Chemical aspects of photodynamic therapy:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
London [u.a.]
Gordon and Breach
2000
|
| Schriftenreihe: | Advanced chemistry texts
1 |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XVI, 305 S. graph. Darst. |
| ISBN: | 9056992481 |
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Datensatz im Suchindex
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|---|---|
| adam_text | Contents
Preface xiii
Acronyms xv
Chapter 1 Introduction 1
1.1 Definition of Area of Study 1
1.2 Historical Aspects 3
1.2.1 Vitamin D and Rickets 4
1.2.2 Phototherapy of Psoriasis 6
1.2.3 Neonatal Hyperbilirubinemia 7
1.2.4 Cancer 9
Bibliography 13
Chapter 2 Physical Matters 15
2.1 Light 15
2.2 Light Sources 19
2.2.1 Sunlight 19
2.2.2 Incandescent Lamps 19
2.2.3 Arc Lamps 19
2.2.4 Light-emitting Diodes 20
2.2.5 Lasers 21
2.3 Light Absorption 23
2.3.1 The Beer-Lambert Law 23
2.3.2 Excitation 24
2.3.2.1 Multiplicity 24
2.3.2.2 Probability 25
2.4 Emission 27
2.5 Jablonski Diagram 28
2.6 Quantum Efficiency 30
2.7 Intermolecular Electronic Excitation Transfer 31
2.8 Singlet Oxygen Quantum Yields 32
Bibliography 37
Chapter 3 Singlet Oxygen 39
3.1 General 39
3.2 Generation of Singlet Oxygen 42
3.2.1 Chemical Methods 42
3.2.2 Physical Methods 42
; CHEMICAL ASPECTS OF PHOTODYNAMIC THERAPY vii
I
CONTENTS
3.3 Chemical Reactions 47
3.3.1 Alkenes — the ene Reaction 47
3.3.2 Electron-rich Alkenes 49
3.3.3 Conjugated Dienes — Diels-Alder Addition 52
3.3.4 Miscellaneous Reactions 54
Bibliography 56
Chapter 4 Photodynamic Action 57
4.1 Definition 57
4.2 Discovery and Development 57
4.3 Photodynamic Agents — Structural Types 64
4.3.1 General Considerations 64
4.3.2 Structural Types 64
4.4 Mechanism of Photodynamic Action 70
4.4.1 The Type I Mechanism — Electron Transfer 70
4.4.2 The Type II Mechanism — Energy Transfer 74
4.4.3 Distinguishing between Type I and Type II
Photooxygenation Processes 76
4.4.3.1 Tests for radical intermediates (Type I
mechanism) 80
4.4.3.2 Tests for singlet oxygen (Type II mechanism) 81
4.4.4 The Overall Mechanistic Picture 83
Bibliography 87
Chapter 5 Some Other Examples of Photomedicine 89
5.1 Introduction 89
5.2 Sunscreens 89
5.2.1 Sunlight and the Skin 89
5.2.2 Artificial Sunscreens 92
5.3 Skin Carcinogenesis 93
5.4 Phototherapy of Rickets (Osteomalacia) 94
5.5 Psoriasis 100
5.5.1 Photosensitisers for PUVA 100
5.5.2 Mechanism 102
5.6 Phototherapy of Neonatal Hyperbilirubinemia 103
5.6.1 Photofragmentation 104
5.6.2 Photoisomerisation/Photosolubilisation 107
5.6.2.1 Photochemical configurational isomerisation
(Photobilirubins I) 107
5.6.2.2 Photocyclisation (Photobilirubins II,
lumirubins) 109
Bibliography 113
viii CHEMICAL ASPECTS OF PHOTODYNAMIC THERAPY
CONTENTS
Chapter 6 The Chemistry of Haematoporphyrin Derivative (HpD) 115
6.1 Introduction 115
6.2 Chemistry of HpD Stage I 117
6.3 Chemistry of HpD Stage II 118
6.4 Clinical Development 126
Bibliography 128
Chapter 7 Second Generation Photosensitisers 129
7.1 First Generation Photosensitisers 129
7.1.1 Advantages 129
7.1.2 Disadvantages 129
7.2 Design Criteria for Second Generation Photosensitisers 130
7.2.1 Dark Toxicity 130
7.2.2 Composition 130
7.2.3 Synthesis 130
7.2.4 Solution Behaviour 130
7.2.4.1 Tetraphenylporphyrin sulphonic acids 131
7.2.4.2 Sulphonated metallophthalocyanines 132
7.2.4.3 3-( 1 -Alkyloxyethyl)-3-devinylpyropheo-
phorbide a 135
7.2.4.4 Spacing of hydrophilic substituents on the
hydrophobic framework 136
7.2.5 Delivery Systems 137
7.2.6 Photophysical Properties 143
7.2.7 Red Absorption 144
Bibliography 147
Chapter 8 Porphyrin Photosensitisers 149
8.1 Introduction 149
8.2 Porphyrin Sources 149
8.3 Porphyrins Derived from Haemoglobin 156
8.4 Synthetic Porphyrins 159
8.4.1 General Approaches 159
8.4.2 Specific Examples 166
8.5 Endogenous Porphyrin: 8-ALA as a Pro-drug 173
Bibliography 174
Chapter 9 Chlorins and Bacteriochlorins 177
9.1 Structural Definition 177
9.2 Absorption Spectra 178
9.3 Naturally Derived Chlorins and Bacteriochlorins 183
9.4 Chlorins Derived from Protohaem 186
9.4.1 From Degteroporphyrin (88) 187
9.4.2 From Protoporphyrin (61) 188
9.4.3 From Photoprotoporphyrin (132) 189
CHEMICAL ASPECTS OF PHOTODYNAMIC THERAPY ix
FOREWORD
9.5 Chlorins and Bacteriochlorins by Total Synthesis 190
9.5.1 By Reduction 190
9.5.2 By Other |},p -Addition Reactions 193
9.5.3 By Meso-P Cyclisation 193
Bibliography 198
Chapter 10 Phthalocyanines and Naphthalocyanines 199
10.1 Structural Considerations 199
10.2 Spectra 201
10.3 5-Azaporphyrins 203
10.4 Benzoporphyrins 203
10.5 Phthalocyanines 203
10.5.1 General 203
10.5.2 Synthesis 211
10.5.3 PDT Photosensitisers 219
10.5.3.1 Zinc(ll) phthalocyanine 219
10.5.3.2 Sulphonic acids 220
10.5.3.3 Hydroxyphthalocyanines 220
10.5.3.4 Axial ligand variation 221
10.6 Naphthalocyanines 222
Bibliography 223
Chapter 11 Other Photosensitisers 225
11.1 Cyanine Dyes 225
11.1.1 Merocyanine 540 225
11.1.2 Indocyanine Green 226
11.2 Hypericin 226
11.3 Phenothiazines 226
11.4 Porphycenes 227
11.5 Squaraines 229
11.6 Texaphyrins 229
11.7 Xanthenes 231
11.8 Conjugated Photosensitisers 233
Bibliography 235
Chapter 12 Photobleaching 237
12.1 Definitions 237
12.2 Potential Value of Photobleaching in PDT 238
12.3 Kinetic Studies 238
12.4 Product Studies 241
12.4.1 Photomodification 241
12.4.1.1 Protoporphyrin 241
12.4.1.2 m-THPP 243
12.4.1.3 m-THPC 244
x CHEMICAL ASPECTS OF PHOTODYNAMIC THERAPY
CONTENTS
12.4.1.4 Purpurins 244
12.4.1.5 Haematoporphyrin 245
12.4.2 Photobleaching 246
12.4.2.1 m-THPC and m-THPBC 246
12.4.2.2 Other photosensitisers related to porphyrins 246
12.5 Biological Systems 248
12.5.1 In vitro Studies 248
12.5.2 In vivo Studies 248
Bibliography 256
Chapter 13 Biological Aspects 257
13.1 Biological Assay 257
13.1.1 Preliminary Physical Tests 257
13.1.2 In vitro Bioassays 258
13.1.3 Intermediate Bioassays 259
13.1.4 In vivo Bioassays 260
13.1.4.1 Tumour photonecrotic activity 260
13.1.4.2 Tumour selectivity 261
13.2 Localisation 262
13.2.1 Protein Binding 264
13.2.2 Intracellular Localisation 264
13.2.3 Localisation in vivo 265
13.3 Photosensitiser Excretion 268
13.4 Mechanisms of Tumour Destruction 269
Bibliography 270
Chapter 14 Clinical and Commercial Developments: Prospects for
the Future 271
14.1 Introduction 271
14.2 PhotofrinR (also referred to as porfimer sodium) 272
14.3 Second Generation Drugs at the Clinical Stage 273
14.3.1 5-ALA (104) 273
14.3.2 m-THPC (77) 274
14.3.3 Tin Etiopurpurin — SnEt2 275
14.3.4 Mono-L-aspartylchlorin e6 — MACE (125) 275
14.3.5 3-(1-Hexyloxyethyl)-3-devinylpyropheophorbide a (75) 275
14.3.6 Sulphonated Aluminium Phthalocyanine 275
14.3.7 Benzoporphyrin Derivative (131) 275
14.3.8 Lutetium Texaphyrin (187) 276
14.3.9 Porphycenes 276
14.4 Comparative Data 276
14.5 Future Prospects 277
14.5.1 Synthesis of New Sensitisers 277
14.5.2 Light Sources 277
CHEMICAL ASPECTS OF PHOTODYNAMIC THERAPY xi
CONTENTS
14.5.3 New Clinical Directions in PDT 278
14.5.3.1 Psoriasis 278
14.5.3.2 Arthritis 278
14.5.3.3 Age-related Macular Degeneration (AMD) 278
14.5.3.4 Other Conditions and Treatments 278
14.5.3.5 Microbicidal Activity 278
Bibliography 289
Index 291
xii CHEMICAL ASPECTS OF PHOTODYNAMIC THERAPY
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| spelling | Bonnett, Raymond Verfasser aut Chemical aspects of photodynamic therapy Raymond Bonnett London [u.a.] Gordon and Breach 2000 XVI, 305 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Advanced chemistry texts 1 Advanced chemistry texts 1 (DE-604)BV014045603 1 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=019897929&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Bonnett, Raymond Chemical aspects of photodynamic therapy Advanced chemistry texts |
| title | Chemical aspects of photodynamic therapy |
| title_auth | Chemical aspects of photodynamic therapy |
| title_exact_search | Chemical aspects of photodynamic therapy |
| title_full | Chemical aspects of photodynamic therapy Raymond Bonnett |
| title_fullStr | Chemical aspects of photodynamic therapy Raymond Bonnett |
| title_full_unstemmed | Chemical aspects of photodynamic therapy Raymond Bonnett |
| title_short | Chemical aspects of photodynamic therapy |
| title_sort | chemical aspects of photodynamic therapy |
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