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Cell-penetrating peptides : design, development and applications / edited by Makoto Oba and Yosuke Demizu. -- Weinheim, Germany : Wiley-VCH, 2023. – (58.174213/C393) |
Contents
Preface x/i
1 Introduction 1
Part I Design 15
2 Classification 17
2.1 Introduction 17
2.2 Physicochemical Properties 17
2.3 Chemical Structure 21
2.4 Origin 22
2.5 Cargo 23
3 Arginine-Rich Cell-Penetrating Peptides: Recent Advances of Design and Applications for Intracellular Delivery 29
3.1 Introduction 29
3.2 Arginine-Rich Peptides with Unnatural Amino Acids 30
3.3 E-Hairpin Arginine Peptides for Enhanced Stabilization Under Cytosolic Condition 31
3.4 Cyclic Arginine-Rich Peptides 31
3.5 Cancer-Targeting Cell-Penetrating Peptides 32
3.6 Assembly System Using Arginine-Rich Cell-Penetrating Peptides 33
3.7 Gene Interaction of Arginine-Rich Cell-Penetrating Peptides 34
3.8 Development of Arginine-Rich Cell-Penetrating Peptides for the Delivery of Genes and Oligonucleotides 34
3.9 Molecular Coating with Arginine-Rich Cell-Penetrating Peptides 35
3.10 Enhanced Cytosolic Release using Arginine-Rich Cell-Penetrating Peptides as Additives 36
3.11 Effective Usage of Arginine-Rich Cell-Penetrating Peptides for Extracellular Vesicles, Exosomes 36
3.12 Conclusion 38
Declaration of Competing Interest 39
Author Contribution 39
4 Cationic Peptide 45
4.1 Cationic Peptide 45
5 Amphipathic Peptide 57
5.1 Introduction 57
5.2 α-Helical Peptides 57
5.3 β-Sheet Peptides 62
5.4 Polyproline Type II Helical Peptides 63
5.5 Others 64
6 Hydrophobic CPPs 69
6.1 MPG 69
6.2 SP 72
6.3 MTS 72
6.4 Hydrophobic MPS 72
6.5 MTS1 72
6.6 TP10 72
6.7 Pep-7 73
6.8 TLM 73
6.9 hCT(9-32)-br 73
6.10 C105Y 73
6.11 M918 74
6.12 PFV 74
6.13 Peptl 74
6.14 hCT(18-32)-br 74
6.15 P4 74
6.16 AA3H 75
6.17 L1-7 75
7 Foldamer 79
7.1 Introduction 79
7.2 β-Amino Acids 80
7.3 γ-Amino Acids 83
7.4 α,α-Disubstituted Amino Acids 84
7.5 Others 86
7.6 Summary 89
Part II Mechanism 109
8 Peptide Structure: Electrophysiological Analysis, Nuclear Magnetic Resonance Analysis, and Molecular Dynamics Simulation of Direct Penetration of Celt-Penetrating Peptides through Bilayer Lipid Membranes 111
8.1 Introduction 111
8.2 Electrophysiological Analysis of the Direct Penetration of CPPs 113
8.3 Solid-state NMR Analysis of the Direct Penetration of CPPs 128
8.4 Molecular Dynamics Simulation of CPP-Membrane Interactions 129
9 Cellular Uptake Mechanisms of Arginine-Rich Cell-Penetrating Peptides 141
9.1 Introduction 141
9.2 Endocytosis Mechanisms of Arginine-Rich Cell-Penetrating Peptides 143
9.3 Membrane Penetration Mechanisms of Arginine-Rich Peptides 144
9.4 Molecular Dynamic Simulation for Understanding Membrane Penetration of Arginine-Rich Cell-Penetrating Peptides 147
9.5 Multilamellar Formation of Membranes for Membrane Penetration of Arginine-Rich Peptides 148
9.6 Enhanced Membrane Penetration of Arginine-Rich Peptides by Induction of Positive Curvature 148
9.7 Internalization Mechanisms into Bacterial Cells 149
9.8 Toxicity 149
9.9 Importance of Controlled Intracellular Localization of Arginine-Rich Cell-Penetrating Peptides After Uptake for the Delivery of Functional Moleculess 150
9.10 Conclusion 151
Declaration of Competing Interest 151
Author Contribution 152
10 Endosomal Escape 159
10.1 Endosomal Escape 159
11 Pharmacokinetics of Therapeutic and Diagnostic Agents Conjugated with Cell-Penetrating Peptides 183
11.1 Introduction 183
11.2 Pharmacokinetics of CPPs 184
11.3 Pharmacokinetics of CPP-Conjugates for CNS Disorders 186
11.4 Pharmacokinetics of CPP-Conjugates for Infectious Diseases 187
11.5 Pharmacokinetics of CPP-Conjugates for Inflammatory Diseases 189
11.6 Pharmacokinetics of CPP-Conjugates for Cancer Treatment 190
11.7 Future Perspective 196
Part III Delivery Toot 203
12 Drug Delivery 205
12.1 Introduction 205
12.2 Delivery by Arg-Rich Peptides 206
12.3 Delivery by Cationic Peptides 209
12.4 Delivery by Amphipathic Peptides 210
12.5 Delivery by Hydrophobic Peptides 211
12.6 Delivery by Foldamers 212
13 Peptide and Protein Delivery 219
13.1 Introduction 219
13.2 The Delivery of Protein by CPPs 224
13.3 The Delivery of Peptides by CPPs 229
14 Cell-Penetrating Peptides for Nucleic Acid Delivery - An Update 237
14.1 Introduction 237
14.2 Characteristics of CPPs 239
14.3 Mechanism of CPP Internalization 239
14.4 CPPs Used as Conjugates for Nucleic Acid Delivery 242
14.5 CPPs Used as Nanoparticles for Nucleic Acid Delivery 243
14,6 CPP Functionalization for a More Specific Delivery 247
14.7 Conclusions 250
15 PPMOs: A Case Study for Cell-Penetrating Peptide Application 263
15.1 Introduction 263
15.2 Peptide Development 267
15.3 Platform Technology 270
16 Celt-Penetrating Peptide-Conjugated Polymer Micelle for pDNA/siRNA Delivery 285
16.1 Introduction 285
16.2 at-Conjugated Polymer Micelles 288
16.3 Multifunctional Peptide-Conjugated Polymer Micelles 297
16.4 Conclusions and Future Perspective 307
17 Lipid-Based Nanoparticles Using Ceil-Penetrating Peptides 315
17.1 Introduction 315
17.2 Cell-Penetrating Peptides 316
17.3 Lipid-based Nanoparticles 320
17.4 CPP-Modified Lipid Nanoparticles 321
17.5 Improving CPP-LNPs 324
17.6 Conclusion 324
Part IV Application 329
18 Cell-Penetrating Peptides as Tools to Facilitate Oral Delivery of Biopharmaceuticals 331
18.1 Introduction 331
18.2 Challenges for Oral Delivery of Biopharmaceuticals 331
18.3 Cell-Penetrating Peptides as Carriers for Oral Delivery of Biopharmaceuticals 333
18.4 In vivo Methods and Data Reporting when Studying Intestinal Absorption of Biopharmaceuticals 343
18.5 Mechanism of Cell-Penetrating Peptide-Mediated Cargo Delivery Across the Intestinal Barrier 347
18.6 Perspectives 349
19 "Intranasal Delivery" 355
19.1 Enhanced Systemic Absorption of Biologics by Coadministration with CPPs 355
19.2 Enhanced Nose-to-Brain Delivery of Biologics by Coadministration with CPPs 357
19.3 Mechanistic Insight for Enhanced Nose-to-Brain Drug Delivery with CPPs 358
19.4 Therapeutic Effects After Enhanced Nose-to-Brain Delivery of Biologics 360
19.5 Perspectives 362
20 Clinical Trials 367
20.1 Introduction 367
20.2 Peptides 367
20.3 Proteins 373
20.4 Low-Molecular-Weight (LMW) Drugs 374
20.5 Nucleic Acids 375
20.6 Fluorescent Dye 376
21 Plant 381
21.1 Introduction 381
21.2 CPP Design and Availability for Plant Cells 382
21.3 Artificial CPP for Plant Cells 383
21.4 Internalization Mechanism 386
21.5 Polypeptide-Based Carriers for Material Delivery 389
21.6 Perspective 393
Index 397
