Handbook of Polyester Drug Delivery Systems PDF by MNV Ravikumar

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Handbook of Polyester Drug Delivery Systems
Edited by MNV Ravikumar
Handbook of Polyester Drug Delivery Systems


Contents

Foreword xvii
Preface xix
1. Overview of Synthesis of Functional Polyesters 1
Stanislaw Slomkowski
1.1 Introduction 1
1.2 Basics of Synthesis of Polyesters 4
1.2.1 Synthesis by Ring-Opening
Polymerization of Cyclic Monomers 4
1.2.2 Synthesis by Polycondensation 10
1.2.3 Synthesis by Enzymatic
Polymerization 11
1.3 Polyesters with Functional Groups 12
1.3.1 Primary Functional Groups in
Polyesters 12
1.3.2 Polyesters with Fluorescent Labels 17
1.3.3 Polyesters with Polymerizable
Groups 22
1.3.4 Polyesters with Terminal Chain
Transfer Groups Serving as
Macro-Transfer Agents in Reversible
Addition–Fragmentation Chain
Transfer (RAFT) Polymerization 23
1.3.5 Polyesters with Functional Groups
for Click Chemistry 23
1.3.6 Polyesters Modified with Succinic
Anhydride and N-Hydroxysuccinimide 24
1.4 Conclusions 25
2. Biodegradable Fatty Acid Polyesters 33
Konda Reddy Kunduru, Arijit Basu, and Abraham J. Domb
2.1 Introduction 33
2.2 Importance of Fatty Acids in Biodegradable
Polymers 35
2.3 Synthesis of Fatty Acid-Based Biodegradable
Polyesters 36
2.4 Degradation and Elimination 43
2.5 Stability of Fatty Acid-Based Polyesters 46
2.6 Biocompatibility 47
2.7 Biomedical Applications 49
2.8 Conclusions and Future Perspectives 52
3. Enzymatically Synthesized Polyesters for Drug Delivery 61
Shengfan Lu, Jianxun Ding, Jinjin Chen, Wei Wang,
Xiuli Zhuang, and Xuesi Chen
3.1 Introduction 62
3.2 Enzymatic Syntheses of Polyesters 63
3.2.1 Enzymatic ROP 64
3.2.2 Enzymatic PC 66
3.3 Postpolymerization Functionalization of ESPs 67
3.4 ESP-Based Drug Delivery Platforms 68
3.4.1 ESP–Drug Conjugates 69
3.4.2 Drug-Encapsulated ESP-Based
Platforms 71
3.5 Conclusions and Outlook 73
4. Overview of Methods of Making Polyester Nano- and
Microparticulate Systems for Drug Delivery 81
Nadim Ahamad, Dadi A. Srinivasa Rao, and
Dhirendra S. Katti
4.1 Introduction 81
4.2 Methods for Synthesis of Micro-/Nanoparticles 84
4.2.1 Conventional Methods for Micro-/
Nanoparticle Synthesis 84
4.2.1.1 One-step fabrication
methods 84
4.2.1.2 Two-step fabrication 89
4.2.1.3 Multistep fabrication 92
4.2.2 Advanced Methods for Particles
Synthesis 95
4.2.2.1 Microfluidics 95
4.2.2.2 Particle replication in
non-wetting template
(PRINT) 98
4.3 Scalability for Large-Scale Production 101
4.4 Recovery and Purification Methods 103
4.4.1 Evaporation under Reduced
Pressure 103
4.4.2 Dialysis 103
4.4.3 Filtration 104
4.4.4 Centrifugation 104
4.5 Drying and Storage of Particles 105
4.5.1 Drying of Particles 105
4.5.1.1 Freeze drying 105
4.5.1.2 Spray drying 106
4.5.2 Storage of particles 107
4.6 Challenges and Future Prospects 107
4.7 Summary 112
5. Electrospun Biodegradable Polyester
Micro-/Nanofibers for Drug Delivery and
Their Clinical Applications 125
Xin Zhao, Divia Hobson, Zhi Yuan (William) Lin,
and Wenguo Cui
5.1 Introduction 126
5.2 Drug Incorporation Techniques 128
5.2.1 Blending 128
5.2.2 Coaxial Process 130
5.2.3 Emulsion Electrospinning 130
5.2.4 Surface Modification 130
5.2.5 Other Electrospinning Techniques 131
5.3 Types of Drugs Released 131
5.3.1 Hydrophobic Drugs 131
5.3.2 Hydrophilic Drugs 132
5.3.3 Growth Factor Delivery 133
5.3.4 DNA and siRNA Delivery 134
5.3.5 Other Types of Drugs 136
5.4 Clinical Applications 137
5.4.1 Wound Dressings 137
5.4.2 Cancer Therapy 138
5.4.3 Adhesion Barrier 140
5.4.4 Tissue Engineering 142
5.4.4.1 Vascular tissue engineering 142
5.4.4.2 Bone tissue engineering 144
5.4.4.3 Tendon tissue engineering 145
5.4.4.4 Skin tissue engineering 147
5.5 Conclusion and Future Prospects 148
6. Overview of Polylactide-co-Glycolide Drug
Delivery Systems 159
Hongkee Sah
6.1 Introduction 159
6.2 Microspheres 160
6.2.1 Long-Acting Release (LAR)
Microspheres 160
6.2.2 Embolic Drug-Eluting Microspheres 164
6.2.3 Aesthetic Microspheres 164
6.3 Implants 166
6.3.1 Subdermal Implants 166
6.3.2 Intravitreal Implant 166
6.4 In situ Formation of a Solid Implant from
a Flowable Liquid 167
6.5 PLGA-Based Micelles 170
6.6 PLGA-Based Nanoparticles 171
6.7 Biodegradable Composite Scaffolds 174
6.8 Nanofibers 175
6.9 Drug-Eluting Metallic Stent (DES) 177
6.10 Summary 179
7. Overview of Polycaprolactone-Based Drug Delivery
System 187
Aurelio Salerno
7.1 Introduction 188
7.2 Overview of PCL Properties Relevant for
TE Applications 190
7.3 Processing of PCL for the Fabrication of
Drug Delivery Devices 193
7.4 Conclusions 204
8. Engineered PLGA Nanosystems for Enhanced Blood
Compatibility 213
Y. M.Thasneem and Chandra P. Sharma
8.1 Introduction 213
8.2 Poly(Lactic-co-Glycolic Acid): The Need to
Engineer the Surface 214
8.3 Biocompatibility 215
8.4 What Makes PLGA a Biocompatible Polymer? 216
8.5 Hemocompatibility 216
8.6 Events Occurring at the Material–Blood
Interface 217
8.7 Bio–Nano Interface 217
8.8 An Insight into the Protein Corona on PLGA
Nanoparticles 219
8.9 Hemolysis 220
8.10 Hemolytic Potential of PLGA Nanoparticles 221
8.11 Thrombogenecity 221
8.12 PLGA Nanoparticles Interaction with the
Coagulation Cascade 223
8.13 Complement Activation 224
8.14 Physicochemical Characteristics of
Nanoparticle Modulate the Complement
Activation 225
8.14.1 Size and Curvature 225
8.14.2 Surface Charge and Functional
Groups 226
8.14.3 Surface Projected Polymers 227
8.15 Complement Activation Mediated by PLGA
Nanoparticles 228
8.16 Interaction with the Lympho-Reticular/
Mononuclear Phagocyte System 228
8.17 Physicochemical Characteristics Influencing
Macrophage-Mediated Phagocytosis 229
8.18 Cytokines as a Biomarker of Nanoparticle
Mediated Immunomodulation 230
8.19 Clearance of Nanoparticles in Circulation 231
8.20 Strategies to Enhance Circulation Half-Time
of Nanoparticles 232
8.20.1 PEGylation 232
8.20.2 Non-ionic Hydrophilic Polymers 233
8.20.3 Recombinant PEG Mimetics 234
8.20.4 HESylation 234
8.20.5 Cell-Based Biomimetic Systems 234
8.20.6 Pathogen-Inspired Immune Evasion 235
8.21 Conclusion 236
9. Peroral Polyester Drug Delivery Systems 243
Matilde Durán-Lobato, Maria Ángeles Holgado,
Josefa Álvarez-Fuentes, José L. Arias,
Mercedes Fernández-Arévalo, and
Lucía Martín-Banderas
9.1 Introduction 243
9.2 Oral Chemotherapy 251
9.2.1 PLGA-Based Nanoformulations 251
9.2.2 PCL-Based Nanoformulations 255
9.2.3 Oral Chemoprevention 257
9.3 Oral Antibiotic Therapy 258
9.3.1 PLGA-Based Nanoformulations 259
9.3.2 PCL-Based Nanoformulations 260
9.4 Oral Vaccination 263
9.4.1 PLGA-Based Nanoformulations 263
9.4.2 PCL-Based Nanoformulations 265
9.5 Oral Delivery of Proteins 266
9.5.1 PLGA-Based Nanoformulations 267
9.5.2 PCL-Based Nanoformulations 271
9.6 Conclusions 272
10. Overview of Polyester Nanosystems for Nasal
Administration 291
Imran Vhora, Sushilkumar Patil, Hinal Patel,
Jitendra Amrutiya, Rohan Lalani, and
Ambikanandan Misra
10.1 Introduction 292
10.2 Physicochemical Diversity of Polyesters 294
10.2.1 Polyesters from Biological Sources 294
10.2.1.1 Polymers of α-hydroxy
acids 294
10.2.1.2 Polyhydroxyalkanoates 297
10.2.2 Polyesters from Petrochemical
Sources 298
10.2.2.1 Poly-e-caprolactone 298
10.2.2.2 Aliphatic copolyesters 299
10.2.2.3 Other polyesters 299
10.3 Preparation of Polyester Nanosystems 304
10.3.1 Emulsification–Solvent Evaporation
Method 304
10.3.2 Emulsification–Solvent Diffusion
Method 305
10.3.3 Salting Out 306
10.3.4 Nanoprecipitation (Solvent
Displacement) Method 307
10.3.5 Dialysis 314
10.3.6 Supercritical Fluid (SCF)
Technology 314
10.4 Drug Release and Degradation of Polyester
Nanosystems 316
10.5 Therapeutic Outcomes of Nasal
Administration of Polyester Nanoparticles 319
10.5.1 Polyesters of Poly-α-Hydroxy Acids 325
10.5.2 Other Polyesters 330
10.6 Future Perspective 332
10.7 Conclusion 335
11. Polyester Particles for Drug Delivery to the Skin:
Local and Systemic Applications 353
Ana Luiza S. Aguillera Forte, Ana Melero,
Ruy C. Ruver Beck, and Claus-Michael Lehr
11.1 Introduction 354
11.2 Skin Structure and Transport of Substances 356
11.3 Topical Application of Polyester Particles 361
11.3.1 Local Applications 361
11.3.2 Systemic Applications 367
11.3.3 Transcutaneous Immunization (TCI) 369
11.4 Conclusions 370
12. Aliphatic Polyester Protein Drug Delivery Systems 379
Brian Amsden
12.1 Introduction 379
12.2 The Nature of Proteins 381
12.3 Aliphatic Polyesters 382
12.4 Formulations 386
12.4.1 Micro- and Nanoparticles 386
12.4.2 Modified Monomers 394
12.4.3 Injectable in situ Forming
Semisolid Implants 395
12.4.4 Injectable Viscous Liquid Implants 396
12.4.5 Elastomers 398
12.4.6 Hydrogels 402
12.4.7 Formulation Manufacture and
Quality by Design 405
12.5 Conclusions 406
13. Biodegradable Polyester-Based
Multi-Compartmental Delivery Systems for Oral
Nucleic Acid Therapy 417
Husain Attarwala and Mansoor Amiji
13.1 Oral Nucleic Acid Therapies 418
13.1.1 Oral Gene Therapy 418
13.1.2 Opportunities in Oral Nucleic
Acid Therapy 419
13.1.3 Extracellular and Intracellular
Barriers to Oral Nucleic Acid Therapy 420
13.2 Polyester-Based Multicompartmental
Formulations 422
13.2.1 Biodegradable Polyesters:
Chemistry and Properties 422
13.2.2 Rationale of Designing Polyester
Multicompartmental Systems for
Gene Delivery 423
13.2.3 Examples of Polyester-Based
Systems for Gene Therapy 425
13.3 Illustrative Example of Gene Therapy with
Nanoparticles-in-Microsphere Oral System 425
13.3.1 NiMOS Formulation 425
13.3.2 Oral Biodistribution and Gene
Transfection Studies 427
13.3.3 Efficacy of Oral IL-10 Gene
Therapy in Inflammatory Bowel
Disease Model 428
13.4 Illustrative Example of Gene Silencing with
Nanoparticles-in-Microsphere Oral System 431
13.4.1 NiMOS Formulation for Delivery of
siRNA Duplexes 431
13.4.2 Oral Administration of TNF-α and
Cyclin D1 siRNA and Gene Silencing
Studies 432
13.4.3 Efficacy of Oral Gene Silencing in
Inflammatory Bowel Disease Model 433
13.5 Illustrative Examples of Polyester-Based
Oral DNA Vaccines 436
13.6 Summary 437
14. PLGA Nano- and Microparticles for VEGF Delivery 445
Teresa Simon-Yarza, Paula Diaz-Herraez,
Simon Pascual-Gil, Elisa Garbayo, Felipe Prosper,
and Maria J. Blanco-Prieto
14.1 Introduction 445
14.1.1 Discovery and Biological Aspects
of Vascular Endothelial Growth
Factor 445
14.1.2 Therapeutic Possibilities of VEGF 446
14.1.2.1 Therapeutic uses of
VEGF linked to its ability
to increase tissue
perfusion and wound healing 447
14.1.2.2 Therapeutic uses of VEGF
related to its neurotrophic
and neuroprotective effects 452
14.2 How to Improve VEGF Therapy 454
14.3 PLGA Particulates for VEGF Delivery: State
of the Art 458
14.3.1 Particle Preparation and Composition 459
14.3.2 Therapeutic Benefits 461
14.4 Conclusions 465
15. Polyester Nano- and Microsystems for Vaccine
Delivery 479
Rajeev Sharma, Nishi Mody, Surbhi Dubey,
Udita Agrawal, and Suresh P. Vyas
15.1 Introduction 479
15.2 Nanotechnology in Vaccine Delivery 480
15.2.1 Routes of Administration of
Nanovaccines 482
15.2.1.1 Oral route 482
15.2.1.2 Nasal route 482
15.2.1.3 Intradermal route 482
15.2.1.4 Intramuscular route 483
15.2.1.5 Subcutaneous route 483
15.3 Polymer-Based Vaccination 484
15.4 Poly(d-l-Lactide-co-Glycolide)
(PLGA)/PLA-Based Nano- and
Microparticulate Systems as a Versatile
Platform in Vaccine Delivery 485
15.4.1 PLGA/ PLA Nano- and
Microparticles as Vaccine
Adjuvants and Challenges 488
15.4.2 Recent Developments and
Strategies to Enhance Immune
Responses 490
15.5 Poly-ε-Caprolactone (PCL) for Vaccine
Delivery 497
15.6 γ–PGA for Vaccine Delivery 503
15.7 Conclusion 505
16. Mucosal Immunization Using Polyester-Based
Particulate Systems 521
Diana Gaspar, Carina Peres, Helena Florindo,
and António J. Almeida
16.1 Introduction 521
16.2 Overcoming Mucosal Barriers: Mechanistic
Issues 526
16.2.1 Advances in the Search for New
Antigen–Polyester Delivery Systems 531
16.2.2 Oral Immunization 532
16.2.3 Nasal Immunization 536
16.2.4 Ocular Immunization 543
16.2.5 Vaginal Immunization 545
16.2.6 Rectal Immunization 546
16.3 Conclusions 547
17. Aliphatic Polyester Micro- and Nanosystems for
Treating HIV, Tuberculosis, and Malaria 563
Alejandro Sosnik
17.1 Introduction 563
17.1.1 Poverty-Related Diseases 563
17.1.1.1 Bacterial PRDs 569
17.1.1.2 Viral PRDs 570
17.1.1.3 Parasitic PRDs 571
17.2 Polyesters in Drug Delivery 574
17.2.1 Polyester-Based Particles in the
Release of ARVs 575
17.2.2 Polyester Particles in the Release of
Antituberculosis Drugs 580
17.2.3 Polyester Particles in the Release of
Antimalarials 582
17.3 Conclusions and Future Perspectives 583
18. Polyester Nano- and Microtechnologies for Tissue
Engineering 595
Namdev B. Shelke, Matthew Anderson, Sana M. Idrees,
Jonathan Nip, Sonia Donde, Xiaojun Yu,
Gloria Gronowicz, Sangamesh G. Kumbar
18.1 Introduction 596
18.2 Applications of Nano-/Microfabricated
Polyester Devices 602
18.2.1 Bone Tissue Engineering 602
18.2.2 Cartilage Tissue Engineering 610
18.2.3 Ligament and Tendon Tissue
Engineering 615
18.2.4 Nerve Tissue Engineering 624
18.2.5 Muscle Tissue Engineering 629
18.3 Conclusions 634
19. Polyester Particles for Curcumin Delivery 651
Murali M. Yallapu, Meena Jaggi, and
Subhash C. Chauhan
19.1 Unmet Needs in Chemotherapy and Role
of Curcumin 652
19.1.1 Evidence of Curcumin’s Medicinal
Value within the Literature 652
19.1.2 Safety and New Approaches 654
19.1.3 Particles for Curcumin Delivery 655
19.2 Particle Technology 656
19.3 Polyester Particles for Curcumin Delivery 656
19.3.1 Design and Development 659
19.3.2 Curcumin Encapsulation/Loading
and Release 660
19.4 Therapeutic Implications 662
19.5 Steps toward Translation 665
19.6 Conclusion 665
20. Polyester Carriers for Enzyme Delivery 675
Raisa Kiseleva and Alexey Vertegel
20.1 Therapeutic Enzymes 676
20.2 Challenges in Enzyme Drug Development
and Methods to Overcome 680
20.3 Polyester Carriers for Enzymatic Drugs 683
20.3.1 Synthesis and Encapsulation of
Enzymes in Polyester Nanoparticles 684
20.3.2 Polyester Carriers for Delivery of
Anti-inflammatory Enzymes 687
20.3.3 Polyester Carriers for Thrombolytic
Enzymes 693
20.3.4 Polyester Carriers and Cancer
Treatment Enzymes 696
20.3.5 Polyester Carriers for Antibacterial
Enzymes 697
20.4 Future of Polyester Carriers for Delivery of
Enzymatic Drugs 698
 

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