Glucose Sensing (eBook)

PREFACE 6
CONTRIBUTORS 7
CONTENTS 10
N-PHENYLBORONIC ACID DERIVATIVES OF ARENECARBOXIMDES AS SACCHARIDE PROBES WITH VIRTUAL SPACER DESIGN 20
1.1. INTRODUCTION 20
1.2. N-PHENYLBORONIC ACID ARENECARBOXIMIDES AS SACCHARIDE PROBES WITH VIRTUAL OR CO SPACER DESIGN 21
1.3. SUBSTITUENT EFFECTS ON MONOBORONIC ACID DERIVATIVES OF N-PHENYLl, 8-NAPHTHALENEDICARBOXIMIDES 22
1.4. POSITIONAL ISOMERS OF NAPHTHALENE DICARBOXIMIDES 32
1.5. CONCLUSION 35
1.6. SUMMARY AND OUTLOOK 36
1.7. ACKNOWLEDGMENTS 36
1.8. REFERENCES 36
GENESIS OF FLUOROPHORE FORMATION IN MACROCYCLE SOLUTIONS AND THE DETECTION OF GLUCOSE AND RELATED SUGARS 40
2.1. INTRODUCTION 40
2.2. THE DISCOVERY OF NEW FUNCTIONAL FLUOROPHORES 40
2.3. THE MECHANISM OF SUGARINDUCED SIGNAL TRANSDUCTION 47
2.4. A HIGHLY CONVENIENT NEW AUTOMATED HPLC POSTCOLUMN DETECTION METHOD FOR MONITORING GLUCOSE AND RELATED BIOMOLECULES 53
2.5. DETECTION OF GLUCOSE IN HUMAN BLOOD PLASMA AND PROGRESS TOWARDS CONCURRENT DETERMINATION OF GLUCOSE AND FRUCTOSE 57
2.6. CONCLUSION 61
2.7. ACKNOWLEDGMENTS 61
2.8. REFERENCES 61
TWO-COMPONENT OPTICAL SUGAR SENSING USING BORONIC ACID-SUBSTITUTED VIOLOGENS WITH ANIONIC FLUORESCENT DYES 65
3.1. INTRODUCTION 65
3.2. BACKGROUND AND ILLUSTRATION OF TWO-COMPONENT GLUCOSE SENSING - PYRANINE (HPTS) AND BORONIC ACID-FUNCTIONALIZED VIOLOGEN (o-BBV2+) 68
3.3. VARIATIONS IN VIOLOGEN QUENCHER - BIPYRIDINIUM AND PHENANTHROLINIUM QUENCHERS 74
3.4. VARIATIONS IN FLUORESCENT REPORTER - SULFONAMIDE DERIVATIVES OF HPTS 89
3.5. IMMOBILIZATION OF THE SENSING COMPONENTS - A GLUCOSE SENSITIVE THIN FILM HYDROGEL 98
3.6. SUMMARY AND FUTURE DIRECTIONS 101
3.7. REFERENCES 102
IMPLANTABLE CONCANAVLIN A BASED SENSORS FOR INTERSTITIAL FLUID GLUCOSE SENSING IN DIABETICS 106
4.1. INTRODUCTION 106
4.2. CONCANAVALIN A AND DEXTRAN 109
4.3. FLUORESCENT BASED ASSAY 113
4.4. SENSING MODALITIES 117
4.5. SUMMARY 128
4.6. REFERENCES 128
FLUORESCENCE BIOSENSORS FOR CONTINUOUSLY MONITORING THE BLOOD GLUCOSE LEVEL OF DIABETIC PATIENTS 133
5.1. INTRODUCTION 133
5.2. GLUCOSE OXIDASE FROM ASPERGILLUS NIGER 135
5.3. THERMOSTABLE GLUCOSE DEHYDROGENASE FROM THERMOPLASMA ACIDOPHILUM 137
5.4. A FLUORESCENCE COMPETITIVE ASSAY BY USING THE STABLE GLUCOKINASE 139
5.5. CONCLUSIONS 142
5.6. ACKNOWLEDGMENT 143
5.7. REFERENCES 143
MICROCAPSULES AS "SMART TATTOO'' GLUCOSE SENSORS: ENGINEERING SYSTEMS WITH ENZYMES AND GLUCOSE-BINDING SENSING ELEMENTS 147
6.1. THE "SMART TATTOO" CONCEPT 147
6.2. LBL NANOFILMS AND POLYELECTROLYTE MICROCAPSULES 150
6.3. GLUCOSE SENSORS FROM NANOENGINEERED CAPSULES 152
6.4. ENZYME-BASED MICROCAPSULE SENSORS 158
6.5. GLUCOSEBINDING PROTEINS IN MICROCAPSULES 172
6.6. CONCLUSIONS 176
6.7. ACKNOWLEDGEMENT 177
6.8. REFERENCES 177
NON-INVASIVE MONITORING OF DIABETES: Specificity, compartmentalization, and calibration issues 180
7.1. INTRODUCTION 180
7.2. SPECIFICITY OF NI GLUCOSE MEASUREMENTS 182
7.3. COMPARTMENTALIZATION OF GLUCOSE VALUES 187
7.4. CALIBRATION MODELS AND PATIENT-SPECIFIC CALIBRATION 187
7.5. THERMO-OPTICAL RESPONSE OF HUMAN SKIN 188
7.6. ENHANCING SPECIFICITY BY AFFINITY CAPTURE AGENTS 205
7.7. CONCLUSIONS 210
7.8. REFERENCES 211
OPTICAL ENZYME-BASED GLUCOSE BIOSENSORS 215
8.1. ABSTRACT 215
8.2. INTRODUCTION 215
8.3. OPTICAL TRANSDUCTION USING COMMON OPTICAL TRANSDUCERS 217
8.4. IMMOBILIZATION OF GLUCOSE OXIDASE 221
8.5. CONSTRUCTION OF GLUCOSE BIOSENSOR 229
8.6. PERFORMANCE OF OPTICAL GLUCOSE BIOSENSOR 233
8.7. IMPLICATION OF THE DISSOLVED OXYGEN CONCENTRATION 237
8.8. ENHANCEMENT OF ENZYME STABILITY 238
8.9. ANALYTICAL FEATURE AND APPLICATION 240
8.10. CONCLUSION 242
8.11. ACKNOWLEDGMENT 243
8.12. REFERENCES 243
SACCHARIDE RECOGNITION BY BORONIC ACID FLUOROPHORE/CYCLODEXTRIN COMPLEXES IN WATER 251
9.1. ADVANCES IN SYNTHETIC RECEPTORS FOR SACCHARIDES 251
9.2. SACCHARIDE RECOGNITION BY BORONIC ACID FLUOROPHORE ß-CYCLODEXTRIN COMPLEXES 256
9.3. FUTURE PERSPECTIVE OF SUPRAMOLECULAR CYCLODEXTRIN COMPLEX SENSORS 268
9.4. ACKNOWLEDGEMENT 270
9.5. REFERENCES 271
PLASMONIC GLUCOSE SENSING 273
10.1. INTRODUCTION 273
10.2. OPTICAL PROPERTIES OF GOLD NANOPARTICLES 274
10.3. PREPARATION OF LIGAND FUNCTIONALIZED GOLD NANOPARTICLES FOR GLUCOSE SENSING AND OTHER APPLICATIONS 275
10.4. PLASMONIC GLUCOSE SENSING 278
10.5. CONCLUSIONS AND FUTURE DIRECTIONS 294
10.6. ACKNOWLEDGMENTS 294
10.7. REFERENCES 294
OPTICALLY-BASED AFFINITY BIOSENSORS FOR GLUCOSE 297
11.1. INTRODUCTION 297
11.2. DEVELOPMENT OF OPTICALLY BASED BIOSENSORS 299
11.3. COMPETITIVE OPTICAL AFFINITY GLUCOSE BIOSENSORS 303
11.4. DYNAMICS OF AFFINITY BIOSENSORS 312
11.5. RECENT DEVELOPMENTS IN AFFINITY BASED GLUCOSE BIOSENSOR SYSTEMS 313
11.6. INTEGRAL BIOSENSOR PROTEINS 318
11.7. ENHANCEMENTS OF OPTICAL GLUCOSE BIONSENSORS BASED ON AFFINITY PRINCIPLES 319
11.8. CONCLUSION 321
11.9. REFERENCES 321
RECENT CHEMILUMINESCENCE APPLICATIOINS FOR GLUCOSE SENSING 325
12.1. INTRODUCTION 325
12.2. CHEMILUMINESCENCE FOR THE DETERMINATION OF GLUCOSE 326
12.3. CHEMILUMINOGENIC BIOSENSOR 327
12.4. CAPILLARY ELECTROPHORESIS FOR GLUCOSE DETERMINATION 331
12.5. GLUCOSE SENSING: RECENT APPROACHES FOR CLINICAL USE IN DIABETES CARE 333
12.6. ACKNOWLEDGEMENT 335
12.7. REFERENCES 335
THE GLUCOSE BINDING PROTEIN AS GLUCOSE SENSOR 337
13.1. INTRODUCTION 337
13.2. PROTEIN ENGINEERING 338
13.3. POLARITY SENSITIVE PROBES 340
13.4. STRATEGIES FOR LOW-COST GLUCOSE SENSING 340
13.5. APPLICATION OF THE GBP-BASED BIOSENSOR IN CELL CULTURE 343
13.6. VALIDATION 344
13.7. REFERENCES 345
FLUORESCENT TICT SENSORS FOR SACCHARIDES 346
14.1. INTRODUCTION 346
14.2. RESULTS AND DISCUSSION 346
14.3. CONCLUSIONS 358
14.4. EXPERIMENTAL 358
14.5. ACKNOWLEDGMENTS 363
14.6. REFERENCES 363
GLUCOSE SENSING AND GLUCOSE DETERMINATION USING FLUORESCENT PROBES AND MOLECULAR RECEPTORS 364
15.1. ABSTRACT 364
15.2. INTRODUCTION 365
15.3. DETERMINATION OF GLUCOSE VIA GOx AND FLUORESCENT MOLECULAR PROBES 367
15.4. CONTINOUS SENSING OF GLUCOSE USING FLUORESCENT SENSOR MEMBRANES 371
15.5. SENSING GLUCOSE VIA METAL-LIGAND COMPLEXES WITH A BORONIC ACID AS THE RECOGNITION SITE 377
15.6. SENSING GLUCOSE VIA THIN FILMS OF ORGANIC CONDUCTING POLYMERS (OCPs) 378
15.7. SENSING GLUCOSE VIA OXYGEN-SENSITIVE NANOPARTICLES 380
15.8. SENSING GLUCOSE VIA THE INITRINSIC FLUORESCENCE OF GLUCOSE OXIDASE 380
15.9. IMAGING TECHNIQUES FOR GLUCOSE AND GLUCOSE OXIDASE 381
15.10. REFERENCES 386
BORONIC ACID-BASED FLUORESCENCE SENSORS FOR GLUCOSE MONITORING 389
16.1. INTRODUCTION 389
16.2. FACTORS THAT AFFECT THE BINDING BETWEEN BORONIC ACIDS AND DIOLS 390
16.3. VARIOUS TYPES OF BORONIC ACID-BASED FLUORESCENT REPORTER COMPOUNDS AVAILABLE 392
16.4. APPROACHES AVAILABLE FOR THE CONSTRUCTION OF THE APPROPRIATE 3-DIMENSIONAL SCAFFOLD FOR THE SELECTIVE RECOGNITION OF THE TARGET SUGAR 404
16.5. CONCLUSION 406
16.6. ACKNOWLEDGEMENT 406
16.7. REFERENCES 406
DEVELOPMENT OF SMART CONTACT LENSES FOR OPHTHALMIC GLUCOSE MONITORING 410
17.1. INTRODUCTION 410
17.2. GLUCOSE SENSING USING BORONICACID PROBES IN SOLUTION 413
17.3. LENS FEASIBITY STUDY 419
17.4. RATIONALE DESIGN OF NEW GLUCOSE SENSING PROBES 424
17.5. GLUCOSE SENSING PROBES BASED ON THE QUINOLINIUM MOIETY 425
17.6. PROBE LEACHING, INTERFERENTS AND SHELF LIFE 433
17.7. FUTURE DEVELOPMENTS BASED ON THIS TECHNOLOGY 435
17.8. CONCLUDING REMARKS 437
17.9. ACKNOWLEDGEMENTS 438
17.10. REFERENCES 438
INDEX 449