Collective fluorescence switching of counterion-assembled dyes in polymer nanoparticles

Nature Communications

Volumn 5, Issue , 2014, Pages

  Reisch, Andreas ^a   Didier, Pascal ^a   Richert, Ludovic ^a   Oncul, Sule ^a   Arntz, Youri ^a   Mély, Yves ^a   Klymchenko, Andrey S ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COUNTERION; FLUORESCENT DYE; FLUORINATED TETRAPHENYLBORATE; INORGANIC SALT; IONIC LIQUID; NANOMATERIAL; OCTADECYL RHODAMINE B; POLYMER; QUANTUM DOT; UNCLASSIFIED DRUG; NANOPARTICLE; OCTADECYL RHODAMINE B CHLORIDE; RHODAMINE; TETRAPHENYLBORON;

BIODEGRADATION; DYE; ENERGY EFFICIENCY; FLUORESCENCE; PARTICLE SIZE; POLYMER; RESOLUTION; SIGNAL-TO-NOISE RATIO; TOXICITY;

ARTICLE; BRIGHTNESS; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYTOTOXICITY TEST; ENERGY TRANSFER; EXCITATION; FLUORESCENCE; FLUORESCENCE SWITCHING; HUMAN; HUMAN CELL; LIGHT; SIGNAL NOISE RATIO; ATOMIC FORCE MICROSCOPY; CHEMISTRY; DIAGNOSTIC USE; FLUORESCENCE MICROSCOPY; NANOTECHNOLOGY;

FLUORESCENT DYES; MICROSCOPY, ATOMIC FORCE; MICROSCOPY, FLUORESCENCE; NANOPARTICLES; NANOTECHNOLOGY; POLYMERS; RHODAMINES; SIGNAL-TO-NOISE RATIO; TETRAPHENYLBORATE;

EID: 84902245633     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms5089     Document Type: Article

References (56)

1. Davis, M. E., Chen, Z. & Shin, D. M. Nanoparticle therapeutics: an emerging treatment modality for cancer. Nat. Rev. Drug Discov. 7, 771-782 (2008).
2. Michalet, X. et al. Quantum dots for live cells, in vivo imaging, and diagnostics. Science 307, 538-544 (2005). (Pubitemid 40165671)
3. Medintz, I. L., Uyeda, H. T., Goldman, E. R. & Mattoussi, H. Quantum dot bioconjugates for imaging, labelling and sensing. Nat. Mater. 4, 435-446 (2005). (Pubitemid 40774047)
4. Bonacchi, S. et al. Luminescent silica nanoparticles: extending the frontiers of brightness. Angew. Chem. Int. Ed. 50, 4056-4066 (2011).
5. Sun, Y. P. et al. Quantum-sized carbon dots for bright and colorful photoluminescence. J. Am. Chem. Soc. 128, 7756-7757 (2006).
6. Jain, R. A. The manufacturing techniques of various drug loaded biodegradable poly(lactide-co-glycolide) (PLGA) devices. Biomaterials 21, 2475-2490 (2000).
7. Wagh, A. et al. Polymeric nanoparticles with sequential and multiple FRET cascade mechanisms for multicolor and multiplexed imaging. Small 9, 2129-2139 (2013).
8. Wagh, A., Qian, S. Y. & Law, B. Development of biocompatible polymeric nanoparticles for in vivo NIR and FRET imaging. Bioconjug. Chem. 23, 981-992 (2012).
9. Kasha, M., Rawls, H. R. & El-Bayoumi, M. A. The exciton model in molecular spectroscopy. Pure Appl. Chem. 11, 371-392 (1965).
10. Kaeser, A. & Schenning, A. P. H. J. Fluorescent nanoparticles based on selfassembled π-conjugated systems. Adv. Mater. 22, 2985-2997 (2010).
11. Nguyen, T. Q., Wu, J., Doan, V., Schwartz, B. J. & Tolbert, S. H. Control of energy transfer in oriented conjugated polymer-mesoporous silica composites. Science 288, 652-656 (2000). (Pubitemid 30241564)
12. Bopp, M. A., Sytnik, A., Howard, T. D., Cogdell, R. J. & Hochstrasser, R. M. The dynamics of structural deformations of immobilized single light-harvesting complexes. Proc. Natl Acad. Sci. USA 96, 11271-11276 (1999). (Pubitemid 29487370)
13. Peng, H. Q. et al. Artificial light-harvesting system based on multifunctional surface-cross-linked micelles. Angew. Chem. Int. Ed. 51, 2088-2092 (2012).
14. Menke, S. M., Luhman, W. A. & Holmes, R. J. Tailored exciton diffusion in organic photovoltaic cells for enhanced power conversion efficiency. Nat. Mater. 12, 152-157 (2013).
15. Achyuthan, K. E. et al. Fluorescence superquenching of conjugated polyelectrolytes: applications for biosensing and drug discovery. J. Mater. Chem. 15, 2648-2656 (2005). (Pubitemid 41048659)
16. Thomas III, S. W., Joly, G. D. & Swager, T. M. Chemical sensors based on amplifying fluorescent conjugated polymers. Chem. Rev. 107, 1339-1386 (2007). (Pubitemid 46736542)
17. Jones, R. M., Bergstedt, T. S., Thomas Buscher, C., McBranch, D. & Whitten, D. Superquenching and its applications in J-aggregated cyanine polymers. Langmuir 17, 2568-2571 (2001). (Pubitemid 35330502)
18. Dickson, R. M., Cubittt, A. B., Tsient, R. Y. & Moerner, W. E. On/off blinking and switching behaviour of single molecules of green fluorescent protein. Nature 388, 355-358 (1997). (Pubitemid 27334808)
19. Nirmal, M. et al. Fluorescence intermittency in single cadmium selenide nanocrystals. Nature 383, 802-804 (1996). (Pubitemid 26372658)
20. Vanden Bout, D. A. et al. Discrete intensity jumps and intramolecular electronic energy transfer in the spectroscopy of single conjugated polymer molecules. Science 277, 1074-1077 (1997). (Pubitemid 27371623)
21. Hofkens, J. et al. Probing photophysical processes in individual multichromophoric dendrimers by single-molecule spectroscopy. J. Am. Chem. Soc. 122, 9278-9288 (2000).
22. Lin, H. et al. Collective fluorescence blinking in linear J-aggregates assisted by long-distance exciton migration. Nano Lett. 10, 620-626 (2010).
23. Würthner, F. Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures. Chem. Commun. 1564-1579 (2004). (Pubitemid 39089105)
24. Klymchenko, A. S. et al. Highly lipophilic fluorescent dyes in nano-emulsions: Towards bright non-leaking nano-droplets. RSC Adv. 2, 11876-11886 (2012).
25. Bwambok, D. K. et al. Near-infrared fluorescent NanoGUMBOS for biomedical imaging. ACS Nano 3, 3854-3860 (2009).
26. Yao, H. & Ashiba, K. Highly fluorescent organic nanoparticles of thiacyanine dye: a synergetic effect of intermolecular H-aggregation and restricted intramolecular rotation. RSC Adv. 1, 834-838 (2011).
27. Chen, L. D., Mandal, D., Pozzi, G., Gladysz, J. A. & Bühlmann, P. Potentiometric sensors based on fluorous membranes doped with highly selective ionophores for carbonate. J. Am. Chem. Soc. 133, 20869-20877 (2011).
28. Bakker, E. & Pretsch, E. Lipophilicity of tetraphenylborate derivatives as anionic sites in neutral carrier-based solvent polymeric membranes and lifetime of corresponding ion-selective electrochemical and optical sensors. Anal. Chim. Acta 309, 7-17 (1995).
29. Schubert, S., Delaney, Jr J. T. & Schubert, U. S. Nanoprecipitation and nanoformulation of polymers: from history to powerful possibilities beyond poly(lactic acid). Soft Matter 7, 1581-1588 (2011).
30. Astete, C. E. & Sabliov, C. M. Synthesis and characterization of PLGA nanoparticles. J. Biomater. Sci. Polym. Ed. 17, 247-289 (2006). (Pubitemid 47279194)
31. Macdonald, R. I. Characteristics of self-quenching of the fluorescence of lipidconjugated rhodamine in membranes. J. Biol. Chem. 265, 13533-13539 (1990).
32. Middleton, J. C. & Tipton, A. J. Synthetic biodegradable polymers as orthopedic devices. Biomaterials 21, 2335-2346 (2000).
33. Baldo, M. A., Soos, Z. G. & Forrest, S. R. Local order in amorphous organic molecular thin films. Chem. Phys. Lett. 347, 297-303 (2001). (Pubitemid 33628519)
34. Colby, K. A. et al. Electronic energy migration on different time scales: concentration dependence of the time-resolved anisotropy and fluorescence quenching of lumogen red in poly(methyl methacrylate). J. Phys. Chem. A 114, 3471-3482 (2010).
35. Yeow, E. K. L. et al. The dynamics of electronic energy transfer in novel multiporphyrin functionalized dendrimers: A time-resolved fluorescence anisotropy study. J. Phys. Chem. B 104, 2596-2606 (2000). (Pubitemid 33685476)
36. Berberan-Santos, M. N., Choppinet, P., Fedorov, A., Jullien, L. & Valeur, B. Multichromophoric cyclodextrins. 6. Investigation of excitation energy hopping by Monte-Carlo simulations and time-resolved fluorescence anisotropy. J. Am. Chem. Soc. 121, 2526-2533 (1999). (Pubitemid 29153463)
37. Berberan-Santos, M. N. et al. Multichromophoric cyclodextrins. 3. Investigation of dynamics of energy hopping by frequency-domain fluorometry. J. Phys. Chem. 100, 15-20 (1996). (Pubitemid 126817228)
38. Vogelsang, J. et al. A reducing and oxidizing system minimizes photobleaching and blinking of fluorescent dyes. Angew. Chem. Int. Ed. 47, 5465-5469 (2008).
39. Orrit, M. Chemical and physical aspects of charge transfer in the fluorescence intermittency of single molecules and quantum dots. Photochem. Photobiol. Sci. 9, 637-642 (2010).
40. Frantsuzov, P., Kuno, M., Jankó, B. & Marcus, R. A. Universal emission intermittency in quantum dots, nanorods and nanowires. Nat. Phys. 4, 519-522 (2008).
41. Cichos, F., von Borczyskowski, C. & Orrit, M. Power-law intermittency of single emitters. Curr. Opin. Colloid Interface Sci. 12, 272-284 (2007). (Pubitemid 350001266)
42. Rust, M. J., Bates, M. & Zhuang, X. Sub-diffraction-limit imaging by stochastic optical reconstruction microscopy (STORM). Nat. Methods 3, 793-795 (2006). (Pubitemid 44445825)
43. van de Linde, S. et al. Direct stochastic optical reconstruction microscopy with standard fluorescent probes. Nat. Protoc. 6, 991-1009 (2011).
44. Shroff, H., Galbraith, C. G., Galbraith, J. A. & Betzig, E. Live-cell photoactivated localization microscopy of nanoscale adhesion dynamics. Nat. Methods 5, 417-423 (2008). (Pubitemid 351619100)
45. van de Linde, S., Wolter, S., Heilemann, M. & Sauer, M. The effect of photoswitching kinetics and labeling densities on super-resolution fluorescence imaging. J. Biotechnol. 149, 260-266 (2010).
46. Würthner, F., Kaiser, T. E. & Saha-Möller, C. R. J-aggregates: From serendipitous discovery to supramolecular engineering of functional dye materials. Angew. Chem. Int. Ed. 50, 3376-3410 (2011).
47. Hoeben, F. J. M., Jonkheijm, P., Meijer, E. W. & Schenning, A.P.H.J. About supramolecular assemblies of p-conjugated systems. Chem. Rev. 105, 1491-1546 (2005).
48. Zondervan, R., Kulzer, F., Orlinskii, S. B. & Orrit, M. Photoblinking of rhodamine 6G in poly(vinyl alcohol): Radical dark state formed through the triplet. J. Phys. Chem. A 107, 6770-6776 (2003).
49. De Schryver, F. C. et al. Energy dissipation in multichromophoric single dendrimers. Acc. Chem. Res. 38, 514-522 (2005). (Pubitemid 41128403)
50. Genovese, D. et al. Energy transfer processes in dye-doped nanostructures yield cooperative and versatile fluorescent probes. Nanoscale 6, 3022-3036 (2014).
51. Adronov, A. & Frechet, J. M. J. Light-harvesting dendrimers. Chem. Commun. 1701-1710 (2000).
52. Rao, K. V., Datta, K. K. R., Eswaramoorthy, M. & George, S. J. Light-harvesting hybrid assemblies. Chemistry 18, 2184-2194 (2012).
53. Danhier, F. et al. PLGA-based nanoparticles: an overview of biomedical applications. J. Control Release 161, 505-522 (2012).
54. Velapoldi, R. A. & Tonnesen, H. H. Corrected emission spectra and quantum yields for a series of fluorescent compounds in the visible spectral region. J. Fluoresc. 14, 465-472 (2004).
55. Godet, J. et al. Specific implications of the HIV-1 nucleocapsid zinc fingers in the annealing of the primer binding site complementary sequences during the obligatory plus strand transfer. Nucleic Acids Res. 39, 6633-6645 (2011).
56. Livesey, A. K. & Brochon, J. C. Analyzing the distribution of decay constants in pulse-fluorimetry using the maximum entropy method. Biophys. J. 52, 693-706 (1987).