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Recent Advances in Analytical Techniques (Volume 2) Novel D evelopments in Pharmaceutical and Biomedi cal A nalysis Edited by Prof. Atta-ur-Rahman, FRS Honorary Life Fellow,Kings College,University of Cambridge,UK Prof. Sibel A. Ozkan Faculty of Pharmacy, Ankara University,Turkey & Dr. Rida Ahmed Postdoctoral Fellow,TCM and Ethnomedicine Innovation & Development Laboratory,School of Pharmacy, Hunan University of Chinese Medicine, Changsha 410208, P.R. China (cid:53)(cid:72)(cid:70)(cid:72)(cid:81)(cid:87)(cid:3)(cid:36)(cid:71)(cid:89)(cid:68)(cid:81)(cid:70)(cid:72)(cid:86)(cid:3)(cid:76)(cid:81)(cid:3)(cid:36)(cid:81)(cid:68)(cid:79)(cid:92)(cid:87)(cid:76)(cid:70)(cid:68)(cid:79)(cid:3)(cid:55)(cid:72)(cid:70)(cid:75)(cid:81)(cid:76)(cid:84)(cid:88)(cid:72)(cid:86) Volume # 2 Novel Developments in Pharmaceutical and Biomedical Analysis Editors: Atta-ur-Rahman, FRS, Sibel A. Ozkan and Rida Ahmed ISSN (Online): 2542-5625 ISSN (Print): 2542-5617 ISBN (Online): 978-1-68108-574-6 ISBN (Print): 978-1-68108-575-3 © 2018, Bentham eBooks imprint. Published by Bentham Science Publishers – Sharjah, UAE. All Rights Reserved. BENTHAM SCIENCE PUBLISHERS LTD. End User License Agreement (for non-institutional, personal use) This is an agreement between you and Bentham Science Publishers Ltd. Please read this License Agreement carefully before using the ebook/echapter/ejournal (“Work”). Your use of the Work constitutes your agreement to the terms and conditions set forth in this License Agreement. If you do not agree to these terms and conditions then you should not use the Work. Bentham Science Publishers agrees to grant you a non-exclusive, non-transferable limited license to use the Work subject to and in accordance with the following terms and conditions. This License Agreement is for non-library, personal use only. 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Email: [email protected] CONTENTS PREFACE ................................................................................................................................................ i LIST OF CONTRIBUTORS .................................................................................................................. ii CHAPTER 1 ADVANCES IN VALIDATED CHROMATOGRAPHIC ASSAY OF SOLID DOSAGE FORMS AND THEIR DRUG DISSOLUTION STUDIES ................................................ 1 Sevinc Kurbanoglu, Ozgur Esim, Ayhan Savaser, Sibel A. Ozkan and Yalcin Ozkan INTRODUCTION .......................................................................................................................... 2 Classification of Solid Oral Dosage Forms ............................................................................ 2 Extracts ......................................................................................................................... 2 Powders ......................................................................................................................... 5 Granules ........................................................................................................................ 5 Pellicles ......................................................................................................................... 5 Pills ............................................................................................................................... 5 Capsules ........................................................................................................................ 6 Lozenges, Troches, Pastilles ......................................................................................... 6 Oromucosal Preparations ............................................................................................. 6 Tablets ........................................................................................................................... 6 Pellets ............................................................................................................................ 7 Quality Control of Solid Oral Dosage Forms ......................................................................... 7 Uniformity of Dosage Units .......................................................................................... 8 Disintegration ............................................................................................................... 8 Dissolution .................................................................................................................... 9 Importance of Dissolution in Pharmacy ................................................................................. 18 Comparison of Dissolution Profiles .............................................................................. 18 In Vitro and In Vivo Relationships and Bioequivalence Challenges in Dissolution Method Development .................................................................................................... 20 Liquid Chromatography in Dissolution Testing ..................................................................... 21 Validation in Chromatographic Analysis ................................................................................ 23 System Suitability Tests ................................................................................................. 25 Linearity and Range ...................................................................................................... 25 Limit of Detection .......................................................................................................... 26 Limit of Quantification .................................................................................................. 26 Accuracy ........................................................................................................................ 26 Precision ....................................................................................................................... 26 Selectivity ...................................................................................................................... 27 Sensitivity ...................................................................................................................... 27 Robustness ..................................................................................................................... 27 Stability ......................................................................................................................... 27 Development of Method for Drug Dissolution Testing .......................................................... 28 CONCLUSION ............................................................................................................................... 34 CONSENT FOR PUBLICATION ................................................................................................ 34 CONFLICT OF INTEREST ......................................................................................................... 34 ACKNOWLEDGEMENTS ........................................................................................................... 34 REFERENCES ............................................................................................................................... 35 CHAPTER 2 NOVEL VALIDATED UHPLC METHOD FOR THE ESTIMATION OF DRUG ACTIVE COMPOUNDS ........................................................................................................................ 44 Mehmet Gumustas, Bengi Uslu and Sibel A. Ozkan INTRODUCTION .......................................................................................................................... 45 Liquid Chromatographic Techniques ..................................................................................... 48 Stationary Phases (Columns) ........................................................................................ 50 UHPLC Over HPLC ............................................................................................................... 55 Detector Types for UHPLC .................................................................................................... 57 UV-VIS Detectors .......................................................................................................... 59 Tunable UV (TUV) Detector ......................................................................................... 60 Photo Diode Array (PDA) Detector .............................................................................. 60 Fluorescence (FLR) Detector ....................................................................................... 60 Refractive Index (RI) Detector ...................................................................................... 61 Evaporative Light Scattering (ELS) Detector ............................................................... 62 Mass Spectrometer (MS) Detector ................................................................................ 62 Application on Drug Assay ..................................................................................................... 63 CONCLUDING REMARKS ......................................................................................................... 81 FUTURE DEMANDS ..................................................................................................................... 82 CONSENT FOR PUBLICATION ................................................................................................ 83 CONFLICT OF INTEREST ......................................................................................................... 83 ACKNOWLEDGEMENTS ........................................................................................................... 83 REFERENCES ............................................................................................................................... 83 CHAPTER 3 HILIC BASED LC/MS FOR METABOLITE ANALYSIS ....................................... 98 Emirhan Nemutlu and Sedef Kır INTRODUCTION .......................................................................................................................... 98 Separation Mechanism ............................................................................................................ 108 PARAMETERS EFFECTS ON SEPARATIONS ....................................................................... 110 Stationary Phase Effects ......................................................................................................... 110 Mobile Phase Effects on Separation ....................................................................................... 113 Organic Phase ............................................................................................................... 114 pH .................................................................................................................................. 114 Ionic Strength ................................................................................................................ 117 Detectors ....................................................................................................................... 117 Sample Preparation ...................................................................................................... 118 Development Steps of HILIC Method .................................................................................... 120 CONCLUSION ............................................................................................................................... 122 CONSENT FOR PUBLICATION ................................................................................................ 122 CONFLICT OF INTEREST ......................................................................................................... 122 ACKNOWLEDGEMENTS ........................................................................................................... 122 REFERENCES ............................................................................................................................... 122 CHAPTER 4 IN VITRO METHODS FOR THE EVALUATION OF OXIDATIVE STRESS .... 131 Hande Gürer Orhan, Sibel Suzen, Tamás Bálint Csont, Miroslav Pohanka, Bożena Nejman-Faleńczyk, Grzegorz Węgrzyn and Luciano Saso INTRODUCTION .......................................................................................................................... 132 1. DETERMINATION OF LIPID, PROTEIN AND DNA OXIDATION PRODUCTS AS BIOMARKERS OF EXPOSURE TO REACTIVE OXYGEN SPECIES ................................ 132 1.1. Lipid Oxidation Products as Biomarkers ......................................................................... 134 Aldehydes ...................................................................................................................... 134 Isoprostanes .................................................................................................................. 136 1.2. Protein Oxidation Products as Biomarkers ...................................................................... 136 Protein Carbonyls ......................................................................................................... 137 Oxidized Amino Acids ................................................................................................... 138 1.3. DNA Oxidation Products as Biomarkers ......................................................................... 139 2. DETECTION OF FREE RADICALS IN BIOLOGICAL SAMPLES BY ELECTRON PARAMAGNETIC RESONANCE SPECTROSCOPY ............................................................. 140 3. FLUORESCENT ASSAYS FOR DETECTION OF REACTIVE OXYGEN AND NITROGEN SPECIES IN BIOLOGICAL SYSTEMS ............................................................... 144 4. VOLTAMMETRY OF LOW MOLECULAR WEIGHT ANTIOXIDANTS. ..................... 148 5. MEASUREMENT OF OXIDATIVE STRESS IN BACTERIA ............................................ 150 5.1. Direct and Indirect Probe-based Measurement of ROS ................................................... 151 5.2. Measurement of the Oxidative Damage to Biomolecules ............................................... 152 Measurement of Protein Damage ................................................................................. 153 Measurement of Lipid Peroxidation .............................................................................. 154 5.3. Measurement of Antioxidants .......................................................................................... 155 CONCLUSIONS ............................................................................................................................. 156 CONSENT FOR PUBLICATION ................................................................................................ 156 CONFLICT OF INTEREST ......................................................................................................... 156 ACKNOWLEDGEMENTS ........................................................................................................... 156 REFERENCES ............................................................................................................................... 156 CHAPTER 5 THE APPLICATION OF VIBRATIONAL SPECTROSCOPY IN STUDIES OF STRUCTURAL POLYMORPHISM OF DRUGS ............................................................................... 173 Przemysław Zalewski, Gabriela Wiergowska, Joanna Goscianska, KorneliaLewandowska and Judyta Cielecka-Piontek INTRODUCTION .......................................................................................................................... 174 Polymorphism of Active Pharmaceutical Substance .............................................................. 175 The Influence of Polymorphism and Amorphization on the Physicochemical Properties of Active Pharmaceutical Ingredients and Excipients ................................................................. 175 Vibrational Methods Used for Identification of Crystalline and Amorphous Forms of Active Pharmaceutical Ingredients and Excipients ............................................................................ 176 Infrared Absorption Spectroscopy ................................................................................ 177 Attenuated Total Reflectance Spectroscopy .................................................................. 178 Raman Spectroscopy ..................................................................................................... 178 Polymorphism of Excipients ................................................................................................... 185 Methods of Stabilization of Polymorphic and Amorphous Forms of Active Pharmaceutical Ingredients ............................................................................................................................... 186 CONCLUDING REMARKS ......................................................................................................... 192 CONSENT FOR PUBLICATION ................................................................................................ 192 CONFLICT OF INTEREST ......................................................................................................... 192 ACKNOWLEDGEMENTS ........................................................................................................... 192 REFERENCES ............................................................................................................................... 193 CHAPTER 6 ELECTROCHEMICAL BIOSENSORS BASED ON CONDUCTIVE POLYMERS AND THEIR APPLICATIONS IN BIOMEDICAL ANALYSIS ....................................................... 208 Sławomira Skrzypek and Paweł Krzyczmonik INTRODUCTION .......................................................................................................................... 208 CONDUCTIVE POLYMERS ....................................................................................................... 209 NANOSTRUCTURED MATERIALS .......................................................................................... 211 Quantum Dots ......................................................................................................................... 211 Core-type Quantum Dots .............................................................................................. 212 Core-shell Quantum Dots ............................................................................................. 212 Alloyed Quantum Dots .................................................................................................. 213 Carbon Nanostructured Materials ................................................................................ 213 Fullerenes and Nanotubes ............................................................................................. 213 Graphene ....................................................................................................................... 214 Functionalization with Nanoparticles ........................................................................... 216 Functionalization with Organic Compounds ................................................................ 216 Functionalization with Polymers .................................................................................. 216 Functionalization with Biomaterials ............................................................................. 217 TYPES OF DETECTION IN BIOSENSORS .............................................................................. 218 Potentiometric Detection ........................................................................................................ 218 Amperometric Detection ......................................................................................................... 220 Detection of Oxygen ...................................................................................................... 220 Detection of Hydrogen Dioxide .................................................................................... 221 Detection of NADH ....................................................................................................... 221 BIOSENSORS ................................................................................................................................. 221 Glucose Biosensors ................................................................................................................. 222 Cholesterol Biosensors ............................................................................................................ 229 Biosensor Based on Laccase ................................................................................................... 233 Urea Biosensors ...................................................................................................................... 236 Affinity Biosensors ................................................................................................................. 240 CONCLUDING REMARKS ......................................................................................................... 241 CONSENT FOR PUBLICATION ................................................................................................ 241 CONFLICT OF INTEREST ......................................................................................................... 242 ACKNOWLEDGEMENTS ........................................................................................................... 242 REFERENCES ............................................................................................................................... 242 CHAPTER 7 NEW TRENDS IN ELECTROCHEMICAL SENSORS MODIFIED WITH CARBON NANOTUBES AND GRAPHENE FOR PHARMACEUTICAL ANALYSIS ................ 249 Burcin Bozal-Palabiyik, Burcu Dogan-Topal, Sibel A. Ozkan and Bengi Uslu INTRODUCTION .......................................................................................................................... 249 CARBON NANOTUBES ............................................................................................................... 252 The Structure and Properties of CNTs .................................................................................... 252 Synthesis and Characterization of CNTs ................................................................................ 253 Preparation of CNT-Based Electrodes .................................................................................... 254 Advantages and Limitations of CNT-Modified Electrodes .................................................... 259 Applications of CNTs in Pharmaceutical Analysis ................................................................ 260 GRAPHENE .................................................................................................................................... 267 The Structure and Properties of Graphene .............................................................................. 267 Synthesis and Characterization of Graphene .......................................................................... 268 Preparation of Graphene-Based Electrodes ............................................................................ 269 Advantages and Limitations of Graphene-Modified Electrodes ............................................ 271 Applications of Graphene in Pharmaceutical Analysis .......................................................... 272 CONCLUSION ............................................................................................................................... 277 ABBRAVIATIONS ......................................................................................................................... 277 CONSENT FOR PUBLICATION ................................................................................................ 279 CONFLICT OF INTEREST ......................................................................................................... 279 ACKNOWLEDGEMENTS ........................................................................................................... 279 REFERENCES ............................................................................................................................... 279 CHAPTER 8 ELECTROCHEMICAL NANOBIOSENSORS IN PHARMACEUTICAL ANALYSIS ............................................................................................................................................... 302 Sevinc Kurbanoglu, Sibel A. Ozkan and Arben Merkoçi INTRODUCTION .......................................................................................................................... 303 (Bio)Receptors ........................................................................................................................ 304 Immobilization of the Biological Materials ............................................................................ 306 Adsorption ..................................................................................................................... 307 Encapsulation ................................................................................................................ 307 Entrapment .................................................................................................................... 307 Covalent Binding ........................................................................................................... 308 Crosslinking .................................................................................................................. 308 Transducer Part of the Biosensors .......................................................................................... 308 Nanomaterials in Nanobiosensing .......................................................................................... 309 Applications of Electrochemical Nanobiosensors in Pharmaceutical Analysis ..................... 311 a. Antibiotics, Antibacterials and Antimicrobials ................................................................... 311 b. Cardiac Stimulant ................................................................................................................ 312 c. Antineoplastic Agents ......................................................................................................... 313 d. Antiviral Drugs ................................................................................................................... 317 e. Antidepressant and Antipsychotic Drugs ............................................................................ 317 f. Antiemetic Drugs ................................................................................................................. 318 g. Adrenergic Agonist ............................................................................................................. 319 h. Antiparasitic ........................................................................................................................ 320 i. Antimalarial ......................................................................................................................... 320 j. Vitamins, Minerals, Antioxidants, Nutritional Drugs .......................................................... 320 k. Analgesic, Anti-inflammatory Drugs .................................................................................. 321 l. Pesticides ............................................................................................................................. 322 CONCLUSIONS ............................................................................................................................. 325 ABBREVIATIONS ......................................................................................................................... 326 CONSENT FOR PUBLICATION ................................................................................................ 327 CONFLICT OF INTEREST ......................................................................................................... 327 ACKNOWLEDGEMENTS ........................................................................................................... 327 REFERENCES ............................................................................................................................... 328 CHAPTER 9 OPTICAL SENSOR ARRAYS FOR PHARMACEUTICAL AND BIOMEDICAL ANALYSES .............................................................................................................................................. 354 Pavel Anzenbacher, Jr and Mehmet Gokhan Caglayan INTRODUCTION .......................................................................................................................... 354 Chemometric Analysis of Optical Array Sensors ................................................................... 358 Principal Component Analysis ............................................................................................... 361 Linear Discriminant Analysis ....................................................................................... 362 Support Vector Machines .............................................................................................. 362 Hierarchical Cluster Analysis ....................................................................................... 363 Neural Networks ............................................................................................................ 364 Optical Array Sensing in Pharmaceutical and Biomedical Analyses ..................................... 364 CONCLUSION ............................................................................................................................... 372 CONSENT FOR PUBLICATION ................................................................................................ 373 CONFLICT OF INTEREST ......................................................................................................... 373 ACKNOWLEDGEMENTS ........................................................................................................... 373 REFERENCES ............................................................................................................................... 373 CHAPTER 10 APPLICATIONS OF IONIC LIQUIDS IN CHEMICAL SCIENCE .................... 382 Imran Ali Zeid, A. Alothman, Abdulrahman Alwarthan and Hassan Y. Aboul-Enein INTRODUCTION .......................................................................................................................... 382 Significance of the Ionic Liquids ............................................................................................ 383 Applications of the Ionic Liquids ........................................................................................... 384 Extraction ...................................................................................................................... 384 Separation ..................................................................................................................... 390 Liquid Chromatography ................................................................................................ 390 Capillary Electrophoresis ............................................................................................. 392 Gas Chromatography .................................................................................................... 394