Molecular tools for G-protein coupled receptors: Synthesis, pharmacological characterization and [3H]-labeling of subtype-selective ligands for histamine H4 and NPY Y2 receptors
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| Main Author: | |
|---|---|
| Format: | Thesis Book |
| Language: | English |
| Published: |
2014
|
| Subjects: | |
| Online Access: | Volltext https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-305058 Inhaltsverzeichnis |
| Physical Description: | X, 229 S. Ill., graph. Darst. |
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MARC
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| 100 | 1 | |a Baumeister, Paul |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Molecular tools for G-protein coupled receptors |b Synthesis, pharmacological characterization and [3H]-labeling of subtype-selective ligands for histamine H4 and NPY Y2 receptors |c vorgelegt von Paul Baumeister |
| 264 | 1 | |c 2014 | |
| 300 | |a X, 229 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
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| adam_text | V
CONTENTS
1 INTRODUCTION 1
1.1 G-PROTEIN-COUPLED RECEPTORS 2
1.1.1 GPCRS AS DRUG TARGETS AND THEIR CLASSIFICATION 2
1.1.2 G-PROTEIN ACTIVATION, LIGAND CLASSIFICATION AND SIGNAL
TRANSDUCTION 2
1.1.3 G-PROTEIN INDEPENDENT SIGNALING, P-ARRESTIN AND FUNCTIONAL
SELECTIVITY 5
1.2 HISTAMINE AND THE HISTAMINE RECEPTOR FAMILY 5
1.2.1 HISTAMINE AS ENDOGENOUS LIGAND 5
1.2.2 HISTAMINE RECEPTORS AND THEIR LIGANDS 6
1.2.2.1 THE HISTAMINE HJ RECEPTOR 7
1.2.2.2 THE HISTAMINE H
2
RECEPTOR 7
1.2.2.3 THE HISTAMINE H
3
RECEPTOR 10
1.2.2.4 THE HISTAMINE H
4
RECEPTOR 11
1.3 NPY AND THE NPY RECEPTOR FAMILY IS
1.3.1 NEUROPEPTIDE Y 15
1.3.2 NPY RECEPTORS AND THEIR LIGANDS 15
1.3.2.1 THE NPY Y
2
RECEPTOR AND ITS LIGANDS 15
1.3.2.2 LIGANDS FOR THE NPY Y
T
, Y
4
AND Y
S
RECEPTORS 17
1.4 RECEPTOR-IIGAND BINDING ASSAYS 19
1.4.1 RADIOLIGAND BINDING METHODS 20
1.4.1.1 SELECTION OF RADIOLIGANDS 20
1.4.2 RADIOLIGANDS FOR THE H
2
, H
4
AND NPY Y
2
RECEPTOR 21
1.5 REFERENCES 22
2 SCOPE AND OBJECTIVES 37
2.1 REFERENCES 40
3 SYNTHESIS AND PHARMACOLOGICAL CHARACTERIZATION OF 2-ARYLBENZIMIDAZOLES
AS POTENT AND
SELECTIVE HISTAMINE H
4
RECEPTOR LIGANDS 43
3.1 INTRODUCTION 44
HTTP://D-NB.INFO/1058695894
VI
3.2 CHEMISTRY 45
3.3 PHARMACOLOGICAL RESULTS AND DISCUSSION 52
3.3.1 HISTAMINE RECEPTOR SUBTYPE AFFINITIES OF THE SYNTHESIZED COMPOUNDS
53
3.3.1.1 VARIATION OF THE SUBSTITUTION PATTERN 53
3.3.1.2 STRUCTURAL VARIATIONS OF ARYLBENZIMIDAZOLE-TYPE HH
4
R LIGANDS 53
3.3.1.3 INTRODUCTION OF A PROPIONYL GROUP 56
3.3.1.4 FUNCTIONAL ACTIVITIES AT RECOMBINANT HUMAN HISTAMINE RECEPTOR
SUBTYPES ...59
3.3.2 INHIBITION OF THE HH
4
R AGONISTIC EFFECT OF 3.16 BY STANDARD H
4
R ANTAGONISTS 62
3.3.2.1 POTENCIES, EFFICACIES AND AFFINITIES AT THE MH
4
R 63
3.3.3 MUSCARINIC RECEPTOR SUBTYPE AFFINITIES OF 3.16 ON CHO-MI AND CHO-M
2
CELLS... 65
3.4 SUMMARY AND OUTLOOK 65
3.5 EXPERIMENTAL SECTION 68
3.5.1 CHEMISTRY 68
3.5.1.1 GENERAL CONDITIONS 68
3.5.2 CHEMISTRY 69
3.5.2.1 PREPARATION OF THE IMIDAZOLE 3.2 69
3.5.2.2 PREPARATION OF THE BENZIMIDAZOLES 3.7-3.10 70
3.5.2.3 PREPARATION OF THE BENZIMIDAZOLYLPHENYL CHLOROALKYL ETHER
3.11-3.15 72
3.5.2.4 PREPARATION OF THE IMIDAZOLE DERIVATIVES 3.16-3.20 74
3.5.2.5 PREPARATION OF THE BENZIMIDAZOLYLPHENOXYALKYLAMINES 3.22-3.23 77
3.5.2.6 PREPARATION OF THE GUANIDINE 3.26 79
3.5.2.7 PREPARATION OF N-PROPIONYL GUANIDINE 3.30 80
3.5.2.8 PREPARATION OF THE CARBOXYLIC AMIDES 3.31-3.37 81
3.5.2.9 PREPARATION OF THE HISTAMINE HOMOLOG 3.41 86
3.5.2.10 PREPARATION OF THE SECONDARY AMINE 3.45 87
3.5.2.11 PREPARATION OF THE PRIMARY AMINES 3.48-3.50 88
3.5.2.12 PREPARATION OF THE PRIMARY AMINES 3.58-3.60 90
3.5.2.13 PREPARATION OF THE AMINES 3.62-3.73 93
VII
3.5.2.14 PREPARATION OF THE AMIDE 3.75 100
3.5.2.15 PREPARATION OF THE AMIDE 3.76 101
3.5.3 PHARMACOLOGICAL METHODS 102
3.5.3.1 COMPETITION BINDING EXPERIMENTS ON MEMBRANE PREPARATIONS OF SF9
INSECT
CELLS 102
3.5.3.2 STEADY-STATE [Y-
33
P]GTPASE ACTIVITY ASSAY 103
3.5.3.3 [
3S
S]GTPYS BINDING ASSAY 103
3.5.3.4 RADIOLIGAND BINDING ASSAY USING HEK293 CELLS EXPRESSING THE MH
4
R 104
3.5.3.5 RADIOLIGAND BINDING STUDIES ON HM,R OR HM
2
R EXPRESSING CHO-K9 CELLS 104
3.5.3.6 DATA ANALYSIS AND PHARMACOLOGICAL PARAMETERS 105
3.6 REFERENCES 107
4 SYNTHESIS AND PHARMACOLOGICAL CHARACTERIZATION OF VUF 8430 DERIVATIVES
AS HISTAMINE H
RECEPTOR LIGANDS ILL
4.1 INTRODUCTION 112
4.2 CHEMISTRY 113
4.3 PHARMACOLOGICAL RESULTS AND DISCUSSION 115
4.4 SUMMARY AND OUTLOOK 117
4.5 EXPERIMENTAL SECTION 119
4.5.1 CHEMISTRY 119
4.5.1.1 GENERAL CONDITIONS 119
4.5.1.2 PREPARATION OF THE ISOTHIOUREA DERIVATIVES 4.2 AND 4.3 119
4.5.1.3 PREPARATION OF A/-ACYLATED ISOTHIOUREA DERIVATIVES 4.4-4.11 120
4.5.1.4 PREPARATION OF THE GUANIDINE DERIVATIVES 4.12-4.39 123
4.5.1.5 PREPARATION OF THE DICARBAMIMIDOTHIOATE 4.40 134
4.5.1.6 PREPARATION OF VUF 8430 ANALOG 4.43 135
4.5.2 PHARMACOLOGICAL METHODS 136
4.5.2.1 GENERAL 136
4.5.2.2 COMPETITION BINDING EXPERIMENTS ON MEMBRANE PREPARATIONS OF SF9
INSECT
CELLS 136
VIII
4.6 REFERENCES 137
5 [
3
H]UR-DE257: A SELECTIVE AND HIGHLY POTENT TRITIUM-LABELED
SQUARAMIDE-TYPE HISTAMINE
H
2
RECEPTOR ANTAGONIST 141
5.1 INTRODUCTION 142
5.2 RESULTS AND DISCUSSION 143
5.2.1 RADIOSYNTHESIS 143
5.2.2 DETERMINATION OF BINDING CONSTANTS OF [
3
H]UR-DE257 144
5.2.3 AUTORADIOGRAPHY 153
5.3 SUMMARY 155
5.4 EXPERIMENTAL SECTION 156
5.4.1 GENERAL CONDITIONS FOR RADIOSYNTHESIS 156
5.4.2 SYNTHESIS OF
/V-[6-(3,4-DIOXO-2-{3-[3-(PIPERIDIN-L-YLMETHYL)PHENOXY]PROPYL-
AMINO}-CYCLOBUT-L-ENYLAMINO)HEXYL]-[2,3-
3
H
2
]PROPIONAMIDE ([
3
H]UR-DE257): 156
5.4.3 PHARMACOLOGICAL METHODS 157
5.4.3.1 HISTAMINE RADIOLIGAND BINDING ASSAYS ON MEMBRANE PREPARATIONS OF
SF9 INSECT
CELLS 157
5.4.3.2 RADIOLIGAND BINDING ASSAY AT HEK293T CRE-LUC HH
2
R CELLS 158
5.4.4 AUTORADIOGRAPHY 159
5.5 REFERENCES 160
6 [
3
H]JNJ7777120: A TRITIUM-LABELED HISTAMINE H
4
RECEPTOR ANTAGONIST 163
6.1 INTRODUCTION 164
6.2 CHEMISTRY 165
6.2.1 OPTIMIZATION OF THE SYNTHESIS 165
6.2.2 RADIOSYNTHESIS OF L
J
H]JNJ7777120 166
6.3 RESULTS AND DISCUSSION 168
6.3.1 HISTAMINE RECEPTOR SUBTYPE AFFINITIES 168
6.3.2 PHARMACOLOGICAL CHARACTERIZATION OF [
3
H]JNJ7777120 (6.4B) ON SF9 CELL
MEMBRANES 169
6.3.2.1 SATURATION BINDING OF (
3
HJJNJ7777120 AT THE HH
4
R 169
IX
6.3.2.2 KINETICS AT THE HH,R 170
6.3.2.3 COMPETITION BINDING AT THE HH
4
R 171
6.3.2.4 MEMBRANES OF SF9 CELLS EXPRESSING THE MH
4
R 172
6.3.3 SATURATION BINDING AT HEK293-SF-H
4
R-HIS6 CELLS 173
6.4 SUMMARY AND CONCLUSION 174
6.5 EXPERIMENTAL SECTION 176
6.5.1 CHEMISTRY 176
6.5.1.1 GENERAL 176
6.5.1.2 PREPARATION OF THE INDOL DERIVATIVES 6.4A AND 6.5 176
6.5.2 PREPARATION OF [
3
H]JNJ7777120 (6.4B) 178
6.5.3 RADIOLIGAND BINDING ASSAY FOR THE HHR 180
6.5.4 SATURATION BINDING ASSAY FOR THE MH
4
R 180
6.6 REFERENCES 181
7 SUBTYPE-SELECTIVE NONPEPTIDE RADIOLIGANDS FOR THE NPY Y
2
RECEPTOR 185
7.1 INTRODUCTION 186
7.2 RESULTS AND DISCUSSION 186
7.2.1 SYNTHESIS OF [
3
H]UR-PLN208 186
7.2.2 PHARMACOLOGICAL CHARACTERIZATION OF [
3
H]UR-PLN208 AND COLD ANALOGS AT CHO-
HY
2
R CELLS 188
7.2.2.1 DETERMINATION OF BINDING CONSTANTS OF [
3
H]UR-PLN208 188
7.2.2.2 ASSOCIATION AND DISSOCIATION KINETICS OF [
3
H]UR-PLN208 190
7.2.2.3 COMPETITION BINDING EXPERIMENTS 191
7.2.2.4 CALCIUM ASSAY ON HY
2
R-EXPRESSING CHO CELLS 193
7.2.3 PHARMACOLOGICAL CHARACTERIZATION OF (
3
H]UR-PLN208 AND NON-LABELED ANALOGS ON
THE HY
2
R AT SF9 INSECT CELL MEMBRANES 194
7.2.3.1 HY
2
R
ANTAGONIST ACTIVITY OF BIIE
0246 AND RELATED COMPOUNDS IN THE STEADY-
STATE [Y-
33
P]GTPASE ASSAY 194
7.2.3.2 SATURATION BINDING OF [
3
H]UR-PLN208 USING HY
2
R-INSECT CELL MEMBRANE
PREPARATIONS 196
X
7.2.4 STABILITY OF ARGININAMIDE-TYPE NPY Y
2
R ANTAGONISTS 197
7.3 SUMMARY AND OUTLOOK 199
7.4 EXPERIMENTAL SECTION 200
7.4.1 GENERAL 200
7.4.2 SYNTHESIS OF
(25)-N-[2-(3,5-DIOXO-L,2-DIPHENYL-L,2,4-TRIAZOLIDIN-4-YL)ETHYL]-N
A
-{2-
[L-({2-OXO-2-[4-(6-OXO-6,LL-DIHYDRO-5H-DIBENZO[6,E]AZEPIN-LL-YL)PIPERAZIN-L-
YL]ETHYL})CYCLOPENTYL]ACETYI}-W
-([2,3-
3
H2]PROPANOYL)ARGININAMIDE ((
3
H]UR-PLN208)
201
7.4.3 INVESTIGATION OF THE CHEMICAL STABILITY 202
7.4.4 PHARMACOLOGICAL METHODS 203
7.4.4.1 CELL CULTURE 203
7.4.4.2 SPECTROFLUORIMETRIC CA
2
* ASSAY (FURA-2 ASSAY) 203
7.4.4.3 RADIOLIGAND BINDING ASSAY 203
7.4.4.4 STEADY-STATE GTPASE ACTIVITY ASSAY 204
7.4.4.5 SATURATION BINDING OF [
3
H]UR-PLN208 AT THE HY
2
R ON MEMBRANE PREPARATIONS
OF SF9 INSECT CELLS 204
7.5 REFERENCES 206
8 SUMMARY 209
9 APPENDIX 213
9.1 SYNTHESIS AND APPLICATION OF THE FIRST RADIOLIGAND TARGETING THE
ALLOSTERIC BINDING
POCKET OF CHEMOKINE RECEPTOR CXCR3 214
9.1.1 ABSTRACT 214
9.1.2 GENERAL CONDITIONS FOR RADIOSYNTHESIS: 214
9.1.3 RADIOSYNTHESIS OF [
3
H]W-{L-[3-(4-ETHOXYPHENYL)-4-OXO-3,4-DIHYDROPYRIDO[2,3-
D]PYRIMIDIN-2-YL]ETHYL}-2-[4-FLUORO-3-(TRIFLUOROMETHYL)PHENYL]-/V-[(L-METHYLPIPERIDIN-4-
YL)METHYL]ACETAMIDE (RAMX3)
215
9.2 NONSPECIFIC BINDING OF [
3
H]JNJ7777120 AT THE HH
4
R IN SF9 CELL MEMBRANES (CF.
CHAPTER 6) 219
9.3 NONSPECIFIC BINDING OF (
3
H]UR-PLN208 AT CHO-HY
2
R CELLS (CF. CHAPTER 7) 219
9.4 NMR-SPECTRA OF SELECTED COMPOUNDS 220
9.5 HPLC PURITY DATA 223
|
| any_adam_object | 1 |
| author | Baumeister, Paul |
| author_facet | Baumeister, Paul |
| author_role | aut |
| author_sort | Baumeister, Paul |
| author_variant | p b pb |
| building | Verbundindex |
| bvnumber | BV042043966 |
| classification_rvk | VS 5075 |
| collection | ebook |
| ctrlnum | (OCoLC)890027067 (DE-599)BVBBV042043966 |
| dewey-full | 610 |
| dewey-hundreds | 600 - Technology (Applied sciences) |
| dewey-ones | 610 - Medicine and health |
| dewey-raw | 610 |
| dewey-search | 610 |
| dewey-sort | 3610 |
| dewey-tens | 610 - Medicine and health |
| discipline | Chemie / Pharmazie Medizin |
| format | Thesis Book |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV042043966 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T01:11:15Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-027485173 |
| oclc_num | 890027067 |
| open_access_boolean | 1 |
| owner | DE-384 DE-473 DE-BY-UBG DE-703 DE-1051 DE-824 DE-29 DE-12 DE-91 DE-BY-TUM DE-19 DE-BY-UBM DE-1049 DE-92 DE-739 DE-898 DE-BY-UBR DE-355 DE-BY-UBR DE-706 DE-20 DE-1102 |
| owner_facet | DE-384 DE-473 DE-BY-UBG DE-703 DE-1051 DE-824 DE-29 DE-12 DE-91 DE-BY-TUM DE-19 DE-BY-UBM DE-1049 DE-92 DE-739 DE-898 DE-BY-UBR DE-355 DE-BY-UBR DE-706 DE-20 DE-1102 |
| physical | X, 229 S. Ill., graph. Darst. |
| psigel | ebook |
| publishDate | 2014 |
| publishDateSearch | 2014 |
| publishDateSort | 2014 |
| record_format | marc |
| spelling | Baumeister, Paul Verfasser aut Molecular tools for G-protein coupled receptors Synthesis, pharmacological characterization and [3H]-labeling of subtype-selective ligands for histamine H4 and NPY Y2 receptors vorgelegt von Paul Baumeister 2014 X, 229 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Regensburg, Univ., Diss., 2014 G-Protein gekoppelter Rezeptor (DE-588)7723480-7 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Pharmakologie (DE-588)4045687-0 gnd rswk-swf Rezeptor (DE-588)4049722-7 gnd rswk-swf Neuropeptid Y (DE-588)4317370-6 gnd rswk-swf Histaminrezeptor (DE-588)4257968-5 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content G-Protein gekoppelter Rezeptor (DE-588)7723480-7 s Chemische Synthese (DE-588)4133806-6 s Pharmakologie (DE-588)4045687-0 s DE-604 Neuropeptid Y (DE-588)4317370-6 s Rezeptor (DE-588)4049722-7 s Histaminrezeptor (DE-588)4257968-5 s Erscheint auch als Online-Ausgabe urn:nbn:de:bvb:355-epub-305058 http://epub.uni-regensburg.de/30505/ Verlag kostenfrei Volltext https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-305058 Resolving-System DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027485173&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Baumeister, Paul Molecular tools for G-protein coupled receptors Synthesis, pharmacological characterization and [3H]-labeling of subtype-selective ligands for histamine H4 and NPY Y2 receptors G-Protein gekoppelter Rezeptor (DE-588)7723480-7 gnd Chemische Synthese (DE-588)4133806-6 gnd Pharmakologie (DE-588)4045687-0 gnd Rezeptor (DE-588)4049722-7 gnd Neuropeptid Y (DE-588)4317370-6 gnd Histaminrezeptor (DE-588)4257968-5 gnd |
| subject_GND | (DE-588)7723480-7 (DE-588)4133806-6 (DE-588)4045687-0 (DE-588)4049722-7 (DE-588)4317370-6 (DE-588)4257968-5 (DE-588)4113937-9 |
| title | Molecular tools for G-protein coupled receptors Synthesis, pharmacological characterization and [3H]-labeling of subtype-selective ligands for histamine H4 and NPY Y2 receptors |
| title_auth | Molecular tools for G-protein coupled receptors Synthesis, pharmacological characterization and [3H]-labeling of subtype-selective ligands for histamine H4 and NPY Y2 receptors |
| title_exact_search | Molecular tools for G-protein coupled receptors Synthesis, pharmacological characterization and [3H]-labeling of subtype-selective ligands for histamine H4 and NPY Y2 receptors |
| title_full | Molecular tools for G-protein coupled receptors Synthesis, pharmacological characterization and [3H]-labeling of subtype-selective ligands for histamine H4 and NPY Y2 receptors vorgelegt von Paul Baumeister |
| title_fullStr | Molecular tools for G-protein coupled receptors Synthesis, pharmacological characterization and [3H]-labeling of subtype-selective ligands for histamine H4 and NPY Y2 receptors vorgelegt von Paul Baumeister |
| title_full_unstemmed | Molecular tools for G-protein coupled receptors Synthesis, pharmacological characterization and [3H]-labeling of subtype-selective ligands for histamine H4 and NPY Y2 receptors vorgelegt von Paul Baumeister |
| title_short | Molecular tools for G-protein coupled receptors |
| title_sort | molecular tools for g protein coupled receptors synthesis pharmacological characterization and 3h labeling of subtype selective ligands for histamine h4 and npy y2 receptors |
| title_sub | Synthesis, pharmacological characterization and [3H]-labeling of subtype-selective ligands for histamine H4 and NPY Y2 receptors |
| topic | G-Protein gekoppelter Rezeptor (DE-588)7723480-7 gnd Chemische Synthese (DE-588)4133806-6 gnd Pharmakologie (DE-588)4045687-0 gnd Rezeptor (DE-588)4049722-7 gnd Neuropeptid Y (DE-588)4317370-6 gnd Histaminrezeptor (DE-588)4257968-5 gnd |
| topic_facet | G-Protein gekoppelter Rezeptor Chemische Synthese Pharmakologie Rezeptor Neuropeptid Y Histaminrezeptor Hochschulschrift |
| url | http://epub.uni-regensburg.de/30505/ https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-305058 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027485173&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT baumeisterpaul moleculartoolsforgproteincoupledreceptorssynthesispharmacologicalcharacterizationand3hlabelingofsubtypeselectiveligandsforhistamineh4andnpyy2receptors |