Quinoline carboxamides as modulators of Breast Cancer Resistance Protein (ABCG2): Investigations on potency, selectivity, mechanism of action, cytotoxicity, stability and drug-like properties
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| Main Author: | |
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| Format: | Thesis Book |
| Language: | English |
| Published: |
2014
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| Subjects: | |
| Online Access: | Volltext https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-295899 Inhaltsverzeichnis |
| Physical Description: | XVI, 171 S. Ill., graph. Darst. |
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| 100 | 1 | |a Bauer, Stefanie |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Quinoline carboxamides as modulators of Breast Cancer Resistance Protein (ABCG2) |b Investigations on potency, selectivity, mechanism of action, cytotoxicity, stability and drug-like properties |c von Stefanie Bauer |
| 264 | 1 | |c 2014 | |
| 300 | |a XVI, 171 S. |b Ill., graph. Darst. | ||
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Record in the Search Index
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| adam_text |
CONTENTS IX
CONTENTS
1 GENERAL INTRODUCTION 1
1.1 THE ABC
PROTEIN SUPERFAMILY 1
1.2 PHYSIOLOGICAL AND
PHARMACOLOGICAL FUNCTIONS
OF ABC
TRANSPORTERS 2
1.2.1 STRUCTURES AND
CELLULAR MECHANISMS OF ABC TRANSPORTERS 2
1.2.2 ABC TRANSPORTERS AND
THE PHENOMENON
OF MULTIDRUG RESISTANCE 4
1.2.3 ABC TRANSPORTERS
EXPRESSED AT THE
BLOOD-BRAIN BARRIER 6
1.3 REFERENCES 8
2 SCOPE AND OBJECTIVES 11
2.1 REFERENCES 12
3 MODULATION OF THE BREAST CANCER RESISTANCE PROTEIN (ABCG2) 13
3.1 INTRODUCTION 13
3.1.1 THE ABCG2 TRANSPORTER 13
3.1.2 BCRP INHIBITORS 14
3.2 OBJECTIVE 15
3.3 MATERIALS AND
METHODS IS
3.3.1 DRUGS AND
CHEMICALS 15
3.3.2 TEST COMPOUNDS 16
3.3.3 NEW FLUORESCENT ABCG2
MODULATORS 24
3.3.4 CELL CULTURE 24
3.3.5 CELL BASED
ASSAYS FOR
THE DETERMINATION OF ABC TRANSPORTER
MODULATION 25
3.3.5.1 ABCG2 MODULATION:
HOECHST 33342 AND
PHEOPHORBIDE A MICROPLATE
ASSAYS 25
3.3.5.2 MITOXANTRONE MICROPLATE
ASSAY FOR THE
DETERMINATION OF ABCG2 MODULATION 27
3.3.5.3 CALCEIN-AM EFFLUX ASSAY
FOR THE DETERMINATION OF ABCB1
MODULATION 28
3.3.5.4 CALCEIN-AM EFFLUX ASSAY
FOR THE DETERMINATION OF ABCC1
MODULATION 28
3.3.6 CHEMOSENSITIVITY ASSAYS 29
3.3.7 CHEMICAL STABILITY
OF ABCG2
MODULATORS IN HUMAN AND
MOUSE PLASMA 29
3.3.7.1 DETERMINATION
OF THE ACTIVITY OF UNSPECIFIC ESTERASES 30
3.3.7.2 ASSAY PROCEDURE 30
3.3.7.3 HPLC AND
HPLC-MS ANALYSIS 31
3.3.8 ABC TRANSPORTER
MODULATION IN A BLOOD-BRAIN
BARRIER MODEL 31
3.4 RESULTS AND
DISCUSSION 33
3.4.1 INHIBITION OF ABCB1,
ABCC1
AND ABCG2 33
3.4.2 FLUORESCENCE PROPERTIES
OF SELECTED
ABCG2 MODULATORS 39
HTTP://D-NB.INFO/1049961749
X
CONTENTS
3.4.3 ALTERNATIVE FLUORESCENCE
BASED ABCG2 INHIBITION
ASSAYS 40
3.4.4 EFFECT OF CO-ADMINISTRATION OF ABCG2
INHIBITORS WITH TOPOTECAN ON THE PROLIFERATION
OF MCF-7/TOPO
CELLS 44
3.4.5 CHEMICAL STABILITY
OF SELECTED ABCG2
TRANSPORTER MODULATORS
UNDER
PHYSIOLOGICAL CONDITIONS 48
3.4.5.1 CHEMICAL STABILITY
IN CULTURE MEDIUM
AND HUMAN
CPD PLASMA 49
3.4.5.2 CHEMICAL STABILITY
IN MOUSE
PLASMA 50
3.4.5.3 ESTERASE ACTIVITY
IN HUMAN
AND MURINE
PLASMA 55
3.4.6 EFFECT OF SELECTED ABCG2 TRANSPORTER
MODULATORS ON THE TRANSPORT
OF DAUNORUBICIN
IN A
BLOOD-BRAIN BARRIER
MODEL 55
3.5 SUMMARY AND
CONCLUSIONS 58
3.6 REFERENCES 60
4 DRUG-LIKE PROPERTIES OF NEW
ABCG2 MODULATORS 65
4.1 INTRODUCTION 65
4.1.1 TRENDS IN MEDICINAL CHEMISTRY
AND DRUG
DEVELOPMENT 65
4.1.2 THE 'RULE OF FIVE' 65
4.1.3 PLASMA PROTEIN
BINDING 66
4.2 MATERIALS AND
METHODS 68
4.2.1 DRUGS AND
CHEMICALS 68
4.2.2 SOLUBILITY 68
4.2.2.1 COMPARISON OF SOLUBILITIES IN DIFFERENT MEDIA 68
4.2.2.2 FLUORESCENCE SPECTRA OF HOECHST 33342 AFTER
INTERCALATION IN DNA IN THE
ABSENCE AND PRESENCE
OF TEST
COMPOUNDS 69
4.2.3 PLASMA PROTEIN
BINDING
STUDIES 69
4.2.3.1 ULTRAFILTRATION 69
4.2.3.2 ISOTHERMAL TITRATION
CALORIMETRY 70
4.2.3.3 EQUILIBRIUM DIALYSIS 70
4.2.3.4 PROTEIN BINDING
ANALYSIS VIA
FLUORESCENT SPECTROSCOPY 71
4.2.3.5 HPLC-BASED METHODS
TO DETERMINE
PROTEIN BINDING
OF SELECTED
ABCG2
MODULATORS 72
4.3 RESULTS AND
DISCUSSION 73
4.3.1 SOLUBILITY OF SELECTED ABCG2 MODULATORS 73
4.3.1.1 COMPUTATIONAL CALCULATIONS 73
4.3.1.2 SOLUBILITY IN DMSO AND
PBS 74
4.3.1.3 FLUORESCENCE SPECTRA OF THE HOECHST 33342
DYE IN THE
PRESENCE OF
DIFFERENT MODULATORS 75
4.3.2 EXTENT OF PLASMA PROTEIN
BINDING 76
4.3.2.1 ULTRAFILTRATION AND
ITC 76
4.3.2.2 EQUILIBRIUM DIALYSIS 76
CONTENTS XI
4.3.2.3 INVESTIGATIONS ON FLUORESCENT MODULATORS
TO DETERMINE
PROTEIN BINDING 77
4.3.2.4 DETERMINATION
OF LIPOPHILICITY PARAMETERS
BY HPLC. 82
4.3.3 PH-DEPENDENT FLUORESCENCE OF ABCG2 MODULATORS 83
4.4 SUMMARY AND
CONCLUSIONS 86
4.5 REFERENCES 87
5 CHARACTERIZATION OF HUMAN BRAIN TUMOR CELL LINES 91
5.1 MALIGNANT BRAIN
TUMORS 91
5.1.1 CLASSIFICATION 91
5.1.2 INCIDENCE AND
MORTALITY 91
5.1.3 THE BLOOD-BRAIN
BARRIER AND
BRAIN
CANCER THERAPY 92
5.2 MATERIALS AND
METHODS 94
5.2.1 DRUGS AND
CHEMICALS 94
5.2.2 CELL LINES
AND
CULTURE CONDITIONS 94
5.2.3 CELL STAINING 95
5.2.4 GENETIC STABILITY - KARYOLOGY 95
5.2.5 CHEMOSENSITIVITY AGAINST COMMON
CYTOSTATIC DRUGS
AND GROWTH
KINETICS 95
5.2.6 TUMORIGENICITY AND
GROWTH
KINETICS OF SUBCUTANEOUS TUMORS
IN NUDE MICE 96
5.2.7 HISTOLOGY 96
5.2.8 INDUCTION OF BCRP OVEREXPRESSION IN
BRAIN TUMOR
CELLS 96
5.2.9 ABC TRANSPORTER DETECTION
BY WESTERN
BLOT ANALYSIS 97
5.2.9.1 CELL LYSIS
AND
PROTEIN QUANTIFICATION 97
5.2.9.2 SDS-PAGE AND WESTERN
BLOT 97
5.2.10 ABC TRANSPORTER DETECTION
BY FLOW
CYTOMETRY 98
5.3 RESULTS AND
DISCUSSION 100
5.3.1 MORPHOLOGY 100
5.3.2 IN VITRO
GROWTH OF BRAIN TUMOR CELLS 101
5.3.3 ANEUPLOIDY 102
5.3.4 CHEMOSENSITIVITY AGAINST
CYTOSTATIC DRUGS 104
5.3.5 CHARACTERIZATION AND
GROWTH KINETICS
OF HUMAN
BRAIN TUMOR
CELL LINES
IN A
SUBCUTANEOUS TUMOR
MODEL IN NUDE MICE 112
5.3.5.1 IN VIVO
GROWTH KINETICS 112
5.3.5.2 HISTOLOGY 113
5.3.6 INVESTIGATIONS ON ABCG2 INDUCED
CELL LINES 113
5.3.6.1 WESTERN
BLOT ANALYSIS
OF WILDTYPE AND INDUCED
CELL LINES 113
5.3.6.2 DETERMINATION
OF ABCG2
OVEREXPRESSION
BY FLOW CYTOMETRY 115
5.3.6.3 HOECHST 33342 ASSAY
USING ABCG2
INDUCED CANCER CELLS 116
5.3.6.4 CHEMOSENSITIVITY OF LN-18/TOPO CELLS
AGAINST SELECTED CYTOSTATICS 118
XII
CONTENTS
5.3.7 ABC TRANSPORTER EXPRESSION
IN HMEC-1
CELLS 119
5.4 SUMMARY. 121
5.5 REFERENCES 122
6 TOWARDS AN ATPASE
ASSAY FOR THE HUMAN ABCG2 TRANSPORTER 125
6.1 INTRODUCTION 125
6.2 MATERIALS AND
METHODS 125
6.2.1 MATERIALS 125
6.2.2 TRANSFORMATION OF E.
COLI 126
6.2.3 GENERAL PROCEDURES
FOR PREPARATION
OF PLASMID ONA 127
6.2.3.1 MINI- AND
MAXL-PREP 127
6.2.3.2 RESTRICTION ENZYME
DIGESTION AND
DEPHOSPHORYLATION OF PLASMID
ENDS 127
6.2.3.3 AGAROSE GEL
ELECTROPHORESIS 127
6.2.3.4 PURIFICATION OF PCR PRODUCTS AND
RECOVERY OF DNA FRAGMENTS
FROM AGAROSE
GELS.
128
6.2.4 PREPARATION OF THE S-ABCG2 CONSTRUCT
VIA SEQUENTIAL
OVERLAP EXTENSION
PCR 128
6.2.4.1 PCR LA FOR THE
S-ABCG2 CONSTRUCT 130
6.2.4.2 PCR LB FOR THE
S-ABCG2 CONSTRUCT 131
6.2.4.3 PCR 2 FOR THE
S-ABCG2 CONSTRUCT 131
6.2.5 PREPARATION OF THE S-ABCB1
CONSTRUCT 132
6.2.6 SUBDONING OF THE S-ABCB1
AND THE
S-ABCG2 CONSTRUCT INTO
PVL1392 VECTOR 134
6.2.7 SF9 INSECT CELL
CULTURE AND
GENERATION OF RECOMBINANT BACULOVIRUSES 135
6.2.8 RECOMBINANT TRANSPORTER EXPRESSION
IN PVL1392/S-ABCG2-LNFECTED SF9
CELLS 136
6.2.8.1 IMMUNOLOGICAL DETECTION
OF ABCG2
EXPRESSION 136
6.2.8.2 MEMBRANE PREPARATION 136
6.2.9 ATPASE ASSAY FOR THE
HUMAN BCRP 137
6.2.9.1 PRINCIPLE 137
6.2.9.2 ATPASE ASSAY PROTOCOL 138
6.3 RESULTS AND
DISCUSSION 142
6.3.1 RESULTS OF DNA SEQUENCING 142
6.3.2 ABCG2 EXPRESSION
IN SF9
CELLS 144
6.3.2.1 INFECTION
TIME 144
6.3.2.2 GLYCOSYLATION OF THE ABCG2 TRANSPORTER 146
6.3.3 OPTIMIZATION,
VALIDATION AND
APPLICATION OF THE ABCG2 ATPASE ASSAY 148
6.3.3.1 SET-UP OF THE ATPASE ASSAY FOR
THE HUMAN
BCRP 148
6.3.3.2 MODE OF ATPASE INHIBITION 150
6.3.3.3 CHOLESTEROL-LOADED ABCG2
SF9 MEMBRANES 153
6.3.3.4 EFFECT OF CHAPS
ON BASAL AND
DRUG-STIMULATED ABCG2-ATPASE ACTIVITY 154
6.4 SUMMARY AND
CONCLUSIONS 158
CONTENTS XIII
6.5 REFERENCES 159
7 SUMMARY 163
A APPENDIX: EXPRESSION OF ABCG2 AT THE MURINE BLOOD-BRAIN BARRIER -
IMMUNOHISTOCHEMICAL INVESTIGATIONS 167
A.1 INTRODUCTION 167
A.2 MATERIALS AND
METHODS 168
A.2.1 DRUGS AND
CHEMICALS 168
A.2.2 PARAFFIN EMBEDDING
AND SECTIONING 168
A.2.3 IMMUNOPEROXIDASE STAINING 168
A.3 RESULTS 169
A.4 SUMMARY AND
CONCLUSIONS 171
A.5 REFERENCES 171 |
| any_adam_object | 1 |
| author | Bauer, Stefanie |
| author_facet | Bauer, Stefanie |
| author_role | aut |
| author_sort | Bauer, Stefanie |
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| building | Verbundindex |
| bvnumber | BV041733139 |
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| collection | ebook |
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| 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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| physical | XVI, 171 S. Ill., graph. Darst. |
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| spelling | Bauer, Stefanie Verfasser aut Quinoline carboxamides as modulators of Breast Cancer Resistance Protein (ABCG2) Investigations on potency, selectivity, mechanism of action, cytotoxicity, stability and drug-like properties von Stefanie Bauer 2014 XVI, 171 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Regensburg, Univ., Diss., 2014 Chinolinderivate (DE-588)4147702-9 gnd rswk-swf ABC-Transporter (DE-588)4472594-2 gnd rswk-swf Amide (DE-588)4279702-0 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Chinolinderivate (DE-588)4147702-9 s Amide (DE-588)4279702-0 s ABC-Transporter (DE-588)4472594-2 s DE-604 Erscheint auch als Online-Ausgabe urn:nbn:de:bvb:355-epub-295899 http://epub.uni-regensburg.de/29589/ Verlag kostenfrei Volltext https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-295899 Resolving-System DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027179882&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Bauer, Stefanie Quinoline carboxamides as modulators of Breast Cancer Resistance Protein (ABCG2) Investigations on potency, selectivity, mechanism of action, cytotoxicity, stability and drug-like properties Chinolinderivate (DE-588)4147702-9 gnd ABC-Transporter (DE-588)4472594-2 gnd Amide (DE-588)4279702-0 gnd |
| subject_GND | (DE-588)4147702-9 (DE-588)4472594-2 (DE-588)4279702-0 (DE-588)4113937-9 |
| title | Quinoline carboxamides as modulators of Breast Cancer Resistance Protein (ABCG2) Investigations on potency, selectivity, mechanism of action, cytotoxicity, stability and drug-like properties |
| title_auth | Quinoline carboxamides as modulators of Breast Cancer Resistance Protein (ABCG2) Investigations on potency, selectivity, mechanism of action, cytotoxicity, stability and drug-like properties |
| title_exact_search | Quinoline carboxamides as modulators of Breast Cancer Resistance Protein (ABCG2) Investigations on potency, selectivity, mechanism of action, cytotoxicity, stability and drug-like properties |
| title_full | Quinoline carboxamides as modulators of Breast Cancer Resistance Protein (ABCG2) Investigations on potency, selectivity, mechanism of action, cytotoxicity, stability and drug-like properties von Stefanie Bauer |
| title_fullStr | Quinoline carboxamides as modulators of Breast Cancer Resistance Protein (ABCG2) Investigations on potency, selectivity, mechanism of action, cytotoxicity, stability and drug-like properties von Stefanie Bauer |
| title_full_unstemmed | Quinoline carboxamides as modulators of Breast Cancer Resistance Protein (ABCG2) Investigations on potency, selectivity, mechanism of action, cytotoxicity, stability and drug-like properties von Stefanie Bauer |
| title_short | Quinoline carboxamides as modulators of Breast Cancer Resistance Protein (ABCG2) |
| title_sort | quinoline carboxamides as modulators of breast cancer resistance protein abcg2 investigations on potency selectivity mechanism of action cytotoxicity stability and drug like properties |
| title_sub | Investigations on potency, selectivity, mechanism of action, cytotoxicity, stability and drug-like properties |
| topic | Chinolinderivate (DE-588)4147702-9 gnd ABC-Transporter (DE-588)4472594-2 gnd Amide (DE-588)4279702-0 gnd |
| topic_facet | Chinolinderivate ABC-Transporter Amide Hochschulschrift |
| url | http://epub.uni-regensburg.de/29589/ https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-295899 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027179882&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT bauerstefanie quinolinecarboxamidesasmodulatorsofbreastcancerresistanceproteinabcg2investigationsonpotencyselectivitymechanismofactioncytotoxicitystabilityanddruglikeproperties |