Synthesis and structure-activity relationships of inhibitors of bacterial hyaluronidase: An approach to obtain compounds with drug-like properties
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
2014
|
| Schlagworte: | |
| Online-Zugang: | kostenfrei https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-298551 Inhaltsverzeichnis |
| Beschreibung: | VIII, 176 S. Ill., graph. Darst. |
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| adam_text | SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS
OF INHIBITORS OF BACTERIAL HYALURONIDASE:
AN APPROACH TO OBTAIN COMPOUNDS
WITH
DRUG-LIKE PROPERTIES
DISSERTATION
ZUR ERIANGUNG DES DOKTORGRADES DER NATURWISSENSCHAFTEN (DR. RER. NAT.)
DER FAKULTAT FUR PHARMAZIE UND CHEMIE
DER UNIVERSITAT REGENSBURG
VORGELEGT VON
CAROTIN MEYER
AUS BAD SODEN-SALMUNSTER
2014
HTTP://D-NB.INFO/105220256X
CONTENTS
V
CONTENTS
1 INTRODUCTION 1
1.1 HYALURONIC ACID 2
1.1.1 STRUCTURE AND PHYSICOCHEMICAL PROPERTIES 2
1.1.2 HYALURONAN METABOLISM AND PHYSIOLOGICAL FUNCTIONS 3
1.2 HYALURONIDASES 3
1.2.1 OCCURRENCE AND CLASSIFICATION 3
1.2.2 HYALURONIDASES FROM EUKARYOTES 5
1.2.3 HYALURONIDASES FROM PROKARYOTES 6
1.2.4 HYALURONIDASE INHIBITORS 8
1.3 METHODS FOR THE DETERMINATION OF HYALURONIDASE ACTIVITY 9
1.3.1 MORGAN-ELSON ASSAY 10
1.3.2 TURBIDIMETRIC ASSAY 12
1.4 INFLUENCE OF THE PH VALUE ON ENZYMATIC ACTIVITY 12
1.5 REFERENCES 14
2 SCOPE AND OBJECTIVES 23
3 SCREENING OF COMMERCIALLY AVAILABLE DRUGS FOR HYALURONIDASE INHIBITION
25
3.1 INTRODUCTION 26
3.2 MATERIALS AND METHODS 27
3.2.1 MATERIALS AND METHODS 27
3.2.2 MORGAN-ELSON ASSAY 27
3.2.2.1 GENERAL PROCEDURES 27
3.2.2.2 CALCULATION OF ENZYME INHIBITION AND IC50 VALUES 29
3.2.3 TURBIDIMETRIC ASSAY 29
3.2.3.1 GENERAL PROCEDURES 29
3.2.3.2 CUVETTE ASSAY 30
3.2.3.3 96-WELL MICROTITER PLATE ASSAY 30
3.2.3.4 COMPOUND SOLUBILITY 31
3.2.3.5 CALCULATION OF ENZYME INHIBITION AND
IC50
VALUES 31
3.2.3.6 DETERMINATION OF TURBIDITY IN THE INCUBATION MIXTURE THE
PRESENCE OF PLASMA
PROTEINS 32
3.3 INHIBITORY ACTIVITY OF SELECTED NON-STEROIDAL ANTI-INFLAMMATORY
DRUGS 32
3.3.1 SALICYLATES 32
3.3.2 ACETIC ACID DERIVATIVES 34
3.3.3 PROPIONIC ACID DERIVATIVES 36
3.3.4 W-ANTHRANILIC ACIDS AND
CELECOXIB 38
VI CONTENTS
3.3.5 MISCELLANEOUS COMPOUNDS 39
3.4 INHIBITORY ACTIVITY OF DIFLUNISAL IN THE PRESENCE OF PLASMA PROTEINS
41
3.5 PEAK PLASMA CONCENTRATIONS OF COMMERCIAL DRUGS 46
3.6 SUMMARY AND CONCLUSION 48
3.7 REFERENCES 50
4 DIFLUNISAL ANALOGS AS INHIBITORS OF BACTERIAL HYALURONIDASE 53
4.1 INTRODUCTION 54
4.2 CHEMISTRY 56
4.3 PHARMACOLOGICAL RESULTS AND DISCUSSION . 58
4.3.1 GENERAL CONDITIONS 58
4.3.2 INHIBITORY ACTIVITIES OF BIPHENYL-2-CARBOXYLIC ACID DERIVATIVES 59
4.3.3 INHIBITORY ACTIVITIES OF BIPHENYL-3-CARBOXYLIC ACID DERIVATIVES 60
4.3.4 INHIBITORY ACTIVITIES OF BIPHENYL-4-CARBOXYLIC ACID DERIVATIVES 63
4.3.5 INHIBITORY ACTIVITIES OF 4-HYDROXYBIPHENYL-3-CARBOXYLIC ACID
ANALOGS 66
4.4 INHIBITORY ACTIVITIES OF SELECTED COMPOUNDS ON SPNHYL 69
4.5 INHIBITORY ACTIVITIES OF VITAMIN C PALMITATE IN THE PRESENCE OF
PALLADIUM CATALYST 70
4.6 SUMMARY AND CONCLUSION 71
4.7 EXPERIMENTAL SECTION 73
4.7.1 GENERAL CONDITIONS 73
4.7.2 CHEMISTRY 75
4.7.2.1 PREPARATION OF COMPOUNDS 4.24-4.46 75
4.8 REFERENCES 92
5 LNDOLE-2-CARBOXYLIC ACIDS AND 2-(6,7-DICHLORO-1
H-INDOL-2-YL)-1,3,4-
OXADIAZOLES AS INHIBITORS OF BACTERIAL HYALURONIDASES 95
5.1 INTRODUCTION 96
5.2 CHEMISTRY 99
5.2.1 SYNTHESIS OF 2-(6,7-DICHLORO-1
H-INDOL-2-YL)-1,3,4-OXADIAZOLES 99
5.2.2 SYNTHESIS OF 1
H-INDOLE-2-CARBOXYLIC ACID
COMPOUNDS 100
5.3 PHARMACOLOGICAL RESULTS AND DISCUSSION 102
5.3.1 GENERAL CONDITIONS 102
5.3.2 INHIBITION OF HYALURONIDASES BY 2-(1
H-INDOL-2-YL)-1,3,4-OXADIAZOLES 102
5.3.3 INHIBITION OF HYALURONIDASES BY 6,7-DICHLORO-1
H-INDOLE-2-CARBOXYLIC ACID DERIVATIVES.
103
5.3.4 INHIBITION OF HYALURONIDASES BY 5-BENZYLOXY- AND 5-HYDROXY-1
H-INDOLE-2-CARBOXYLIC
ACID DERIVATIVES 106
5.4 INHIBITORY ACTIVITIES OF SELECTED COMPOUNDS ON SPNHYL 108
5.5 SUMMARY 109
5.6 EXPERIMENTAL SECTION 110
5.6.1 GENERAL CONDITIONS 110
5.6.2 CHEMISTRY 110
CONTENTS VII
5.6.2.1 PREPARATION OF COMPOUNDS 5.1, 5.32 110
5.6.2.2 PREPARATION OF ETHYL 2-ACETYLPENTANOATE (5.3) 111
5.6.2.3 PREPARATION OF COMPOUNDS 5.4-5.5, 5.34-5.36 112
5.6.2.4 PREPARATION OF COMPOUNDS 5.6, 5.7, 5.37-5.39 113
5.6.2.5 PREPARATION OF COMPOUNDS 5.9-5.11 114
5.6.2.6 PREPARATION OF COMPOUNDS 5.12-5.14 115
5.6.2.7 PREPARATION OF FERT-BUTYL 4-(BROMOMETHYL)BENZOATE (5.15) 116
5.6.2.8 PREPARATION OF COMPOUNDS 5.16-5.21, 5.40-5.44 117
5.6.2.9 PREPARATION OF COMPOUNDS 5.22-5.31, 5.45-5.52, 5.60 120
5.6.2.10 PREPARATION OF COMPOUNDS 5.53-5.59 125
5.7 REFERENCES 128
6 2-PHENYLINDOLIZINES AS HYALURONIDASE INHIBITORS 131
6.1 INTRODUCTION 132
6.2 CHEMISTRY 133
6.3 PHARMACOLOGICAL RESULTS AND DISCUSSION 135
6.3.1 GENERAL CONDITIONS 135
6.3.2 INHIBITORY ACTIVITY OF 2-PHENYLINDOLIZINE COMPOUNDS 136
6.4 SUMMARY 138
6.5 EXPERIMENTAL SECTION 139
6.5.1 GENERAL CONDITIONS 139
6.5.2 CHEMISTRY 139
6.5.2.1 PREPARATION OF COMPOUNDS 6.4-6.6 139
6.5.2.2 PREPARATION OF ETHYL 2-METHYLISONICOTINOATE
30
6.8 140
6.5.2.3 PREPARATION OF COMPOUNDS 6.15-6.19 140
6.5.2.4 PREPARATION OF COMPOUNDS 6.20-6.22 142
6.5.2.5 PREPARATION OF COMPOUNDS 6.25, 6.26 144
6.6 REFERENCES 145
7 CHARACTERIZATION OF SNAKE VENOMS REGARDING HYALURONIDASE ACTIVITY 147
7.1 INTRODUCTION 148
7.2 MATERIALS AND METHODS 150
7.2.1 DETERMINATION OF PROTEIN CONTENT 150
7.2.2 SDS-POLYACRYLAMIDE GEL ELECTROPHORESIS (SDS-PAGE) 150
7.2.3 ZYMOGRAPHY 151
7.2.4 COLORIMETRIC HYALURONIDASE ACTIVITY ASSAY (MORGAN-ELSON ASSAY) 152
7.2.4.1 GENERAL PROCEDURES 152
7.2.4.2 DETERMINATION OF HYALURONIDASE ACTIVITY 152
7.2.5 TURBIDIMETRIC HYALURONIDASE ACTIVITY ASSAY 153
7.2.6 PLASMA PROTEIN BINDING 153
7.3 RESULTS AND DISCUSSION 154
7.3.1 PROTEIN CONTENT AND DETERMINATION OF MOLECULAR MASS 154
7.3.2 HYALURONIDASE ACTIVITY 155
W
7.3.3 INFLUENCE OF PH ON ENZYMATIC ACTIVITY 157
7.3.4 INHIBITORY ACTIVITIES OF SELECTED COMPOUNDS ON SNAKE VENOM
HYALURONIDASES 159
7.3.5 PLASMA PROTEIN BINDING OF SELECTED COMPOUNDS 161
7.4 SUMMARY AND CONCLUSION 163
7.5 REFERENCES 164
8 SUMMARY 167
9 APPENDIX 171
9.1 ABBREVIATIONS 172
|
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| spelling | Meyer, Carolin Verfasser aut Synthesis and structure-activity relationships of inhibitors of bacterial hyaluronidase An approach to obtain compounds with drug-like properties von Carolin Meyer 2014 VIII, 176 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Regensburg, Univ., Diss., 2014 Struktur-Aktivitäts-Beziehung (DE-588)4183784-8 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Inhibitor (DE-588)4027007-5 gnd rswk-swf Hyaluronidasen (DE-588)4204239-2 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Hyaluronidasen (DE-588)4204239-2 s Inhibitor (DE-588)4027007-5 s Chemische Synthese (DE-588)4133806-6 s DE-604 Struktur-Aktivitäts-Beziehung (DE-588)4183784-8 s Erscheint auch als Online-Ausgabe urn:nbn:de:bvb:355-epub-298551 http://epub.uni-regensburg.de/29855/ Verlag kostenfrei Volltext https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-298551 Resolving-System DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027269718&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Meyer, Carolin Synthesis and structure-activity relationships of inhibitors of bacterial hyaluronidase An approach to obtain compounds with drug-like properties Struktur-Aktivitäts-Beziehung (DE-588)4183784-8 gnd Chemische Synthese (DE-588)4133806-6 gnd Inhibitor (DE-588)4027007-5 gnd Hyaluronidasen (DE-588)4204239-2 gnd |
| subject_GND | (DE-588)4183784-8 (DE-588)4133806-6 (DE-588)4027007-5 (DE-588)4204239-2 (DE-588)4113937-9 |
| title | Synthesis and structure-activity relationships of inhibitors of bacterial hyaluronidase An approach to obtain compounds with drug-like properties |
| title_auth | Synthesis and structure-activity relationships of inhibitors of bacterial hyaluronidase An approach to obtain compounds with drug-like properties |
| title_exact_search | Synthesis and structure-activity relationships of inhibitors of bacterial hyaluronidase An approach to obtain compounds with drug-like properties |
| title_full | Synthesis and structure-activity relationships of inhibitors of bacterial hyaluronidase An approach to obtain compounds with drug-like properties von Carolin Meyer |
| title_fullStr | Synthesis and structure-activity relationships of inhibitors of bacterial hyaluronidase An approach to obtain compounds with drug-like properties von Carolin Meyer |
| title_full_unstemmed | Synthesis and structure-activity relationships of inhibitors of bacterial hyaluronidase An approach to obtain compounds with drug-like properties von Carolin Meyer |
| title_short | Synthesis and structure-activity relationships of inhibitors of bacterial hyaluronidase |
| title_sort | synthesis and structure activity relationships of inhibitors of bacterial hyaluronidase an approach to obtain compounds with drug like properties |
| title_sub | An approach to obtain compounds with drug-like properties |
| topic | Struktur-Aktivitäts-Beziehung (DE-588)4183784-8 gnd Chemische Synthese (DE-588)4133806-6 gnd Inhibitor (DE-588)4027007-5 gnd Hyaluronidasen (DE-588)4204239-2 gnd |
| topic_facet | Struktur-Aktivitäts-Beziehung Chemische Synthese Inhibitor Hyaluronidasen Hochschulschrift |
| url | http://epub.uni-regensburg.de/29855/ https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-298551 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027269718&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT meyercarolin synthesisandstructureactivityrelationshipsofinhibitorsofbacterialhyaluronidaseanapproachtoobtaincompoundswithdruglikeproperties |