Synthesis and characterization of neuropeptide Y analogues for tumour diagnosis and therapie:
Gespeichert in:
| 1. Verfasser: | |
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| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
2006
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | 200 Bl. graph. Darst. 30 cm |
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Datensatz im Suchindex
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| adam_text | 9
TABLE OF CONTENTS
TITLE PAGE 1
DEDICATION PAGE 2
DETAILS ABOUT TIME SCHEDULE AND SUPERVISION 3
BIBLIOGRAPHISCHE BESCHREIBUNG 4
SUMMARY 5
ZUSAMMENFASSUNG 7
TABLE OF CONTENTS 9
ABBREVIATIONS 16
CHAPTER 1 20
Introduction: Peptide Hormones as Potential
Radiopharmaceuticals in Tumour Diagnosis and Therapy
1.1 Introduction to Concept 21
1.2 Role of Peptide Receptors in Cancer 22
1.3 Peptide Synthesis 25
1.3.1 Insoluble Solid Support/Resins 26
1.3.2 Protecting Groups in SPPS 26
1.3.2.1 Boc Protecting Group 27
1.3.2.2 Fmoc Protecting Group 27
1.3.3. Activation Procedures 28
1.3.4 Fmoc Solid Phase Peptide Synthesis 28
1.4 Incorporation of Radioactivity into Peptides 30
1.4.1 Direct Labelling 30
1.4.1.1 Radiolabelling of Peptides with 123I 31
1.4.2 Chelate or Indirect Labelling 32
1.4.3 Prelabelling Method 33
1.4.4 Postlabelling Method 33
1.4.4.1 Radiolabelling of Peptides with 18F 34
10
1.5 Bifunctional Chelating Agents 35
1.5.1 DTPA 35
1.5.2 DOTA 36
1.5.3 TETA 37
1.5.4 NOTA 37
1.5.5 HYNIC 37
1.6 Radionuclides 39
1.7 Evaluation of Radiopeptides 43
1.8 Pharmacokinetics 44
1.9 Comparison of in vitro Peptide Receptor Expression in Normal 46
Tissues and Tumours
1.9.1 Somatostatin Receptors 46
1.9.2 Vasoactive Intestinal Peptide (VIP) 51
1.9.3 Bombesin/Gastrin Releasing Peptide (GRP) Analogues 52
1.9.4 a-Melanocyte Stimulating Hormone (a-MSH) Peptide Analogues 55
1.9.5 Neurotensin Receptors 56
1.9.6 Cholecystokinin (CCK) Receptors 57
1.9.7 Substance P 58
1.9.8 Neuropeptide Y (NPY) 58
1.9.8.1 Radiolabelling of NPY and PYY Analogues for 60
Tumour Diagnosis
1.9.8.2 Fluorescence labelling of NPY and PYY Analogues 62
for Cell Intemalization Studies
1.9.9 Calcitonin 63
1.9.10 Oxytocin 63
1.9.11 Endothelin 63
1.9.12 Orexin 64
1.10 Conclusions 64
1.11 Aims and Scope of the Presented Work 65
11
CHAPTER 2 66_
Materials 66
2.1 Equipment 67
2.2 Chemicals 70
2.2.1 Amino Acids 70
2.2.2 General Chemicals 70
2.3 Cells, Medium and Solutions for the Cell Culture 72
2.3.1 Cell Lines 72
2.3.2 Medium and Solutions 72
Chapter 3 74
Experimental Methods 74
3.1 Peptide Synthesis 75
3.1.1 Manual Peptide Synthesis (Amino Acid Coupling) 75
3.1.1.1 Removal of Fluorenylmethoxycarbonyl (Fmoc) Group from 75
the Resin
3.1.1.2 Coupling of the First Amino Acid on Rink Amide Resin 75
3.1.2 Automatic Peptide Synthesis 75
3.1.2.1 N-Terminal Protection and Labelling(s) at Lys4 Side 76
Chain in NPY Sequence
3.2 Labelling with 5(6)-Carboxyfluorescein (CF) 77
3.3 Labelling with (NaHis-ac) 78
3.4 Labelling with DOTA 78
3.5 Detection of Resin-Bound Amino Group (Kaiser Test) 79
3.6 Labelling with 186Re(CO)3 or69JGa 79
3.6.1 Labelling of (NaHis-ac)-NPY Analogues with 186Re(CO)3 79
3.6.2 Labelling of DOTA-NPY Analogues with 69JGa 79
3.7 Purification of Peptides 80
3.7.1 Purification through Preparative HPLC 80
12
3.7.2 Purification through Semi-Preparative HPLC 80
3.8 Metabolic Stability Study 80
3.9 Improvement of Metabolic Stability of Y1/Y2 Receptor-Selective 81
NPY Analogues
3.9.1 Incorporation of p-ACC Building Blocks 81
3.9.2 N-Terminus Acetylation of the Peptide 81
3.10 Cell Culture 82
3.10.1 Mediums used in Cell Culture 82
3.10.2 Thawing the Cells 82
3.10.3 Passaging the Cells 83
3.11 Binding Assays 83
3.12 Internalization Studies with the Fluorescent Ligands 84
3.12.1 Displacement of CF-NPY Analogues by 10 jxM Unlabelled NPY 84
3.12.2 Time Course of Internalization 84
3.12.3 Confocal LASER Scanning Microscopy (CLSM) 85
3.13 Radiolabelling 85
3.13.1 Labelling of DOTA-Peptide with 86Y 85
3.13.2 Radio-HPLC(86Y-DOTA-[Ahx524]NPY) 85
3.13.3 Biological Samples 85
3.13.4 Radio-Instant Thin Layer Chromatography (Radio-ITLC) 86
3.14 Biodistribution Studies in Rodents 86
3.14.1 Animal Preparation 86
3.14.2 Ex vivo Autoradiography 87
3.14.3 microPET® Imaging Studies 87
3.14.4 Image Analysis 88
3.14.5 Statistical Analysis of Experimental Data 89
CHAPTER 4 90
Results of Experimental Work 90
4.1 Unlabelled Peptides 92
13
4.1.1 Receptor Binding Assays with Unlabelled Peptides 94
4.2 Preparation of 5(6)- Carboxyfluorescein (CF)-labelled Peptides 97
4.3 Metabolic Stability Study 98
4.3.1 Digestion Pattern of NPY by Trypsin 98
4.3.2 Metabolic Stability Study in Human Blood Plasma 98
4.3.2.1 Metabolic Stability of NPY (used as positive control) 99
4.3.2.2 Metabolic Stability of NPY Yi Receptor-Selective Analogues 101
4.3.2.3 Metabolic Stability of NPY Y2 Receptor-Selective Analogues104
4.4 Internalization Studies with the Fluorescent Ligands 107
4.4.1 Receptor Binding Affinity of CF-NPY Analogues 107
4.4.2 Principle of Internalization 109
4.4.3 Displacement of the CF-NPY from SK-N-MC, MCF-7 and 110
SMS-KAN Cells
4.4.4 Time-Course of Internalization 111
4.4.5 Confocal LASER Scanning Microscopy (CLSM) 113
4.5 Chelation of NPY Analogues 116
4.5.1 Preparation of 186Re(CO)3-(NaHis-ac) labelled Peptides 117
4.5.1.1 Labelling with (NaHis-ac) 117
4.5.1.2 Labelling with 186Re(CO)3 118
4.5.1.3 Receptor Binding Affinity of 186Re(CO)3-(NaHis-ac)-NPY 119
Analogues
4.5.2 Preparation of 697Ga-DOTA labelled Peptides 123
4.5.2.1 Labelling with DOTA tris(tert-butyl ester) 125
4.5.2.2 Receptor Binding Affinity of DOTA-NPY Analogues 124
4.6.2.3 Labelling of DOTA-Peptides with 69 7Ga 126
4.6 Radiolabelling 127
4.6.1 Radiolabelling of DOTA-Peptides with 68Ga 127
14
4.6.2 Radiolabelling and Biodistribution of DOTA-[Ahx5 24]NPY with 86Y 128
4.6.2.1 Radiolabelling 128
4.6.2.2 Biodistribution of 86Y-DOTA-[Ahx5-24]NPY 128
4.6.3 Metabolism of 86Y-DOTA-[Ahx524]NPY 130
4.7 Peptide YY (PYY) Y2 Receptor-Selective Analogues with 131
Improved Metabolic Stability
4.7.1 Preparation of CF-labelled Peptides 131
4.7.2 Metabolic Stability in Human Blood Plasma 132
4.7.3 Displacement of 3[H]propionyl-NPY by 10 }iM CF-PYY(3-36) and 133
CF-PYY(13-36) in SMS-KAN Cells
4.7.4 Chelation of PYY(3-36) and PYY(13-36) 134
4.7.4.1 Labelling with DOTA tris(tert-butyl ester) 134
4.7.4.2 Labelling with (NaHis-ac) 136
4.8 Improvement of Metabolic Stability by Introducing (3-ACC 137
Building Blocks
4.8.1 Incorporation of p-ACC Building Blocks in the Growing 138
Peptide Sequences
4.8.2 CF-labelling of (3-ACC Building Block Containing Peptides 138
4.8.3 Metabolic Stability of p-ACC Building Blocks Containing Peptides 139
in Human Blood Plasma
4.8.4 Labelling with DOTA tris(tert-butyl ester) 139
4.8.5 Receptor Binding Affinity of p-ACC Building Blocks Containing 141
Peptides on Various NPY Receptor Expressing Cells
4.8.6 Displacement of 3[H]propionyl-NPY by 10 nM 142
Ac-[Lys(pAla-DOTA)23, pAla24, pACC3234]NPY(23-36)
4.8.7 Internalization Studies of p-ACC Building Blocks containing 142
Peptides on various NPY Receptor Expressing Cells
4.8.7.1 Time-Course of Internalization 142
4.8.7.2 Confocal LASER Scanning Microscopy (CLSM) 143
15
CHAPTER 5 146
Discussion 146
5.1 Structure-Activity Relationship 147
5.2 Metabolic Stability 149
5.3 Receptor-mediated Cell Internalization 151
5.4 Labelling NPY Analogues with 186Re(CO)3-(NaHis-ac) 153
5.5 Labelling NPY Analogues with DOTA 154
5.6 697Ga-DOTA Labelling 154
5.7 Radiolabelling of DOTA-[Ahx524]NPY with 86Y and Biodistribution 155
in Nude Mice
5.8 Improvement of Metabolic Stability of NPY Analogues 155
5.8.1 Incorporation of p-ACC Building Blocks 156
5.8.2 Development of PYY Analogues 156
5.9 Summarizing the Discussion 157
5.11 Conclusion 160
CHAPTER 6 161
REFERENCES 161
CURRICULUM VITAE 184
PUBLICATIONS POSTER PRESENTATIONS 185
ORAL PRESENTATIONS 187
ACKNOWLEDGEMENTS 188
ZUSAMMENFASSUNG DER WISSENSCHAFTLICHEN ERGEBNISSE ZUR 189
DISSERTATION
|
| any_adam_object | 1 |
| author | Khan, Irfan Ullah |
| author_facet | Khan, Irfan Ullah |
| author_role | aut |
| author_sort | Khan, Irfan Ullah |
| author_variant | i u k iu iuk |
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| bvnumber | BV035256945 |
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| dewey-full | 616.994 |
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| dewey-ones | 616 - Diseases |
| dewey-raw | 616.994 |
| dewey-search | 616.994 |
| dewey-sort | 3616.994 |
| dewey-tens | 610 - Medicine and health |
| discipline | Medizin |
| format | Thesis Book |
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| spelling | Khan, Irfan Ullah Verfasser aut Synthesis and characterization of neuropeptide Y analogues for tumour diagnosis and therapie vorgelegt von Irfan Ullah Khan 2006 200 Bl. graph. Darst. 30 cm txt rdacontent n rdamedia nc rdacarrier Leipzig, Univ., Diss., 2006 Strahlentherapie (DE-588)4057833-1 gnd rswk-swf Neuropeptid Y (DE-588)4317370-6 gnd rswk-swf Diagnostik (DE-588)4113303-1 gnd rswk-swf Analyse (DE-588)4122795-5 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Tumor (DE-588)4078460-5 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Neuropeptid Y (DE-588)4317370-6 s Analyse (DE-588)4122795-5 s Chemische Synthese (DE-588)4133806-6 s DE-604 Tumor (DE-588)4078460-5 s Diagnostik (DE-588)4113303-1 s Strahlentherapie (DE-588)4057833-1 s b DE-604 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017062520&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Khan, Irfan Ullah Synthesis and characterization of neuropeptide Y analogues for tumour diagnosis and therapie Strahlentherapie (DE-588)4057833-1 gnd Neuropeptid Y (DE-588)4317370-6 gnd Diagnostik (DE-588)4113303-1 gnd Analyse (DE-588)4122795-5 gnd Chemische Synthese (DE-588)4133806-6 gnd Tumor (DE-588)4078460-5 gnd |
| subject_GND | (DE-588)4057833-1 (DE-588)4317370-6 (DE-588)4113303-1 (DE-588)4122795-5 (DE-588)4133806-6 (DE-588)4078460-5 (DE-588)4113937-9 |
| title | Synthesis and characterization of neuropeptide Y analogues for tumour diagnosis and therapie |
| title_auth | Synthesis and characterization of neuropeptide Y analogues for tumour diagnosis and therapie |
| title_exact_search | Synthesis and characterization of neuropeptide Y analogues for tumour diagnosis and therapie |
| title_full | Synthesis and characterization of neuropeptide Y analogues for tumour diagnosis and therapie vorgelegt von Irfan Ullah Khan |
| title_fullStr | Synthesis and characterization of neuropeptide Y analogues for tumour diagnosis and therapie vorgelegt von Irfan Ullah Khan |
| title_full_unstemmed | Synthesis and characterization of neuropeptide Y analogues for tumour diagnosis and therapie vorgelegt von Irfan Ullah Khan |
| title_short | Synthesis and characterization of neuropeptide Y analogues for tumour diagnosis and therapie |
| title_sort | synthesis and characterization of neuropeptide y analogues for tumour diagnosis and therapie |
| topic | Strahlentherapie (DE-588)4057833-1 gnd Neuropeptid Y (DE-588)4317370-6 gnd Diagnostik (DE-588)4113303-1 gnd Analyse (DE-588)4122795-5 gnd Chemische Synthese (DE-588)4133806-6 gnd Tumor (DE-588)4078460-5 gnd |
| topic_facet | Strahlentherapie Neuropeptid Y Diagnostik Analyse Chemische Synthese Tumor Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017062520&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT khanirfanullah synthesisandcharacterizationofneuropeptideyanaloguesfortumourdiagnosisandtherapie |