Contents

Cover

Title page

Copyright page

Preface

Section I: Production and Derivatives of Chitosan

Chapter 1: Chitin and Chitosan: History, Composition and Properties
1. 1.1 Chitin
2. 1.2 Chitosan
3. 1.3 Conclusion
4. References
Chapter 2: Nitrogenated Polysaccharides – Chitin and Chitosan, Characterization and Application
1. 2.1 Introduction
2. 2.2 Extraction of Nitrogenated Polysaccharides from Natural Sources
3. 2.3 Research Methods of Nitrogenated Polysaccharides
4. 2.4 Characterization of Nitrogenated Polysaccharides
5. 2.5 Properties of Nitrogenated Polysaccharides
6. 2.6 Applications
7. 2.7 Conclusion
8. References
Chapter 3: Enzymes for Production of Chitin, Chitosan, and Chitooligosaccharide and Determination of Activities of Enzymes Using Chitinous Substrates
1. 3.1 Introduction
2. 3.2 Fermentation Methods for Production of Enzymes
3. 3.3 Methods for Purification of Enzymes
4. 3.4 Storage Conditions of Enzyme
5. 3.5 Commercial Enzymes
6. 3.6 Determinations of Enzyme Activities Using Chitinous Materials
7. 3.7 Conclusion
8. Acknowledgement
9. References
Chapter 4: Production of Chitin, Chitosan, and Chitooligosaccharide from Shrimp and Crab Shells Using Green Technology and Applications of Their Composite Materials
1. 4.1 Introduction
2. 4.2 Microorganisms for Production of Chitin and Chitosan Using Green Technology
3. 4.3 Production of Chitin Using Microorganisms
4. 4.4 Production of Chitosan from Chitin Using Chitin Deacetylase from Microorganisms
5. 4.5 Production of Crude Chitooligosaccharide from Shrimp and Crab Shells Using Fermentation Technology
6. 4.6 Applications of Chitin, Chitosan, Chitooligosaccharides and Their Composite Materials
7. 4.7 Conclusion
8. Acknowledgement
9. References
Chapter 5: Chitosan and Its Derivatives: Overview of Commercial Applications in Diverse Fields
1. 5.1 History
2. 5.2 Synthesis of Chitosan
3. 5.3 General Properties
4. 5.4 Biological Properties
5. 5.5 Physicochemical Aspects
6. 5.6 Molecular Weight
7. 5.7 Stability
8. 5.8 Fabrication
9. 5.9 Self-Assembly
10. 5.10 Strategies Self-Assembly
11. 5.11 Chief Significance
12. 5.12 Various Forms
13. 5.13 Chemical Modification
14. 5.14 Technologic Features for Medicinal Utilization
15. 5.15 Synthetic Procedure of Chitosan Nanoparticles
16. 5.16 Modified Chitosan
17. 5.17 Carboxymethyl Chitosan (CMC)
18. 5.18 Michael Reaction
19. 5.19 Antioxidant
20. 5.20 Antibacterial Properties
21. 5.21 Antimicrobial Activity
22. 5.22 Antiviral Activity
23. 5.23 Biological Adhesive
24. 5.24 Bonding Purposes
25. 5.25 Biodegradation
26. 5.26 Parameter Moving Transfection Competence
27. 5.27 Conjugation
28. 5.28 Functionalization of Chitosan
29. 5.29 Schiff’s Base Formation
30. 5.30 Reductive Amination
31. 5.31 Chitosan–Proteins Interaction
32. 5.32 Absorption Enhancer
33. 5.33 Chitosan–Starch Blends
34. 5.34 Application in Various Fields
35. 5.35 Conclusion
36. References
Chapter 6: Chitin and Chitosan-Complexes and Their Applications
1. 6.1 Introduction
2. 6.2 Synthesis of Chitosan from Chitin
3. 6.3 Different Properties of Chitosan
4. 6.4 Polyelectrolyte Complexes of Chitosan
5. 6.5 Complexes of Polyelectrolyte between Chitosan and Naturally Occurring Polymers
6. 6.6 Various Useful and Important Applications of Chitosan
7. 6.7 Conclusion
8. Acknowledgement
9. References
Chapter 7: Enzymes from Genetically Modified Microorganisms for Production of Chitin, Chitosan, and Chitooligosaccharide
1. 7.1 Introduction
2. 7.2 Enzymes for Production of Chitin/Chitosan, and Chitooligosaccharide
3. 7.3 Enzyme and DNA Technology for Production of Chitin, Chitosan, and CTO
4. 7.4 Determinations of Enzyme Activities Using Chitinous Materials
5. 7.5 Conclusion
6. References

Section II: Chitosan in Textile and Food Industry

Chapter 8: Chitosan Applications for the Food Industry
1. 8.1 Introduction
2. 8.2 Biological Activities of Chitosan and Its Derivatives
3. 8.3 Chitosan and Its Derivatives for Food Applications
4. 8.4 Nutritional Aspects of Chitin and Chitosan
5. 8.5 Preparation of Chitin and Chitosan Oligomers and Their Applications in the Food Industry as Health Supplements
6. 8.6 Future Trends: Chitosan-Based Nanotechnology for Food Applications
7. 8.7 Conclusion
8. Acknowledgements
9. References
Chapter 9: Chitosan: Sustainable and Environmental-Friendly Resource for Textile Industry
1. 9.1 Introduction
2. 9.2 Chitosan and Chitosan Resources
3. 9.3 Chitosan Treatment of Textiles
4. 9.4 Textile Functionalities Achieved
5. 9.5 Effluent Treatment Applications
6. 9.6 Future Perspectives and Conclusion
7. References

Section III: Chitosan in Biomedical Applications

Chapter 10: Perspectives of Chitin- and Chitosan-Based Scaffolds Dressing in Regenerative Medicine
1. 10.1 Introduction
2. 10.2 Scaffold Characteristics
3. 10.3 Fabrication Techniques
4. 10.4 Applications of Chitin and Chitosan as Regenerative Medicine
5. 10.5 Conclusion
6. References
Chapter 11: Chitin – and Chitosan-Based Scaffolds
1. 11.1 Introduction
2. 11.2 Scaffold Components
3. 11.3 Scaffold Requirements
4. 11.4 Chitin – and Chitosan-Based Scaffolds Fabrication Techniques
5. 11.5 Applications of Chitin and Chitosan for Regeneration of Various Tissues
6. 11.6 Chitin – and CS-Based Scaffolds for Drug and Growth Factors Delivery
7. 11.7 Chitin – and CS-Based Scaffolds/Dressings in Market
8. 11.8 Conclusions
9. 11.9 Future perspectives
10. Abbreviations
11. References
Chapter 12: Nanopolymer Chitosan in Cancer and Alzheimer Biomedical Application
1. 12.1 Introduction
2. 12.2 Chitosan Applications in Cancer
3. 12.3 Chitosan Applications in Alzheimer’s
4. 12.4 Conclusion
5. References
Chapter 13: Biomedical Significance of Chitin- and Chitosan-Based Nanocomposites
1. 13.1 Introduction
2. 13.2 Biomedical Applications
3. 13.3 Conclusion
4. References
Chapter 14: Potential Biomedical Applications of Chitosan – and Chitosan-Based Nanomaterials
1. 14.1 Introduction
2. 14.2 Production of Chitin and Chitosan
3. 14.3 Bioactivities of Chitin and Chitosan
4. 14.4 Biomedical Application of Chitin – and Chitosan-Based Nanomaterials
5. 14.5 Conclusion and Future Perspective
6. Acknowledgement
7. References

Section IV: Chitosan in Agriculture and Water Treatment

Chapter 15: Practical and Plausible Implications of Chitin- and Chitosan-Based Nanocomposites in Agriculture
1. 15.1 Introduction
2. 15.2 Applications of Chitin and Chitosan Nanocomposite in Agriculture
3. 15.3 Conclusion
4. References
Chapter 16: Scope of Electrospun Chitosan Nanofibrous Web for its Potential Application in Water Filtration
1. 16.1 Introduction
2. 16.2 Chitosan as an Efficient Material for Water Purification/Disinfection
3. 16.3 Electrospinning Process
4. 16.4 Electrospun Chitosan Nanofibers Embedded with Silver Nanoparticles for Filtration of Water Contaminated with Bacteria
5. 16.5 Chitosan-Based Nanocomposites for Water Filtration
6. 16.6 Current Challenges and Future Perspectives
7. References
Chapter 17: Application of Chitin/Chitosan and its Derivatives as Adsorbents, Coagulants, and Flocculants
1. 17.1 Introduction
2. 17.2 Chitin and Chitosan
3. 17.3 Properties of Chitin and Chitosan
4. 17.4 Modification of Chitin and Chitosan
5. 17.5 Application of Natural Polymers in Wastewater Treatment as Promising Adsorbents
6. 17.6 Chitin and Chitosan as a New Type of Polymer Coagulant/Flocculants
7. 17.7 Future Directions for Research
8. 17.8 Conclusion
9. Acknowledgments
10. References

Index

End User License Agreement

List of Illustrations

Chapter 1

Figure 1.1 Extraction of chitin.
Figure 1.2 Extraction of chitin by alkaline solution.
Figure 1.3 Structural comparison of chitin and cellulose.
Figure 1.4 Antiparallel and parallel arrangements of different allomorphs of chitin.
Figure 1.5 Extraction of chitosan.
Figure 1.6 Structure of chitosan.

Chapter 2

Figure 2.1 X-ray diffractogram of α-chitin (a) and α-chitosan (b).
Figure 2.2 Measurement of width of crystalline peak.
Figure 2.3 Illustration of method for determining the crystallinity degree of α-chitin sample.
Figure 2.4 Illustration of method for determining the crystallinity degree of α-chitosan sample.
Figure 2.5 Illustration of ¹H NMR spectrum of chitosan solution.
Figure 2.6 Illustration of solid state CP/MAS ¹³C NMR spectrum of chitin.
Figure 2.7 N-acetylglucosamine unit of chitin.
Figure 2.8 Image of orthorhombic (1) and monoclinic (2) crystalline unit cells.
Figure 2.9 X-ray diffractograms of (a) α – and (b) β-chitins.
Figure 2.10 Dependence of interplanar distance, d (010), of β-chitin on volume of quest molecules.
Figure 2.11 Theoretical isotherms sorption of water vapor by completely amorphous chitin (1) and chitosan (2) at 25 °C.

Chapter 3

Figure 3.1 (a) The structure of chitin with 100% degree of acetylation; (b) The structure of chitosan with 100% degree of deacetylation; (c) Structure of chitin and chitosan with various degree of acetylation [1].
Figure 3.2 Steps for production of chitin, chitosan, and chitooligosaccharide.
Figure 3.3 General method for the purification of crude enzyme.

Chapter 4

Figure 4.1 Flow chart for production of chitin, chitosan, and chitooligosaccharides by green technology [23].

Chapter 5

Figure 5.1 Preparation of chitosan from shrimp shells.
Figure 5.2 Chemical structure of chitosan.
Figure 5.3 Biological properties.
Figure 5.4 Chitosan under oxidative condition.
Figure 5.5 Order of monomer arrangement in acidic condition.
Figure 5.6 Schematic diagram of chitosan to form fabrication.
Figure 5.7 Various mechanism by chitosan based derivatives.
Figure 5.8 Self-assembly of amiphilic chitosan derivatives.
Figure 5.9 Chief significant of chitosan based material.
Figure 5.10 Various forms of chitosan.
Figure 5.11 Chemically modification of chitosan.
Figure 5.12 Medical utilization of chitosan.
Figure 5.13 Development of chitosan nanoparticles.
Figure 5.14 Overall modification of chitosan.
Figure 5.15 Chemical structure of carboxymethyl chitosan.
Figure 5.16 Michael reaction of chitosan.
Figure 5.17 Synthetic path of N,O-quaternized.
Figure 5.18 Reactive oxygen species.
Figure 5.19 General structure of photo-cross-linkable-Az-CH-LA.
Figure 5.20 Binding purpose.
Figure 5.21 Chitosan biodegradation.
Figure 5.22 Factor affecting of chitosan based.
Figure 5.23 Enzymatic assembly reaction.
Figure 5.24 Chitosan via the imine linkage.
Figure 5.25 Amination of chitosan.
Figure 5.26 Chitosan via the Mannich.
Figure 5.27 Diagram of Az-chitosan chains.
Figure 5.28 Schematic diagram of skin repair.
Figure 5.29 Ionic interaction.
Figure 5.30 Schematic diagram of chitosan-based biosensor.
Figure 5.31 Role of enzyme activity.
Figure 5.32 Reaction of tyrosinase.
Figure 5.33 Enzyme immobilization.
Figure 5.34 The structure of hyaluronan.

Chapter 6

Figure 6.1 Structure of chitin (a) and chitosan (b).
Figure 6.2 Deacetylation of chitin produces chitosan.
Figure 6.3 Different steps involved in preparation of chitosan from the shell of crustaceans. This method is adopted from RiZvezdova et al., [7].
Figure 6.4 Various chemical properties of chitosan.
Figure 6.5 Biological properties of chitosan.
Figure 6.6 Different types of chitosan-based polyelectrolyte complexes.
Figure 6.7 Different potential bio-applications of chitosan complexes.

Chapter 7

Figure 7.1 Chemical structures of chitin and chitosan. Chitosan: m>60%; chitin: m<60%.
Figure 7.2 Target DNA in DNA of microorganisms.
Figure 7.3 Steps for cloning.

Chapter 8

Figure 8.1 Molecular structures of cellulose, chitin, and chitosan.
Figure 8.2 Effects of chitosan on capsule size (e and f) and the number of capsular polysaccharides (d and g) in Cryptococcus neoformans cells, and the exopolymeric matrix of biofilms (e and h). Scale bars in all pictures represent 2 µm [65].
Figure 8.3 Schiff’s base obtained from the reaction between free amino groups of chitosan and aldehydes.
Figure 8.4 Synthesis of N,N,N-trimethylchitosan [78].
Figure 8.5 Mono (2-methacryloyl oxyethyl) acid phosphate (chitosan-MAP) and vinylsulfonic acid sodium salt (chitosan-VSS) grafted onto synthesized chitosan by Jung et al. [82].
Figure 8.6 Scanning Electron Microscope (SEM) photographs of chitosan and chitosan/TPP nanoparticles [114].
Figure 8.7 Digital photographs of carboxymethyl chitosan hydrogel beads prepared in different binary aqueous-alcohol solvents. The percentage amount below each photograph represents the concentration of alcohol used for the preparation of that bead [130].

Chapter 9

Figure 9.1 Chitosan chain from resources to applications.
Figure 9.2 Chitosan production steps.
Figure 9.3 Textile materials functionalized with chitosan.
Figure 9.4 Application array for chitosan treated textiles.

Chapter 11

Figure 11.1 Elements of tissue engineering triad for new tissue formation by allowing cells to migrate, adhere, and produce tissue. Source of the cell act as a productive template and is able to produce large amount of cells through cell growth (a), scaffold architecture and material provide conductive template which gives proper support and strength for the growth of new tissue (b) and bioactive molecules induce proper signals for the system to mentor cells to differentiate, proliferate and perform metabolic activities (c).
Figure 11.2 Different components of scaffold: (a) polymers, (b) cells/growth factors, (c) therapeutic molecules and (d) bioactive molecules.

Chapter 12

Figure 12.1 Basic chemical structure of chitosan (adopted from [12]).
Figure 12.2 Trends in recent reports on the use of chitosan in cancer-related studies (Pubs: Publications). (Information obtained from ISI Web of Knowledge. Accessed on 12/08/2016.)
Figure 12.3 Trends in recent reports on the use of chitosan in Alzheimer’s studies (Pubs: Publications). (Information obtained from ISI Web of Knowledge. Accessed on 12/08/2016.)
Figure 12.4 The schematic model of “turn on-off” complex of chitosan functionalized QDs as noncytotoxic platform for cancer therapy-diagnostic (reproduced from [77]).
Figure 12.5 The schematic model of chitosan functionalized dual drugs in cancer drug delivery strategies (reproduced from [89]).
Figure 12.6 Pictorial depiction of (a) blocking interaction between chitosan/N-trimethyl chitosan and Aβ (40), binding modes of (b) deacetylated chitosan, and (c) quartenarized N-trimethyl chitosan with full length of Aβ (40) (adopted from [162]).

Chapter 13

Figure 13.1 Biomedical applications of chitin- and chitosan-based nanocomposites.

Chapter 14

Figure 14.1 Structure of chitin and chitosan.
Figure 14.2 Example of a three-step process for the synthesis of Chitin and Chitosan from fish scales.
Figure 14.3 Various bioactivities of chitin – and chitosan-based nanomaterials.
Figure 14.4 Antitumor activity of chitosan nanomaterials.
Figure 14.5 The schematic representation of antimicrobial mechanism of action of chitosan.
Figure 14.6 Wound dressing application of chitosan and their derivatives.

Chapter 15

Figure 15.1 Agricultural implications of chitin- and chitosan-based nanocomposites.

Chapter 16

Figure 16.1 Structure of chitosan [13].
Figure 16.2 Deacetylation process by which chitosan is obtained from chitin [20].
Figure 16.3 Conversion of chitosan to a polycationic electrolyte at pH < 6.0 [20].
Figure 16.4 Mechanism of flocculation of particles using chitosan.
Figure 16.5 Removal of metal ions by chitosan [20].
Figure 16.6 Mechanism of killing of the bacteria present in water by chitosan.
Figure 16.7 Principle of electrospinning process [43].
Figure 16.8 SEM images of nanofibers of chitosan hydrolysed for 48 h in aqueous 80% acetic acid 7 wt% [(a) magnification: ×10,000, (b) magnification: ×1100) [35].
Figure 16.9 SEM images of electrospun fibers at different acid concentration (wt%): (a) 10, (b) 30, (c) 50, (d) 70, and (e) 90; 4 kV/cm, 7 wt% chitosan (106,000 g/mol) [36].
Figure 16.10 The bacterial growth inhibition halos against Escherichia coli (a) PVA/Chitosan nanofibers, (b) AgNPs/PVA/chitosan nanofibers with 5 mmol/L Ag, and (c) AgNPs/PVA/chitosan nanofibers with 10 mmol/L Ag [39].
Figure 16.11 Log reduction of E. coli concentration in PBS samples after soaking 10 mg of nanofibers containing (a) 0, (b) 2, and (c) 4 wt% AgNO₃ [31].
Figure 16.12 Log reduction of E. coli concentration after dynamic filtration of bacterial suspension through CS/PVA ENMs containing 0 wt%, 2 wt%, and 4 wt% AgNO₃ [31].
Figure 16.13 Static and dynamic silver release test [31].
Figure 16.14 Three-tier composite structure [41].

List of Tables

Chapter 1

Table 1.1 Percentage of chitin produced from different sources [3].
Table 1.2 Examples of sources of extraction of chitin [5].

Chapter 2

Table 2.1 Positions of the main diffraction peaks and interplanar distances for α-chitin and α-chitosan.
Table 2.2 Characteristics IR-bands of chitin samples [23, 48–54].
Table 2.3 Characteristics IR-bands of chitosan samples [54–60].
Table 2.4 Coefficients in equation of Mark-Houwink-Sakurada.
Table 2.5 Characteristics of crystalline unit cells of chitins, chitosan and natural cellulose CI_β.
Table 2.6 X-ray diffraction patterns of α – and β-chitins.
Table 2.7 Value of A_m,a as function of DA.

Chapter 3

Table 3.1 Fermentation methods and optimal conditions for the productions of chitinase, chitosanase, chitin deacetylase and protease.
Table 3.2 Purifications of chitinase, chitosanase, chitin deacetylase, and protease.
Table 3.3 Optimal conditions for enzyme activities.

Chapter 4

Table 4.1 Producing of chitin from shrimp and crab shells using various microorganisms under different conditions deproteination (DP), demineralization (DM).
Table 4.2 Production of chitosan from chitin using deacetylase
Table 4.3 Production of chitosanase from various bacteria strains under different fermentation conditions.
Table 4.4 Agriculture sector application of chitosan and chitooligosaccharides.
Table 4.5 Applications of chitosan composite materials

Chapter 7

Table 7.1 List of enzymes for production of chitin, chitosan, and chitooligosaccharide (CTO).
Table 7.2 Microorganisms for target genes and host for gene expression.
Table 7.3 Determinations of enzyme activities using chitinous materials.

Chapter 8

Table 8.1 Antioxidant properties of chitosan and its derivatives (2008–2013).
Table 8.2 Chitosan-based particulate systems for the encapsulation of nutrients (2008–2013).

Chapter 11

Table 11.1 Different applications of CT and CS in bone tissue engineering.
Table 11.2 Applications of CT and CS in the field of cartilage tissue engineering.
Table 11.3 Chitin – and CS-based membranes and scaffolds in drug delivery.
Table 11.4 Chitin – and CS-based membranes and scaffolds in delivery of growth factors.
Table 11.5 Chitin – and CS-based marketed scaffolds/dressings [177–181].

Chapter 12

Table 12.1 Applications of chitosan for cancer drug delivery system.
Table 12.2 Chitosan in cancer therapy applications.
Table 12.3 Biosensing applications of chitosan biomedical diagnosis.
Table 12.4 Pharmaceutical formulation and drug delivery applications of chitosan in Alzheimer’s disease.

Chapter 14

Table 14.1 Application of chitosan based nanomaterials in drug delivery.

Chapter 16

Table 16.1 Copper (Cu), Chromium (Cr), Iron (Fe), Zinc (Zn) removal percentage [27]
Table 16.2 Relative effectiveness of various antimicrobial agents [23].
Table 16.3 Properties of chitosan and PEO solutions [33].

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Library of Congress Cataloging-in-Publication Data
Names: Ahmed, Shakeel, 1989- editor. | Ikram, Saiqa, editor.
Title: Chitosan : derivatives, composites and applications/edited by Shakeel Ahmed and Saiqa Ikram.
Description: Hoboken, NJ, USA : Wiley, 2017. | Includes bibliographical references and index.|
Identifiers: LCCN 2017023345 (print) | LCCN 2017024016 (ebook)| ISBN 9781119364818 (epub) | ISBN 9781119364801 (pdf) | ISBN 9781119363507 (cloth)
Subjects: LCSH: Chitosan–Biotechnology. | Chitosan–Industrial applications.
Classification: LCC TP248.65.C55 (ebook) | LCC TP248.65.C55 C547 2017 (print) | DDC 660.6–dc23
LC record available at https://lccn.loc.gov/2017023345

Preface

Many books are devoted to the description of polymers that are not of biopolymers or the polymers which are originating from the natural resources; the techniques for their mass/industrial production, their art, value, and their distribution reflecting the wealth of the information existing in the field of science and engineering to therapeutics. On the other hand, there is no book exclusively devoted to the fascinating topic of biopolymers especially to “Chitosan” and its unique properties and applications. A few books contain scattered chapters and details on chitosan emphasizing the possibilities of locating fragments of information elsewhere. However, again there is no book that is solely devoted to chitosan and its versatile applications. In the meantime, the expanded applications of chitosan are on the rise in many fields, making a book that covers both past and novel applications of this “Biopolymer for the Future” as well as its properties and ways in which to manipulate them, crucial.

The main aim in compiling this book is to present, in easy-to-follow sequence, a description of chitosan production methods and of techniques which can be used to estimate and modify its physical and chemical properties. This book offers a full description not only of the traditional and recent developments following applications of chitosan in the fields of biotechnology, environmental studies, food, medicine, water treatments, drug delivery including all therapeutically usages, but also topics which have never been covered in the literature, making it of utmost importance to industry and academia.

We hope that this book will assist all levels of readers. It is dedicated not only to academic community but also to the researchers and industrialist who will find this book to be a source of knowledge as well as a launching pad for novel ideas and inventions. In particular, this book is expected to be of interest to the people involved in formulations, water-treating methods, food scientists, technologists, industrial chemists and engineers. Potential readers also include both professional and dedicated non-professional environmentalists, agriculturists, and those working on the development of novel chitosan-based matrices and their applications. Finally, it is expected that this book will find a prominent place in the traditional universities and research institutions libraries where chemistry, biotechnology, medicine as well as environmental studies, and other practical and theoretical mechanized topics are taught, studied, and implemented.

Shakeel Ahmed and Saiqa Ikram
Delhi, India
June 2017

Chitosan

Derivatives, Composites and Applications

Preface

Section I
PRODUCTION AND DERIVATIVES OF CHITOSAN