Protein kinases as drug targets:
Saved in:
| Format: | Book |
|---|---|
| Language: | English |
| Published: |
Weinheim
Wiley-VCH-Verl.
2011
|
| Series: | Methods and principles in medicinal chemistry
49 |
| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XXI, 373 S. Ill., graph. Darst. |
| ISBN: | 9783527317905 |
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IMAGE 1
CONTENTS
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 3
1.2 OPTIMIZATION OF A BIOCHEMICAL KINASE ASSAY 4 1.2.1 STEP 1:
IDENTIFICATION OF A SUBSTRATE AND CONTROLLING OF THE LINEARITY BETWEEN
SIGNAL AND KINASE CONCENTRATION 4 1.2.2 STEP 2: ASSAY WALL AND
OPTIMIZATION OF THE REACTION BUFFER 6 1.2.3 STEP 3: THE MICHAELIS-MENTEN
CONSTANT K M AND THE ATP
CONCENTRATION 10
1.2.4 STEP 4: SIGNAL LINEARITY THROUGHOUT THE REACTION TIME AND
DEPENDENCE ON THE KINASE CONCENTRATION 12 1.2.5 STEP 5: ASSAY VALIDATION
BY MEASUREMENT OF THE IC 50 OF REFERENCE INHIBITORS 25
1.3 MEASURING THE BINDING AFFINITY AND RESIDENCE TIME OF UNUSUAL KINASE
INHIBITORS 15 1.3.1 WASHOUT EXPERIMENTS 18 1.3.2 SURFACE PLASMON
RESONANCE 19 1.3.3 CLASSICAL METHODS WITH FLUORESCENT PROBES 21
1.3.4 PREINCUBATION OF TARGET AND INHIBITOR 22 1.3.5 REPORTER
DISPLACEMENT ASSAY 22 1.3.6 IMPLICATIONS FOR DRUG DISCOVERY 25
1.4 ADDRESSING ADME ISSUES OF PROTEIN KINASE INHIBITORS IN EARLY DRUG
DISCOVERY 26
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/1006150048
DIGITALISIERT DURCH
IMAGE 2
VI CONTENTS
1.4.1 INTRODUCTION 26
1.4.2 EXPERIMENTAL APPROACHES TO DRUG ABSORPTION 30 1.4.2.1 MEASURING
SOLUBILITY 30 1.4.2.2 MEASURING IIPOPHILICITY AND IONIZATION 30 1.4.2.3
MEASURING PERMEABILITY 31 1.4.2.4 TRANSPORTER ASSAYS ADDRESSING P-GP
INTERACTION 33
1.4.3 EXPERIMENTAL APPROACHES TO DRUG METABOLISM 34 1.4.3.1 BACKGROUND
AND CONCEPTS 34 1.4.3.2 MEASURING METABOLIC STABILITY 37 1.4.3.3
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 45
2.1.1 KINASE INHIBITORS FOR DISSECTION OF SIGNALING PATHWAYS 46 2.1.2
CELLULAR KINASE ASSAYS FOR DRUG DISCOVERY APPLICATIONS 46 2.2 FACTORS
THAT INFLUENCE CELLULAR EFFICACY OF KINASE INHIBITORS 47 2.2.1
COMPETITION FROM ATP 47 2.2.2 SUBSTRATE PHOSPHORYLATION LEVELS 51 2.2.3
ULTRASENSITIVITY OF KINASE SIGNALING CASCADES 51 2.2.4 CELL PERMEABILITY
52
2.2.5 CELLULAR KINASE CONCENTRATIONS 53 2.2.6 EFFECTS OF INHIBITORS NOT
RELATED TO SUBSTRATE PHOSPHORYLATION 54 2.3 ASSAYS FOR MEASUREMENT OF
CELLULAR KINASE ACTIVITY 55
2.3.1 ANTIBODY-BASED DETECTION 56 2.3.2 HIGH-CONTENT SCREENING 59 2.3.3
USE OF GENETICALLY ENGINEERED CELL LINES 60 2.3.4 GENETICALLY ENCODED
BIOSENSORS 61 2.3.5 LABEL-FREE TECHNOLOGIES 62 2.3.6 ANALYSIS OF KINASE
FAMILY SELECTIVITY 62 2.3.7 SILAC 62
2.3.8 AFFINITY CHROMATOGRAPHY WITH IMMOBILIZED KINASE INHIBITORS 63 2.4
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 69
3.2 CHEMICAL GENETICS 71
3.2.1 ENGINEERING ASKA LIGAND-KINASE PAIRS 71 3.3 THE APPLICATION OF
ASKA TECHNOLOGY IN MOLECULAR BIOLOGY 76 3.3.1 IDENTIFICATION OF KINASE
SUBSTRATES 76
IMAGE 3
CONTENTS VII
3.3.2 STUDIES ON KINASE INHIBITION 76
3.3.3 ALTERNATIVE APPROACHES TO SPECIFICALLY TARGETING KINASES OF
INTEREST 78 3.4 CONCLUSIONS AND OUTLOOK 80
REFERENCES SI
PART TWO MEDICINAL CHEMISTRY 85
4 RATIONAL DRUG DESIGN OF KINASE INHIBITORS FOR SIGNAL TRANSDUCTION
THERAPY 87 GYOE'RGY KERI, LAESZLOE OERFI, AND GABOR NAEMETH
4.1 THE CONCEPT OF RATIONAL DRUG DESIGN 88 4.2 3D STRUCTURE-BASED DRUG
DESIGN 89 4.3 IIGAND-BASED DRUG DESIGN 92
4.3.1 ACTIVE ANALOGUE APPROACH 92 4.3.2 3D QUANTITATIVE
STRUCTURE-ACTIVITY RELATIONSHIPS 92 4.4 TARGET SELECTION AND VALIDATION
93 4.5 PERSONALIZED THERAPY WITH KINASE INHIBITORS 96 4.5.1 TARGET
FISHING: KINASE INHIBITOR-BASED AFFINITY CHROMATOGRAPHY 97 4.6 THE NCL*
TECHNOLOGY AND EXTENDED PHARMACOPHORE MODELING
(PREDICTION-ORIENTED QSAR) 99 4.7 NON-ATP BINDING SITE-DIRECTED OR
ALLOSTERIC KINASE INHIBITORS 101 4.8 THE MASTER KEYS FOR MULTIPLE TARGET
KINASE INHIBITORS 202 4.8.1 APPLICATION OF KINATOR* FOR THE
SECOND-GENERATION KINASE
INHIBITORS 205
4.9 CONCLUSIONS 107
REFERENCES 109
5 KINASE INHIBITORS IN SIGNAL TRANSDUCTION THERAPY 115 GYOERGY KIN,
LAESZLOE OERFI, AND GABOR NEMETH 5.1 VEGFR (VASCULAR ENDOTHELIAL GROWTH
FACTOR RECEPTOR) 125 5.2 FLT3 (FMS-LIKE TYROSINE KINASE 3) 226 5.3
BCR-ABL (BREAKPOINT CLUSTER REGION-ABELSON MURINE LEUKEMIA
VIRAL ONCOGENE HOMOLOGUE) 228 5.4 EGFR (EPIDERMAL GROWTH FACTOR
RECEPTOR) 218 5.5 IGFR (INSULIN-LIKE GROWTH FACTOR RECEPTOR) 220 5.6
FGFR (FIBROBLAST GROWTH FACTOR RECEPTOR) 220 5.7 PDGFR (PLATELET-DERIVED
GROWTH FACTOR RECEPTOR) 222 5.8 C-KIT 222
5.9 MET (MESENCHYMAL-EPITHELIAL TRANSITION FACTOR) 222 5.10 SRC 123
5.11 P38 MAPKS (MITOGEN-ACTIVATED PROTEIN KINASES) 123 5.12 ERK1/2 124
5.13 JNK (C-JUN N-TERMINAL KINASE, MAPK8) 226 5.14 PKC (PROTEIN KINASE
C) 226 5.15 CDKS (CYCLIN-DEPENDENT KINASES) 127
IMAGE 4
VIII CONTENTS
5.16
5.17 5.18 5.19
5.20 5.21 5.21.1 5.21.2
AURORAS 227 AKT/PKB (PROTEIN KINASE B) 229 PHOSPHOINOSITIDE 3-KINASES
229 SYK (SPLEEN TYROSINE KINASE) 130
JAK (JANUS KINASE) 230 KINASE INHIBITORS IN INFLAMMATION AND INFECTIOUS
DISEASES 232 INFLAMMATION 232 INFECTION 132
REFERENCES 134
6 DESIGN PRINCIPLES OF DEEP POCKET-TARGETING PROTEIN KINASE INHIBITORS
245 ALEXANDER C. BACKES, GERHARD MUELLER, AND PETER C. SENNHENN 6.1
INTRODUCTION 145
6.2 CLASSIFICATION OF PROTEIN KINASE INHIBITORS 247 6.3 TYPE II
INHIBITORS 150
6.4 COMMON FEATURES OF TYPE II INHIBITORS 154 6.5 DESIGN STRATEGIES FOR
TYPE II INHIBITORS 255 6.5.1 F2B APPROACH 260
6.5.2 B2F APPROACH 266
6.5.3 B2B APPROACH 269
6.5.4 HYBRID (F2B + B2F) APPROACH 173 6.6 COMPARATIVE ANALYSIS OF THE
DIFFERENT DESIGN STRATEGIES 280 6.7 CONCLUSIONS AND OUTLOOK 287
REFERENCES 290
7 FROM DISCOVERY TO CLINIC: AURORA KINASE INHIBITORS AS NOVEL TREATMENTS
FOR CANCER 195 NICOLA HERON 7.1 INTRODUCTION 195
7.2 BIOLOGICAL ROLES OF THE AURORA KINASES 195 7.3 AURORA KINASES AND
CANCER 296
7.4 IN VITRO PHENOTYPE OF AURORA KINASE INHIBITORS 197 7.5 AURORA KINASE
INHIBITORS 203
7.5.1 THE DISCOVERY OF AZD1152 203 7.5.1.1 ANILINOQUINAZOLINES: ZM447439
203 7.5.1.2 NEXT-GENERATION QUINAZOLINES: HETEROCYCLIC ANALOGUES 204
7.5.1.3 AMINO-THIAZOLO AND PYRAZOLO ACETANILIDE QUINAZOLINES 208 7.5.2
MK-0457 (VX-680) 214 7.5.3 PHA-739358 215
7.5.4 MLN8054 219
7.5.5 AT9283 220
7.6 X-RAY CRYSTAL STRUCTURES OF AURORA KINASES 221 7.7 SUMMARY 222
REFERENCES 222
IMAGE 5
CONTENTS IX
PART THREE APPLICATION OF KINASE INHIBITORS TO THERAPEUTIC
INDICATION AREAS 229
8 DISCOVERY AND DESIGN OF PROTEIN KINASE INHIBITORS:
TARGETING THE CELL CYCLE IN ONCOLOGY 232 MOKDAD MEZNA, GEORGE
KONTOPIDIS, AND CAMPBELL MCLNNES 8.1 PROTEIN KINASE INHIBITORS IN
ANTICANCER DRUG DEVELOPMENT 231 8.2 STRUCTURE-GUIDED DESIGN OF
SMALL-MOLECULE INHIBITORS
OF THE CYCLIN-DEPENDENT KINASES 233 8.3 CATALYTIC SITE INHIBITORS 234
8.4 ATP SITE SPECIFICITY 236
8.5 ALTERNATE STRATEGIES FOR INHIBITING CDKS 239 8.6 CYCLIN GROOVE
INHIBITORS (CGI) 240 8.7 INHIBITION OF CDK-CYCLIN ASSOCIATION 242 8.8
RECENT DEVELOPMENTS IN THE DISCOVERY AND THE DEVELOPMENT
OF AURORA KINASE INHIBITORS 242 8.9 DEVELOPMENT OF AURORA KINASE
INHIBITORS THROUGH SCREENING AND STRUCTURE-GUIDED DESIGN 244 8.10 AURORA
KINASE INHIBITORS IN CLINICAL TRIALS 248 8.11 PROGRESS IN THE
IDENTIFICATION OF POTENT AND SELECTIVE POLO-LIKE
KINASE INHIBITORS 250 8.12 DEVELOPMENT OF SMALL-MOLECULE INHIBITORS OF
PLK1 KINASE ACTIVITY 252 8.13 DISCOVERY OF BENZTHIAZOLE PLK1 INHIBITORS
254 8.14 RECENT STRUCTURAL STUDIES OF THE PLKL KINASE DOMAIN 255 8.15
ADDITIONAL SMALL-MOLECULE PLK1 INHIBITORS REPORTED 256 8.16 THE POLO-BOX
DOMAIN 257 8.17 FUTURE DEVELOPMENTS 259
REFERENCES 259
9 MEDICINAL CHEMISTRY APPROACHES FOR THE INHIBITION OF THE P38 MAPK
PATHWAY 271 STEFAN LAUFER L, SIMONA MARGUTTI, DOWINIK HAEUSER 9.1
INTRODUCTION 271
9.2 P38 MAP KINASE BASICS 271
9.3 P38 ACTIVITY AND INHIBITION 275
9.4 FIRST-GENERATION INHIBITORS 278 9.5 PYRIDINYL-IMIDAZOLE INHIBITOR:
SB203580 278 9.6 N-SUBSTITUTED IMIDAZOLE INHIBITORS 282 9.7
N.N'-DIARYLUREA-BASED INHIBITORS: BIRB796 286
9.8 STRUCTURALLY DIVERSE CLINICAL CANDIDATES 288 9.9 MEDICINAL CHEMISTRY
APPROACH ON VX-745-IIKE COMPOUNDS 297 9.10 CONCLUSION AND PERSPECTIVE
FOR THE FUTURE 301 REFERENCES 302
IMAGE 6
X CONTENTS
10 CELLULAR PROTEIN KINASES AS ANTIVIRAL TARGETS 305
LUIS M. SCHANG
10.1 INTRODUCTION 305
10.2 ANTIVIRAL ACTIVITIES OF THE PHARMACOLOGICAL CYCLIN-DEPENDENT KINASE
INHIBITORS 320 10.2.1 RELEVANT PROPERTIES OF CDKS AND PCIS 310 10.2.2
ANTIVIRAL ACTIVITIES OF PCIS 327
10.2.2.1 ANTIVIRAL ACTIVITIES OF PCIS AGAINST HERPESVIRUSES 327 10.2.2.2
ANTIVIRAL ACTIVITIES OF PCIS AGAINST HIV 332 10.2.2.3 ANTIVIRAL
ACTIVITIES OF PCIS AGAINST OTHER VIRUSES 335 10.2.3 PCIS CAN BE USED IN
COMBINATION THERAPIES 336
10.2.4 PCIS INHIBIT VIRAL PATHOGENESIS 337 10.3 ANTIVIRAL ACTIVITIES OF
INHIBITORS OF OTHER CELLULAR PROTEIN KINASES 338 10.4 CONCLUSION 339
REFERENCES 342
11 PROSPECTS FOR TB THERAPEUTICS TARGETING MYCOBACTERIUM TUBERCULOSIS
PHOSPHOSIGNALING NETWORKS 349 YOSSEF AV-GAY AND TOM ALBER 11.1
INTRODUCTION 349
11.2 RATIONALE FOR SER/THR PROTEIN KINASES AND PROTEIN PHOSPHATASES AS
DRUG TARGETS 350 11.3 DRUG TARGET VALIDATION BY GENETIC INACTIVATION 351
11.4 STPK MECHANISMS, SUBSTRATES, AND FUNCTIONS 352 11.5 M. TUBERCULOSIS
STPK INHIBITORS 355
11.6 CONCLUSIONS AND PROSPECTS 359 REFERENCES 359
INDEX 365 |
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| owner | DE-20 DE-M49 DE-BY-TUM DE-19 DE-BY-UBM DE-355 DE-BY-UBR |
| owner_facet | DE-20 DE-M49 DE-BY-TUM DE-19 DE-BY-UBM DE-355 DE-BY-UBR |
| physical | XXI, 373 S. Ill., graph. Darst. |
| publishDate | 2011 |
| publishDateSearch | 2011 |
| publishDateSort | 2011 |
| publisher | Wiley-VCH-Verl. |
| record_format | marc |
| series | Methods and principles in medicinal chemistry |
| series2 | Methods and principles in medicinal chemistry |
| spelling | Protein kinases as drug targets ed. by Bert Klebl ... Weinheim Wiley-VCH-Verl. 2011 XXI, 373 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Methods and principles in medicinal chemistry 49 Arzneistoffträger (DE-588)4278196-6 gnd rswk-swf Enzyminhibitor (DE-588)4152479-2 gnd rswk-swf Proteinkinasen (DE-588)4175996-5 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Proteinkinasen (DE-588)4175996-5 s Enzyminhibitor (DE-588)4152479-2 s Arzneistoffträger (DE-588)4278196-6 s DE-604 Klebl, Bert Sonstige oth Methods and principles in medicinal chemistry 49 (DE-604)BV035418617 49 X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3527467&prov=M&dok_var=1&dok_ext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=022571071&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Protein kinases as drug targets Methods and principles in medicinal chemistry Arzneistoffträger (DE-588)4278196-6 gnd Enzyminhibitor (DE-588)4152479-2 gnd Proteinkinasen (DE-588)4175996-5 gnd |
| subject_GND | (DE-588)4278196-6 (DE-588)4152479-2 (DE-588)4175996-5 (DE-588)4143413-4 |
| title | Protein kinases as drug targets |
| title_auth | Protein kinases as drug targets |
| title_exact_search | Protein kinases as drug targets |
| title_full | Protein kinases as drug targets ed. by Bert Klebl ... |
| title_fullStr | Protein kinases as drug targets ed. by Bert Klebl ... |
| title_full_unstemmed | Protein kinases as drug targets ed. by Bert Klebl ... |
| title_short | Protein kinases as drug targets |
| title_sort | protein kinases as drug targets |
| topic | Arzneistoffträger (DE-588)4278196-6 gnd Enzyminhibitor (DE-588)4152479-2 gnd Proteinkinasen (DE-588)4175996-5 gnd |
| topic_facet | Arzneistoffträger Enzyminhibitor Proteinkinasen Aufsatzsammlung |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=3527467&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=022571071&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV035418617 |
| work_keys_str_mv | AT kleblbert proteinkinasesasdrugtargets |