Bioorganometallics: biomolecules, labeling, medicine
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| Format: | Buch |
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| Sprache: | English |
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Wiley-VCH
2006
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| Beschreibung: | XVIII, 444 S. Ill., graph. Darst. |
| ISBN: | 352730990X 9783527309900 |
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| 245 | 1 | 0 | |a Bioorganometallics |b biomolecules, labeling, medicine |c ed. by Gérard Jaouen |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2006 | |
| 300 | |a XVIII, 444 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 4 | |a Metallorganische Chemie - Biomolekül | |
| 650 | 4 | |a Metallorganische Verbindungen - Pharmazeutische Chemie | |
| 650 | 4 | |a Bioorganic chemistry | |
| 650 | 4 | |a Organometallic Compounds |x chemistry | |
| 650 | 4 | |a Organometallic Compounds |x pharmacology | |
| 650 | 4 | |a Organometallic Compounds |x therapeutic use | |
| 650 | 4 | |a Organometallic compounds | |
| 650 | 4 | |a Organometallic compounds |x Physiological effect | |
| 650 | 4 | |a Pharmaceutical Preparations | |
| 650 | 0 | 7 | |a Pharmazeutische Chemie |0 (DE-588)4132158-3 |2 gnd |9 rswk-swf |
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Datensatz im Suchindex
| _version_ | 1804133563246837760 |
|---|---|
| adam_text | I VII
Contents
Preface V
List of Contributors XVII
1 A Novel Field of Research:
Bioorganometallic Chemistry, Origins, and Founding Principles 1
drardJaouen, Wolfgang Beck, and Michael J. McGlinchey
1.1 Introduction 1
1.2 Organometallics and Therapy 4
1.2.1 The Founding Father 4
1.2.2 The First Significant Organometallic Drug 5
1.2.3 Arsenic Compounds after Ehrlich 6
1.2.4 Organometallic Mercury Compounds 7
1.2.5 The Current Re evaluation:
Considerations of Efficacy, Toxicity and Selectivity 7
1.3 Toxicology and the Environment 10
1.4 Bioanalytical Methods Based on Special Properties of Organometallic
Complexes 12
1.5 Naturally occurring Organometallics and Synthetic Models 17
1.6 Organometallic Chemistry and Aqueous Solvents 26
1.7 Conclusions 30
References 31
2 Ruthenium Arene Anticancer Complexes 39
Michael Melchart and Peter J. Sadler
2.1 Introduction 39
2.2 Metal based Anticancer Complexes 40
2.3 Chemistry of Ru Arenes 42
2.3.1 Synthesis 42
2.3.2 Structure 45
2.3.3 Chirality 46
Bioorganometallics: Biomokculcs. Labeling, Medicine. Edited by Gerard Jaouen
Copyright © 2006 Wiley VCH Verlag GmbH Co. KGaA, Weinhcim
ISBN: 3 527 3O99O X
VIIII Contents
2.4 Biological Activity 47
2.4.1 Antibacterial 47
2.4.2 Anticancer 47
2.4.3 Biodistribution and Metabolism 49
2.5 Mechanism of Action 50
2.5.1 Nucleobase and DNA Binding 50
2.5.2 Amino Acids and Proteins 58
2.5.3 Aquation 60
2.6 Conclusions 61
References 62
3 Organometallics Targeted to Specific Biological Sites:
the Development of New Therapies 65
Gerard Jaouen, Siden Top, and Anne Vessieres
3.1 Introduction 65
3.2 Overview of Previous Developments 66
3.3 Metal Complex SERMs (Selective Estrogen Receptor Modulators) 68
3.3.1 Inorganic Complexes of Platinum 69
3.3.2 Carborane Derivatives with Estrogenic Properties 70
3.3.3 Titanocene Dichloride Derivative of Tamoxifen 72
3.3.4 Cyclopentadienyl Rhenium Tricarbonyl Derivatives of Tamoxifen
Derivatives 74
3.3.5 Ferrocene Tamoxifen Derivatives (Ferrocifens) 76
3.3.6 Ruthenocene Tamoxifen Derivatives 79
3.3.7 Conclusion for SERMs 80
3.4 The Alkyne Cobalt Carbonyl Complexes 80
3.5 Ferroquine, a New Weapon in the Fight Against Malaria:
the Archetypical Bioorganometallic Approach 82
3.5.1 The Problem of Malaria 82
3.5.2 Ferroquine: a Bioorganometallic Approach 84
3.5.3 Conclusion for Ferroquine 86
3.6 Other Examples of Organometallics Complexes Tested for their
Biological Activities 86
3.7 Conclusion 87
References 90
4 Radiopharmaceuticals 97
Roger Alberto
4.1 What are Radiopharmaceuticals? 97
4.1.1 Radiopharmaceutical Drug Finding and Drug Development 99
4.1.2 Organometallic Complexes in Radiopharmaceutical Routines 101
4.2 Organometallic Aquo ions 103
Contents I IX
4.3 The Prototype [99Tc(OH2)3(CO)3]+, Synthesis and Properties 106
4.3.1 Coordination Chemistry with [99Tc(OH2)3(CO)3]+ 109
4.3.2 Organometallic Chemistry in Water with [99Tc(OH2)3(CO)3]+ 115
4.4 Combining [99Tc(OH2)3(CO)3]+ with Targeting Vectors 118
4.5 Perspectives 121
References 122
5 Conjugates of Peptides and PNA with Organometallic Complexes:
Syntheses and Applications 125
Nils Metzler Nolte
5.1 Introduction 125
5.2 Conjugates of Organometallics with Small Peptides 127
5.2.1 Organometallics as Templates for the Induction of Secondary
Structural Elements in Peptides 128
5.2.1.1 Derivatives of l,l Ferrocene Dicarboxylic Acid 128
5.2.1.2 Other Derivatives 134
5.2.2 Peptides as Ligands for Organometallics 136
5.3 Conjugates of Organometallics with Natural Peptides 139
5.3.1 Organometallic Derivatives of Enkephalins 140
5.3.2 Organometallic Derivatives of Peptide Hormones 142
5.3.2.1 Substance P and Neurokinin A 142
5.3.2.2 Angiotensin 144
5.3.2.3 Bradykinin 146
5.3.2.4 Gonadotropin releasing Hormone 146
5.3.2.5 Secretin 147
5.3.3 Organometallic Derivatives of Other Peptides 148
5.3.3.1 Nuclear Localization Signal 148
5.3.3.2 Glutathione 148
5.3.3.3 Papain Inhibitors 149
5.3.3.4 Alamethicin 150
5.3.3.5 Others 150
5.3.4 Enzymatic Degradation of Organometallic Peptide Derivatives 152
5.4 Conjugates of Organometallics with PNA 153
5.4.1 Conjugates of PNA Monomers 153
5.4.2 Conjugates of PNA Oligomers 158
5.5 Applications 159
5.5.1 Organometallic Protecting Groups for Peptide Synthesis 159
5.5.1.1 Ferrocene derived Protecting Groups 159
5.5.1.2 Aminocarbene derived Protecting Groups 160
5.5.2 Peptide Synthesis 162
5.5.2.1 Template Synthesis of Peptides with Organometallics 162
5.5.2.2 Ugi Four component Reaction 163
5.5.2.3 Ruthenium mediated Coupling of Aryl Ethers for the Synthesis
of Cyclic Peptides 164
XI Contents
5.5.3 Labeling of Peptides 166
5.5.3.1 HPLC with Electrochemical Detection (HPLC ECD) 266
5.5.3.2 Radioactive Labels 168
5.5.4 Host guest Chemistry and Biosensors 170
References 173
6 Labeling of Proteins with Organometallic Complexes:
Strategies and Applications 181
Michele Salmain
6.1 Introduction 181
6.2 Redox Probes 182
6.2.1 Amperometric Biosensors 182
6.2.1.1 Diffusional Mediators 183
6.2.1.2 Electron Relays 184
6.2.1.3 Electrical Wiring 188
6.2.2 HPLC and Immunoassays 190
6.2.3 Enzyme Structural Studies 191
6.2.4 Other applications 192
6.3 Luminescent Probes 193
6.3.1 Long lived Probes 193
6.3.2 Electron Tunneling Studies 195
6.4 Heavy Metal Probes 196
6.4.1 Structural Analysis of Proteins by X ray Crystallography 196
6.4.2 Cryo electron Microscopy 201
6.4.3 Pharmacological Studies 201
6.5 Metallo carbonyl Probes for Infrared Spectroscopy 202
6.6 Conclusions and Outlook 208
References 210
7 Organometallic Bioprobes 215
C. Richard Stephenson
7.1 Introduction 215
7.2 The Definition of the Terms Bioprobes and Molecular Bioprobes 225
7.3 Response Strategies for the Read out of Information 217
7.4 Organometallic Components for Organometallic Bioprobes
Opening up the Advantages of IR based Read out Methods 220
7.5 Selectivity of Responses in IR based Read out Methods 226
7.5.1 Solvent induced Effects 227
7.5.2 Responses to pH 230
7.5.3 Responses to Alkali Metal Ion Concentrations 233
7.5.4 Responses to n stacking Interactions between Organic Structures 235
7.6 Examples of Organometalcarbonyl Bioprobe Structures 237
7.7 Use of Organometallic Bioprobes with Proteins 242
Contents I XI
7.8 Power of Genetics in the Design of Bioprobe Experiments 247
7.8.1 Remote and Local Response Capabilities 248
7.8.2 Functional and Dysfunctional Probes 250
7.8.3 Functional and Dysfunctional Receptors 250
7.8.4 Functional and Dysfunctional Probes and Receptors to Study
the Induction of nod Gene Expression 250
7.9 Conclusions 254
References 255
8 Organometallic Complexes as Tracers in Non isotopic Immunoassay 263
Michele Salmain and Anne Vessieres
8.1 Introduction 263
8.2 Principle of an Immunoassay 264
8.3 Obtaining Specific Antibodies 266
8.4 Synthesis of the Organometallic Tracers 267
8.4.1 Preparation of Tracers Labeled with Ferrocene 267
8.4.1.1 Preparation of a Tracer for Lidocaine 271
8.4.1.2 Preparation of a Tracer for Theophylline 271
8.4.1.3 Preparation of a Tracer for Triiodothyronine 271
8.4.1.4 Labeling of Antibodies (IgG) 272
8.4.2 Preparation of a Tracer for Diphenylhydantoin Labeled with a
(Cyclopentadienyl)dicarbonyl Iron (Fp) Entity 272
8.4.3 Synthesis of Tracers Labeled with a Cymantrene
(Cyclopentadienyl Manganese Tricarbonyl) Entity 273
8.4.3.1 Preparation of Tracers for Nortriptyline and Phenobarbital 273
8.4.3.2 Preparation of a Tracer for Chlortoluron 273
8.4.3.3 Preparation of a Tracer for Biotin 274
8.4.4 Synthesis of Diphenylhydantoin Bearing a Benchrotrene
(Benzene chromium Tricarbonyl) Entity 275
8.4.5 Synthesis of Tracers Bearing an Alkyne Dicobalt Hexacarbonyl
Moiety 275
8.4.5.1 Preparation of Tracers for Cortisol and Atrazine 275
8.4.5.2 Preparation of a Tracer for Carbamazepine 277
8.4.6 Synthesis of Cationic Tracers 278
8.4.6.1 Tracers Labeled with a Cobaltocenium Entity 278
8.4.6.2 Cationic Tracers Including a Ferrocene Entity 279
8.4.7 Synthesis of a Tracer Bearing a Rhenium Tricarbonyl Fragment 280
8.5 Examples of Mono and Multi metalloimmunoassays (MIA) 281
8.5.1 Metalloimmunoassay Using Atomic Absorption Spectroscopy 281
8.5.2 Detection by Fourier transform Infrared Spectroscopy
(Carbonyl Metalloimmuno Assay, CM I A) 283
8.5.2.1 Mono immunoassays by CMIA 285
8.5.2.2 Multi immunoassay by CMIA 286
8.5.2.3 New Developments in the CMIA Method 287
XIII Contents
8.5.3 Electrochemical Detection 288
8.5.3.1 Homogeneous Ferrocene mediated Amperometric Immunoassay 288
8.5.3.2 Homogeneous Electrochemical Immunoassay
(Square Wave Voltammetry) 289
8.5.3.3 Electrochemical Flow Immunoassay System 291
8.5.4 Detection by Fluorescence Polarization (FP) 293
8.6 Use of Organometallic Complexes as Substrates or Co substrates
for Enzyme Immunoassay 294
8.6.1 Organometallic Complexes Used as Enzyme Substrates 294
8.6.2 Organometallic Complexes Used as Enzyme Co substrates
(Redox Mediators) 295
8.6.2.1 Flow Injection Immunoassay with Electrochemical Detection 295
8.6.2.2 Dual Enzyme Immunoassay with Amperometric Detection 296
8.6.2.3 Dual Enzyme Immunoassay Using Electrochemical Microscopy
Detection 297
8.7 Conclusion 298
References 300
9 Cenosensors Based on Metal Complexes 303
Shigeori Takenaka
9.1 Introduction 303
9.2 Metal Complexes as DNA Probes 303
9.2.1 Cationic Metal Complexes 303
9.2.2 Metal Complexes Conjugated with a DNA Fragment or DNA binding
Ligand 305
9.3 Electrochemical Analysis of the Interaction of Metal Complexes with
dsDNA 306
9.4 Gene Detection Based on a Cationic Metal Complex or Metal Complex
Conjugated with DNA binding Ligand 308
9.5 Gene Detection Based on Ferrocenyl Oligonucleotides as a Metal
Complex Conjugated with DNA Fragments 312
9.6 Conclusion 317
References 318
10 Supramolecular Host Recognition Processes with Biological Compounds,
Organometallic Pharmaceuticals, and Alkali metal Ions as Guests 321
Richard H. Fish
10.1 Introduction 321
10.2 Host 1 323
10.2.1 Synthesis, Structure, and Aqueous Stability 323
10.2.2 Molecular Recognition of Aromatic and Aliphatic Amino Acids 324
10.2.3 Molecular Recognition of Substituted Aromatic Carboxylic Acids 328
10.2.4 Molecular Recognition of Aromatic and Aliphatic Carboxylic Acids 329
10.2.5 Discussion of the Molecular Recognition Process with Host 1 332
Contents I XIII
10.2.6 Conclusions for Host 1: Non covalent Interactions with Various
Guests 333
10.3 A New Host,
trans [Cp*RhTi1 (N3) l methylcytosine)(|i OH)]2(OTf)2 2 334
10.3.1 Molecular Recognition Studies with Aromatic Amino Acids:
H bonding as the Critical Recognition Parameter 334
10.3.2 Conclusions for Molecular Recognition with Host 2 338
10.4 Computer Docking Experiments of Organometallic Pharmaceuticals
at Estrogen Receptor Binding Sites: Selective, Non Covalent
Interactions with Hormone Proteins 338
10.5 Organometallic Ionophores 342
10.5.1 Structure and Selectivity to Alkali Metal Ions 342
10.5.2 Specific Fluoride Receptors 348
10.5.3 Conclusions for Organometallic Ionophores 350
10.6 Overall Conclusions for Molecular Recognition 350
References 351
11 Structure and Mechanism of Metalloenzyme Active Sites 353
Juan C. Fontecilla Camps
11.1 Introduction 353
11.2 Copper 354
11.2.1 Quercentine 2,3 dioxygenase 354
11.2.2 Amines Oxidases 355
11.2.3 CuZn Superoxide Dismutases (SOD) 356
11.2.4 Multicopper Oxidases 357
11.2.4.1 Laccases 357
11.2.4.2 Nitrous Oxide Reductase (NOR) 358
11.2.4.3 Copper Homeostasis 359
11.3 Iron 359
11.3.1 Cytochrome c Oxidase (COX) 360
11.3.2 Oxygenases 361
11.3.3 Ribonucleotide Reductase (RR) 363
11.3.4 S adenosyl Methionine (SAM) dependent Radical Enzymes 364
11.4 Manganese 366
11.4.1 Superoxide Dismutases 366
11.4.2 Phosphoprotein Phosphatases (PPPs) 367
11.4.3 Oxalate Decarboxylases (Pyruvate Carboxylase) 368
11.4.4 Arginases 369
11.4.5 The Photosynthetic Oxygen evolving Center (OEC) of
Photosystem II (PSII) 370
11.5 Molybdenum and Tungsten 371
11.5.1 DMSO Reductase Family 372
11.5.2 Xanthine Oxidoreductase (XOR) Family 374
11.5.3 Sulfite Oxidase Family 3 75
XIV Contents
11.5.4 Aldehyde Ferredoxin Oxidoreductase Family 376
11.5.5 Carbon Monooxide Dehydrogenase (CODHMo) 377
11.6 Nickel 378
11.6.1 Carbon Monoxide Dehydrogenase 378
11.6.2 Acetyl Coenzyme A synthase (ACS) 380
11.6.3 NiFe Hydrogenases 384
11.7 Zinc 385
11.7.1 Carbonic Anhydrases (CA) 386
11.7.2 Alcohol Dehydrogenases (ADH) 387
11.7.3 Metallo (3 lactamases 389
11.7.4 Alkaline Phosphatases 390
11.7.5 Metallopeptidases 390
11.7.6 Other Zn dependent Enzymes 391
11.7.6.1 D aminoacylase 391
11.7.6.2 GTP Cyclohydrolase I 392
11.7.6.3 Enzymes Containing Zn S Bonds 392
11.8 Conclusions 393
References 393
12 Synthetic Models for Bioorganometallic Reaction Centers 403
Rachel C. Linck and Thomas B. Rauchfuss
12.1 Introduction 403
12.2 Fe only Hydrogenase 404
12.2.1 Overview 404
12.2.2 Structure of the Active Site 404
12.2.3 Proposed Mechanism 406
12.2.4 Fundamental Chemistry of Fe2(SR)2(CO)6, Including
Cyano Derivatives 406
12.2.5 Modeling the Azadithiolate Cofactor 408
12.2.6 Reactions of Model Complexes with H2 409
12.2.7 H2 Production Catalysts 409
12.2.8 Modeling Diferrous Dithiolates 411
12.3 NiFe Hydrogenases 412
12.3.1 Overview 412
12.3.2 Structure of the Active Site 412
12.3.3 Proposed Mechanism 423
12.3.4 Models for the Fe Site 414
12.3.5 Structural Models for the Bimetallic Site 415
12.3.6 Functional Models 417
UA Acetyl CoA Synthase 418
12.4.1 Overview 418
12.4.2 Structure of the Active Site 418
12.4.3 Proposed Mechanism 419
12.4.4 Spectroscopic Models for Proximal Nickel 419
Contents I XV
12.4.5 Structural Models for the Dinickel Site 420
12.4.6 Functional Models 421
12.4.6.1 Transmetalation of Methyl 421
12.4.6.2 Thioester Forming Steps 422
12.5 Anaerobic Carbon Monoxide Dehydrogenase 422
12.5.1 Overview 422
12.5.2 Structure of the Active Site 423
12.5.3 Proposed Mechanisms 423
12.5.4 Functional Studies 424
12.5.5 Structural Models 424
12.6 Aerobic Carbon Monoxide Dehydrogenase 425
12.6.1 Overview 425
12.6.2 Structure of the Active Sites and Proposed Mechanisms 425
12.6.3 Structural and Functional Models 426
12.7 Methyl Coenzyme M Reductase 427
12.7.1 Overview 427
12.7.2 Structure of the Active Site 427
12.7.3 Proposed Mechanism 428
12.7A Structural/Functional Models 429
12.8 Conclusions 430
References 431
Subject Index 437
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| id | DE-604.BV020008128 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T20:10:42Z |
| institution | BVB |
| isbn | 352730990X 9783527309900 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-013329739 |
| oclc_num | 254469166 |
| open_access_boolean | |
| owner | DE-703 DE-19 DE-BY-UBM DE-91G DE-BY-TUM DE-20 DE-29T DE-83 DE-11 DE-188 |
| owner_facet | DE-703 DE-19 DE-BY-UBM DE-91G DE-BY-TUM DE-20 DE-29T DE-83 DE-11 DE-188 |
| physical | XVIII, 444 S. Ill., graph. Darst. |
| publishDate | 2006 |
| publishDateSearch | 2006 |
| publishDateSort | 2006 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Bioorganometallics biomolecules, labeling, medicine ed. by Gérard Jaouen Weinheim Wiley-VCH 2006 XVIII, 444 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Metallorganische Chemie - Biomolekül Metallorganische Verbindungen - Pharmazeutische Chemie Bioorganic chemistry Organometallic Compounds chemistry Organometallic Compounds pharmacology Organometallic Compounds therapeutic use Organometallic compounds Organometallic compounds Physiological effect Pharmaceutical Preparations Pharmazeutische Chemie (DE-588)4132158-3 gnd rswk-swf Metallorganische Verbindungen (DE-588)4038906-6 gnd rswk-swf Biomolekül (DE-588)4135124-1 gnd rswk-swf Metallorganische Chemie (DE-588)4602390-2 gnd rswk-swf Metallorganische Chemie (DE-588)4602390-2 s Biomolekül (DE-588)4135124-1 s DE-604 Metallorganische Verbindungen (DE-588)4038906-6 s Pharmazeutische Chemie (DE-588)4132158-3 s Jaouen, Gérard Sonstige (DE-588)130516546 oth HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013329739&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Bioorganometallics biomolecules, labeling, medicine Metallorganische Chemie - Biomolekül Metallorganische Verbindungen - Pharmazeutische Chemie Bioorganic chemistry Organometallic Compounds chemistry Organometallic Compounds pharmacology Organometallic Compounds therapeutic use Organometallic compounds Organometallic compounds Physiological effect Pharmaceutical Preparations Pharmazeutische Chemie (DE-588)4132158-3 gnd Metallorganische Verbindungen (DE-588)4038906-6 gnd Biomolekül (DE-588)4135124-1 gnd Metallorganische Chemie (DE-588)4602390-2 gnd |
| subject_GND | (DE-588)4132158-3 (DE-588)4038906-6 (DE-588)4135124-1 (DE-588)4602390-2 |
| title | Bioorganometallics biomolecules, labeling, medicine |
| title_auth | Bioorganometallics biomolecules, labeling, medicine |
| title_exact_search | Bioorganometallics biomolecules, labeling, medicine |
| title_full | Bioorganometallics biomolecules, labeling, medicine ed. by Gérard Jaouen |
| title_fullStr | Bioorganometallics biomolecules, labeling, medicine ed. by Gérard Jaouen |
| title_full_unstemmed | Bioorganometallics biomolecules, labeling, medicine ed. by Gérard Jaouen |
| title_short | Bioorganometallics |
| title_sort | bioorganometallics biomolecules labeling medicine |
| title_sub | biomolecules, labeling, medicine |
| topic | Metallorganische Chemie - Biomolekül Metallorganische Verbindungen - Pharmazeutische Chemie Bioorganic chemistry Organometallic Compounds chemistry Organometallic Compounds pharmacology Organometallic Compounds therapeutic use Organometallic compounds Organometallic compounds Physiological effect Pharmaceutical Preparations Pharmazeutische Chemie (DE-588)4132158-3 gnd Metallorganische Verbindungen (DE-588)4038906-6 gnd Biomolekül (DE-588)4135124-1 gnd Metallorganische Chemie (DE-588)4602390-2 gnd |
| topic_facet | Metallorganische Chemie - Biomolekül Metallorganische Verbindungen - Pharmazeutische Chemie Bioorganic chemistry Organometallic Compounds chemistry Organometallic Compounds pharmacology Organometallic Compounds therapeutic use Organometallic compounds Organometallic compounds Physiological effect Pharmaceutical Preparations Pharmazeutische Chemie Metallorganische Verbindungen Biomolekül Metallorganische Chemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013329739&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT jaouengerard bioorganometallicsbiomoleculeslabelingmedicine |