Radioligand binding studies with muscarinic receptor subtypes: investigations on new McN-A-343 analogues, (stereo-)structure-activity relationships of muscarinic antagonists related to cycrimine and pridinol, and development of dimethindene analogues as M2-selective antagonists
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| Format: | Book |
| Language: | English |
| Published: |
2000
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| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Frankfurt (Main), Univ., Diss., 2000 |
| Physical Description: | IV, 205 S. graph. Darst. : 21 cm |
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| adam_text | RADIOLIGAND BINDING STUDIES WITH MUSCARINIC RECEPTOR SUBTYPES
INVESTIGATIONS ON NEW MCN-A-343 ANALOGUES, (STEREO-)STRUCTURE-ACTIVITY
RELATIONSHIPS OF MUSCARINIC ANTAGONISTS RELATED TO CYCRIMINE AND
PRIDINOL, AND DEVELOPMENT OF DIMETHINDENE ANALOGUES AS M 2 -SELECTIVE
ANTAGONISTS DISSERTATION ZUR ERLANGUNG DES DOKTORGRADES DER
NATURWISSENSCHAFTEN VOFGELEGT BEIM FACHBEREICH CHEMISCHE UND
PHARMAZEUTISCHE WISSENSCHAFTEN DER JOHANN WOLFGANG GOETHE-UNIVERSITAT IN
FRANKFURT AM MAIN VON CHRISTINE KEIM AUS KASSEL FRANKFURT AM MAIN 2000
(DF1) TABLE OF CONTENTS TABLE OF CONTENTS 1 INTRODUCTION AND AIMS OF THE
THESIS 1 1.1 INTRODUCTION 1 1.1.1 HISTORICAL BACKGROUND 1 1.1.2
PHARMACOLOGICAL SUBCLASSIFICATION AND NOMENCLATURE OF MUSCARINIC
RECEPTOR SUBTYPES 1 1.1.3 SUBTYPE-SELECTIVE MUSCARINIC LIGANDS 4 1.1.3.1
AGONISTS 4 1.1.3.2 ANTAGONISTS 6 1.1.4 CLONING STUDIES AND MOLECULAR
STRUCTURE OF MUSCARINIC RECEPTORS 10 1.1.5 RECEPTOR-EFFECTOR COUPLING OF
MUSCARINIC RECEPTORS 12 1.1.6 LOCALIZATION AND FUNCTION OF MUSCARINIC
RECEPTORS 14 1.1.6.1 MUSCARINIC RECEPTORS IN THE BRAIN 15 1.1.6.2
MUSCARINIC RECEPTORS IN THE PERIPHERY 16 1.1.7 RADIOLIGAND BINDING
STUDIES WITH CLONED MUSCARINIC RECEPTORS 19 1.1.7.1 THE USE OF CLONED
RECEPTORS - BENEFITS AND LIMITATIONS 19 1.1.7.2 LIMITATIONS OF RECEPTOR
BINDING STUDIES 20 1.1.8 THERAPEUTIC AND DIAGNOSTIC POTENTIAL OF
SELECTIVE MUSCARINIC LIGANDS 21 1.1.8.1 CENTRAL NERVOUS SYSTEM 22
1.1.8.2 PERIPHERAL ORGANS AND TISSUES 25 1.1.9 STEREOSELECTIVITY 26
1.1.9.1 PFEIFFER S RULE AND EUDISMIC ANALYSIS 27 1.1.9.2 THE
FOUR-BINDING-SUBSITE MODEL 29 1.2 AIMS OF THE THESIS 32 1.2.1 ANALOGUES
OF MCN-A-343 32 1.2.2 HYDROXYMETHYL ANALOGUES OF THE MUSCARINIC
ANTAGONISTS CYCRIMINE AND PRIDINOL - (STEREO-)STRUCTURE-ACTIVITY
RELATIONSHIPS 35 1.2.2.1 DI(4-F-PHENYL) ANALOGUES 37 1.2.2.2
HYDROXYMETHYL COMPOUNDS RELATED TO CYCRIMINE 38 1.2.3 ANTAGONISTS
RELATED TO DIMETHINDENE 40 TABLE OF CONTENTS 2 MATERIALS AND METHODS 49
2.1 DRUGS AND CELLS 49 2.1.1 COMMERCIALLY AVAILABLE DRUGS 49 2.1.2 GIFTS
49 2.1.3 SYNTHESES 49 2.1.4 CHIRALITY 50 2.1.5 SALTS OF COMPOUNDS AND
STOCK SOLUTIONS 50 2.1.6 PREPARATIONS OF BUFFERS AND SOLUTIONS 51 2.1.7
CHINESE HAMSTER OVARY CELLS (CHO-K1) 51 2.2 METHODS 52 2.2.1 CELL
CULTURE 52 2.2.2 PREPARATION OF MEMBRANE HOMOGENATES 52 2.2.2.1 CHO-K1
CELLS 52 2.2.2.2 PROTEIN ASSAY 53 2.2.3 RADIOLIGAND BINDING STUDIES ON
MUSCARINIC RECEPTOR SUBTYPES 53 2.2.3.1 SATURATION BINDING EXPERIMENTS
54 2.2.3.2 HOMOLOGOUS COMPETITION BINDING EXPERIMENTS 54 2.2.3.3
HETEROLOGOUS COMPETITION BINDING EXPERIMENTS 55 2.2.4 DATA ANALYSIS AND
STATISTICS 55 3 RESULTS 59 3.1 SATURATION BINDING EXPERIMENTS 59 3.2
COMPETITION EXPERIMENTS - GENERAL CONSIDERATIONS 62 3.3 MCN-A-343
ANALOGUES 63 3.3.1 4-F-PHEPYMCN AND PHEPYMCN 65 3.3.2 ANALOGUES
CONTAINING AN ESTER FUNCTION INSTEAD OF THE CARBAMOYI MOIETY 66 3.3.3
1-NAPHTHYL ANALOGUES 69 3.4 HYDROXYMETHYL ANALOGUES OF THE MUSCARINIC
ANTAGONISTS CYCRIMINE AND PRIDINOL - (STEREO-)STRUCTURE-ACTIVITY
RELATIONSHIPS 72 3.4.1 DI(4-F-PHENYL) ANALOGUES 75 TABLE OF CONTENTS
3.4.2 HYDROXYMETHYL ANALOGUES OF CYCRIMINE AND PRIDINOL AND THEIR
CORRESPONDING SILANES AND GERMANES 80 3.4.2.1 ENANTIOMERS OF CARBON
COMPOUNDS, SILANES AND GERMANES 80 3.4.2.2 DIPHENYL AND DICYCLOPENTYL
DERIVATIVES OF CARBON COMPOUNDS, SILANES AND GERMANES 86 3.5 ANTAGONISTS
RELATED TO DIMETHINDENE 93 3.5.1 SUBSTITUTIONS IN THE INDENE SYSTEM 97
3.5.2 DERIVATIVES WITH VARIATIONS OF THE CENTRE OF CHIRALITY 99 3.5.3
ANALOGUES WITH VARIATIONS OF THE HETEROAROMATIC SYSTEM 100 3.5.4
MODIFICATIONS OF THE TERMINAL BASIC MOIETY 101 3.5.5 ANALOGUES WITH
MODIFIED LENGTH OF THE AMINOALKYL CHAIN 103 3.5.6 DIMETHINDENE-RELATED
COMPOUNDS WITH ESTER AND AMIDE GROUPS 105 3.5.7 FULVENES 106 3.5.8
ANTIHISTAMINIC PROPERTIES OF SELECTED ANALOGUES 109 4 DISCUSSION 4.1
SATURATION BINDING EXPERIMENTS 4.2 COMPETITION EXPERIMENTS - GENERAL
CONSIDERATIONS 4.3 4.4 MCN-A-343 ANALOGUES 4.3.1 ANTAGONISTS WITH A
PHENYL-SUBSTITUTED CHIRAL CARBON ATOM 4.3.2 ANALOGUES CONTAINING AN
ESTER FUNCTION 4.3.3 1-NAPHTHYL ANALOGUES 111 111 111 111 112 115 119
HYDROXYMETHYL ANALOGUES OF THE MUSCARINIC ANTAGONISTS CYCRIMINE AND
PRIDINOL - (STEREO-)STRUCTURE-ACTIVITY RELATIONSHIPS 123 4.4.1
DI(4-FLUORO-PHENYL) ANALOGUES 123 4.4.1.1 AFFINITY AND
RECEPTOR-SELECTIVITY 124 4.4.1.2 INFLUENCE OF THE RING SIZE OF THE
N-HETEROCYCLE 125 4.4.1.3 N-METHYLATION 126 4.4.1.4 C/SI-EXCHANGE 127
4.4.1.5 INFLUENCE OF THE FLUORINE-SUBSTITUTION IN THE PHENYL RINGS -
COMPARISON WITH NON-FLUORINATED COMPOUNDS 128 4.4.1.6 COMPARISON WITH
HYDROXY COMPOUNDS 128 III TABLE OF CONTENTS 4.4.2 HYDROXYMETHYL
ANALOGUES OF CYCRIMINE AND PRIDINOL AND THEIR CORRESPONDING SILANES AND
GERMANES 130 4.4.2.1 COMPARISON WITH EXISTENT FUNCTIONAL AND BINDING
DATA 131 4.4.2.2 AFFINITY AND RECEPTOR-SELECTIVITY 132 4.4.2.3
N-METHYLATION 135 4.4.2.4 SILA-AND GERMA-SUBSTITUTION 136 4.4.2.5
STEREOSELECTIVITY AND EUDISMIC ANALYSIS 138 4.4.2.6
PHENYL/CYCLOPENTYL-EXCHANGE AND FOUR-BINDING-SUBSITE MODEL 145 4.5
ANTAGONISTS RELATED TO DIMETHINDENE 150 4.5.1 INFLUENCE OF SUBSTITUTIONS
IN THE INDENE SYSTEM 150 4.5.2 INFLUENCE OF VARIATIONS AT THE CENTRE OF
CHIRALITY 151 4.5.3 ANALOGUES WITH AN ALTERED HETEROAROMATIC SYSTEM 152
4.5.4 MODIFICATIONS OF THE TERMINAL BASIC MOIETY 153 4.5.5 INFLUENCE OF
A MODIFIED AMINOALKYL CHAIN LENGTH 155 4.5.6 INFLUENCE OF ADDITIONAL
ESTER AND AMIDE FUNCTIONS 157 4.5.7 FULVENES - 1 5 7 4.5.8 HISTAMINE
H^AFFINITY AND INVERSE STEREOSELECTIVITY 158 4.5.9 COMPARISON OF
COMPOUND 50 WITH OTHER M2-SELECTIVE ANTAGONISTS 160 4.5.10 DIAGNOSTIC
AND THERAPEUTIC IMPLICATIONS 161 5 SUMMARY 163 6 ZUSAMMENFASSUNG 171 7
ABBREVIATIONS 179 8 REFERENCES 183 IV
|
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| spelling | Keim, Christine 1972- Verfasser (DE-588)122826426 aut Radioligand binding studies with muscarinic receptor subtypes investigations on new McN-A-343 analogues, (stereo-)structure-activity relationships of muscarinic antagonists related to cycrimine and pridinol, and development of dimethindene analogues as M2-selective antagonists vorgelegt von Christine Keim 2000 IV, 205 S. graph. Darst. : 21 cm txt rdacontent n rdamedia nc rdacarrier Frankfurt (Main), Univ., Diss., 2000 Ligand Biochemie (DE-588)4606532-5 gnd rswk-swf Muscarinrezeptor (DE-588)4170773-4 gnd rswk-swf Bindestelle (DE-588)4145563-0 gnd rswk-swf Isotopenmarkierung (DE-588)4176811-5 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Ligand Biochemie (DE-588)4606532-5 s Isotopenmarkierung (DE-588)4176811-5 s Bindestelle (DE-588)4145563-0 s Muscarinrezeptor (DE-588)4170773-4 s DE-604 GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009406658&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Keim, Christine 1972- Radioligand binding studies with muscarinic receptor subtypes investigations on new McN-A-343 analogues, (stereo-)structure-activity relationships of muscarinic antagonists related to cycrimine and pridinol, and development of dimethindene analogues as M2-selective antagonists Ligand Biochemie (DE-588)4606532-5 gnd Muscarinrezeptor (DE-588)4170773-4 gnd Bindestelle (DE-588)4145563-0 gnd Isotopenmarkierung (DE-588)4176811-5 gnd |
| subject_GND | (DE-588)4606532-5 (DE-588)4170773-4 (DE-588)4145563-0 (DE-588)4176811-5 (DE-588)4113937-9 |
| title | Radioligand binding studies with muscarinic receptor subtypes investigations on new McN-A-343 analogues, (stereo-)structure-activity relationships of muscarinic antagonists related to cycrimine and pridinol, and development of dimethindene analogues as M2-selective antagonists |
| title_auth | Radioligand binding studies with muscarinic receptor subtypes investigations on new McN-A-343 analogues, (stereo-)structure-activity relationships of muscarinic antagonists related to cycrimine and pridinol, and development of dimethindene analogues as M2-selective antagonists |
| title_exact_search | Radioligand binding studies with muscarinic receptor subtypes investigations on new McN-A-343 analogues, (stereo-)structure-activity relationships of muscarinic antagonists related to cycrimine and pridinol, and development of dimethindene analogues as M2-selective antagonists |
| title_full | Radioligand binding studies with muscarinic receptor subtypes investigations on new McN-A-343 analogues, (stereo-)structure-activity relationships of muscarinic antagonists related to cycrimine and pridinol, and development of dimethindene analogues as M2-selective antagonists vorgelegt von Christine Keim |
| title_fullStr | Radioligand binding studies with muscarinic receptor subtypes investigations on new McN-A-343 analogues, (stereo-)structure-activity relationships of muscarinic antagonists related to cycrimine and pridinol, and development of dimethindene analogues as M2-selective antagonists vorgelegt von Christine Keim |
| title_full_unstemmed | Radioligand binding studies with muscarinic receptor subtypes investigations on new McN-A-343 analogues, (stereo-)structure-activity relationships of muscarinic antagonists related to cycrimine and pridinol, and development of dimethindene analogues as M2-selective antagonists vorgelegt von Christine Keim |
| title_short | Radioligand binding studies with muscarinic receptor subtypes |
| title_sort | radioligand binding studies with muscarinic receptor subtypes investigations on new mcn a 343 analogues stereo structure activity relationships of muscarinic antagonists related to cycrimine and pridinol and development of dimethindene analogues as m2 selective antagonists |
| title_sub | investigations on new McN-A-343 analogues, (stereo-)structure-activity relationships of muscarinic antagonists related to cycrimine and pridinol, and development of dimethindene analogues as M2-selective antagonists |
| topic | Ligand Biochemie (DE-588)4606532-5 gnd Muscarinrezeptor (DE-588)4170773-4 gnd Bindestelle (DE-588)4145563-0 gnd Isotopenmarkierung (DE-588)4176811-5 gnd |
| topic_facet | Ligand Biochemie Muscarinrezeptor Bindestelle Isotopenmarkierung Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009406658&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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