Novel selective ligands for μ-opioid and β2-adrenergic receptors: synthesis and biological investigations = Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren
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| Main Author: | |
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| Format: | Thesis Book |
| Language: | English |
| Published: |
Erlangen ; Nürnberg
[2018]
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis Inhaltsverzeichnis |
| Physical Description: | 284 Seiten Illustrationen, Diagramme 21 cm |
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MARC
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| 100 | 1 | |a Dengler, Daniela Gisela |d 1988- |e Verfasser |0 (DE-588)1169347991 |4 aut | |
| 245 | 1 | 0 | |a Novel selective ligands for μ-opioid and β2-adrenergic receptors |b synthesis and biological investigations = Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren |c vorgelegt von Daniela Gisela Dengler |
| 246 | 1 | 3 | |a Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren |
| 246 | 1 | 3 | |a Novel selective ligands for mu-opioid and beta-2-adrenergic receptors |
| 246 | 1 | 3 | |a Neuartige selektive Liganden für My-Opioid- und Beta-2-Adrenorezeptoren |
| 246 | 1 | 1 | |a Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren |
| 264 | 1 | |a Erlangen ; Nürnberg |c [2018] | |
| 300 | |a 284 Seiten |b Illustrationen, Diagramme |c 21 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 502 | |b Dissertation |c Friedrich-Alexander-Universität Erlangen-Nürnberg |d 2018 | ||
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| 650 | 0 | 7 | |a Opiatrezeptor |0 (DE-588)4172636-4 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Agonist |0 (DE-588)4380725-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Beta-2-Rezeptor |0 (DE-588)4254128-1 |2 gnd |9 rswk-swf |
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| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-030628890 | |
Record in the Search Index
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| adam_text |
TABLE OF CONTENTS
1.
INTRODUCTION.
1
1.1 PHARMACOLOGY OF
PAIN.1
1.2 EMERGING DRUG TARGETS FOR THE TREATMENT OF
PAIN.3
1.2.1 N-METHYL-D-ASPARTATE (NMDA)
RECEPTOR.3
1.2.2 IMIDAZOLINE 12
RECEPTOR.4
1.2.3 RHOA AND RHO KINASE (ROCK)
PROTEINS.5
1.2.4 HISTAMINE H3
RECEPTOR.
6
1.2.5 NEUROKININ NK1
RECEPTOR.
7
1.2.6 LYSOPHOSPHATIDIC ACID (LPA)
RECEPTORS.9
1.2.7 CANNABINOID (CB)
RECEPTOR.
11
1.2.8 OPIOID RECEPTORS (OR,
OP).
12
1.2.9 UNMET MEDICAL NEED FOR TREATING
PAIN.15
1.3 DEVELOPMENT OF 6-PROTEIN BIASED POR AGONISTS AS NOVEL PROMISING
ANALGESICS
.
16
2. OBJECTIVES OF THE
THESIS.
22
3. NOVEL SELECTIVE P-OPIOID RECEPTOR
AGONISTS.
25
3.1 SYNTHESIS AND CHEMICAL CHARACTERIZATION OF PZM21
.
25
3.1.1 SYNTHESIS OF
PZM21.
25
3.1.2 CHEMICAL CHARACTERIZATION OF
PZM21.26
3.1.2.1 NMR ANALYSES OF
PZM21.
26
3.1.2.2 OPTICAL PURITY OF
PZM21.
32
3.1.2.3 ABSOLUTE CONFIGURATION OF
PRECURSORS:.32
3.2 PREDICTION OF THE BINDING MODE OF PZM21 VIA SAR STUDIES136
.
34
3.2.1 DESIGN AND SYNTHESES OF STRUCTURAL
ANALOGS.34
3.2.2 SAR-STUDIES FOR EVALUATION OF THE BINDING MODE
.
39
3.3 FURTHER STRUCTURAL
ANALOGS.
42
3.3.1 DESIGN AND SYNTHESIS OF FURTHER DERIVATIVES
.
42
3.3.1.1 ANALOGS WITH VARIATIONS ON THE METHYL GROUP AT THE
STEREOCENTER.44
3.3.1.2 ANALOGS WITH REPLACEMENTS FOR THE UREA MOIETY
.
46
3.3.1.3 ANALOGS WITH A SHORTENED SIDE
CHAIN.46
3.3.1.4 ANALOGS WITH VARIATIONS ON THE DIMETHYLAMINO GROUP
.
47
3.3.1.5 ANALOGS WITH REPLACEMENTS FOR THE PHENOL CORE.
50
3.3.1.6 ANALOGS WITH REPLACEMENTS FOR THE THIOPHENE CORE.
3.3.2 BIOLOGICAL EVALUATION OF STRUCTURAL
ANALOGS.52
3.3.2.1 ANALOGS WITH VARIATIONS ON METHYL GROUP AT THE STEREOCENTER
.
52
3.3.2 2 ANALOGS WITH REPLACEMENTS FOR THE UREA
MOIETY.
54
3.3.2.3 ANALOGS WITH A SHORTENED SIDE
CHAIN.55
3.3.2.4 ANALOGS WITH VARIATIONS ON THE DIMETHYLAMINO GROUP
.
55
3.3.2.5 ANALOGS WITH REPLACEMENTS FOR THE PHENOL CORE
.
56
3.3.2 6 ANALOGS WITH REPLACEMENTS FOR THE THIOPHENE CORE
.
58
3.4 LN-VITRO METABOLIC STABILITY OF
PZM21.59
3.4.1 MICROSOMAL STABILITY
ASSAY.
59
3.4.1.1 RAT LIVER
MICROSOMES.
59
3.4.1.2 MOUSE LIVER
MICROSOMES.
62
3.4.1.3 HYPOTHETICAL MAIN
METABOLITES.
64
3.4.2 SYNTHESES OF POSSIBLE
METABOLITES.65
3.4.3 CHARACTERIZATION AND BIOLOGICAL EVALUATION OF PUTATIVE MAIN
METABOLITES.67
3.4.3.1 LC-MS
ANALYSES.
67
34.3.2 BINDING AFFIN
ITIES.
68
3.5 MOLECULAR TOOLS FOR NANOBODY SCREENINGS AND CRYSTALLOGRAPHY TRIALS
.
70
3.5.1 BIOTINYLATED VERSION OF PZM21 FOR NANOBODY SCREENINGS
.
70
3.5.1.1 DESIGN AND SYNTHESIS OF A BIOTINYLATED POR LIGAND
.
70
3.5.1.2 BIOLOGICAL
EVALUATION.
73
3.5.1.3 NOVEL STRATEGY FOR BIOTIN
ATTACHMENT.74
3.5.2 COVALENT ANALOGS FOR CRYSTALLOGRAPHY
TRIALS.75
3.5.2.1 DESIGN AND SYNTHESIS OF IRREVERSIBLE
LIGANDS.75
3.5 2.2 BIOLOGICAL EVALUATION OF COVALENT
ANALOGS.80
4. NEGATIVE ALLOSTERIC MODULATORS (NAMS) TARGETING SS2 ADRENERGIC
RECEPTORS.86
4.1 STRUCTURE-ACTIVITY RELATIONSHIP (SAR) STUDIES OF AS408 AND
STRUCTURAL ANALOGS.88
4.1.1 DESIGN AND SYNTHESIS OF STRUCTURAL ANALOGS OF AS408
.
88
4.1.1.1 DESIGN OF STRUCTURAL
ANALOGS.88
4.1.1.2 CHEMICAL SYNTHESES OF STRUCTURAL
ANALOGS.90
4.1.1.3 FUNCTIONAL CHARACTERIZATION OF ANALOGS FOR SAR STUDIES:
.
91
4.2 FURTHER FUNCTIONAL CHARACTERIZATION OF NEGATIVE ALLOSTERIC
MODULATORS (NAMS).93
4.2.1 INVESTIGATIONS ON THE MODULATION OF G PROTEIN COUPLING EFFICACIES
93
4.2.2 DISSOCIATION EXPERIMENTS ON AS408 AND SELECTED ANALOGS
.
100
4.2.2.1 AGONIST DISSOCIATION
EXPERIMENTS.
100
4.2.2 2 ANTAGONIST DISSOCIATION
EXPERIMENTS.
104
5.
SUMMARY.106
6.
ZUSAMMENFASSUNG.
113
7. MATERIAL AND M
ETHODS.
120
7.1 BIOLOGICAL
EXPERIMENTS.
120
7.1.1 FUNCTIONAL CHARACTERIZATION OF P-OPIOID RECEPTOR LIGANDS
.
120
7.1.2 LN-VITRO METABOLIC
STABILITY.
120
7.1.3 FUNCTIONAL CHARACTERIZATION OF SS-ADRENERGIC RECEPTOR LIGANDS
.
121
7.2
CHEMISTRY.123
7.2.1 GENERAL
PROCEDURES.
123
7.2.2 SYNTHETIC PROCEDURES AND COMPOUND CHARACTERIZATION
.
126
7.2.3 X-RAY CRYSTALLOGRAPHY ANALYSES OF PZM21 INTERMEDIATES
.
254
8.
ABBREVIATIONS.
262
9.
REFERENCES.
268
10. CURRICULUM V
ITAE.284 |
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| author | Dengler, Daniela Gisela 1988- |
| author_GND | (DE-588)1169347991 |
| author_facet | Dengler, Daniela Gisela 1988- |
| author_role | aut |
| author_sort | Dengler, Daniela Gisela 1988- |
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| bvnumber | BV045240666 |
| ctrlnum | (OCoLC)1136361139 (DE-599)DNB1168666686 |
| discipline | Biologie |
| format | Thesis Book |
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| genre_facet | Hochschulschrift |
| id | DE-604.BV045240666 |
| illustrated | Illustrated |
| indexdate | 2024-08-01T00:30:42Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-030628890 |
| oclc_num | 1136361139 |
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| owner_facet | DE-29T DE-29 DE-355 DE-BY-UBR |
| physical | 284 Seiten Illustrationen, Diagramme 21 cm |
| publishDate | 2018 |
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| spelling | Dengler, Daniela Gisela 1988- Verfasser (DE-588)1169347991 aut Novel selective ligands for μ-opioid and β2-adrenergic receptors synthesis and biological investigations = Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren vorgelegt von Daniela Gisela Dengler Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren Novel selective ligands for mu-opioid and beta-2-adrenergic receptors Neuartige selektive Liganden für My-Opioid- und Beta-2-Adrenorezeptoren Erlangen ; Nürnberg [2018] 284 Seiten Illustrationen, Diagramme 21 cm txt rdacontent n rdamedia nc rdacarrier Dissertation Friedrich-Alexander-Universität Erlangen-Nürnberg 2018 Morphinantagonist (DE-588)4248332-3 gnd rswk-swf Opiatrezeptor (DE-588)4172636-4 gnd rswk-swf Agonist (DE-588)4380725-2 gnd rswk-swf Beta-2-Rezeptor (DE-588)4254128-1 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Opiatrezeptor (DE-588)4172636-4 s Morphinantagonist (DE-588)4248332-3 s DE-604 Beta-2-Rezeptor (DE-588)4254128-1 s Agonist (DE-588)4380725-2 s B:DE-101 application/pdf http://d-nb.info/1168666686/04 Inhaltsverzeichnis DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030628890&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Dengler, Daniela Gisela 1988- Novel selective ligands for μ-opioid and β2-adrenergic receptors synthesis and biological investigations = Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren Morphinantagonist (DE-588)4248332-3 gnd Opiatrezeptor (DE-588)4172636-4 gnd Agonist (DE-588)4380725-2 gnd Beta-2-Rezeptor (DE-588)4254128-1 gnd |
| subject_GND | (DE-588)4248332-3 (DE-588)4172636-4 (DE-588)4380725-2 (DE-588)4254128-1 (DE-588)4113937-9 |
| title | Novel selective ligands for μ-opioid and β2-adrenergic receptors synthesis and biological investigations = Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren |
| title_alt | Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren Novel selective ligands for mu-opioid and beta-2-adrenergic receptors Neuartige selektive Liganden für My-Opioid- und Beta-2-Adrenorezeptoren |
| title_auth | Novel selective ligands for μ-opioid and β2-adrenergic receptors synthesis and biological investigations = Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren |
| title_exact_search | Novel selective ligands for μ-opioid and β2-adrenergic receptors synthesis and biological investigations = Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren |
| title_full | Novel selective ligands for μ-opioid and β2-adrenergic receptors synthesis and biological investigations = Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren vorgelegt von Daniela Gisela Dengler |
| title_fullStr | Novel selective ligands for μ-opioid and β2-adrenergic receptors synthesis and biological investigations = Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren vorgelegt von Daniela Gisela Dengler |
| title_full_unstemmed | Novel selective ligands for μ-opioid and β2-adrenergic receptors synthesis and biological investigations = Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren vorgelegt von Daniela Gisela Dengler |
| title_short | Novel selective ligands for μ-opioid and β2-adrenergic receptors |
| title_sort | novel selective ligands for μ opioid and β2 adrenergic receptors synthesis and biological investigations neuartige selektive liganden fur μ opioid und β2 adrenorezeptoren |
| title_sub | synthesis and biological investigations = Neuartige selektive Liganden für μ-Opioid- und β2-Adrenorezeptoren |
| topic | Morphinantagonist (DE-588)4248332-3 gnd Opiatrezeptor (DE-588)4172636-4 gnd Agonist (DE-588)4380725-2 gnd Beta-2-Rezeptor (DE-588)4254128-1 gnd |
| topic_facet | Morphinantagonist Opiatrezeptor Agonist Beta-2-Rezeptor Hochschulschrift |
| url | http://d-nb.info/1168666686/04 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030628890&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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