Capillary Electrophoresis

Transcription

1 edited by Suvardhan Kanchi Salvador Sagrado Myalowenkosi Sabela Krishna Bisetty Capillary Electrophoresis Trends and Developments in Pharmaceutical Research

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3 Capillary Electrophoresis

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5 Capillary Electrophoresis Trends and Developments in Pharmaceutical Research edited by Suvardhan Kanchi Salvador Sagrado Myalowenkosi Sabela Krishna Bisetty

6 Published by Pan Stanford Publishing Pte. Ltd. Penthouse Level, Suntec Tower 3 8 Temasek Boulevard Singapore editorial@panstanford.com Web: British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library. Capillary Electrophoresis: Trends and Developments in Pharmaceutical Research Copyright 2017 by Pan Stanford Publishing Pte. Ltd. All rights reserved. This book, or parts thereof, may not be reproduced in any form or by any means, electronic or mechanical, including photocopying, recording or any information storage and retrieval system now known or to be invented, without written permission from the publisher. For photocopying of material in this volume, please pay a copying fee through the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, USA. In this case permission to photocopy is not required from the publisher. ISBN (Hardcover) ISBN (ebook) Printed in the USA

7 Contents Preface xiii 1. Capillary Electrophoresis: A Versatile Technique in Pharmaceutical Analysis 1 Imran Ali, Zeid A. Alothman, Abdulrahman Alwarthan, and Hassan Y. Aboul-Enein 1.1 Introduction Theory of Capillary Electrophoresis Types of Capillary Electrophoresis Instrumentation Sample Introduction Capillary Electrophoresis Capillary Power Supply Background Electrolyte Detection UV/Vis absorbance detectors Conductivity detectors Amperometric detectors Thermooptical absorbance detectors Fluorescence detectors Atomic absorption spectroscopy detectors Inductively coupled plasma detectors Mass detectors Miscellaneous detectors Indirect detection Data Integration Sample Preparation Method Development and Optimization Validation of Methods Applications Conclusion 45

8 vi Contents 2. Recent Applications of Chiral Capillary Electrophoresis in Pharmaceutical Analysis 71 José María Saz and María Luisa Marina 2.1 Introduction Chiral Selectors Added to BGE for Enantioseparation of Chiral Drugs by CCE Cyclodextrins Macrocyclic Antibiotics Polysaccharides Other Chiral Selectors Applications of CCE in Pharmaceutical Analysis Analysis of Pharmaceutical Formulations Analysis of Illicit Drugs Analysis of Biological Samples A Mini-Review on Enantiomeric Separation of Ofloxacin using Capillary Electrophoresis: Pharmaceutical Applications 117 Suvardhan Kanchi, Myalowenkosi Sabela, Deepali Sharma, and Krishna Bisetty 3.1 Introduction Role of CE in Pharmaceutical Analysis Challenges Involved in the Enantiomeric Separation of Ofloxacin Developments in Enanatiomeric Separation of Ofloxacin Recent Developments in Enantiomeric Separation of Ofloxacin Applications of Nanotechnology in Enantiomeric Separation of Ofloxacin Role of Computational Techniques in Enantiomeric Separation of Ofloxacin Molecular Modeling Molecular Dynamic Simulations Conclusion Nano-Stationary Phases for Capillary Electrophoresis Techniques 147 Chaudhery Mustansar Hussain and Sagar Roy 4.1 Introduction 148

9 Contents vii 4.2 Different Types of Nanoparticles/ Nanomaterials Synthetic Strategies for Immobilization for Nano-Stationary Phases Evaluation of Nano-Stationary Phases Conclusion Capillary Electrophoresis Coupled to Mass Spectrometry for Enantiomeric Drugs Analysis 165 Vítězslav Maier, Martin Švidrnoch, and Jan Petr 5.1 Enantioseparation of Pharmaceutical Products Basic Concepts of Enantioseparation by Capillary Electrophoresis Capillary Electrophoresis with Mass Spectrometry Electrospray Ionization in Hyphenation of CE with MS Interfacing of CE-ESI-MS Sheathless Interface Sheath Liquid Interface Liquid-Junction Interface Compatibility of Capillary Electrophoresis and Mass Spectrometry Basic Principles of Partial Filling Technique Cyclodextrin as CS for CE-MS Enantioseparation Experimental Setup without Restrictions of the CD Entering MS Ion Source Counter-Current Mode for CD-Mediated Enantioseparation by CE-ESI-MS Partial Filling Technique Employing Neutral Derivatives of CDs Combination of PFT and Counter- Current Migration for CD-Mediated CE-ESI-MS Enantioseparation Enantioseparation using MEKC-MS Crown Ethers Mediated Enantioseparations by CE-MS 200

10 viii Contents 5.9 Macrocyclic Antibiotics as CS for CE-MS Non-Aqueous Capillary Electrophoresis-Mass Spectrometry for Enantioseparation Enantioseparation by CEC-MS Specifics of Quantitative Analysis of Enantiomers by CE-MS Enantioselective Drug Plasma Protein-Binding Studies by Capillary Electrophoresis 225 Laura Escuder-Gilabert, Yolanda Martín-Biosca, Salvador Sagrado, and María José Medina-Hernández 6.1 Introduction Plasma Proteins Capillary Electrophoresis for Enantioselective Protein-Binding Experiments Combination of CE with other Separation Techniques CE for Direct Enantioselective Protein-Binding Evaluation Experimental Design and Mathematical Models in Protein-Binding Studies Mathematical Models and Deficiencies Experimental Design and Verification of the Assumptions Examples Illustrating the Direct Approach Strategy Studies on the Application of Capillary Electrophoresis for Evaluating Enantioselective Plasma Protein Binding of Chiral Drugs Conclusion Clinical Use of Capillary Zone Electrophoresis: New Insights into Parkinson s Disease 259 Pedro Rada, Luis Betancourt, Sergio Sacchettoni, Juan Félix del Corral, Hilarión Araujo, and Luis Hernández 7.1 Introduction Parkinson s Disease Basal Ganglia Circuitry 261

11 Contents ix In Vivo Monitoring of Brain Molecules Capillary Zone Electrophoresis GABA in the Ventrolateral Nucleus of the Thalamus in Two PD Patients Sample Preparation Running Conditions Result Polyamine Putrescine and Parkinson s Disease Blood Sampling Running Conditions Putrescine Levels in RBCs and Plasma of PD Patients Electrophoretically Mediated Microanalysis for Evaluation of Enantioselective Drug Metabolism 277 Yolanda Martín-Biosca, Laura Escuder-Gilabert, Salvador Sagrado, and María José Medina-Hernández 8.1 Introduction Enzymatic Reactions in CE: Electrophoretically Mediated Microanalysis Evaluation of Enantioselective Metabolism by EMMA Study of Stereoselectivity of Flavin-Containing Monooxygenase Isoforms using Cimetine as Substrate Characterization of the Enantioselective CYP3A4 Catalyzed N-demethylation of Ketamine Evaluation of Enantioselective Metabolism of Verapamil and Fluoxetine by the at-inlet EMMA Mode Conclusion Capillary Electrophoresis for the Quality Control of Intact Therapeutic Monoclonal Antibodies 305 Anne-Lise Marie, Grégory Rouby, Emmanuel Jaccoulet, Claire Smadja, Nguyet Thuy Tran, and Myriam Taverna 9.1 Introduction Impurities and Drug-Related Substances 308

12 x Contents Process-Related Impurities Product-Related Substances Chemical degradations Biochemical degradations Physical degradations Identity and Heterogeneity of mabs Source of Natural Heterogeneity of Proteins: Post-Translational Modifications Identity Control Issues after mab Compounding Quality Control of mabs at Different Stages of Their Production In-process Controls Control of Drug-Related Substances Capillary zone electrophoresis Capillary gel electrophoresis Capillary isoelectric focusing Control of Compounded mab before Patient Administration Conclusion Molecular Simulation of Chiral Selector Enantiomer Interactions through Docking: Antimalarial Drugs as Case Study 363 Myalowenkosi Sabela, Suvardhan Kanchi, Deepali Sharma, and Krishna Bisetty 10.1 Introduction Procedure Experimental Protocol Simulation Protocol Ligand and receptor preparation Minimization Molecular properties HOMO-LUMO calculations Docking Score ligand poses and analysis Results and Discussion 372

13 Contents xi Experimental Enantioseparation Score Ligand Poses and Analysis Analysis of Enantioselective Interaction Enantioresolution Conclusion and Future Prospect 380 Index 385

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15 Preface Capillary electrophoresis (CE) has recently received widespread recognition as an analytical technique of choice and has become an established method that can be used in numerous analytical laboratories, including industrial and academic sectors, and in pharmaceutical and biochemical research and quality control, which are the most important fields of CE applications. Considering the rapid growth of CE, this book seeks to broaden the understanding of modern CE applications, developments, and prospects focused on molecules of pharmaceutical interest. Accordingly, this book describes recent developments and applications that are related to compounds of pharmaceutical interest, such as drugs, natural products, metabolites, and impurities in formulations. It also discusses about the latest pharmaceutical applications in quality control, drug and disease monitoring, drug metabolism, estimation of physicochemical properties, etc. It describes how various methods can be developed for sample preparation (e.g., in-capillary pre-concentration techniques), capillary coating, stationary phases, (enantio-) separations (e.g., use of nanoparticles and bio-macromolecules as chiral selectors), and miniaturization among others. The book also attempts to offer new trends involving the use of molecular simulations, currently used to broaden the understanding of pseudo separation mechanisms. The book is aimed at beginners in this field as some fundamentals of CE technique have been introduced. It clearly outlines the procedures that can be used to hurdle over several barriers in a range of analytical problems. Some of these barriers include detection limits, signal detection, changing capillary environment, and reproducible and improvement on resolution separations of analytes and hyphenation of mass spectrometry with CE. Each chapter outlines a specific electrophoretic variant with detailed instructions and some standard operating procedures. The reported works have been summarized in the form of tables wherever necessary. Overall, the book provides a comparative assessment of related techniques on mode

16 xiv Preface selection, methods development, detection, and quantitative analysis and estimation of pharmacokinetic parameters. In that respect, we are confident that this book will meet its desired goal to render assistance to lovers of electrophoresis. Suvardhan Kanchi Salvador Sagrado Myalowenkosi Sabela Krishna Bisetty Spring 2017