A. A. Heikal, J. W. Perry, S. Barlow, Z. Hu, D. McCord-Maughon, T. C. Parker, H. Rockel, S. Thayumanavan, S. R. Marder, D. Beljonne, and J.-L. Bredas, "Structure-property relationships for two-photon absorbing chromophores: Bis-donor diphenylpolyene and Bisstyrylbenzene derivatives," J. Am. Chem. Soc. 122, 9500-9510 (2000)
26. M. Albota, D. Beljonne, J.-L. Bredas, J. E. Ehrlich, J.-Y. Fu, A. A. Heikal, S. E. Hess, T. Kogej, M. D. Levin, S. R. Marder, D. McCord-Maughon, J. W. Perry, H. Rockel, M. Rumi, G. Subramaniam, W. W. Webb, X-L. Wu, and C. Xu, "Design of organic molecules with large two-photon absorption cross sections," Science 281, 1653-1656 (1998). (Pubitemid 28435576)
27. B. A. Reinhardt, L. L Brott, S. J. Clarson, A. G. Dillard, J. C. Bhatt, R. Kannan, L. Yuan, G. S. He, and P. N. Prasad, "Highly active two-photon dyes: design, synthesis, and characterization toward application," Chem. Mater. 10, 1863-1874 (1998). (Pubitemid 128485501)
28. P. C. Cheng, S. J. Pan, K.-S. Kim, W. S. Liou, and M. S. Park, "Highly efficient upconverters for multiphoton fluorescence microscopy," J. Microsc. 189, 199-212 (1998). (Pubitemid 28172725)
29. H. Y. Woo, J. W. Hong, B. Liu, A. Mikhailovsky, D. Korystov, and G. C. Bazan, "Water-soluble 2.2paracyclophane chromophores with large two-photon action cross sections," J. Am. Chem. Soc. 123, 820-821 (2005). (Pubitemid 40144268)
30. A. Margineanu, J. Hofkens, M. Cotlet, S. Habuchi, A. Stefan, J. Qu, C. Kohl, K. Mullen, J. Vercammen, Y. Engelborghs, T. Gensch, and F. C. De Schryver, "Photophysics of a water-soluble rylene dye: comparison with other fluorescent molecules for biological applications," J. Phys. Chem. B 108, 12242-12251 (2004).
31. S. J. K. Pond, O. Tsutsumi, M. Rumi, O. Kwon, E. Zojer, J.-L. Bredas, S. R. Marder, and J. W. Perry, "Metal-ion sensing fluorophores with large two-photon absorption cross sections: aza-crown ether substituted donor-acceptor-donor distyrlbenzenes," J. Am. Chem. Soc. 136, 9291-9306 (2004). (Pubitemid 38989447)
32. H. M. Kim, M-Y. Jeong, H. C. Ahn, S.-J. Jeon, and B. R. Cho, "Two-photon sensor for metal ions derived from azacrown ether," J. Org. Chem. 69, 5749-5751 (2004). (Pubitemid 39079633)
33. A. Miyawaki, O. Griesbeck, R. Heim, and R. Y. Tsien, "Dynamic and quantitative Ca2+ measurements using improved chameleons," Proc. Natl. Acad. Sci. U.S.A., 96, 2135-2140 (1999) (Pubitemid 29117880)
34. S. R. Adams, V. Lev- Ram, R. Y. Tsien, and Y. Roger, "A new caged Ca2+, azid-1, is far more photosensitive than nitrobenzyl-based chelators," Chem. Biol. 4, 867-878 (1997). (Pubitemid 28000626)
35. M. Taki, J. L. Wolford, and T. V. O'Halloran, "Emission ratiometric imaging of intracellular zinc: design of a benzoxazole fluorescent sensor and its application in two-photon microscopy," J. Am. Chem. Soc. 126, 712-713 (2004). (Pubitemid 38114344)
36. C. J. Chang, E. M. Nolan, J. Jaworski, K.-I. Okamoto, Y. Hayashi, M. Sheng, and S. J. Lippard, "ZP8, a neuronal zinc sensor with improved dynamic range; imaging zinc in hippocampal slices with twophoton microscopy," Inorg. Chem. 43, 6774-6779 (2004).
37. S. Charier, O. Ruel, J.-B. Baudin, D. Alcor, J.-F. Alleman, A. Meglio, and L. Jullien, "An efficient fluorescent probe for ratiometric pH measurements in aqueous solutions," Angew. Chem., Int. Ed. 43, 4785-4788 (2004). (Pubitemid 39278590)
38. M. H. V. Werts, S. Gmouh, O. Mongin, H. Pons, and M. Blanchard- Desce, "Strong Modulation of two-photon excited fluorescence of quadripolar dyes by deprotonation," J. Am. Chem. Soc. 126, 16294-16295 (2004). (Pubitemid 40081907)
39. G. Piszczek, B. P. Maliwal, I. Gryczynski, J. Dattelbaum, and J. R. Lakowicz, "Multiphoton ligand-enhanced excitation of lanthanides," J. Fluoresc. 11, 101-107 (2001). (Pubitemid 33818251)
40. T. Y. Ohulchanskyy, H. E. Pudavar, S. M. Yarmoluk, V. M. Yashchuk, E. J. Bergey, and P. N. Prasad, "A monomethine cyanine dye cyan 40 for two-photon-excited fluorescence detection of nucleic acids and their visualization in live cells," Photochem. Photobiol. 77, 138-145 (2003).
41. N. J. Meltola, R. Wahlroos, and A. E. Soini, "Hydrophilic labeling reagents of dipyrrylmethene-BF2 dyes for two-photon excited fluorometry: syntheses and photophysical characterization," J. Fluoresc. 14, 635-647 (2004)
42. N. J. Meltola, A. E. Soini, and P. E. Hanninen, "Syntheses of novel dipyrrylmethene-BF2 dyes and their performance as labels in two-photon excited fluoroimmunoassay," J. Fluoresc. 14, 129-138 (2004).
43. J. M. Hales, D. J. Hagan, E. W. Van Stryland, K. J. Schafer, A. M. Morales, K. D. Belfield, P. Pacher, O. Kwon, and J. L. Bredas, "Resonant enhancement of two-photon absorption in substituted fluorene molecules," J. Chem. Phys. 121, 3152-3160 (2004)
44. J. M. Hales, K. J. Schafer, A. M. Morales, K. D. Belfield, D. J. Hagan, and E. W. Van Stryland, "Nonlinear optical spectroscopic characterization of a series of fluorene derivatives," Proc. SPIE 5211, 21-30, (2003).
45. J. Lackowicz, in Principles of Fluorescence Spectroscopy, Plenum Press, New York (1999).
46. R. Bacallao and E. H. K. Stelzer, "Preservation of biological specimens for observation in a confocal fluorescence microscope and operational principles of confocal fluorescence microscopy," Methods Cell Biol. 31, 437-452 (1989).
47. J. Garin, E. Melendez, F. L. Merchan, P. Merino, J. Orduna, and T. Tejere, "Synthesis of unsymmetrical diheteroarylbenzenes: benzazole and quinazoline derivatives," J. Heterocycl. Chem. 28, 359-363 (1991).
48. R. P. Haugland, in Methods in Molecular Biology: Monoclonal Antibody Protocols, Vol. 45, Chap. 22, W. C. Davis, Ed., pp. 205-214, Humana Press, Totowa, N. J. (1995).
49. T. A. Bewley, "A novel procedure for determining protein concentrations from absorption spectra of enzyme digests," Anal. Biochem. 123, 55-65 (1982). (Pubitemid 12053338)