Biofunctionalization of Nanomaterials

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1 Nanotechnologies for the Life Sciences Volume 7 Biofunctionalization of Nanomaterials Edited by Challa S. S. R. Kumar Ist Edition WILEY- VCH WILEY-VCH Verlag GmbH & Co. KGaA

2 The Editor of this Book Dr. Challa S. S. R. Kumar The Center for Advanced Microstruclures and Devices (CAMD) Louisiana State University 6980 Jefferson Highway BATON ROUGE. LA USA All books published by Wiley-VCH are carefully produced. Nevertheless, authors. editors, and publisher do not Warrant the Information containcd in these books, including this book, to bc lrec ol errors. Readers are advised to keep in rnind that statements. data. illustrations, procedural details or other items may inadvertently bc inaecurate. Library of Congress Card No.: applied for British Library Cataloging-in-Publication Data: A catalogue record for this book is available from the British Library. Bibliographie Information published by Die Deutsche Bibliothek Die Deutsche Bibliothek lists this publicalion in the Deutsche Nationalbibliografic; detailed bibliographic data is available in the Internet at WILEY-VCH Verlag GmbH & Co. KGaA. Weinheim All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form - by photoprinting. microfilm, or any other means - nor transmitted or translated into a machine language without written permission from the publishers. Registered names. trademarks. etc. used in this book, even when not speeifieally marked as such, are not to be considered unprotected by law. Printed in the Föderal Republic of Gcrmany. Printed on aeid-free paper. Typesetting Asco Typcsctters, Hong Kong Printing Strauss GmbH, Mörlenbach Binding ]. Schäffer GmbH i. G., Grünstadt ISBN-13: ISBN-10:

Contents Preface List of Contributors XIII XVII 1 Biofunctionalization of Fluorescent Nanoparticles 1 Michael J. Murcia and Christoph A. Naumann 1.1 Introduction 1 1.

3 Contents Preface List of Contributors XIII XVII 1 Biofunctionalization of Fluorescent Nanoparticles 1 Michael J. Murcia and Christoph A. Naumann 1.1 Introduction Fluorescent Nanoparticle Probes Dye-doped Nanoparticles Quantum Dots (QDs) Metal Nanoparticles Hybrid Architectures Involving Fluorescent Nanoprobes Metal--Dye Dye-doped Silica Shells Quantum Dot-containing Microspheres Bioconjugation of Fluorescent Nanoparticles General Considerations Overview Common Coupling Reactions Bioconjugation of Polymeric Nanoparticles Noncovalent Approaches Covalent Approaches Bioconjugation of Quantum Dots Noncovalent Approaches Covalent Approaches Bioconjugation of Metallic Nanoprobes Noncovalent Approaches Covalent Approaches Design of Biocompatible Coatings General Considerations Overview Colloidal Stability Biocompatible Surfaces Cytotoxicity Nanoparticle-stabilizing Coatings Low Cytotoxicity Coatings Applications Biosensing Polymeric Sensors Quantum Dot Sensors

1.5.1.3 1.5.2 1.5.2.1 1.5.2.2 2 2.1 2.2 2.3 2.4 2.4.1 2.4.2 2.4.3 2.4.4 2.4.4.1 2.4.4.2 2.5 2.5.1 2.5.2 2.5.3 2.6 3 3.1 3.

4 Metallic Sensors Fluorescent Nanoparticles as Labels in Biological Imaging Dye-doped Nanoparticles Quantum Dots Biofunctionalization of Carbon Nanotubes Elena Bekyarova, Robert C. Haddon, and Vladimir Parpura Introduction Carbon Nanotubes -- Types, Structures and Properties Synthesis of Carbon Nanotubes Approaches to Aqueous Solubilization of Carbon Nanotubes Chemical Modifications Use of Water-compatible Surfactants Functionalization with Water-soluble Polymers Interaction and Functionalization with Biological Molecules Noncovalent Biofunctionalization Covalent Biofunctionalization Applications of Biofunctionalized Carbon Nanotubes Assembly of Electronic Devices Biosensing Substrates for Neuronal Growth Concluding Remarks Biofunctionalization of Magnetic Nanoparticles Yong Gao Introduction Functionalization of Magnetic Nanoparticles for In Vitro Protein/Cell Separation Functionalization of Magnetic Nanoparticles for Biochemical/Chemical 80 Synthesis of Therapeutic Drugs and Their Intermediates 3.4 Functionalization of Magnetic Nanoparticles for In Vivo Bio-imaging, 82 Drug Targeting and Tumor Hyperthermia Treatments MR Imaging Targeted Drug Delivery Magnetic Hyperthermia 3.5 Conclusions Biofunctionalization of Gold Nanoparticles 99 Ming Zheng and Xueying Huang 4.1 Introduction General Synthetic Routes 99

4.2.1 4.2.1.1 4.2.1.2 4.2.1.3 4.2.2 4.3 4.4 4.5 4.6 4.6.1 4.6.2 4.6.3 5 5.1 5.2 5.

5 Direct Synthesis of Ligand-protected Au NPs Strongly Ionic Ligand-protected Au NPs Weakly Ionic Ligand-protected Au NPs Au NPs Protected with Neutral Ligands Ligand Exchange Reaction Preparative-scale Synthesis and Solution-phase Characterization of DNA-directed Nanoparticle Assemblies Bifunctional Proteins for Programmable Assembly of Nanoparticles Strategies for Eliminating Nonspecific Interactions and Enabling Specific Binding with Biomolecules Biological Applications Nucleic Acids Proteins Cells and Virus Biofunctionalization of Phospholipid Polymer Nanoparticles Junji Watanabe, Jongwon Park, Tomomi Ito, Madoka Takai, and Kazuhiko Ishihara Introduction Nanofabrication for Biomedical Applications Nano-scaled Processing Key Materials for Nanofabrication Design of Bioconjugate Nanoparticles Bioconjugate Phospholipid Polymer Solution Properties by Fluorescence Probe Bioconjugate Nanoparticles Surface Elemental Analysis by X-ray Photoelectron Spectroscopy Surface ^-Potential on Nanoparticles Particle Size by Dynamic Light Scattering and Morphology by Scanning Electron Microscope Determination of Active Ester Groups on Nanoparticles Biofunction on Nanoparticles Design of Sequential Enzymatic Reaction Amplified Signal on Nanoparticles Application for Molecular Diagnosis Example of C-reactive Protein Detection Using Nanoparticles High-performance Diagnosis in Serum Conclusions

6 Biofunctionalization of Metallic Nanoparticles and Microarrays for 150 Biomolecular Detection Grit Festag, Uwe Klenz, Thomas Henkel, Andrea Csáki, and Wolfgang Fritzsche 6.1 Introduction 6.1.1 Applications 6.

6 6 Biofunctionalization of Metallic Nanoparticles and Microarrays for 150 Biomolecular Detection Grit Festag, Uwe Klenz, Thomas Henkel, Andrea Csáki, and Wolfgang Fritzsche 6.1 Introduction Applications Array Fabrication Detection Methods Optical Absorbance SPR Imaging Raman Scattering Electrical Detection Electrochemical Detection Gravimetric Nanoparticles and their Biofunctionalization Types of Nanoparticles used for Biomolecular Detection Metal Nanoparticles Core/Shell Particles Magnetic Nanoparticles Quantum Dots Synthesis of Gold (Silver) Nanoparticles Biofunctionalization Modification of Gold Nanoparticles with Oligonucleotides/DNA Modification of Gold Nanoparticles with Proteins Biofunctionalization of other Metal Nanoparticles Biological Applications of Gold Nanoparticles Substrates and their Biofunctionalization Molecular Thin Films Self-assembly Monolayers Optimization of Gold Nanoparticle-based Microarrays for DNA Detection Nanoporous Gels Outlook Conjugation of Nanomaterials with Proteins 183 Mohammed J. Meziani, Yi Lin, and Ya-Ping Sun 7.1 Introduction Coupling of Inorganic Nanoparticles with Proteins Chemical Functionalization Methods Protein-assisted Assemblies of Inorganic Nanoparticles Crosslinking Route through Protein Recognition Template-directed Approach Supercritical Fluid Methods 195

7.2.3.1 BSA-conjugated Silver Nanoparticles 196 7.2.3.2 BSA-conjugated Semiconductor Nanoparticles 197 7.2.3.3 Assembly and Disassembly of Nanoparticles through Protein Isomeric 202 Conversion 7.

7 BSA-conjugated Silver Nanoparticles BSA-conjugated Semiconductor Nanoparticles Assembly and Disassembly of Nanoparticles through Protein Isomeric 202 Conversion 7.3 Coupling of Carbon Nanotubes and Proteins Non-specific Adsorption Specific Conjugation and Biorecognition Conclusions and Perspectives 221 Acknowledgment Stabilization and Functionalization of Metallic Nanoparticles: the 235 Peptide Route Raphaël Lévy and R. Christopher Doty 8.1 Introduction Metallic Nanoparticles -- An Overview Metallic Nanoparticles -- Preparation Metallic Nanoparticles -- Optical Properties Metallic Nanoparticles -- Applications Stabilization and Functionalization of Metallic Nanoparticles -- The 248 Peptide Route Peptides, Proteins and Nanoscale Science Peptide Toolbox for Bionanotechnology Peptides as Capping Ligands Interactions of Amino Acids with Noble Metals Peptides as Reducing Agent and Template in Metallic Nanoparticle Synthesis Rational Design of a Peptide Capping Ligands for Gold Nanoparticles: CALNN Combinatorial Exploration of Peptides as Capping Ligands: the CALNN Family Peptide-capped Silver Nanoparticles Peptides as Capping Ligands for Fluorescent and Magnetic Nanoparticles Peptide Extensions to Introduce Functionalities Biotin and Strep-tag II Peptide-DNA Hybrids His-tag and Nickel Nitrilotriacetic Acid (Ni-NTA) Chromatography of Peptide-capped Nanoparticles Size-exclusion Chromatography Affinity Chromatography Recognition of Materials Peptide-based Linkers A Peptide-Peptide Linker Based on Leucine-zipper Sequences A Peptide-DNA Linker Based on Metallopeptides A Peptide-Texas Red Linker Obtained by Phage Display Biologically Active Peptides 259

8.3.9 Self-assembling Peptides 260 8.3.9.1 Fibers and Nanotubes 260 8.3.9.2 Peptide-based Amphiphiles 262 8.

8 8.3.9 Self-assembling Peptides Fibers and Nanotubes Peptide-based Amphiphiles Concluding Remarks Folate-linked Lipid-based Nanoparticles for Tumor-targeted Gene 270 Therapy Yoshiyuki Hattori and Yoshie Maitani 9.1 Introduction Gene Delivery and Expression System Nanoparticles for Gene Delivery System Folate-linked Vectors Folate Receptors Folate Receptor-targeting Liposomes Folate-linked Lipid-based Nanoparticles Formulations Nanoplex and Transfection Activity In Vitro Selectivity of Folate-linked Nanoparticle Transfection Activity In Vivo Application of Suicide Gene Therapy Conclusions 291 List of Abbreviations Magnetic Core Conducting Polymer Shell Nanocomposites for DNA 299 Attachment and Hybridization Jean-Paul Lellouche 10.1 Introduction Chemical Design of DPyr- and DCbz-containing Monomers: 301 Introduction of Molecular Diversity 10.3 Synthetic Approaches for Mono- and Dicarboxylated 302 DPyr-/DCbz-based Monomers 10.4 Oxidative Polymerization of DPyr-/DCbz-based Monomers around 305 Magnetite Nanoparticles General Considerations Characterization of Magnetically Responsive PolyDPyr- and 307 PolyDCbz-Magnetite Nanocomposites 10.5 Development of a DNA-based Biological System for Nanocomposite 311 Parallel Screening Covalent Attachment of an NH2-5 -modified 20-mer DNA Probe onto NCs 313 towards DNA-Biofunctionalized NCs. Covalent Amide Bond Chemistry and Resulting NC-Supported DNA Hybridizations Attachment of a Biotin- 5 -modified 20-mer DNA Probe to 318 DNA-biofunctionalized NCs. Quasi-covalent Linkage Using the Streptavidin--Biotin System and the Resulting NC-supported DNA Hybridizations Storage: Medium-term Stability of Some PolyDPyr-/PolyDCbz-Magnetite NCs 320

10.6 Typical Experimental Procedures for NC Fabrication and NC-Supported 320 DNA Hybridizations 10.6.1 Typical Optimized Procedures for NC Fabrication Including Magnetite 320 Preparation 10.6.1.1 Magnetite Preparation Using the Oxidative Hydrolysis of Iron(II) Sulfate in an 320 Alkaline KOH Medium 10.

9 10.6 Typical Experimental Procedures for NC Fabrication and NC-Supported 320 DNA Hybridizations Typical Optimized Procedures for NC Fabrication Including Magnetite 320 Preparation Magnetite Preparation Using the Oxidative Hydrolysis of Iron(II) Sulfate in an 320 Alkaline KOH Medium PolyDPyr-Magnetite Nanocomposites PolyDCbz-Magnetite Nanocomposites Covalent Attachment of an Aminated NH2 5 -modified DNA Probe. Hybridization Experiments onto PolyDPyr-/PolyDCbz-Magnetite NCs. Typical Experimental Procedures Specific Reagents, Buffers and Washing/Assay Solutions Quasi-covalent Attachment of a Biotin-5 -modified DNA Probe and DNA 324 Hybridization Experiments onto Streptavidin-modified PolyDPyr-(5a)/PolyDCbz(5b)-magnetite NCs. Typical Experimental Procedures 10.7 Conclusions and Research Outlook Gelatin Nanoparticles and Their Biofunctionalization 330 Sushma Kommareddy, Dinesh B. Shenoy, and Mansoor M. Amiji 11.1 Introduction Gelatin and Gelatin Derivatives Gelatin Chemical Modification of Gelatin PEGylation Thiolation Other Conjugates of Gelatin Nanoparticulate Carriers of Gelatin and Gelatin Derivatives Desolvation Desolvation Using Ethanol Two-step Desolvation Coacervation Nano-encapsulation by Water-in-oil Emulsion Method Characterization of Gelatin and Modified Gelatin Nanoparticles Loading and Release of Payload from Gelatin Nanoparticles Biocompatibility Studies Applications of Gelatin and Modified Gelatin Nanoparticles Conclusions Index

P. M. Ajayan, L. S. Schadler, P. V. Braun Nanocomposite Science and Technology

P. M. Ajayan, L. S. Schadler, P. V. Braun Nanocomposite Science and Technology Nanocomposite Science and Technology. Edited by P.M. Ajayan, L.S. Schadler, P.V. Braun Copyright ª 2003 WILEY-VCH Verlag GmbH