Chemistry of Bioconjugates E-Book

• Herausgeber: John Wiley & Sons
• Kategorie: Fachliteratur
• Sprache: Englisch

Seitenzahl: 1185

Veröffentlichungsjahr: 2013

Beschreibung

Explores bioconjugate properties and applications of polymers, dendrimers, lipids, nanoparticles, and nanotubes Bioconjugation has enabled breakthroughs across many areas of industry and biomedicine. With its emphasis on synthesis, properties and applications, this book enables readers to understand the connection between chemistry and the biological application of bioconjugated materials. Its detailed descriptions of methods make it possible for researchers to fabricate and take full advantage of bioconjugates for a broad range of applications. Moreover, the book sets the foundation for the development of new applications, including assays, imaging, biosensors, drug delivery, and diagnostics. Chemistry of Bioconjugates features contributions from an international team of leading experts and pioneers in the field. These contributions reflect the authors' firsthand laboratory experience as well as a thorough review of the current literature. The book's six sections examine: * General methods of bioconjugation * Polymer bioconjugates * Organic nanoparticle-based bioconjugates * Inorganic nanomaterial bioconjugates, including metals and metal oxides * Cell-based, hydrogel/microgel, and glyco-bioconjugates * Characterization, physico-(bio)chemical properties, and applications of bioconjugates This comprehensive exploration of bioconjugates includes discussions of polymers, dendrimers, lipids, nanoparticles, and nanotubes. References at the end of each chapter serve as a gateway to the most important original research findings and reviews in the field. By drawing together and analyzing all the latest chemical methods and research findings on the physico-chemical and biochemical properties of bioconjugates, Chemistry of Bioconjugates sheds new light on the significance and potential of bioconjugation. The book is recommended for organic and polymer chemists, biochemists, biomaterial scientists, carbohydrate chemists, biophysicists, bioengineers, and drug and gene delivery scientists.

Leseprobe

CONTENTS

Cover

Title Page

Copyright

Preface

Contributors

Section I: General Methods of Bioconjugation

Chapter 1: Covalent and Noncovalent Bioconjugation Strategies

1.1 INTRODUCTION

1.2 COVALENT BIOCONJUGATION STRATEGIES

1.3 NONCOVALENT BIOCONJUGATION STRATEGIES

1.4 CONCLUSIONS AND OUTLOOK

REFERENCES

Section II: Polymer Bioconjugates

Chapter 2: Bioconjugates Based on Poly(Ethylene Glycol)s and Polyglycerols

2.1 INTRODUCTION

2.2 POLYETHYLENE GLYCOL-BASED BIOCONJUGATES

2.3 LIMITATIONS OF PEG CONJUGATES

2.4 POLYGLYCEROL-BASED CONJUGATES

2.5 CONCLUSIONS

ACKNOWLEDGMENTS

REFERENCES

Chapter 3: Synthetic Polymer Bioconjugate Systems

3.1 INTRODUCTION

3.2 PEPTIDE OR PROTEIN BIOCONJUGATION TECHNIQUES

3.3 CARBOHYDRATE BIOCONJUGATION TECHNIQUES

3.4 CONJUGATION WITH NUCLEIC ACID

3.5 CONJUGATION WITH DRUGS

3.6 CONJUGATION WITH CONTRAST AGENTS

3.7 CONCLUSION AND PERSPECTIVE

REFERENCES

Chapter 4: Natural Polymer Bioconjugate Systems

4.1 INTRODUCTION

4.2 NATURAL POLYMER SYSTEMS

4.3 CONCLUSION AND FUTURE DIRECTIONS

ACKNOWLEDGMENT

REFERENCES

Chapter 5: Dendrimer Bioconjugates: Synthesis and Applications

5.1 INTRODUCTION—DENDRIMERS FOR BIOCONJUGATE CHEMISTRY

5.2 DENDRIMER–DRUG CONJUGATES

5.3 DENDRIMER–CARBOHYDRATE CONJUGATES

5.4 DENDRIMER CONJUGATES WITH IMAGING AGENTS

5.5 DENDRIMER–DNA CONJUGATES

5.6 DENDRIMER–PEPTIDE AND DENDRIMER–PROTEIN CONJUGATES

5.7 CONCLUSIONS AND FUTURE PROSPECTS

REFERENCES

Section III: Organic Nanoparticles Based Bioconjugates

Chapter 6: Bioconjugation Strategies: Lipids, Liposomes, Polymersomes, and Microbubbles

6.1 INTRODUCTION

6.2 LIPIDS AND LIPOSOMES

6.3 MICROBUBBLES AND NANOBUBBLES

6.4 POLYMERSOMES

REFERENCES

Chapter 7: Organic Nanoparticle Bioconjugate: Micelles, Cross-Linked Micelles, and Nanogels

7.1 INTRODUCTION

7.2 POLYMER–PROTEIN NANOPARTICULATE BIOCONJUGATES

7.3 POLYMER–ODN/DNA NANOPARTICULATE BIOCONJUGATES

7.4 POLYMER–CARBOHYDRATE NANOPARTICULATE BIOCONJUGATES

7.5 POLYMER–BIOACTIVE MOLECULE NANOPARTICULATE BIOCONJUGATES

7.6 POLYMER–DRUG NANOPARTICULATE BIOCONJUGATES

7.7 POLYMER-IMAGING AGENTS NANOPARTICULATE BIOCONJUGATES

REFERENCES

Chapter 8: Carbon Nanotubes and Fullerene C60 Bioconjugates

8.1 INTRODUCTION

8.2 CARBON NANOTUBES—THE CYLINDERS

THE BUCKMINSTERFULLERENE, C60—THE BUCKYBALL

8.4 CARBON NANOTUBES–-BIOCONJUGATES THROUGH COVALENT FUNCTIONALIZATION

8.5 CARBON NANOTUBES—BIOCONJUGATES THROUGH NONCOVALENT FUNCTIONALIZATION

8.6 BUCKMINSTERFULLERENE—BIOCONJUGATES THROUGH FUNCTIONALIZATION OR CHEMICAL MODIFICATION

8.7 CONCLUSIONS AND FUTURE TRENDS

REFERENCES

Section IV: Inorganic Nanomaterials Bioconjugates (Metals, Metal Oxides—Quantum Dots, Iron-Oxide)

Chapter 9: Gold Nanomaterials Bioconjugates

9.1 PEPTIDES/PROTEINS

9.2 ODN/DNA

9.3 CARBOHYDRATES

9.4 DRUGS

9.5 IMAGING AGENTS

9.6 BIOACTIVE (MACRO)MOLECULES

9.7 CONCLUSION

REFERENCES

Chapter 10: Methods for Magnetic Nanoparticle Synthesis and Functionalization

10.1 SYNTHESIS OF MAGNETIC NP CORES

10.2 IMMOBILIZATION OF CARBOHYDRATES ONTO MAGNETIC NPS

10.3 FUNCTIONALIZATION OF MAGNETIC NPS FOR DELIVERY OF THERAPEUTIC AGENTS

10.4 FUNCTIONALIZATION OF MAGNETIC NPS FOR NUCLEIC ACID DELIVERY

10.5 CONJUGATION OF MAGNETIC NPS WITH ANTIBODIES

10.6 CONCLUSION

REFERENCES

Chapter 11: Quantum Dots Bioconjugates

11.1 INTRODUCTION

11.2 SYNTHESIS OF WATER-SOLUBLE QDS

11.3 BIOCONJUGATION OF WATER-SOLUBLE QDS

11.4 CONCLUSION

REFERENCES

Chapter 12: Silica Nanoparticle Bioconjugates

12.1 INTRODUCTION

12.2 DRUGS

12.3 IMAGING AGENTS

12.4 NUCLEIC ACID (DNA/RNA)

12.5 PEPTIDES/PROTEINS

12.6 CARBOHYDRATES

12.7 BIOACTIVE (MACRO)MOLECULES

12.8 CONCLUSION AND FUTURE TRENDS

REFERENCES

Chapter 13: Polyhedral Oligomeric Silsesquioxanes (POSS) Bioconjugates

13.1 INTRODUCTION

13.2 PREPARATION OF POSS-CONTAINING BIOCONJUGATES

13.3 APPLICATIONS OF POSS-CONTAINING BIOCONJUGATES

13.4 CONCLUSIONS AND OUTLOOK

REFERENCES

Section V: Cell-Based, Hydrogels/Microgels and Glyco-Bioconjugates

Chapter 14: Cell-Based Bioconjugates

14.1 INTRODUCTION

14.2 CLASSIFICATION OF CELL MEMBRANE CONJUGATIONS ON THE BASIS OF MODIFICATION METHODS

14.3 IMMUNOCAMOUFLAGE OF RED BLOOD CELLS

14.4 ISLET TRANSPLANTATION

14.5 CELL SURFACE DECORATION FOR LABELING, MANIPULATION, AND PROGRAMMABLE ADHESION

14.6 VIRUSES, BACTERIA, YEAST CELL CONJUGATION

14.7 CONCLUSIONS

REFERENCES

Chapter 15: Bioresponsive Hydrogels and Microgels

15.1 INTRODUCTION

15.2 BIOSENSING

15.3 CONCLUSION

REFERENCES

Chapter 16: Conjugation Strategies Used for the Preparation of Carbohydrate-Conjugate Vaccines

16.1 INTRODUCTION

16.2 FUTURE DIRECTIONS

16.3 LIST OF ABBREVIATIONS

ACKNOWLEDGMENTS

REFERENCES

Section VI: Characterization, Physico-(Bio)Chemical Properties, and Applications of Bioconjugates

Chapter 17: Properties and Characterization of Bioconjugates

17.1 INTRODUCTION

17.2 POLYMER BIOCONJUGATES

17.3 NANOPARTICLE BIOCONJUGATES

17.4 FULLERENE AND CARBON NANOTUBE BIOCONJUGATES

17.5 DENDRIMER BIOCONJUGATES

17.6 LIPOSOME-BASED BIOCONJUGATES

17.7 MICROGEL AND HYDROGEL BIOCONJUGATES

17.8 CELL-BASED BIOCOJUGATES

17.9 BIOCONJUGATES ON SURFACES

17.10 INTERMOLECULAR FORCES IN BIOLOGY

ACKNOWLEDGMENT

REFERENCES

Chapter 18: Physico-Chemical and Biochemical Properties of Bioconjugates

18.1 INTRODUCTION

18.2 PHYSICAL PROPERTIES

18.3 CHEMICAL PROPERTIES

18.4 BIOCHEMICAL PROPERTIES

REFERENCES

Chapter 19: Applications of Bioconjugates

19.1 INTRODUCTION

19.2 LABELING TAGS AND PROBES

19.3 BIOLOGICAL ASSAYS

19.4 IMAGING in vivo

19.5 BIOSENSORS

19.6 DRUG DELIVERY

19.7 TISSUE ENGINEERING

19.8 GENE DELIVERY

19.9 BIOCOMPATIBILITY

19.10 VACCINES

19.11 IN VITRO AND IN VIVO TARGETING

19.12 DIAGNOSTIC AND AFFINITY SEPARATIONS

19.13 INDUSTRIAL APPLICATIONS

19.14 CONCLUSION

REFERENCES

Index

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Library of Congress Cataloging-in-Publication Data:

Chemistry of bioconjugates : synthesis, characterization, and biomedical applications / edited by Dr. Ravin Narain, Department of Chemical and Materials Engineering, University of Alberta, Edmonton, Alberta, Canada. pages cm Includes index. ISBN 978-1-118-35914-3 (cloth) 1. Bioconjugates. I. Narain, Ravin, editor of compilation. QP517.B49C46 2014 612.1′111–dc23 2013026540

ISBN: 9781118159248

PREFACE

Combining characteristics of different components into one to generate new molecular systems with unique properties by simply linking one or more (macro)molecules is defined as bioconjugation. The ability to create such biohybrids either covalently or non-covalently has allowed major breakthrough in many industrial and biomedical areas such as bioseparation, targeting, detection, biosensing, biological assays, etc. This book provides a comprehensive account on the chemistries involved in the formation of bioconjugates, followed by an extensive review of all the different types of bioconjugates generated so far from polymers, dendrimers, nanoparticles, carbon nanotubes, hydrogels and so on for different bio-related applications. A section is also devoted to the physicochemical and biochemical properties of bioconjugates. Finally, the book also provides a comprehensive account on the significance of bioconjugation which is lacking in many of the current available resources.

The book begins by providing an overview of the chemistry involved in bioconjugation. Different types of bioconjugation strategies available for the modification of biomolecules (proteins, peptides, carbohydrates, polymers, DNA) are presented. Classical bioconjugation approaches are described first, followed by some recent bioconjugation techniques. This section also provides detailed synthetic protocols for some of the most important strategies for bioconjugation.

Polymer bioconjugates are then discussed separately in three sections, namely polyethylene glycol (PEG), synthetic polymer bioconjugates, and natural polymer bioconjugates. PEG has been extensively used in the development of macromolecular therapeutics and most of the current clinically available therapeutics are PEGylated bioconjugates. PEGylation has been used for proteins, anticancer drugs, and other bioactive molecules such as peptides, antibodies, oligonucleotides, aptamers, red blood cells, and more recently, viruses. Conjugation of synthetic polymers to biomolecules is an appealing strategy to produce new biomacromolecules with distinctive properties. Typical conjugation strategies are either “grafting from” or “grafting to” approaches. In “grafting from” approach, monomer-functionalized biomolecules are polymerized to produce synthetic polymer bioconjugates. On the other hand, in “grafting to” approach, biomolecules are immobilized by reactive coupling reactions. Random and site-specific modifications of natural macromolecules have also been extensively studied and, therefore, an elaborated section has been devoted to this area.

The next section is focused on organic nanoparticle bioconjugates. Different chemical strategies used to couple biomolecules with liposomes, micelles, carbon nanotubes, fullerene, and graphene are discussed. Bioconjugation of biomolecules to those organic nanoparticles has become increasingly important in drug formulation and therapeutic delivery. Choosing the right chemistry between the biomolecule and organic nanoparticle has been the focus of great attention in recent years in view of improving the sustained delivery of these bioconjugates to the targeted site effectively. Carbon nanotubes, fullerene, and graphene have unique properties and their coupling with biomolecules have generated unique materials of high potency in biomedical applications.

Inorganic nanomaterials such as gold, iron oxide, quantum dots, and silica have become key players in the biomedical field. Their unique chemical and physical properties have contributed significantly in further development of these nanomaterials. Their surface properties dictate their colloidal stability and biocompatibility. Therefore, in recent years, several strategies have been developed to conjugate bioactive molecules, targeting ligands and other biologically relevant molecules to broaden the applications of these nanomaterials. This section discusses the different chemistries used in bioconjugation of biomolecules on the surface of these most widely used inorganic nanomaterials.

With the rapid development of the chemistries in bioconjugation, it is now possible to prepare cell-based bioconjugates efficiently. Modifying cell surfaces with bioactive molecules or synthetic polymers has been a versatile way to add advanced features and unique properties to inert cells. Creating a nanoscale layer on a cell surface, for example, significantly improves or even completely changes its biological properties as well as introduces new unique properties, such as chemical functionality, surface roughness, surface tension, morphology, surface charge, surface reflectivity, surface conductivity, and optical properties. Recently, surface modification of living cells has been the subject of study for a variety of biological applications such as imaging, transfection, and control of cell surface interactions. Additionally, microgels and hydrogels have emerged as important materials due to their unique features such as encapsulation, swelling, degradation, and controlled dimensions. Such features are further enhanced by conjugating them chemically or physically with other bioactive molecules. This section reviews different approaches in making those biologically relevant bioconjugates. Subsequently, various conjugation strategies for the preparation of carbohydrate-based vaccines and different types of chemistry used for covalent linkage of the individual vaccine components are discussed. Then, both direct and indirect conjugation techniques, as well as different types of linker molecules used to generate the spacing deemed required between carbohydrate and immunogen are presented.

Finally, once the bioconjugates are synthesized, their structures and function need to be properly characterized to fully understand their properties. Therefore, proper tools are required to fully understand the properties of these complex hybrid biomolecules. The techniques used in the full characterization of these bioconjugates are discussed in detail. This section also focuses on the physicochemical and biochemical properties of bioconjugates. The physical properties of conjugates, including their response to temperature, external field (magnetic field, electric field, ultrasound), and light, are discussed. The chemical properties of conjugates, such as their response to a change in the pH and ionic strength, are also summarized. Additionally, the properties of conjugates in response to glutathione (GSH), hydrogen peroxide (H2O2), and glucose are also outlined. These bioconjugates have been implied for a variety of biological applications, including drug and gene delivery applications, biological assays, imaging, and biosensors. The success of these bioconjugates in research laboratories, compared to their precursor biomolecules, has further encouraged their use for industrial applications. Some of these bioconjugates are now used in clinical trials.

Ravin Narain

CONTRIBUTORS

Marya Ahmed, Department of Chemical and Materials Engineering, Alberta Glycomics Centre, University of Alberta, Edmonton, AB, Canada

Keshwaree Babooram, Department of Chemical and Materials Engineering, Alberta Glycomics Centre, University of Alberta, Edmonton, AB, Canada

Mitsuhiro Ebara, Biomaterials Unit, International Center for Materials Nanoarchitectonics (WPI-MANA), National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba, Ibaraki, Japan

Kheireddine El-Boubbou, Department of Chemistry, Michigan State University, East Lansing, Michigan, USA; College of Science and Health Professions, King Saud bin AbdulAziz University for Health Sciences, National Guard Health Affairs, Riyadh, Saudi Arabia

Mohammad H. El-Dakdouki, Department of Chemistry, Michigan State University, East Lansing, Michigan, USA; Department of Chemistry, Beirut Arab University, Beirut, Lebanon

Ali Faghihnejad, Department of Chemical and Materials Engineering, Alberta Glycomics Centre, University of Alberta, Edmonton, AB, Canada

Fang Gao, Centre for Blood Research and the Department of Pathology and Laboratory Medicine, Department of Chemistry, University of British Columbia, Vancouver, BC, Canada

Elizabeth R. Gillies, Department of Chemistry and Department of Chemical and Biochemical Engineering, The University of Western Ontario, London, Canada

Anirban Sen Gupta, Department of Biomedical Engineering, Case Western Reserve University, Cleveland, OH, USA

Rachel Hevey, Alberta Glycomics Center and Department of Chemistry, University of Calgary, Calgary, AB, Canada

Lizhi Hong, Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai, PR China

Jun Huang, Department of Chemical and Materials Engineering, Alberta Glycomics Centre, University of Alberta, Edmonton, AB, Canada

Xuefei Huang, Department of Chemistry, Michigan State University, East Lansing, Michigan, USA

Muhammad Imran ul-Haq, Centre for Blood Research and the Department of Pathology and Laboratory Medicine, Department of Chemistry, University of British Columbia, Vancouver, BC, Canada

Xiaoze Jiang, State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, Shanghai, PR China

Herbert Kavunja, Department of Chemistry, Michigan State University, East Lansing, Michigan, USA

Jayachandran N. Kizhakkedathu, Centre for Blood Research and the Department of Pathology and Laboratory Medicine, Department of Chemistry, University of British Columbia, Vancouver, BC, Canada

Yohei Kotsuchibashi, Department of Chemical and Materials Engineering, Alberta Glycomics Centre, University of Alberta, Edmonton, AB, Canada

Xue Li, Department of Chemistry, University of Alberta, Edmonton, AB, Canada

Chang-Chun Ling, Alberta Glycomics Center and Department of Chemistry, University of Calgary, Calgary, AB, Canada

Lichao Liu, Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai, PR China

Ravin Narain, Department of Chemical and Materials Engineering, Alberta Glycomics Centre, University of Alberta, Edmonton, AB, Canada

Ali Nazemi, Department of Chemistry and Department of Chemical and Biochemical Engineering, The University of Western Ontario, London, Canada

Xiuwei Pan, Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai, PR China

Michael J. Serpe, Department of Chemistry, University of Alberta, Edmonton, AB, Canada

Rajesh A. Shenoi, Centre for Blood Research and the Department of Pathology and Laboratory Medicine, Department of Chemistry, University of British Columbia, Vancouver, BC, Canada

Rajesh Sunasee, Department of Chemistry, State University of New York, Plattsburgh, NY, USA

Maria Vamvakaki, Institute of Electronic Structure and Laser, Foundation for Research and Technology, Hellas, Heraklion, Crete, Greece; Department of Materials Science and Technology, University of Crete, Heraklion, Crete, Greece.

Horst A. von Recum, Department of Biomedical Engineering, Case Western Reserve University, Cleveland, OH, USA

Jingguang Xia, Department of Chemistry, Michigan State University, East Lansing, Michigan, USA

Qian Yang, Department of Civil and Environmental Engineering, University of Maryland, College Park, MD, USA

Hongbo Zeng, Department of Chemical and Materials Engineering, Alberta Glycomics Centre, University of Alberta, Edmonton, AB, Canada

Weian Zhang, Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai, PR China

Zhenghe Zhang, Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai, PR China

Meifang Zhu, State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, Shanghai, PR China

SECTION I

GENERAL METHODS OF BIOCONJUGATION