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Abstract:

A novel surface architecture was developed to generate biocompatible and stable photoswitchable quantum dots (psQDs). Photochromic diheteroarylethenes, which undergo thermally stable photoconversions between two forms with different spectral properties in organic solvents, were covalently linked to an amphiphilic polymer that self-assembles with the lipophilic chains surrounding commercial hydrophobic core-shell CdSe/ZnS QDs. This strategy creates a small (∼7 nm diameter) nanoparticle (NP) that is soluble in aqueous medium. The NP retains and even enhances the desirable properties of the original QD (broad excitation, narrow emission, photostability), but the brightness of its emission can be tailored by light. The modulation of emission monitored by steady-state and time-resolved fluorescence was 35-40%. The psQDs exhibit unprecedented photostability and fatigue resistance over at least 16 cycles of photoconversion. © 2011 American Chemical Society.

Registro:

Documento: Artículo
Título:Photoswitchable water-soluble quantum dots: PcFRET based on amphiphilic photochromic polymer coating
Autor:Díaz, S.A.; Menéndez, G.O.; Etchehon, M.H.; Giordano, L.; Jovin, T.M.; Jares-Erijman, E.A.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Laboratory of Cellular Dynamics, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Göttingen, Germany
Palabras clave:amphiphilic polymer; FRET; nanoparticle coating; photochromism; quantum dots; Amphiphilic polymers; Amphiphilics; Aqueous medium; CdSe/ZnS; Fatigue resistance; FRET; Hydrophobic core; nanoparticle coating; Novel surfaces; Photo-stability; Photo-switchable; Photochromic polymers; Photoconversion; Quantum Dot; quantum dots; Spectral properties; Thermally stable; Time-resolved fluorescence; Water soluble quantum dots; Nanoparticles; Organic solvents; Photochromism; Photopolymers; Plastic coatings; Polymers; Semiconductor quantum dots
Año:2011
Volumen:5
Número:4
Página de inicio:2795
Página de fin:2805
DOI: http://dx.doi.org/10.1021/nn103243c
Título revista:ACS Nano
Título revista abreviado:ACS Nano
ISSN:19360851
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_19360851_v5_n4_p2795_Diaz

Referencias:

  • Walling, M.A., Novak, J.A., Shepard, J.R.E., Quantum Dots for Live Cell and in vivo Imaging (2009) Int. J. Mol. Sci., 10, pp. 441-491
  • Medintz, I.L., Mattoussi, H., Quantum Dot-Based Resonance Energy Transfer and its Growing Application in Biology (2009) Phys. Chem. Chem. Phys., 11, pp. 17-45
  • Clapp, A.R., Medintz, I.L., Mattoussi, H., Förster Resonance Energy Transfer Investigations Using Quantum-Dot Fluorophores (2006) ChemPhysChem, 7, pp. 47-57
  • Morgner, F., Geissler, D., Stufler, S., Butlin, N.G., Lohmannsroben, H.G., Hildebrandt, N., A Quantum-Dot-Based Molecular Ruler for Multiplexed Optical Analysis (2010) Angew. Chem., Int. Ed., 49, pp. 7570-7574
  • Roberti, M.J., Giordano, L., Jovin, T.M., Jares-Erijman, E.A., FRET Imaging by k t/ k f (2011) ChemPhysChem, 12. , DOI: 10.1002/cphc.201000925
  • Giordano, L., Jovin, T.M., Irie, M., Jares-Erijman, E.A., Diheteroarylethenes as thermally stable photoswitchable acceptors in photochromic fluorescence resonance energy transfer (pcFRET) (2002) Journal of the American Chemical Society, 124 (25), pp. 7481-7489. , DOI 10.1021/ja016969k
  • Jares-Erijman, E.A., Jovin, T.M., FRET imaging (2003) Nature Biotechnology, 21 (11), pp. 1387-1395. , DOI 10.1038/nbt896
  • Marriott, G., Mao, S., Sakata, T., Ran, J., Jackson, D.K., Petchprayoon, C., Gomez, T.J., Aaron, H.L., Optical Lock-In Detection Imaging Microscopy for Contrast-Enhanced Imaging in Living Cells (2008) Proc. Natl. Acad. Sci. U. S. A., 105, pp. 17789-17794
  • Yan, Y., Marriott, M.E., Petchprayoon, C., Marriott, G., Optical Switch Probes and Optical Lock-in Detection (OLID) Imaging Microscopy: High-Contrast Fluorescence Imaging within Living Systems (2011) Biochem. J., 433, pp. 411-422
  • Reits, E.A.J., Neefjes, J.J., From Fixed to FRAP: Measuring Protein Mobility and Activity in Living Cells (2001) Nat. Cell Biol., 3, pp. 145-E147
  • Levitt, J.A., Matthews, D.R., Ameer-Beg, S.M., Suhling, K., Fluorescence Lifetime and Polarization-Resolved Imaging in Cell Biology (2009) Curr. Opin. Biotechnol., 20, pp. 28-36
  • Patterson, G., Davidson, M., Manley, S., Lippincott-Schwartz, J., Superresolution Imaging Using Single-Molecule Localization (2010) Annu. Rev. Phys. Chem., 61, pp. 345-367
  • Bates, M., Huang, B., Zhuang, X., Super-Resolution Microscopy by Nanoscale Localization of Photo-Switchable Fluorescent Probes (2008) Curr. Opin. Chem. Biol., 12, pp. 505-514
  • Heilemann, M., Dedecker, P., Hofkens, J., Sauer, M., Photoswitches: Key Molecules for Subdiffraction-Resolution Fluorescence Imaging and Molecular Quantification (2008) Laser Photonics Rev., 3, pp. 180-202
  • Schermelleh, L., Heintzmann, R., Leonhardt, H., A Guide to Super-Resolution Fluorescence Microscopy (2010) J. Cell Biol., 180, pp. 165-175
  • Dertinger, T., Colyer, R., Iyer, G., Weiss, S., Enderlein, J., Fast, Background-free, 3D Super-Resolution Optical Fluctuation Imaging (SOFI) (2009) Proc. Natl. Acad. Sci. U. S. A., 106, pp. 22287-92
  • Medintz, I.L., Trammell, S.A., Mattoussi, H., Mauro, J.M., Reversible Modulation of Quantum Dot Photoluminescence Using a Protein-Bound Photochromic Fluorescence Resonance Energy Transfer Acceptor (2004) Journal of the American Chemical Society, 126 (1), pp. 30-31
  • Jares-Erijman, E., Giordano, L., Spagnuolo, C., Lidke, K., Jovin, T.M., Imaging quantum dots switched on and off by photochromic fluorescence resonance energy transfer (pcFRET) (2005) Molecular Crystals and Liquid Crystals, 430, pp. 257-265. , DOI 10.1080/15421400590946479
  • Erno, Z., Yildiz, I., Gorodetsky, B., Raymo, F.M., Branda, N.R., Optical Control of Quantum Dot Luminescence via Photoisomerization of a Surface-Coordinated, Cationic Dithienylethene (2010) Photochem. Photobiol. Sci., 9, pp. 249-253
  • Piao, X., Zou, Y., Wu, J., Li, C., Yi, T., Multiresponsive Switchable Diarylethene and Its Application in Bioimaging (2009) Org. Lett., 11, pp. 3818-3821
  • Yildiz, I., Deniz, E., Raymo, F.M., Fluorescence Modulation with Photochromic Switches in Nanostructured Constructs (2009) Chem. Soc. Rev., 38, pp. 1859-1867
  • Tian, Z.Y., Yu, J.B., Wu, C.F., Szymanski, C., McNeill, J., Amplified Energy Transfer in Conjugated Polymer Nanoparticle Tags and Sensors (2010) Nanoscale, 2, pp. 1999-2011
  • Irie, M., Diarylethenes for Memories and Switches (2000) Chem. Rev., 100, pp. 1685-1716
  • Hirose, T., Matsuda, K., Irie, M., Self-assembly of photochromic diarylethenes with amphiphilic side chains: Reversible thermal and photochemical control (2006) Journal of Organic Chemistry, 71 (20), pp. 7499-7508. , DOI 10.1021/jo060505t
  • Tomasulo, M., Deniz, E., Sortino, S., Raymo, F.M., Hydrophilic and Photochromic Switches Based on the Opening and Closing of [1,3]Oxazine Rings (2010) Photochem. Photobiol. Sci., 9, pp. 136-140
  • Chen, J., Zeng, F., Wu, S., Chen, Q., Tong, Z., A Core-Shell Nanoparticle Approach to Photoreversible Fluorescence Modulation of a Hydrophobic Dye in AqueousMedia (2008) Chem.-Eur. J., 14, pp. 4851-4860
  • Zhu, L., Wu, W., Zhu, M.-Q., Han, J.J., Hurst, J.K., Li, A.D.Q., Reversibly photoswitchable dual-color fluorescent nanoparticles as new tools for live-cell imaging (2007) Journal of the American Chemical Society, 129 (12), pp. 3524-3526. , DOI 10.1021/ja068452k
  • Chudakov, D.M., Matz, M.V., Lukyanov, S., Lukyanov, K., Fluorescent Proteins and Their Applications in Imaging Living Cells and Tissues (2010) Physiol. Rev., 90, pp. 1103-1163
  • Weng, J., Ren, J., Luminescent Quantum Dots: A Very Attractive and Promising Tool in Biomedicine (2006) Curr. Med. Chem., 13, pp. 897-909
  • Yu, W.W., Semiconductor Quantum Dots: Synthesis and Water-Solubilization for Biomedical Applications (2008) Expert Opin. Biol. Ther., 8, pp. 1571-1581
  • Michalet, X., Pinaud, F.F., Bentolila, L.A., Tsay, J.M., Doose, S., Li, J.J., Sundaresan, G., Weiss, S., Quantum dots for live cells, in vivo imaging, and diagnostics (2005) Science, 307 (5709), pp. 538-544. , DOI 10.1126/science.1104274
  • Hezinger, A.F.E., Tessmar, J., Gopferich, A., Polymer coating of quantum dots - A powerful tool toward diagnostics and sensorics (2008) European Journal of Pharmaceutics and Biopharmaceutics, 68 (1), pp. 138-152. , DOI 10.1016/j.ejpb.2007.05.013, PII S0939641107001956, Interactive Polymers for Pharmaceutical and Biomedical Applications
  • Pellegrino, T., Manna, L., Kudera, S., Liedl, T., Koktysh, D., Rogach, A.L., Keller, S., Parak, W.J., Hydrophobic nanocrystals coated with an amphiphilic polymer shell: A general route to water soluble nanocrystals (2004) Nano Letters, 4 (4), pp. 703-707. , DOI 10.1021/nl035172j
  • Jańczewski, D., Tomczak, N., Khin, Y.W., Han, M.-Y., Vancso, G.J., Designer Multi-Functional Comb-Polymers for Surface Engineering of Quantum Dots on the Nanoscale (2009) Eur. Polym. J., 45, pp. 3-9
  • Kawai, T., Kunitake, T., Irie, M., Novel Photochromic Conducting Polymer Having Diarylethene Derivative in the Main Chain (1999) Chem. Lett., pp. 905-906
  • Wigglesworth, T.J., Myles, A.J., Branda, N.R., High-content photochromic polymers based on dithienylethenes (2005) European Journal of Organic Chemistry, (7), pp. 1233-1238. , DOI 10.1002/ejoc.200400623
  • Ercole, F., Davis, T.P., Evans, R.A., Photo-Responsive Systems and Biomaterials: Photochromic Polymers, Light-Triggered Self-Assembly, Surface Modification, Fluorescence Modulation and beyond (2010) Polym. Chem., 1, pp. 37-54
  • Fernandez-Arguelles, M.T., Yakovlev, A., Sperling, R.A., Luccardini, C., Gaillard, S., Medel, A.S., Mallet, J.-M., Parak, W.J., Synthesis and characterization of polymer-coated quantum dots with integrated acceptor dyes as FRET-based nanoprobes (2007) Nano Letters, 7 (9), pp. 2613-2617. , DOI 10.1021/nl070971d
  • Lin, C.-A.J., Sperling, R.A., Li, J.K., Yang, T.-Y., Li, P.-Y., Zanella, M., Chang, W.H., Parak, W.J., Design of an amphiphilic polymer for nanoparticle coating and functionalization (2008) Small, 4 (3), pp. 334-341. , DOI 10.1002/smll.200700654
  • Giordano, L., Vermeij, R.J., Jares-Erijman, E.A., Synthesis of indole-containing diheteroarylethenes. New probes for photochromic FRET (pcFRET) (2005) Arkivoc, 2005 (12), pp. 268-281. , http://www.arkat-usa.org/ark/journal/2005/I12_Lederkremer/1632/ RL-1632KP%20as%20published%20mainmanuscript.pdf
  • Derfus, A.M., Chan, W.C.W., Bhatia, S.N., Probing the Cytotoxicity of Semiconductor Quantum Dots (2004) Nano Letters, 4 (1), pp. 11-18. , DOI 10.1021/nl0347334
  • Zhelev, Z., Jose, R., Nagase, T., Ohba, H., Bakalova, R., Ishikawa, M., Baba, Y., Enhancement of the photoluminescence of CdSe quantum dots during long-term UV-irradiation: Privilege or fault in life science research? (2004) Journal of Photochemistry and Photobiology B: Biology, 75 (1-2), pp. 99-105. , DOI 10.1016/j.jphotobiol.2004.05.014, PII S1011134404000648
  • Grecco, H.E., Lidke, K.A., Heintzmann, R., Lidke, D.S., Spagnuolo, C., Martinez, O.E., Jares-Erijman, E.A., Jovin, T.M., Ensemble and single particle photophysical properties (two-photon excitation, anisotropy, FRET, lifetime, spectral conversion) of commercial quantum dots in solution and in live cells (2004) Microscopy Research and Technique, 65 (4-5), pp. 169-179. , DOI 10.1002/jemt.20129
  • Niebling, T., Zhang, F., Ali, Z., Parak, W.J., Hemibrodt, W., Excitation Dynamics in Polymer-Coated Semiconductor Quantum Dots with Integrated Dye Molecules: The Role of Reabsorption (2009) J. Appl. Phys., 106, pp. 104701-1047016
  • Wohlfarth, C., Wohlfahrt, B., Condensed Matter Optical Constants. Refractive Indices of Pure Liquids and Binary Liquid Mixtures (Supplement to III/38) (2008) The Landolt-Börnstein Database, 47. , Springer-Verlag: Berlin
  • Schreiber, F., Structure and growth of self-assembling monolayers (2000) Progress in Surface Science, 65 (5-8), pp. 151-256. , DOI 10.1016/S0079-6816(00)00024-1
  • Hanazawa, M., Sumiya, R., Horikawa, Y., Irie, M., Thermally Irreversible Photochromic Systems-Reversible Photocyclization of 1,2-Bis(2-methylbenzo[ b ]thiophen-3-yl)perfluorocycloalkene Derivatives (1992) J. Chem. Soc., Chem. Commun, pp. 206-207
  • Kim, E., Kim, M., Kim, K., Diarylethenes with intramolecular donor-acceptor structures for photo-induced electrochemical change (2006) Tetrahedron, 62 (29), pp. 6814-6821. , DOI 10.1016/j.tet.2006.04.089, PII S0040402006007198
  • Hu, G.H., Lindt, J.T., Amidification of Poly(styrene-co-maleic anhydride) with Amines in Tetrahydrofuran Solution: A Kinetic Study (1992) Polym. Bull., 29, pp. 357-363
  • Sperling, R.A., Pellegrino, T., Li, J.K., Chang, W.H., Parak, W.J., Electrophoretic Separation of Nanoparticles with a Discrete Number of Functional Groups (2006) Adv. Funct. Mater., 16, pp. 943-948
  • Celej, M.S., Jares-Erijman, E.A., Jovin, T.M., Fluorescent N-arylaminonaphthalene Sulfonate Probes for Amyloid Aggregation of α-Synuclein (2008) Biophys. J., 94, pp. 4867-4879

Citas:

---------- APA ----------
Díaz, S.A., Menéndez, G.O., Etchehon, M.H., Giordano, L., Jovin, T.M. & Jares-Erijman, E.A. (2011) . Photoswitchable water-soluble quantum dots: PcFRET based on amphiphilic photochromic polymer coating. ACS Nano, 5(4), 2795-2805.
http://dx.doi.org/10.1021/nn103243c
---------- CHICAGO ----------
Díaz, S.A., Menéndez, G.O., Etchehon, M.H., Giordano, L., Jovin, T.M., Jares-Erijman, E.A. "Photoswitchable water-soluble quantum dots: PcFRET based on amphiphilic photochromic polymer coating" . ACS Nano 5, no. 4 (2011) : 2795-2805.
http://dx.doi.org/10.1021/nn103243c
---------- MLA ----------
Díaz, S.A., Menéndez, G.O., Etchehon, M.H., Giordano, L., Jovin, T.M., Jares-Erijman, E.A. "Photoswitchable water-soluble quantum dots: PcFRET based on amphiphilic photochromic polymer coating" . ACS Nano, vol. 5, no. 4, 2011, pp. 2795-2805.
http://dx.doi.org/10.1021/nn103243c
---------- VANCOUVER ----------
Díaz, S.A., Menéndez, G.O., Etchehon, M.H., Giordano, L., Jovin, T.M., Jares-Erijman, E.A. Photoswitchable water-soluble quantum dots: PcFRET based on amphiphilic photochromic polymer coating. ACS Nano. 2011;5(4):2795-2805.
http://dx.doi.org/10.1021/nn103243c