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Quenched-phosphorescence Detection of Molecular Oxygen

Quenched-phosphorescence Detection of Molecular Oxygen

Dmitri B Papkovsky | Ruslan I Dmitriev

(2018)

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Book Details

Abstract

Significant progress has been made in recent years in quenched-phosphorescence oxygen sensing, particularly in the materials and applications of this detection technology that are open to commercialization, like uses in brain imaging and food packaging. Prompted by this, the editors have delivered a dedicated book that brings together these developments, provides a comprehensive overview of the different detection methodologies, and representative examples and applications.

This book is intended to attract new researchers from various disciplines such as chemistry, physics, biology and medicine, stimulate further progress in the field and assist in developing new applications. Providing a concise summary at the cutting edge, this practical guide for current experts and new potential users will increase awareness of this versatile sensing technology.


Table of Contents

Section Title Page Action Price
Front Cover Cover
Quenched-phosphorescence Detection of Molecular Oxygen: Applications in Life Sciences i
Preface v
Contents vii
Chapter 1 - Fundamentals of Quenched Phosphorescence O2 Sensing and Rational Design of Sensor Materials 1
1.1 Introduction 1
1.2 Mechanism of Oxygen Quenching 2
1.3 Requirements for Phosphorescent Indicators 4
1.4 Brief Overview of the Most Common Indicators 6
1.5 Rational Design of Optical Sensing Materials 9
1.6 Sensitivity and Dynamic Range of Oxygen Sensors 11
1.7 Referenced Oxygen Sensing and Imaging 13
1.8 Artefacts in Oxygen Sensing 14
1.9 Conclusions and Outlook 16
References 16
Chapter 2 - New Polymer-based Sensor Materials and Fabrication Technologies for Large-scale Applications 19
2.1 Introduction 19
2.2 Physical Entrapment of Phosphors Within Inorganic and Organic Matrices 21
2.2.1 Casting of Polymer ‘Cocktails’ 25
2.2.2 Physical Mixing of Phosphors with Ormosils 29
2.2.3 Phosphor Integration in Silicone Rubbers 30
2.2.4 Impregnation of Microporous Membranes and Microparticles with Phosphor Molecules 32
2.2.5 Solvent Crazing 33
2.2.6 Electrospinning 34
2.2.7 Electrophoretic Deposition 35
2.2.8 Layer-by-layer Deposition (LbL) 35
2.3 Covalent and Coordinative Binding of Phosphors to Substrates 36
2.4 Conclusions and Outlook 38
Abbreviations 39
Acknowledgement 39
References 40
Chapter 3 - Evolution of Cell-penetrating Phosphorescent O2 Probes 50
3.1 Evolution of Cell-penetrating Phosphorescent O2 probes 50
3.1.1 Introduction 50
3.1.2 Why and How to Measure Intracellular O2 52
3.1.3 Different Classes of Cell-penetrating O2 Probes and Their Evolution 55
3.1.3.1 Small Molecule Probes and Other Conjugates 55
3.1.3.2 Nanoparticles of First Generation 59
3.1.3.3 Nanoparticles of Second Generation 60
3.1.3.4 Nanoparticles of Third Generation 62
3.2 Conclusions and Future Outlook 63
Acknowledgement 64
References 64
Chapter 4 - Hydrophilic Ir(iii) Complexes for In vitro and In vivo Oxygen Imaging 71
4.1 Introduction 71
4.2 Experimental 73
4.2.1 Synthesis of BTP-PEGn (n = 12, 24, 48) and PPY-PEG24 73
4.2.2 Photophysical Properties in Aqueous Solutions 76
4.2.3 Octanol/Water Partition Coefficients (logPO/W) 76
4.2.4 Fluorescence and Phosphorescence Lifetime Imaging Microscopy 77
4.2.5 Cell Culture and Imaging 77
4.2.6 In vivo Imaging 77
4.3 Results and Discussion 78
4.3.1 Electronic Structures of the Ir(iii) Complexes 78
4.3.2 Hydrophilicity and Photophysical Properties in Water 79
4.3.3 Phosphorescence Quenching by Molecular Oxygen in Solution 81
4.3.4 Temperature Effects on Phosphorescence Quenching by O2 83
4.3.5 Cellular Uptake and Oxygen Response 84
4.3.6 In vivo O2 Imaging by PLIM Measurements 86
4.4 Conclusion 89
Acknowledgement 89
References 89
Chapter 5 - Protection of Triplet Excited State Materials from Oxygen Quenching and Photooxidation in Optical Sensing Applications 91
5.1 Introduction 91
5.2 Phosphorescent Probes with Appended Protective Groups 93
5.2.1 Phosphorescent Dendrimers 93
5.2.2 “Self-healing” Phosphorescent Complexes 97
5.3 Host-guest Complexes and Aggregates 99
5.3.1 Tryptophan Phosphorescence in Proteins 99
5.3.2 Phosphorescence of Cyclodextrin Complexes in the Presence of Oxygen 100
5.3.3 Steroids as Protective Matrixes 103
5.3.4 Gel Matrixes 104
5.4 Application of Oxygen Scavengers 105
5.4.1 Inorganic Oxygen Scavengers 105
5.4.2 Application of Natural Antioxidants 106
5.4.3 Scavengers of Singlet Oxygen 107
5.5 Encapsulation of the Phosphorescent Molecules into Polymers 108
5.6 Inorganic Matrix Materials 110
5.7 Conclusions and Perspectives 111
Acknowledgements 112
References 112
Chapter 6 - Progress in Phosphorescence Lifetime Measurement Instrumentation for Oxygen Sensing 117
6.1 Introduction 117
6.2 The Phosphorescence Emission as a Linear System 120
6.2.1 First Order Phosphorescent Systems 120
6.2.2 Multi-exponential Phosphorescent Systems 121
6.2.3 Lifetime Derived from Modulation Factor and Phase-shift 122
6.2.4 Modelling and Calibration of Phosphorescent Systems 123
6.3 Architecture for Measuring the Frequency Response 123
6.3.1 Modular Architecture of the Phosphorescence Instrument 124
6.3.2 Estimation of the Frequency Response 125
6.4 Multifrequency Measurements and Applications 127
6.4.1 Characterization of the Sensing Phase 128
6.4.2 Selecting the Optimal Single Modulation Frequency for Analyte Determination 130
6.4.3 Using Multi-frequency Information for Oxygen Determination 131
6.5 Noise Analysis and Applications 134
6.5.1 Application to Uncertainty Estimation 136
6.5.2 Application to Optimal Combination of Harmonics 137
6.6 Instrument Development 137
6.7 Conclusions 141
Acknowledgement 142
References 142
Chapter 7 - Optical O2 Sensing in Aquatic Systems and Organisms 145
7.1 Introduction 145
7.2 Optical O2 Sensing Platforms 146
7.2.1 Fiber-optic O2 Opt(r)odes 147
7.2.2 Planar Opt(r)odes for O2 Imaging and Remote Read-out 148
7.2.3 Particle-based Optical O2 Sensors 150
7.3 Challenges Related to Optical O2 Measurements in Aquatic Systems 151
7.3.1 Large O2 Dynamics 151
7.3.2 Extreme Environments Require Special Designs 152
7.3.3 Sensor Stability – from Mechanical Stress to Biofouling 154
7.4 Applications of Optical O2 Sensors 155
7.4.1 Application of Micro-opt(r)odes 155
7.4.1.1 Profiling 156
7.4.1.2 Eddy Correlation Spectroscopy 156
7.4.2 Applications of Bulk Sensors and Sensor Patches 157
7.4.2.1 Respirometry 158
7.4.2.2 Environmental Monitoring 159
7.4.3 Chemical Imaging 159
7.4.3.1 Microscopic O2 Imaging 161
7.4.3.2 O2 Imaging in Sediments 163
7.4.3.3 O2 Imaging on Structurally Complex Samples 165
7.5 Future Challenges 167
7.5.1 Multi-analyte Measurements 167
7.5.2 Special O2 Microniches and Their Impact on Other Processes 168
7.5.3 Low Cost Instrumentation for Long-term Monitoring 168
7.6 Conclusions 168
References 169
Chapter 8 - Monitoring of Extracellular and Intracellular O2 on a Time-resolved Fluorescence Plate Reader 175
8.1 Introduction 175
8.2 Measuring Oxygen 176
8.2.1 Clark Electrodes 176
8.2.2 Phosphorescent Porphyrin-based Probes 176
8.2.2.1 Seahorse XF Analyser 177
8.2.3 Oxygen Sensing Plate Based Assays Using Standard Tissue Culture Plates 179
8.2.3.1 MitoXpress® Oxygen Probes 180
8.2.3.2 MitoXpress-Xtra 181
8.3 Measurement of Intracellular Oxygen 183
8.3.1 MitoXpress-Intra Probe 184
8.3.2 Application of the MitoXpress-Intra Probe 187
8.4 Future Applications of Plate-based Oxygen Monitoring Systems 188
Acknowledgements 190
References 190
Chapter 9 - Monitoring Parameters of Oxygen Transport to Cells in the Microcirculation 193
9.1 Introduction 193
References 203
Chapter 10 - Photoacoustic Imaging of Oxygen 205
10.1 Introduction 205
10.2 Photoacoustic Oxygen Monitoring Using Biological Chromophores (i.e. Hemoglobin) 207
10.3 Photoacoustic Lifetime Measurements for Oxygen Sensing (PALT) 209
10.4 Applying Nanotechnology to PALT 213
10.5 Summary and Discussion 215
Acknowledgements 217
References 217
Chapter 11 - Imaging of Tissue Oxygen Ex vivo 220
11.1 Introduction 220
11.2 Experimental 222
11.2.1 Materials 222
11.2.2 Animals and Tissue Staining 222
11.2.3 Live Tissue Imaging by Confocal FLIM/PLIM Microscopy 223
11.2.4 Analysis of Oxygen Consumption Rate (OCR) in Colonic Mucosa Samples 223
11.2.5 Statistical Analysis and Data Presentation 224
11.3 Results and Discussion 224
11.3.1 Oxygen Imaging in the Colon Tissue 224
11.3.1.1 Staining of Colonic Tissue with O2 Sensing Probes 225
11.3.1.2 Imaging of O2 in Colonic Tissue 225
11.3.1.3 Effect of DSS-induced Colitis on O2 Levels and OCR in Mouse Colonocytes 228
11.3.1.4 Effect of NOX Deficiency on O2 Levels in Mouse Colonic Epithelium 228
11.3.1.5 O2 Imaging in Rat and Human Colonic Epithelium 229
11.3.1.6 Main Findings and Conclusions 230
11.3.2 Ex vivo O2 Imaging in the Urinary Bladder 232
11.3.2.1 Ex vivo and in vivo Staining of the Urinary Bladder Epithelium with Pt-Glc and Other Probes 233
11.3.2.2 Ex vivo Imaging of Intracellular O2 Gradients in Umbrella Cells 234
11.3.2.3 Ex vivo Imaging of O2 in Other Tissue Types of the Urinary Bladder 237
11.3.2.4 Main Findings and Conclusions 237
11.3.3 Ex vivo O2 Imaging in Carotid Arteries 238
11.4 Concluding Remarks 240
Acknowledgements 241
References 241
Chapter 12 - Tracking of Hypoxia and Cancer Metastasis with Iridium(iii)-based O2 Probes 244
12.1 Introduction 244
12.2 Hypoxia Imaging with Poly(N-Vinylpyrrolidone) (PVP)-conjugated Ir(iii) Complex Probe (Ir-PVP) 245
12.2.1 Design of the Ir-PVP Probe 245
12.2.2 Ratiometric Imaging of Hypoxia in Solid Tumours with Ir-PVP Probe 247
12.2.3 Monitoring the Proliferation of Cancer Cells in Live Mice with Ir-PVP Probe 247
12.3 Tracking Cancer Metastasis with Ir(iii)-based Oxygen Nanosensor 249
12.3.1 Design of the Ir(iii)-based Oxygen Nanosensor (Ir-CM) 249
12.3.2 Tracking Lung Cancer Metastasis with Ir-CM Nanosensor 249
12.3.3 Tracking Cancer Metastasis in the Lymph Node with Ir-CM Nanosensor 249
12.4 Ir(iii)-based Successively Activating Phosphorescent Probe for Ultrasensitive Hypoxia Imaging 253
12.4.1 Design of the Successively Activating Phosphorescent Probe (Ir-Im-PEG) 253
12.4.2 Tracking Liver Cancer Metastasis with the Ir-Im-PEG Probe 254
12.5 Conclusion and Perspective 256
Acknowledgement 256
References 257
Chapter 13 - Probing Tissue Oxygenation by Delayed Fluorescence of Protoporphyrin IX 259
13.1 Introduction 259
13.2 Background 260
13.2.1 Oxygen 260
13.2.2 Porphyrins 261
13.2.3 Protoporphyrin IX 261
13.2.4 Delayed Fluorescence Quenching 262
13.2.5 Quenching Constants 264
13.3 Measuring Mitochondrial PO2 265
13.3.1 Aminolevulinic Acid 265
13.3.2 Laboratory Setup 266
13.3.2.1 Excitation Source 266
13.3.2.2 Gated Detector 266
13.3.2.3 Data-acquisition System 267
13.3.2.4 Signal Analysis 267
13.3.2.5 Multi Compartment Measurements 269
13.4 In vivo Cellular Respirometry 270
13.5 Clinical Implementation 271
13.5.1 The Skin as a “Canary” of the Body 271
13.5.2 Priming of the Skin 272
13.5.3 The COMET Measuring System 272
13.5.4 Example Measurements 273
13.6 Conclusion 275
Conflict of Interest Statement 275
References 276
Chapter 14 - Microfluidic Systems and Optical Oxygen Sensors: A Perfect Match for Advancing Bioprocessing and Microbiology 278
14.1 Introduction 278
14.2 Challenges 282
14.3 Sensor Formats 284
14.3.1 Water-soluble/Macromolecular Probes 285
14.3.2 Sensor Layers 285
14.3.3 Micro/Nanoparticles 285
14.4 Sensor Layer Integration and Fabrication 286
14.5 Detection Principles 289
14.6 Applications 291
14.7 Conclusion 293
References 294
Chapter 15 - pO2 Measurements in Biological Tissues by Luminescence Lifetime Spectroscopy: Strategies to Exploit or Minimize Phototoxic Effects in Tumors 298
15.1 Introduction 298
15.2 Assessment of the Tumor Oxygenation with the Phosphorescence Quenching-based Approach 300
15.3 Photodynamic Therapy 301
15.4 Oxygen Consumption During Photodynamic Therapy 305
15.5 Strategies to Minimize Tissue Damage While Measuring the pO2 308
15.5.1 Impact of the Biodistribution and Subcellular Localization of Oxygen-sensitive Molecules on Their Phototoxicity 308
15.5.2 Correlation Between the Production of ROS and the Phototoxicity While Measuring the pO2 310
15.5.3 Alteration of pO2 Measurements by the Luminescence of Oxygen Molecular Probes Photoproducts 311
15.6 Conclusion 313
Acknowledgement 314
References 314
Chapter 16 - In vivo Brain Functional Imaging Using Oxygenation-related Optical Signal 319
16.1 Introduction 319
16.2 Intrinsic Optical Signal (IOS) 321
16.3 Functional Magnetic Resonance Imaging (fMRI) 322
16.4 Functional Near-Infrared Spectroscopy (fNIRS) 323
16.5 Diffuse Optical Tomography (DOT) 324
16.6 Photoacoustic Imaging (PAI) 324
16.7 Phosphorescence Quenching Techniques 326
16.7.1 Soluble Phosphorescent Oxygen-sensitive Probes 326
16.7.2 Phosphorescent Microparticle-based Probes 329
16.7.3 Planar Phosphorescent Oxygen Sensors 329
16.8 Conclusions 330
References 331
Chapter 17 - Applications of Phosphorescent O2 Sensors in Food and Beverage Packaging Systems 335
17.1 Introduction 335
17.2 Monitoring O2 Content in Modified Atmosphere Packaging of Foodstuffs 340
17.2.1 Selection of Oxygen Sensors for Food Packaging Applications 342
17.2.2 Characterisation of O2 Sensors 342
17.2.3 Instruments Used to Monitor O2 on Food Packaging Integrated with O2 Sensors 343
17.2.4 Applications of O2 Sensors for Monitoring O2 Content in Packaged Food Products 344
17.3 Conclusions 357
Acknowledgements 357
References 357
Subject Index 361