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A comprehensive reference on biochemistry, bioimaging, bioanalysis, and therapeutic applications of carbon nanomaterials
Carbon nanomaterials have been widely applied for biomedical applications in the past few decades, because of their unique physical properties, versatile functionalization chemistry, and biological compatibility. This book provides background knowledge at the entry level into the biomedical applications of carbon nanomaterials, focusing on three applications: bioimaging, bioanalysis, and therapy.
Carbon Nanomaterials for Bioimaging, Bioanalysis and Therapy begins with a general introduction to carbon nanomaterials for biomedical applications, including a discussion about the pros and cons of various carbon nanomaterials for the respective therapeutic applications. It then goes on to cover fluorescence imaging; deep tissue imaging; photoacoustic imaging; pre-clinical/clinical bioimaging applications; carbon nanomaterial sensors for cancer and disease diagnosis; targeted cancer therapy; and photothermal/photodynamic therapy. Each chapter briefly introduces the biomedical application and emphasizes the most appropriate carbon nanomaterial(s) for the application.
Carbon Nanomaterials for Bioimaging, Bioanalysis and Therapy is an excellent resource for academic researchers and industrial scientists working on preparation and bio-application of carbon nanomaterials, biomedical engineering, and nanotechnology.
Editors
Yuen Yung Hui, is a Postdoctoral Research Fellow at the Institute of Atomic and Molecular Sciences, Academia Sinica, Taipei, Taiwan, Republic of China.
Huan-Cheng Chang, is a Distinguished Research Fellow at the Institute of Atomic and Molecular Sciences, Academia Sinica, Taipei, Taiwan, Republic of China.
Haifeng Dong, is a Professor at the University of Science and Technology Beijing, P.R. China.
Xueji Zhang, is Professor and Dean in the School of Chemistry & Biological Engineering at the University of Science & Technology Beijing, P.R. China.
List of Contributors xiii
Series Preface xix
Preface xxi
Part I Basics of Carbon Nanomaterials 1
1 Introduction to Carbon Structures 3
Meng-Chih Su and Yuen Yung Hui
1.1 Carbon Age 3
1.2 Classification 4
1.3 Fullerene 4
1.4 Carbon Nanotubes 6
1.4.1 Structure 6
1.4.2 Electronics 8
1.5 Graphene 10
1.5.1 Structure 10
1.5.2 Electronics 11
1.6 Nanodiamonds and Carbon Dots 12
Acknowledgment 13
References 13
2 Using Polymers to Enhance the Carbon Nanomaterial Biointerface 15
Goutam Pramanik, Jitka Neburkova, Vaclav Vanek, Mona Jani, Marek Kindermann, and Petr Cigler
2.1 Introduction 15
2.2 Colloidal Stability of CNMs 16
2.3 Functionalization of CNMs with Polymers 18
2.3.1 Noncovalent Approaches 18
2.3.2 Covalent Approaches 18
2.4 Influence of Polymers on the Spectral Properties of CNMs 19
2.5 Functionalizing CNMs with Antifouling Polymers for Bioapplications 22
2.6 Functionalization of CNMs with Stimuli-Responsive Polymers 26
2.6.1 Carbon Nanoparticles with Thermoresponsive Polymers 27
2.6.2 pH-Responsive Carbon Nanoparticles 27
2.6.3 Redox-Responsive Carbon Nanoparticles 28
2.6.4 Multi-Responsive Carbon Nanoparticles 28
2.7 Functionalization of CNMs with Polymers for Delivery of Nucleic Acids 29
2.8 Outlook 32
Acknowledgments 34
References 34
3 Carbon Nanomaterials for Optical Bioimaging and Phototherapy 43
Haifeng Dong and Yu Cao
3.1 Introduction 43
3.2 Surface Functionalization of Carbon Nanomaterials 43
3.3 Carbon Nanomaterials for Optical Imaging 45
3.3.1 Intrinsic Fluorescence of Carbon Nanomaterials 45
3.3.2 Imaging Utilizing Intrinsic Fluorescence Features of Carbon Nanomaterials 46
3.3.3 Imaging with Fluorescently Labeled Carbon Nanomaterials 51
3.4 Carbon Nanomaterials for Phototherapies of Cancer 51
3.4.1 Photothermal Therapy 52
3.4.2 Photodynamic Therapy 53
3.5 Conclusions and Outlook 56
References 56
Part II Bioimaging and Bioanalysis 63
4 High-Resolution and High-Contrast Fluorescence Imaging with Carbon Nanomaterials for Preclinical and Clinical Applications 65
John Czerski and Susanta K. Sarkar
4.1 Introduction 65
4.2 Survey of Carbon Nanomaterials 66
4.2.1 Fluorescent Nanodiamonds 66
4.2.2 Carbon Nanotubes 66
4.2.3 Graphene 69
4.2.4 Carbon Nanodots 69
4.3 Fluorescent Properties of FNDs and SWCNTs 69
4.3.1 FNDs 69
4.3.2 SWCNTs 71
4.4 Survey of High-Resolution and High-Contrast Imaging 71
4.4.1 General Considerations for Eventual Human Use 71
4.4.2 General Considerations for Achieving High-Resolution and High-Contrast Imaging 72
4.4.2.1 Photoacoustic Imaging (PAI) 72
4.4.2.2 X-ray Computed Tomographic (CT) Imaging 73
4.4.2.3 Magnetic Resonance Imaging (MRI) 73
4.4.2.4 Image Alignment and Drift Correction 74
4.4.3 Preclinical and Clinical Optical Imaging with CNMs 74
4.4.4 Optical Imaging in the Short-Wavelength Window (~650-950 nm) 74
4.4.4.1 Optical Imaging beyond the Diffraction Limit 75
4.4.4.2 Selective Modulation of Emission 75
4.4.4.3 Time-Gated Fluorescence Lifetime Imaging 77
4.4.5 Optical Imaging in the Long-Wavelength Window (~950-1400 nm) 77
4.5 Conclusions 78
References 79
5 Carbon Nanomaterials for Deep-Tissue Imaging in the NIR Spectral Window 87
Stefania Lettieri and Silvia Giordani
5.1 Introduction 87
5.1.1 Transparent Optical Windows in Biological Tissue 87
5.1.2 Near-Infrared Imaging Materials 88
5.2 Carbon Nanomaterials for NIR Imaging 89
5.2.1 Biocompatibility of CNMs 90
5.2.2 Fluorescence of CNMs Probes 91
5.2.3 Covalent and Noncovalent Functionalization 91
5.2.4 CNMs as Bioimaging Platforms 91
5.2.4.1 Fullerene 91
5.2.4.2 Carbon Nanotubes 93
5.2.4.3 Graphene Derivatives 99
5.2.4.4 Carbon Dots 100
5.2.4.5 Carbon Nano-onions 102
5.2.4.6 Nanodiamonds 104
5.3 Conclusions and Outlook 105
Acknowledgments 106
References 106
6 Tracking Photoluminescent Carbon Nanomaterials in Biological Systems 115
Simon Haziza, Laurent Cognet, and François Treussart
Chapter Summary 115
6.1 Introduction 115
6.2 Tracking Cells in Organisms with Fluorescent Nanodiamonds 116
6.3 Monitoring Inter and Intra Cellular Dynamics with Fluorescent Nanodiamonds 120
6.4 Single-Walled Carbon Nanotubes: A Near-Infrared Optical Probe of the Nanoscale Extracellular Space in Live Brain Tissue 127
6.5 Conclusion 131
References 132
7 Photoacoustic Imaging with Carbon Nanomaterials 139
Seunghyun Lee, Donghyun Lee, and Chulhong Kim
Chapter Summary 139
7.1 Introduction 139
7.2 Photoacoustic Imaging Systems 140
7.2.1 Photoacoustic Microscopy 141
7.2.2 Photoacoustic Computed Tomography 142
7.3 Photoacoustic Application of Carbon Nanomaterials 145
7.3.1 Carbon Nanomaterials for Photoacoustic Imaging Contrast Agents 146
7.3.2 Carbon Nanomaterials for Multimodal Photoacoustic Imaging 149
7.3.3 Carbon Nanomaterials for Photoacoustic Image-Guided Therapy 156
7.3.4 Conclusions and Future Perspective 160
Acknowledgments 161
References 162
8 Carbon Nanomaterial Sensors for Cancer and Disease Diagnosis 167
Tran T. Tung, Kumud M. Tripathi, TaeYoung Kim, Melinda Krebsz, Tibor Pasinszki, and Dusan Losic
8.1 Introduction 167
8.2 Detection of VOC by Using Gas/Vapor Sensors for Cancer and Disease Diagnosis 169
8.2.1 Carbon Nanodots (CNDs) and Graphene Quantum Dots (GQDs) for VOC Sensors 171
8.2.2 Carbon Nanotubes (CNTs) for VOC Sensors 173
8.2.3 Graphene for VOC Sensors 176
8.3 Detection of Biomarkers Using Biosensors for Cancer and Disease Diagnosis 179
8.3.1 Carbon Nanodot- and Graphene Quantum Dot-Based Biosensors for Disease Biomarkers Detection 179
8.3.2 Carbon Nanotube-Based Biosensors for Cancer Biomarker Detection 182
8.3.3 Carbon Nanotube-Based Biosensors for Disease Biomarker Detection 186
8.3.4 Graphene-Based Biosensors for Cancer Biomarker Detection 188
8.3.5 Graphene-Based Biosensors for Disease Biomarker Detection 190
8.4 Conclusions and Perspectives 192
Acknowledgments 193
References 193
9 Recent Advances in Carbon Dots for Bioanalysis and the Future Perspectives 203
Jessica Fung Yee Fong, Yann Huey Ng, and Sing Muk Ng
9.1 Introduction 203
9.2 Fundamentals of CDs 205
9.2.1 Synthesis Approaches 205
9.2.2 Optical Properties 206
9.2.2.1 Absorbance and Photoluminescence (PL) 206
9.2.2.2 Quantum Yield (QY) 210
9.2.2.3 Photoluminescence Origins 210
9.2.2.4 Up-Conversion Photoluminescence (UCPL) 211
9.2.2.5 Phosphorescence 212
9.2.3 Physical and Chemical Properties 213
9.2.4 Biosafety Assessments 214
9.3 Bioengineering of CDs for Bioanalysis 216
9.3.1 Functionalization Mechanism and Strategies 216
9.3.1.1 Chemical Functionalization 216
9.3.1.2 Doping 217
9.3.1.3 Coupling with Gold Nanoparticles 217
9.3.1.4 Fabrication onto Solid Polymeric Matrices 218
9.3.2 Biomolecules Grafted on CDs as Sensing Receptors 218
9.3.2.1 Deoxyribonucleic Acid (DNA) 218
9.3.2.2 Aptamers 219
9.3.2.3 Proteins/Peptides 219
9.3.2.4 Biopolymers 220
9.4 Bioanalysis Applications of CDs 221
9.4.1 Biosensing Mechanism/Transduction Schemes 221
9.4.1.1 Fluorescence 222
9.4.1.2 Chemiluminescence (CL) 223
9.4.1.3 Electrochemiluminescence (ECL) 224
9.4.1.4 Electrochemical 224
9.4.2 Uses of CDs in Bioanalysis 225
9.4.2.1 Heavy Metals/Elements 225
9.4.2.2 Reactive Oxygen/Nitrogen Species (ROS/RNS) 226
9.4.2.3 Oligonucleotides 227
9.4.2.4 Small Molecules/Pharmaceutical Drugs/Natural Compounds 228
9.4.2.5 Proteins 230
9.4.2.6 Enzyme Activities and Inhibitor Screening 231
9.4.2.7 pH 232
9.4.2.8 Temperature 234
9.4.3 Solid-State Sensing for Point-of-Care Diagnostic Kits 234
9.4.4 Bioimaging/Real-Time Monitoring 236
9.4.5 Theranostics 238
9.5 Future Perspectives 240
9.5.1 Better Understanding of PL Mechanisms 240
9.5.2 Establishment of Systematic Synthesis Protocol 241
9.5.3 QY Improvement and Spectral Expansion to Longer Wavelength 241
9.5.4 Sensitivity Improvement for Solid-State Sensing 242
9.6 Conclusions 242
References 242
Part III Therapy 265
10 Functionalized Carbon Nanomaterials for Drug Delivery 267
Naoki Komatsu 267
10.1 Introduction 267
10.2 Direct Fabrication of Graphene-Based Composite with Photosensitizer for Cancer Phototherapy 268
10.2.1 Fabrication of Graphene-Based Composite with Chlorin e6 (G-Ce6) 268
10.2.2 Characterization of G-Ce6 268
10.2.3 In vitro Evaluation of G-Ce6 for Cancer Phototherapy 272
10.3 Polyglycerol-Functionalized Nanodiamond Conjugated with Platinum-Based Drug for Cancer Chemotherapy 274
10.3.1 Synthesis of Polyglycerol-Functionalized Nanodiamond Conjugated with Platinum-Based Drug and Targeting Peptide 274
10.3.2 Characterization of Polyglycerol-Functionalized Nanodiamond and the Derivatives 276
10.3.3 In vitro Evaluation of Polyglycerol-Functionalized Nanodiamond Conjugated with Platinum-Based Drug for Cancer Chemotherapy 279
10.4 Polyglycerol-Functionalized Nanodiamond Hybridized with DNA for Gene Therapy 280
10.4.1 Synthesis and Characterization of Polyglycerol-Functionalized Nanodiamond Conjugated with Basic Polypeptides 280
10.4.2 Characterization of Polyglycerol-Functionalized Nanodiamond Hybridized with Plasmid DNA 280
10.5 Conclusions and Perspectives 283
Acknowledgments 285
References 285
11 Multifunctional Graphene-Based Nanocomposites for Cancer Diagnosis and Therapy 289
Ayuob Aghanejad, Parinaz Abdollahiyan, Jaleh Barar, and Yadollah Omidi
11.1 Introduction 289
11.2 Multifunctional Graphene-Based Composites for the Diagnosis/Therapy of Cancer 291
11.2.1 Metal-Graphene Nanocomposites 292
11.2.1.1 Gold-Graphene Composites 292
11.2.1.2 Magnetic Graphene Nanocomposites 294
11.2.2 Polymeric Graphene Nanocomposites 295
11.2.3 Graphene Biomaterials for MR Imaging 299
11.3 Multimodal Graphene-Based Composites for the Radiotherapy of Cancer 300
11.4 Graphene-Based Nanobiomaterials for Cancer Diagnosis 302
11.5 Conclusion 302
Acknowledgment 303
References 303
12 Carbon Nanomaterials for Photothermal Therapies 309
Jiantao Yu, Lingyan Yang, Junyan Yan, Wen-Cheng Wang, Yi-Chun Chen, Hung-Hsiang Chen, and Chia-Hua Lin
12.1 Introduction 309
12.2 GO for PTT 311
12.2.1 PTT-Related Physical and Chemical Properties of GO 311
12.2.2 GO for in vitro PTT 312
12.2.3 GO for in vivo PTT 314
12.3 CNTs and CNHs for PTT 314
12.3.1 Physical and Chemical Properties of CNTs and CNHs Related to PTT 315
12.3.2 CNTs and CNHs for in vitro PTT 316
12.3.3 CNTs and CNHs for in vivo PTT 316
12.4 CDs and GDs for PTT 318
12.4.1 Physical and Chemical Properties of CDs and GDs Related to PTT 318
12.4.2 CDs and GDs for in vitro PTT 319
12.4.3 CDs and GDs for in vivo PTT 319
12.5 Fullerenes for PTT 320
12.5.1 Physical and Chemical Properties of Fullerenes Related to PTT 320
12.5.2 Fullerenes for in vitro PTT 320
12.5.3 Fullerenes for in vivo PTT 321
12.6 Carbon Nanomaterial-Based Nanocomposites for PTT 321
12.6.1 GO-Based Nanocomposites for PTT 322
12.6.2 CNT-Based Nanocomposites for PTT 323
12.6.3 CD- and GD-Based Nanocomposites for PTT 323
12.7 Carbon Nanomaterial-Based Combined Therapy with PTT 324
12.7.1 Chemotherapy 324
12.7.2 RT 324
12.7.3 Photodynamic Therapy (PDT) 325
12.7.4 Gene Therapy 325
12.7.5 Immune Therapy 327
12.7.6 Theranostic Applications 328
12.8 Conclusions and Perspectives 329
References 330
Index 341
Meng-Chih Su1 and Yuen Yung Hui2
1 Department of Chemistry, Sonoma State University, California, USA
2 Institute of Atomic and Molecular Sciences, Academia Sinica, Taipei, Taiwan
Welcome to the Carbon World!
It seems that we already know the chemistry of carbon quite well, mostly in the form of graphite, through its long association with humans in history. Carbon is a simple element, predominantly (99% natural abundance of C-12) containing the same number (6) of protons and neutrons, and therefore is radioactively stable. Of its other isotopes, C-13 (1%) and C-14 (<100?ppm), only C-14 is radioactive with half-life time lasting for a long 5730 year. It has been used routinely for the chronological tracking in archeology. With its relatively low mass, carbon is in the sixth place of all the hundred plus elements known today with an atomic number of Z = 6.
In nature, carbon ranks as the fourth element of cosmic abundance, after hydrogen, helium, and oxygen, and counts for about 20% by weight of all livestock and humans on earth, next only to oxygen (60%). Grouped together with silicon and germanium (4A group) in the Periodic Table of Elements, the chemical reactivity of elemental carbon may be considered inert compared to the neighboring nitrogen (5A) and oxygen (6A) groups because of its thermodynamic stability. Hence, graphite solid is used as a reference state for just about all thermodynamic measurements and data. Of course, such "inertness" is changed completely when carbon is combined with hydrogen, oxygen, and/or nitrogen - a whole world of interesting reactions will occur, and as we have learned in our college organic chemistry courses, the strong carbon chain becomes backbone of all organic molecules.
So, why carbon now? In science, carbon appears as one of the most common elements supporting of and interacting with a vast variety of materials since probably dawn of human civilization and, like a dear old friend, we thought we had known all there was to know about carbon. What is it so special about carbon, among all elements on our planet Earth, that scientists and researchers are now calling it the "carbon age" [1-3]? Specifically, why the carbon nanomaterials? Perhaps there is something about this old friend that we never knew, which can only be revealed as we look carefully into the nanometer regime of carbon. In this section, we trace the development of carbon nanomaterials in order to explore their molecular structures and intrinsic properties, which have shown great potential to many innovate practices and applications both in research and as commercial products.
Carbon nanomaterials have four major allotropes for biomedical applications: carbon nanotube (), graphene (), nanodiamond (), and fullerene; all consisting of only carbon atoms, of which each has its own unique three-dimensional nanostructure. These forms of carbon are often referred to as one-dimensional CNT, two-dimensional GR, three-dimensional ND, and zero-dimensional fullerene, based mainly on its structure and electronic properties.
Graphite is normally viewed as graphene layers stacking up in three dimensions and hence not an allotrope of its own. Multiple forms of carbon, including fullerene, CNT, GR, and ND, present a rich class of solid-state materials that are both environmentally friendly and sustainable among other unique features each of their own.
A brief look in the history and development of carbon nanomaterials here seems in order to reacquaint us with some milestones in the development of new forms of carbon, with an emphasis on their unique structures and general features. A good place to start is when carbon nanoparticles first entered the center stage of science, as Richard Smalley, with help from Robert Curl, boldly introduced the world in 1985 with his soccer ball structure for the C60 molecule, now recognized as buckminsterfullerene (or fullerene, in short). An immense (and somewhat unexpected) passion caught up almost immediately in the science community to search for members of the fullerene family, to learn their chemistry, as well as to explore the possible applications of these new buckyballs. Indeed, C70, C76, C84, and other fullerene siblings were found in no time, all sharing a set of unique features as outlined here.
Fullerene is formed in a hollow cage made out of only carbon atoms with each carbon connected to three immediate neighbors in a small ring configuration, which consists of either five or six members, pentagonal, and hexagonal, respectively. As D'Arcy Thompson pointed out at the turn of the 1900s, no system of hexagons alone can enclose a space; it would need exactly 12 pentagonal rings in combination with a varying number of hexagonal rings to piece together a fullerene cage. This is known as Euler's theorem in geometry and topology, which states that the number of vertexes (V), edges (E), and faces (F) of a simple polyhedron is related by the formula V?-?E?+?F = 2.
For C60, as shown in Figure 1.1 [4], the 60 carbon atoms give V = 60; three bonds per atom and a total of 3?×?60 = 180 bonds, or 180/2 = 90 edges (each edge shared by two atoms). Following Euler's formula, 60 - 90?+?F = 2, C60 has 32 faces (32 rings), i.e. 20 hexagonals and 12 pentagonals. Therefore, fullerenes are defined as "polyhedral closed cages made up entirely of n three-coordinate carbon atoms and having 12 pentagonal and (n/2 - 10) hexagonal faces, where n is greater than or equal to 20." So, C70 has 25 hexagonals, C84 has 32, and so forth. Other polyhedral closed cages made up entirely of n three-coordinate carbon atoms are known as quasi-fullerenes. Also shown in Figure 1.1 is that no two pentagonals can share the same edge, consequently, every carbon atom must belong simultaneously to one pentagonal and two hexagonal rings. Therefore, while C60 is shaped as a true buckyball (spheroidal), other fullerenes such as C70 appear as an oblong figure more resembling a rugby ball rather than a soccer ball.
Figure 1.1 C60 fullerene (or soccer ball) [4].
Fullerenes are stable molecules. C60, for example, weighs only 720?amu in a tiny size of about 1?nm in diameter, likely to survive even in galaxy and interstellar journeys. This had motivated Smalley (based on Harold Kroto's suggestions) to do experiments in searching for new and stable carbon species that may be present in outer space. In an early study of the chemistry of fullerenes [5], both C60 and C70 were discovered become superconducting when doped with alkali metals yielding a record high temperature at the time: 18° in Kelvin. On the other hand, when placed under favorable conditions (mostly photolytic catalyzed reactions), fullerene may become reactive with incoming nucleophiles, converting carbon's sp2 -hybridization to sp3 through nucleophilic additions. During the reaction, the hexagonal benzene rings remain largely inert as nucleophiles interacting with the electrons on the pentagonals. The change in hybridization, accompanied by a conformational change from the curved planar to a three-dimensional structure, is believed to relax the overall surface strain, providing necessary stability for the final product.
In 1996, the Nobel Prize in chemistry was awarded to Robert F. Curl Jr., Harold W. Kroto, and Richard E. Smalley "for their discovery of fullerenes." It is clear now as we look back that the impact brought by the discovery of C60 is not merely the discovery of a new form of carbon in material; rather, it has opened our eyes to see the infinitive possibilities of new structures that can be constructed by familiar elements, carbon and beyond, and the applications never imaginable that they can bring to humans. After all, we may not know carbon, a dear old friend of ours, as well as we have thought we did.
Around 1990, while exploring new forms of fullerenes, Smalley suggested the possibility of tubular fullerene: a straight segment of carbon tube capped, perhaps, by two hemispheres of C60 on both ends of the tube. While Smalley's idea may or may not link directly to the grand entry of CNTs to the scientific world, certainly when Sumio Iijima of NEC (Japan) reported the first observation of multiwall nanotubes () [6] in the following year (1991), the world was brought to witness yet another wave of awes and wonders of another new form of carbon. Iijima was able to demonstrate clearly the presence of concentric nanotubes produced by arc discharge evaporation of graphite, each comprised of 2-50 layers of carbon sheets. At the center, the smallest hollow tube has a diameter of 2.2?nm with additional layers each separated from the adjacent others by 0.34?nm, matching the distance between two adjacent layers in bulk graphite. Two years later, in 1993, single-walled carbon nanotube () was identified for the first time in a lab by Iijima and Ichihashi [7] and, independently, by Bethune et al....
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