In search for potent and selective NPY Y 4 receptor ligands: acylguanidines, argininamides and peptide analogs
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
2012
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| Schlagworte: | |
| Online-Zugang: | Volltext https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-251447 Inhaltsverzeichnis |
| Beschreibung: | XII, 256 S. Ill., graph. Darst. |
Internformat
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| 100 | 1 | |a Kaske, Melanie |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a In search for potent and selective NPY Y 4 receptor ligands |b acylguanidines, argininamides and peptide analogs |c vorgelegt von Melanie Kaske |
| 246 | 1 | 3 | |a In search for potent and selective NPY Y4 receptor ligands |
| 264 | 1 | |c 2012 | |
| 300 | |a XII, 256 S. |b Ill., graph. Darst. | ||
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| 502 | |a Regensburg, Univ., Diss., 2012 | ||
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| adam_text | IMAGE 1
CONTENTS
V
CONTENTS
CHAPTER 1 GENERAL INTRODUCTION 1
1.1 THE NEUROPEPTIDE Y (NPY) FAMILY 2
1.2 MAMMALIAN NPY RECEPTOR SUBTYPES 4
1.2.1 NPY YI, Y 2 AND Y5 RECEPTORS AND THEIR LIGANDS 5
1.2.1.1 THE NPY Y T RECEPTOR 5
1.2.1.2 THE NPY Y 2 RECEPTOR 6
1.2.1.3 THE NPY Y 5 RECEPTOR 8
1.2.2 THE NPY Y 4 RECEPTOR AND ITS LIGANDS 9
1.3 (NON)PEPTIDE LIGANDS FOR NPY RECEPTORS - DEVELOPMENT AND THERAPEUTIC
POTENTIAL 11
1.3.1 NPY RECEPTORS IN HEALTH AND DISEASE 11
1.3.2 NPY RECEPTOR LIGANDS AND THEIR THERAPEUTIC POTENTIAL 13
1.3.3 STRATEGIES FOR THE DEVELOPMENT O F (NON)PEPTIDE NPY RECEPTOR
LIGANDS 15
1.4 REFERENCES 16
CHAPTER 2 SCOPE AND OBJECTIVES 35
CHAPTER 3 A^-ACYLATED HETARYLPROPYLGUANIDINES AS ANTAGONISTS OF THE
HUMAN
NPY Y 4 RECEPTOR: SYNTHESIS AND PHARMACOLOGICAL INVESTIGATIONS 39
3.1 INTRODUCTION 40
3.2 CHEMISTRY 4 1
3.2.1 SYNTHESIS OF THE A^-ACYLATED ARYLPROPYLGUANIDINES 4 1
3.2.2 SYNTHESIS OF ACYLGUANIDINE-TYPE AND CARBAMOYLGUANIDINE-TYPE AMINO
ACID
DERIVATIVES 44
3.3 PHARMACOLOGICAL RESULTS AND DISCUSSION 50
3.3.1 FUNCTIONAL ACTIVITIES AND AFFINITIES AT THE Y 4R AND RECEPTOR
SUBTYPE
SELECTIVITY OF THE W-ACYLATED HETARYLPROPYLGUANIDINES 50
HTTP://D-NB.INFO/1036942465
IMAGE 2
VI CONTENTS
3.3.2 FUNCTIONAL ACTIVITIES AT THE NPY Y 4R AND RECEPTOR SUBTYPE
SELECTIVITY O F
CARBAMOYLGUANIDINE-TYPE AMINO ACID DERIVATIVES 53
3.4 SUMMARY AND CONCLUSION 54
3.5 EXPERIMENTAL SECTION 55
3.5.1 CHEMISTRY 55
3.5.1.1 GENERAL EXPERIMENTAL CONDITIONS 55
3.5.1.2 PREPARATION O F THE GUANIDINYLATING REAGENT 3.4 AND THE N-BOC
PROTECTED
BUILDING BLOCK 3.5 56
3.5.1.3 PREPARATION OF THE 3-(LH-BENZIMIDAZOL-2-YL)PROPAN-L-OL 3.32 57
3.5.1.4 PREPARATION O F 2-(3-PIPERAZINOPROPYL)ISOINDOLINE-L,3-DIONES
3.12 - 3.15 58
3.5.1.5 PREPARATION O F THE 2-[3-(HETARYL)PROPYL]ISOINDOLINE-L,3-DIONES
3.23 - 3.25 AND
3.31 59
3.5.1.6 PREPARATION OF THE 3-HETARYLPROPYLAMINES 3.16 - 3.19 AND 3.26 -
3.28 AND 3.32
BY HYDRAZINOLYSIS OF THE PHTHALIMIDES 6 1
3.5.1.7 PREPARATION OF MONO-BOC-PROTECTED DIAMINES 3.35 AND 3.36 AND
MONO-BOCPROTECTED PIPERAZINE 3.7 64
3.5.1.8 PREPARATION OF A^-ACYLATED AYLPROPYLGUANIDINES 3.40 - 3.52 65
3.5.1.9 PREPARATION OF THE GUANIDINE-TYPE BUILDING BLOCK 3.57 70
3.5.1.10 PREPARATION OF THE CARBAMOYLGUANIDINE-TYPE BUILDING BLOCK 3.68
7 1
3.5.1.11 PREPARATION O F CARBAMOYLGUANIDINE-TYPE AMINO ACID DERIVATIVES
3.73 - 3.77 73
3.5.2 PHARMACOLOGICAL METHODS 75
3.5.2.1 MATERIALS AND CELL CULTURE 75
3.5.2.2 AEQUORIN ASSAY 76
3.5.2.3 FLOW CYTOMETRIC BINDING ASSAY 77
3.6 REFERENCES 78
CHAPTER 4 FT^-ACYLATED PHENYLPIPERAZINYLGUANIDINES AS Y 4R LIGANDS:
SYNTHESIS,
MOLECULAR PHARMACOLOGY AND TOXICITY 8 3
4.1 INTRODUCTION 84
4.2 CHEMISTRY 85
4.3 PHARMACOLOGICAL RESULTS AND DISCUSSION 86
IMAGE 3
CONTENTS
VII
4.3.1 POTENCIES AND SUBTYPE SELECTIVITY OF THE SYNTHESIZED A^-ACYLATED
PIPERAZINYLPROPYLGUANIDINES AT THE NPY Y 4R 86
4.3.2 CYTOTOXICITY O F THE SYNTHESIZED /^-ACYLATED
PIPERAZINYLPROPYLGUANIDINES 87
4.3.2.1 INTRODUCTION 87
4.3.3 HEMOLYTIC PROPERTIES OF SELECTED LIGANDS 89
4.3.4 CYTOTOXICITY OF SELECTED LIGANDS 90
4.4 SUMMARY AND CONCLUSION 93
4.5 EXPERIMENTAL SECTION 94
4.5.1 CHEMISTRY 94
4.5.1.1 GENERAL EXPERIMENTAL CONDITIONS 94
4.5.1.2 PREPARATION OF THE A^-BOC PROTECTED PHENYLPIPERAZINYLGUANIDINE
BUILDING BLOCK
4.3 94
4.5.1.3 PREPARATION OF BIPHENYL- AND CYCLOHEXYLPROPANOIC ACID 4.10 AND
4.11 95
4.5.1.4 PREPARATION OF ACYLGUANIDINES 4.15 - 4 . 1 9 98
4.5.2 PHARMACOLOGICAL METHODS AND TOXICOLOGICAL INVESTIGATIONS 101
4.5.2.1 AEQUORIN ASSAY 101
4.5.2.2 FLOW CYTOMETRIC BINDING ASSAY 101
4.5.2.3 DETERMINATION OF HEMOLYTIC PROPERTIES USING MOUSE ERYTHROCYTES
101
4.5.2.4 CHEMOSENSITIVITY ASSAY 102
4.6 REFERENCES 102
CHAPTER 5 FROM MONOVALENT AND BIVALENT ARGININAMIDE-TYPE NPY YIR LIGANDS
T O YR ANTAGONISTS 105
5.1 INTRODUCTION 106
5.2 PHARMACOLOGICAL INVESTIGATIONS OF ARGININAMIDE-TYPE YTR LIGANDS FOR
ACTIVITY AT THE Y 4R 108
5.2.1 CRITERIA FOR THE SELECTION OF APPROPRIATE MONOVALENT AND BIVALENT
ARGININAMIDE-TYPE STRUCTURES 108
5.2.2 PHARMACOLOGICAL RESULTS AND DISCUSSION 111
5.3 ENANTIOMERS OF ARGININAMIDE DERIVATIVES: STEREODISCRIMINATION AT Y
4R AND
YIR 115
5.3.1 INTRODUCTION 115
IMAGE 4
VIII
CONTENTS
5.3.2 SYNTHESIS O F THE BIVALENT BL BO 3304 DERIVATIVE (S,S)-5.27 115
5.3.3 PHARMACOLOGICAL RESULTS AND DISCUSSION 116
5.4 MONOVALENT BIBO 3304 DERIVATIVES WITH VARYING JV G-SUBSTITUENTS 119
5.4.1 INTRODUCTION 119
5.4.2 CHEMISTRY 119
5.4.3 PHARMACOLOGICAL RESULTS AND DISCUSSION 122
5.5 PHARMACOLOGICAL INVESTIGATIONS ON BIVALENT BIBP 3326 DERIVATIVES AS
LEAD
STRUCTURES FOR THE NPY Y 4R RESEARCH 125
5.5.1 CRITERIA FOR THE SELECTION OF INVESTIGATED STRUCTURES 125
5.5.2 PHARMACOLOGICAL RESULTS AND DISCUSSION 127
5.6 SUMMARY AND OUTLOOK 128
5.7 EXPERIMENTAL SECTION 131
5.7.1 CHEMISTRY 131
5.7.1.1 GENERAL CONDITIONS 131
5.7.2 PREPARATION O F (S)-CONFIGURED BIVALENT COMPOUND (S,S)-5.27 131
5.7.2.1 SYNTHESIS OF THE (/?)- AND (S)-ARGININAMIDE-TYPE BUILDING BLOCKS
(R)- AND (5)-5.44 134
5.7.2.2 SYNTHESIS OF THE SPACERS 5.52, 5.54,5.S6, 5.59, 5.64 AND 5.65
142
5.7.2.3 PREPARATION OF (5)- AND (R)-CONFIGURED MONOVALENT LIGANDS 5.66 -
5.71 148
5.7.3 PHARMACOLOGICAL METHODS 156
5.7.3.1 MATERIALS AND CELL CULTURE 156
5.7.3.2 AEQUORIN ASSAY 157
5.7.3.3 FLOW CYTOMETRIC BINDING ASSAY 157
5.7.3.4 RADIOLIGAND BINDING ASSAY 157
5.8 REFERENCES 158
CHAPTER 6 DERIVATIVES O F TRUNCATED PNPY AND HPP AS POTENT AND SELECTIVE
NPY
Y 4R LIGANDS CONTAINING (J- OR Y-AMINO ACIDS 163
6.1 INTRODUCTION 164
6.2 DESIGN AND PREPARATION OF THE PEPTIDES 165
6.3 CIRCULAR DICHROISM OF THE FOLDAMERS 168
IMAGE 5
CONTENTS
IX
6.4 PHARMACOLOGICAL RESULTS 169
6.4.1 AFFINITY, SUBTYPE SELECTIVITY, POTENCY AND EFFICACY 169
6.4.2 BEHAVIOR IN FUNCTIONAL ASSAYS WITH DIFFERENT READ-OUTS: [CA 2*]J
MOBILIZATION
VS. GTPASE ACTIVITY 172
6.4.2.1 RESULTS OF THE AEQUORIN ASSAY 173
6.4.2.2 RESULTS FROM THE STEADY STATE GTPASE ASSAY 175
6.4.2.3 RESULTS FROM THE FURA-2 ASSAY 177
6.4.3 DISCUSSION OF THE DISCREPANCIES OBSERVED IN DIFFERENT FUNCTIONAL
ASSAYS 178
6.5 SUMMARY AND CONCLUSION 181
6.6 EXPERIMENTAL SECTION 181
6.6.1 CD-MEASUREMENTS 181
6.6.2 PHARMACOLOGICAL METHODS 182
6.6.2.1 MATERIALS AND CELL CULTURE 182
6.6.2.2 AEQUORIN ASSAY 182
6.6.2.3 FLOW CYTOMETRIC BINDING ASSAY 183
6.6.2.4 STEADY STATE GTPASE ASSAY 183
6.6.2.5 CA 2+-ASSAY (FURA-2) 183
6.7 REFERENCES 184
CHAPTER 7 CIS-PENTACIN CONTAINING YR SELECTIVE AGONISTS 189
7.1 INTRODUCTION 190
7.2 CHEMISTRY 191
7.3 REPLACEMENT OF THE AMINO ACID IN POSITION 34 BY CIS-PENTACIN OR
LEUCINE 194
7.3.1 STRUCTURAL OVERVIEW OF THE SYNTHESIZED PEPTIDES 194
7.3.2 PHARMACOLOGICAL RESULTS AND DISCUSSION 197
7.4 SUMMARY, CONCLUSION AND OUTLOOK 201
7.5 EXPERIMENTAL SECTION 202
7.5.1 CHEMISTRY 202
7.5.1.1 GENERAL CONDITIONS 202
7.5.1.2 PREPARATION OF (25,2/?)-2-AMINOCYDOPENTANECARBOXYLIC ACID 202
7.5.1.3 PREPARATION OF (LFI, 2S)-2-AMINOCYDOPENTANECARBOXYLICACID 204
IMAGE 6
X CONTENTS
7.5.1.4 PREPARATION OF FMOC-PROTECTED CIS-2-AMINOPENTANECARBOXYLIC ACID
206
7.5.2 PEPTIDE SYNTHESIS ACCORDING TO A STANDARD FMOC-PROTOCOL 207
7.5.2.1 GENERAL CONDITIONS 207
7.5.2.2 GENERAL PROCEDURE FOR SPPS (FMOC-PROTOCOL) 207
7.5.2.3 SYNTHESIS OF NPY AND HPP ANALOGS 208
7.5.3 PHARMACOLOGY METHODS 212
7.5.3.1 FLOW CYTOMETRIC BINDING ASSAY 212
7.5.3.2 STEADY STATE GTPASE ASSAY 212
7.6 REFERENCES 212
CHAPTER 8 GREEN- AND RED-FLUORESCENT SUBTYPE-SELECTIVE PEPTIDES FOR THE
NPY
Y2, Y 4 AND YS RECEPTOR 215
8.1 INTRODUCTION 216
8.2 CHEMISTRY 217
8.3 NPY RECEPTOR AFFINITY, AGONISM AND SELECTIVITY 220
8.4 FLUORESCENCE PROPERTIES OF THE LABELED PEPTIDES 222
8.4.1 APPLICATION O F SUBTYPE-SELECTIVE FLUORESCENTLY-LABELED PEPTIDES
TO CONFOCAL
LASER SCANNING MICROSCOPY 225
8.4.2 APPLICATION O F FLUORESCENCE-LABELED PEPTIDES IN FLOW CYTOMETRY:
SATURATION,
KINETICS AND COMPETITION BINDING EXPERIMENTS 229
8.5 SUMMARY AND CONCLUSION 233
8.6 EXPERIMENTAL SECTION 234
8.6.1 CHEMISTRY 234
8.6.1.1 GENERAL CONDITIONS 234
8.6.1.2 PREPARATION OF THE FUNCTIONALIZED ARGININE BUILDING BLOCK 8.1
234
8.6.2 PEPTIDES SYNTHESIS ACCORDING T O A STANDARD FMOC-PROTOCOL 236
8.6.2.1 GENERAL CONDITIONS 236
8.6.2.2 GENERAL PROCEDURE FOR THE COUPLING OF THE FUNCTIONALIZED
ARGININE BUILDING BLOCK 237
8.6.2.3 GENERAL PROCEDURE FOR SPPS 237
8.6.3 PREPARATION OF FLUORESCENTLY-LABELED PEPTIDES 238
8.6.3.1 GENERAL CONDITIONS 238
IMAGE 7
CONTENTS
XI
8.6.3.2 GENERAL PROCEDURE FOR PEPTIDE LABELING 238
8.6.4 DETERMINATION OF QUANTUM YIELDS 240
8.6.5 PHARMACOLOGICAL METHODS 242
8.6.5.1 MATERIALS AND CELL CULTURE 242
8.6.5.2 STEADY STATE GTPASE ASSAY 242
8.6.5.3 FLOW CYTOMETRIC BINDING EXPERIMENTS 242
8.6.5.4 CONFOCAL MICROSCOPY 243
8.7 REFERENCES 244
CHAPTER 9 SUMMARY 247
CHAPTER 10 APPENDIX 2 5 1
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| spelling | Kaske, Melanie Verfasser aut In search for potent and selective NPY Y 4 receptor ligands acylguanidines, argininamides and peptide analogs vorgelegt von Melanie Kaske In search for potent and selective NPY Y4 receptor ligands 2012 XII, 256 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Regensburg, Univ., Diss., 2012 Ligand Biochemie (DE-588)4606532-5 gnd rswk-swf Neuropeptid Y (DE-588)4317370-6 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Neuropeptid Y (DE-588)4317370-6 s Ligand Biochemie (DE-588)4606532-5 s DE-604 Erscheint auch als Online-Ausgabe urn:nbn:de:bvb:355-epub-251447 http://epub.uni-regensburg.de/25144/ Verlag kostenfrei Volltext https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-251447 Resolving-System DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=026040989&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Kaske, Melanie In search for potent and selective NPY Y 4 receptor ligands acylguanidines, argininamides and peptide analogs Ligand Biochemie (DE-588)4606532-5 gnd Neuropeptid Y (DE-588)4317370-6 gnd |
| subject_GND | (DE-588)4606532-5 (DE-588)4317370-6 (DE-588)4113937-9 |
| title | In search for potent and selective NPY Y 4 receptor ligands acylguanidines, argininamides and peptide analogs |
| title_alt | In search for potent and selective NPY Y4 receptor ligands |
| title_auth | In search for potent and selective NPY Y 4 receptor ligands acylguanidines, argininamides and peptide analogs |
| title_exact_search | In search for potent and selective NPY Y 4 receptor ligands acylguanidines, argininamides and peptide analogs |
| title_full | In search for potent and selective NPY Y 4 receptor ligands acylguanidines, argininamides and peptide analogs vorgelegt von Melanie Kaske |
| title_fullStr | In search for potent and selective NPY Y 4 receptor ligands acylguanidines, argininamides and peptide analogs vorgelegt von Melanie Kaske |
| title_full_unstemmed | In search for potent and selective NPY Y 4 receptor ligands acylguanidines, argininamides and peptide analogs vorgelegt von Melanie Kaske |
| title_short | In search for potent and selective NPY Y 4 receptor ligands |
| title_sort | in search for potent and selective npy y 4 receptor ligands acylguanidines argininamides and peptide analogs |
| title_sub | acylguanidines, argininamides and peptide analogs |
| topic | Ligand Biochemie (DE-588)4606532-5 gnd Neuropeptid Y (DE-588)4317370-6 gnd |
| topic_facet | Ligand Biochemie Neuropeptid Y Hochschulschrift |
| url | http://epub.uni-regensburg.de/25144/ https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-251447 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=026040989&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT kaskemelanie insearchforpotentandselectivenpyy4receptorligandsacylguanidinesargininamidesandpeptideanalogs AT kaskemelanie insearchforpotentandselectivenpyy4receptorligands |