Polymer-coated nanoparticles: a universal tool for biolabelling experiments.

Water solubilization of nanoparticles is a fundamental prerequisite for many biological applications. To date, no single method has emerged as ideal, and several different approaches have been successfully utilized. These 'phase-transfer' strategies are reviewed, indicating key advantages and disadvantages, and a discussion of conjugation strategies is presented. Coating of hydrophobic nanoparticles with amphiphilic polymers provides a generic pathway for the phase transfer of semiconductor, magnetic, metallic, and upconverting nanoparticles from nonpolar to polar environments. Amphiphilic polymers that include maleimide groups can be readily functionalized with chemical groups for specific applications. In the second, experimental part, some of the new chemical features of such polymer-capped nanoparticles are demonstrated. In particular, nanoparticles to which a pH sensitive fluorophore has been attached are described, and their use for intracellular pH-sensing demonstrated. It is shown that the properties of analyte-sensitive fluorophores can be tuned by using interactions with the underlying nanoparticles.

[1]  Xiaogang Peng,et al.  Highly luminescent, stable, and water-soluble CdSe/CdS core-shell dendron nanocrystals with carboxylate anchoring groups. , 2006, Langmuir : the ACS journal of surfaces and colloids.

[2]  M. Bruchez,et al.  Corrigendum: Immunofluorescent labeling of cancer marker Her2 and other cellular targets with semiconductor quantum dots , 2003, Nature Biotechnology.

[3]  Christine M. Micheel,et al.  Cell Motility and Metastatic Potential Studies Based on Quantum Dot Imaging of Phagokinetic Tracks , 2002 .

[4]  Feng Zhang,et al.  Excitation dynamics in polymer-coated semiconductor quantum dots with integrated dye molecules: The role of reabsorption , 2009 .

[5]  M. Singer SINEs and LINEs: Highly repeated short and long interspersed sequences in mammalian genomes , 1982, Cell.

[6]  Jessica O. Winter,et al.  Recognition Molecule Directed Interfacing Between Semiconductor Quantum Dots and Nerve Cells , 2001 .

[7]  Hans C. Fischer,et al.  Design and characterization of lysine cross-linked mercapto-acid biocompatible quantum dots , 2006 .

[8]  D. Balding,et al.  HLA Sequence Polymorphism and the Origin of Humans , 2006 .

[9]  Huiguang Zhu,et al.  Bilayers as phase transfer agents for nanocrystals prepared in nonpolar solvents. , 2009, ACS nano.

[10]  S. Nie,et al.  Etching colloidal gold nanocrystals with hyperbranched and multivalent polymers: a new route to fluorescent and water-soluble atomic clusters. , 2007, Journal of the American Chemical Society.

[11]  J. Montenegro,et al.  How colloidal nanoparticles could facilitate multiplexed measurements of different analytes with analyte-sensitive organic fluorophores. , 2011, ACS nano.

[12]  L. Liz‐Marzán,et al.  The Assembly of Coated Nanocrystals , 2003 .

[13]  Shimon Weiss,et al.  Bioactivation and cell targeting of semiconductor CdSe/ZnS nanocrystals with phytochelatin-related peptides. , 2004, Journal of the American Chemical Society.

[14]  Walter H. Chang,et al.  Design of an amphiphilic polymer for nanoparticle coating and functionalization. , 2008, Small.

[15]  Manuela Semmler-Behnke,et al.  Biodistribution of PEG-modified gold nanoparticles following intratracheal instillation and intravenous injection. , 2010, Biomaterials.

[16]  Yongcheng Liu,et al.  Detection of pathogens using luminescent CdSe/ZnS dendron nanocrystals and a porous membrane immunofilter. , 2007, Analytical chemistry.

[17]  Huan-Cheng Chang,et al.  Bright fluorescent nanodiamonds: no photobleaching and low cytotoxicity. , 2005, Journal of the American Chemical Society.

[18]  M. Himmel,et al.  Quantum Dot Molecules Assembled with Genetically Engineered Proteins , 2003 .

[19]  Pilar López-Larrubia,et al.  Engineering biofunctional magnetic nanoparticles for biotechnological applications. , 2010, Nanoscale.

[20]  A. Verkman,et al.  Cystic Fibrosis Transmembrane Conductance Regulator-independent Phagosomal Acidification in Macrophages* , 2007, Journal of Biological Chemistry.

[21]  Rebekah Drezek,et al.  Protease-activated quantum dot probes. , 2005, Biochemical and biophysical research communications.

[22]  Valeria Grazú,et al.  Designing novel nano-immunoassays: antibody orientation versus sensitivity , 2010 .

[23]  D. Fernig,et al.  A Generic Approach to Monofunctionalized Protein‐Like Gold Nanoparticles Based on Immobilized Metal Ion Affinity Chromatography , 2006, Chembiochem : a European journal of chemical biology.

[24]  Jayanth Panyam,et al.  Rapid endo‐lysosomal escape of poly(DL‐lactide‐coglycolide) nanoparticles: implications for drug and gene delivery , 2002, FASEB journal : official publication of the Federation of American Societies for Experimental Biology.

[25]  R. Niessner,et al.  Multifunctional nanoparticles for dual imaging. , 2011, Analytical chemistry.

[26]  B. Tycko,et al.  Rapid acidification of endocytic vesicles containing α 2-macroglobulin , 1982, Cell.

[27]  S. Nie,et al.  Quantum dot bioconjugates for ultrasensitive nonisotopic detection. , 1998, Science.

[28]  E. Doris,et al.  A versatile strategy for quantum dot ligand exchange. , 2007, Journal of the American Chemical Society.

[29]  P. Mulvaney,et al.  The preparation of colloidally stable, water-soluble, biocompatible, semiconductor nanocrystals with a small hydrodynamic diameter. , 2009, ACS nano.

[30]  Xiaogang Peng,et al.  Luminescent CdSe/CdS core/shell nanocrystals in dendron boxes: superior chemical, photochemical and thermal stability. , 2003, Journal of the American Chemical Society.

[31]  Tim Liedl,et al.  Cytotoxicity of colloidal CdSe and CdSe/ZnS nanoparticles. , 2005, Nano letters.

[32]  Martin Oheim,et al.  Ion and pH sensing with colloidal nanoparticles: influence of surface charge on sensing and colloidal properties. , 2010, Chemphyschem : a European journal of chemical physics and physical chemistry.

[33]  Moungi G Bawendi,et al.  Oligomeric ligands for luminescent and stable nanocrystal quantum dots. , 2003, Journal of the American Chemical Society.

[34]  Igor L. Medintz,et al.  Quantum dot bioconjugates for imaging, labelling and sensing , 2005, Nature materials.

[35]  P. Mulvaney,et al.  The effects of chemisorption on the luminescence of CdSe quantum dots. , 2006, Langmuir : the ACS journal of surfaces and colloids.

[36]  Erkki Ruoslahti,et al.  Nanocrystal targeting in vivo , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[37]  Robert Langer,et al.  Quantum dot-aptamer conjugates for synchronous cancer imaging, therapy, and sensing of drug delivery based on bi-fluorescence resonance energy transfer. , 2007, Nano letters.

[38]  Dieter Braun,et al.  Size determination of (bio)conjugated water-soluble colloidal nanoparticles : A comparison of different techniques , 2007 .

[39]  Xiaohua Huang,et al.  Cancer cell imaging and photothermal therapy in the near-infrared region by using gold nanorods. , 2006, Journal of the American Chemical Society.

[40]  Philippe Rostaing,et al.  Diffusion Dynamics of Glycine Receptors Revealed by Single-Quantum Dot Tracking , 2003, Science.

[41]  J. Matthew Mauro,et al.  Self-Assembly of CdSe−ZnS Quantum Dot Bioconjugates Using an Engineered Recombinant Protein , 2000 .

[42]  P. Tauc,et al.  Wrapping nanocrystals with an amphiphilic polymer preloaded with fixed amounts of fluorophore generates FRET-based nanoprobes with a controlled donor/acceptor ratio. , 2009, Langmuir : the ACS journal of surfaces and colloids.

[43]  Shuming Nie,et al.  Counting single native biomolecules and intact viruses with color-coded nanoparticles. , 2006, Analytical chemistry.

[44]  Byron Ballou,et al.  Noninvasive imaging of quantum dots in mice. , 2004, Bioconjugate chemistry.

[45]  Sanjiv S Gambhir,et al.  Peptide-labeled near-infrared quantum dots for imaging tumor vasculature in living subjects. , 2006, Nano letters.

[46]  M. Bruchez,et al.  Immunofluorescent labeling of cancer marker Her2 and other cellular targets with semiconductor quantum dots , 2003, Nature Biotechnology.

[47]  Vincent Noireaux,et al.  In Vivo Imaging of Quantum Dots Encapsulated in Phospholipid Micelles , 2002, Science.

[48]  Tymish Y. Ohulchanskyy,et al.  Combined Optical and MR Bioimaging Using Rare Earth Ion Doped NaYF4 Nanocrystals , 2009 .

[49]  Daniele Gerion,et al.  Fluorescent CdSe/ZnS nanocrystal-peptide conjugates for long-term, nontoxic imaging and , 2004 .

[50]  Joachim O. Rädler,et al.  Hydrophobic Nanocrystals Coated with an Amphiphilic Polymer Shell: A General Route to Water Soluble Nanocrystals , 2004 .

[51]  T. Livache,et al.  Biotinylated CdSe/ZnSe nanocrystals for specific fluorescent labeling , 2004 .

[52]  S. Nie,et al.  In vivo cancer targeting and imaging with semiconductor quantum dots , 2004, Nature Biotechnology.

[53]  Hedi Mattoussi,et al.  Avidin: a natural bridge for quantum dot-antibody conjugates. , 2002, Journal of the American Chemical Society.

[54]  Paul Mulvaney,et al.  Complete Quenching of CdSe Nanocrystal Photoluminescence by Single Dye Molecules , 2008 .

[55]  Igor L. Medintz,et al.  Enhancing the stability and biological functionalities of quantum dots via compact multifunctional ligands. , 2007, Journal of the American Chemical Society.

[56]  M. Bawendi,et al.  Synthesis and characterization of nearly monodisperse CdE (E = sulfur, selenium, tellurium) semiconductor nanocrystallites , 1993 .

[57]  Rebekah Drezek,et al.  Forming biocompatible and nonaggregated nanocrystals in water using amphiphilic polymers. , 2007, Journal of the American Chemical Society.

[58]  Martin Oheim,et al.  Synthesis and characterization of polymer-coated quantum dots with integrated acceptor dyes as FRET-based nanoprobes. , 2007, Nano letters.

[59]  M. Gunzburg,et al.  Experimental determination of quantum dot size distributions, ligand packing densities, and bioconjugation using analytical ultracentrifugation. , 2008, Nano letters.

[60]  J. Storhoff,et al.  A DNA-based method for rationally assembling nanoparticles into macroscopic materials , 1996, Nature.

[61]  Guanying Chen,et al.  Ultrasmall monodisperse NaYF(4):Yb(3+)/Tm(3+) nanocrystals with enhanced near-infrared to near-infrared upconversion photoluminescence. , 2010, ACS nano.

[62]  Igor L. Medintz,et al.  Self-assembled quantum dot-peptide bioconjugates for selective intracellular delivery. , 2006, Bioconjugate chemistry.

[63]  J. Matthew Mauro,et al.  Long-term multiple color imaging of live cells using quantum dot bioconjugates , 2003, Nature Biotechnology.

[64]  Shimon Weiss,et al.  Synthesis and Properties of Biocompatible Water-Soluble Silica-Coated CdSe/ZnS Semiconductor Quantum Dots† , 2001 .

[65]  A Paul Alivisatos,et al.  Sorting fluorescent nanocrystals with DNA. , 2002, Journal of the American Chemical Society.

[66]  A Paul Alivisatos,et al.  Discrete nanostructures of quantum dots/Au with DNA. , 2004, Journal of the American Chemical Society.

[67]  Paul Mulvaney,et al.  Synthesis of Nanosized Gold−Silica Core−Shell Particles , 1996 .

[68]  Christine M. Micheel,et al.  Electrophoretic Isolation of Discrete Au Nanocrystal/DNA Conjugates , 2001 .

[69]  D. Maclaurin,et al.  Quantum measurement and orientation tracking of fluorescent nanodiamonds inside living cells. , 2011, Nature nanotechnology.

[70]  Chad A. Mirkin,et al.  Programmed Assembly of DNA Functionalized Quantum Dots , 1999 .

[71]  A. Riedinger,et al.  Ratiometric optical sensing of chloride ions with organic fluorophore-gold nanoparticle hybrids: a systematic study of design parameters and surface charge effects. , 2010, Small.

[72]  H. Mattoussi,et al.  Conjugation of luminescent quantum dots with antibodies using an engineered adaptor protein to provide new reagents for fluoroimmunoassays. , 2002, Analytical chemistry.

[73]  L. Liz‐Marzán,et al.  Stabilization of CdS semiconductor nanoparticles against photodegradation by a silica coating procedure , 1998 .

[74]  Igor L. Medintz,et al.  Synthesis of compact multidentate ligands to prepare stable hydrophilic quantum dot fluorophores. , 2005, Journal of the American Chemical Society.

[75]  J. Ying,et al.  Synthesis of silica-coated semiconductor and magnetic quantum dots and their use in the imaging of live cells. , 2007, Angewandte Chemie.

[76]  Robert Langer,et al.  Poly(ethylene oxide)-modified poly(beta-amino ester) nanoparticles as a pH-sensitive biodegradable system for paclitaxel delivery. , 2003, Journal of controlled release : official journal of the Controlled Release Society.

[77]  C. Bustamante,et al.  Conjugation of DNA to Silanized Colloidal Semiconductor Nanocrystalline Quantum Dots , 2002 .

[78]  Shuhua Liu,et al.  Silica-coated metal nanoparticles. , 2009, Chemistry, an Asian journal.

[79]  Xiaogang Peng,et al.  Conjugation Chemistry and Bioapplications of Semiconductor Box Nanocrystals Prepared via Dendrimer Bridging , 2003 .

[80]  S. Bhatia,et al.  Probing the Cytotoxicity Of Semiconductor Quantum Dots. , 2004, Nano letters.

[81]  Xiaogang Peng,et al.  Photochemical instability of CdSe nanocrystals coated by hydrophilic thiols. , 2001, Journal of the American Chemical Society.

[82]  Yoshio Kobayashi,et al.  Preparation and Properties of Silica-Coated Cobalt Nanoparticles† , 2003 .

[83]  Michael C. Wilson,et al.  Surfactant-assisted synthesis of water-soluble and biocompatible semiconductor quantum dot micelles. , 2005, Nano letters.

[84]  Masato Yasuhara,et al.  Quantum Dots Targeted to the Assigned Organelle in Living Cells , 2004, Microbiology and immunology.

[85]  A. Kornowski,et al.  Tailor-made ligands for biocompatible nanoparticles. , 2006, Angewandte Chemie.

[86]  Igor L. Medintz,et al.  Fluorescence resonance energy transfer between quantum dot donors and dye-labeled protein acceptors. , 2003, Journal of the American Chemical Society.

[87]  James McBride,et al.  Targeting cell surface receptors with ligand-conjugated nanocrystals. , 2002, Journal of the American Chemical Society.

[88]  Jerry S. H. Lee,et al.  Magnetic nanoparticles in MR imaging and drug delivery. , 2008, Advanced drug delivery reviews.

[89]  Moungi G Bawendi,et al.  Compact biocompatible quantum dots functionalized for cellular imaging. , 2008, Journal of the American Chemical Society.

[90]  Wolfgang J. Parak,et al.  Electrophoretic Separation of Nanoparticles with a Discrete Number of Functional Groups , 2006 .

[91]  Dale M. Willard,et al.  CdSe−ZnS Quantum Dots as Resonance Energy Transfer Donors in a Model Protein−Protein Binding Assay , 2001 .

[92]  Xiaogang Peng,et al.  Stabilization of inorganic nanocrystals by organic dendrons. , 2002, Journal of the American Chemical Society.