Protein Kinases as Drug Targets
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1 Methods and Principles in Medicinal Chemistry 49 Protein Kinases as Drug Targets Bearbeitet von Bert Klebl, Gerhard Müller, Michael Hamacher, Raimund Mannhold, Hugo Kubinyi, Gerd Folkers 1st Edition Buch. XXII, 374 S. Hardcover ISBN Format (B x L): 17 x 24 cm Gewicht: 914 g Weitere Fachgebiete > Technik > Verfahrenstechnik, Chemieingenieurwesen, Lebensmitteltechnik > Pharmazeutische Technologie Zu Leseprobe schnell und portofrei erhältlich bei Die Online-Fachbuchhandlung beck-shop.de ist spezialisiert auf Fachbücher, insbesondere Recht, Steuern und Wirtschaft. Im Sortiment finden Sie alle Medien (Bücher, Zeitschriften, CDs, ebooks, etc.) aller Verlage. Ergänzt wird das Programm durch Services wie Neuerscheinungsdienst oder Zusammenstellungen von Büchern zu Sonderpreisen. Der Shop führt mehr als 8 Millionen Produkte.
2 V List of Contributors XI Preface XV A Personal Foreword XVII Part One Hit Finding and Profiling for Protein Kinases: Assay Development and Screening, Libraries 1 1 In Vitro Characterization of Small-Molecule Kinase Inhibitors 3 Doris Hafenbradl, Matthias Baumann, and Lars Neumann 1.1 Introduction Optimization of a Biochemical Kinase Assay Step 1: Identification of a Substrate and Controlling of the Linearity between Signal and Kinase Concentration Step 2: Assay Wall and Optimization of the Reaction Buffer Step 3: The Michaelis Menten Constant K m and the ATP Concentration Step 4: Signal Linearity throughout the Reaction Time and Dependence on the Kinase Concentration Step 5: Assay Validation by Measurement of the IC 50 of Reference Inhibitors Measuring the Binding Affinity and Residence Time of Unusual Kinase Inhibitors Washout Experiments Surface Plasmon Resonance Classical Methods with Fluorescent Probes Preincubation of Target and Inhibitor Reporter Displacement Assay Implications for Drug Discovery Addressing ADME Issues of Protein Kinase Inhibitors in Early Drug Discovery 26 Protein Kinases as Drug Targets. Edited by B. Klebl, G. Müller, and M. Hamacher Copyright Ó 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN:
3 VI Introduction Experimental Approaches to Drug Absorption Measuring Solubility Measuring Lipophilicity and Ionization Measuring Permeability Transporter Assays Addressing P-gp Interaction Experimental Approaches to Drug Metabolism Background and Concepts Measuring Metabolic Stability Measuring CYP450 Inhibition 39 References 39 2 Screening for Kinase Inhibitors: From Biochemical to Cellular Assays 45 Jan Eickhoff and Axel Choidas 2.1 Introduction Kinase Inhibitors for Dissection of Signaling Pathways Cellular Kinase Assays for Drug Discovery Applications Factors that Influence Cellular Efficacy of Kinase Inhibitors Competition from ATP Substrate Phosphorylation Levels Ultrasensitivity of Kinase Signaling Cascades Cell Permeability Cellular Kinase Concentrations Effects of Inhibitors Not Related to Substrate Phosphorylation Assays for Measurement of Cellular Kinase Activity Antibody-Based Detection High-Content Screening Use of Genetically Engineered Cell Lines Genetically Encoded Biosensors Label-Free Technologies Analysis of Kinase Family Selectivity SILAC Affinity Chromatography with Immobilized Kinase Inhibitors Outlook 63 References 64 3 Dissecting Phosphorylation Networks: The Use of Analogue-Sensitive Kinases and More Specific Kinase Inhibitors as Tools 69 Matthias Rabiller, Jeffrey R. Simard and Daniel Rauh 3.1 Introduction Chemical Genetics Engineering ASKA Ligand Kinase Pairs The Application of ASKA Technology in Molecular Biology Identification of Kinase Substrates 76
4 VII Studies on Kinase Inhibition Alternative Approaches to Specifically Targeting Kinases of Interest Conclusions and Outlook 80 References 81 Part Two Medicinal Chemistry 85 4 Rational Drug Design of Kinase Inhibitors for Signal Transduction Therapy 87 György Kéri, László Ó rfi, and Gábor Németh 4.1 The Concept of Rational Drug Design D Structure-Based Drug Design Ligand-Based Drug Design Active Analogue Approach D Quantitative Structure Activity Relationships Target Selection and Validation Personalized Therapy with Kinase Inhibitors Target Fishing: Kinase Inhibitor-Based Affinity Chromatography The NCL TM Technology and Extended Pharmacophore Modeling (Prediction-Oriented QSAR) Non-ATP Binding Site-Directed or Allosteric Kinase Inhibitors The Master Keys for Multiple Target Kinase Inhibitors Application of KinaTor TM for the Second-Generation Kinase Inhibitors Conclusions 107 References Kinase Inhibitors in Signal Transduction Therapy 115 György Kéri, László Ó rfi, and Gábor Németh 5.1 VEGFR (Vascular Endothelial Growth Factor Receptor) Flt3 (FMS-Like Tyrosine Kinase 3) Bcr-Abl (Breakpoint Cluster Region Abelson Murine Leukemia Viral Oncogene Homologue) EGFR (Epidermal Growth Factor Receptor) IGFR (Insulin-Like Growth Factor Receptor) FGFR (Fibroblast Growth Factor Receptor) PDGFR (Platelet-Derived Growth Factor Receptor) c-kit Met (Mesenchymal-Epithelial Transition Factor) Src p38 MAPKs (Mitogen-Activated Protein Kinases) ERK1/ JNK (c-jun N-Terminal Kinase, MAPK8) PKC (Protein Kinase C) CDKs (Cyclin-Dependent Kinases) 127
5 VIII 5.16 Auroras Akt/PKB (Protein Kinase B) Phosphoinositide 3-Kinases Syk (Spleen Tyrosine Kinase) JAK (Janus Kinase) Kinase Inhibitors in Inflammation and Infectious Diseases Inflammation Infection 132 References Design Principles of Deep Pocket-Targeting Protein Kinase Inhibitors 145 Alexander C. Backes, Gerhard Müller, and Peter C. Sennhenn 6.1 Introduction Classification of Protein Kinase Inhibitors Type II Inhibitors Common Features of Type II Inhibitors Design Strategies for Type II Inhibitors F2B Approach B2F Approach B2B Approach Hybrid (F2B þ B2F) Approach Comparative Analysis of the Different Design Strategies Conclusions and Outlook 187 References From Discovery to Clinic: Aurora Kinase Inhibitors as Novel Treatments for Cancer 195 Nicola Heron 7.1 Introduction Biological Roles of the Aurora Kinases Aurora Kinases and Cancer In Vitro Phenotype of Aurora Kinase Inhibitors Aurora Kinase Inhibitors The Discovery of AZD Anilinoquinazolines: ZM Next-Generation Quinazolines: Heterocyclic Analogues Amino-Thiazolo and Pyrazolo Acetanilide Quinazolines MK-0457 (VX-680) PHA MLN AT X-Ray Crystal Structures of Aurora Kinases Summary 221 References 222
6 IX Part Three Application of Kinase Inhibitors to Therapeutic Indication Areas Discovery and Design of Protein Kinase Inhibitors: Targeting the Cell cycle in Oncology 231 Mokdad Mezna, George Kontopidis, and Campbell McInnes 8.1 Protein Kinase Inhibitors in Anticancer Drug Development Structure-Guided Design of Small-Molecule Inhibitors of the Cyclin-Dependent Kinases Catalytic Site Inhibitors ATP Site Specificity Alternate Strategies for Inhibiting CDKs Cyclin Groove Inhibitors (CGI) Inhibition of CDK Cyclin Association Recent Developments in the Discovery and the Development of Aurora Kinase Inhibitors Development of Aurora Kinase Inhibitors through Screening and Structure-Guided Design Aurora Kinase Inhibitors in Clinical Trials Progress in the Identification of Potent and Selective Polo-Like Kinase Inhibitors Development of Small-Molecule Inhibitors of PLK1 Kinase Activity Discovery of Benzthiazole PLK1 Inhibitors Recent Structural Studies of the Plk1 Kinase Domain Additional Small-Molecule PLK1 Inhibitors Reported The Polo-Box Domain Future Developments 259 References Medicinal Chemistry Approaches for the Inhibition of the p38 MAPK Pathway 271 Stefan Laufer L, Simona Margutti, Dowinik Hauser 9.1 Introduction p38 MAP Kinase Basics p38 Activity and Inhibition First-Generation Inhibitors Pyridinyl-Imidazole Inhibitor: SB N-Substituted Imidazole Inhibitors N,N 0 -Diarylurea-Based Inhibitors: BIRB Structurally Diverse Clinical Candidates Medicinal Chemistry Approach on VX-745-Like Compounds Conclusion and Perspective for the Future 301 References 302
7 X 10 Cellular Protein Kinases as Antiviral Targets 305 Luis M. Schang 10.1 Introduction Antiviral Activities of the Pharmacological Cyclin-Dependent Kinase Inhibitors Relevant Properties of CDKs and PCIs Antiviral Activities of PCIs Antiviral Activities of PCIs against Herpesviruses Antiviral Activities of PCIs against HIV Antiviral Activities of PCIs against Other Viruses PCIs Can be Used in Combination Therapies PCIs Inhibit Viral Pathogenesis Antiviral Activities of Inhibitors of Other Cellular Protein Kinases Conclusion 339 References Prospects for TB Therapeutics Targeting Mycobacterium tuberculosis Phosphosignaling Networks 349 Yossef Av-Gay and Tom Alber 11.1 Introduction Rationale for Ser/Thr Protein Kinases and Protein Phosphatases as Drug Targets Drug Target Validation by Genetic Inactivation STPK Mechanisms, Substrates, and Functions M. tuberculosis STPK Inhibitors Conclusions and Prospects 359 References 359 Index 365
Edited by Bert Klebl, Gerhard Müller, and Michael Hamacher. Protein Kinases as Drug Targets WILEY VCH. WILEY-VCH Verlag GmbH & Co.
Edited by Bert Klebl, Gerhard Müller, and Michael Hamacher Protein Kinases as Drug Targets ~ WILEY VCH WILEY-VCH Verlag GmbH & Co. KGaA Contents List of Contributors Preface XV A Personal Foreword XI XVI
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