Natural product chemistry for drug discovery:
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| Format: | Book |
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| Language: | English |
| Published: |
Cambridge
Royal Society of Chemistry
2010
|
| Series: | RSC biomolecular sciences
18 |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XVII, 440 S. Ill., graph. Darst. 24 cm |
| ISBN: | 9780854041930 0854041931 |
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| adam_text | Titel: Natural product chemistry for drug discovery
Autor: Buss, Antony D.
Jahr: 2010
Contents
Section 1 Introduction to Natural Products for Drug Discovery
Chapter 1 Natural Products as Drugs and Leads to Drugs: The
Historical Perspective
David J. Newman and Gordon M. Cragg
1 Ancient History ( 2900 BCE to 1800 CE) 3
2 The Initial Influence of Chemistry upon Drug Discovery 6
2.1 Alkaloids 6
2.2 Aspirin 8
2.3 Digitalis 9
3 20th and 21st Century Drugs/Leads from Nature 10
3.1 Antibacterial and Antifungal Antibiotics 10
3.2 Antiviral Agents 19
3.3 Natural Product Based Antitumour Agents 21
4 Final Comments 23
References 24
Chapter 2 Chemical Space and the Difference Between Natural Products
and Synthetics
Sheo B. Singh and J. Chris Culberson
1 Introduction 28
2 Sources of Organic Compounds and Drug Leads 29
2.1 Natural Products 29
2.2 Natural Product Derivatives 29
3 Synthetic Compounds 30
3.1 Synthetic Compound Libraries 30
3.2 Combinatorial Libraries 30
RSC Biomolecular Sciences No. 18
Natural Product Chemistry for Drug Discovery
Edited by Antony D. Buss and Mark S. Butler
© Royal Society of Chemistry 2010
Published by the Royal Society of Chemistry, www.rsc.org
Contents
3.3 Diversity-Oriented Synthetic (DOS)
Libraries 31
3.4 Fragment Libraries 31
4 Lipinski s Rule of Five for Orally Active
Drugs 32
5 Assessment of Diversity of Libraries with Respect
to Drugs 33
5.1 Molecular Weight 34
5.2 Distribution of Atom Types: H-bond Donors and
Acceptors 35
5.3 Lipophilicities (Log P) 37
5.4 Chiral Centres 37
5.5 Rotatable Bonds, Unsaturations, Rings, Chains
and Ring Topology 38
6 Principal Component Analysis (PCA) 39
7 Conclusions 40
References 42
Chapter 3 Mechanism of Action Studies
James J. La Clair
1 Introduction 44
2 Some Like It Hot: Esperamicin A,, Neocarzinostatin
and Related Enediyne Antibiotics 45
3 To Catch a Mockingbird: Taxol, Epothilone and the
Microtubule 47
4 Notorious: Jasplakinolide, Alias Jaspamide and
Actin 51
5 Invasion of the Pathway Snatchers: Artemisinin 53
6 Once Upon a Time in the Immune System: FK-506,
Cyclosporin A and Rapamycin 55
7 Back to the Cytoskeleton: the Phorboxazoles 56
8 It s a Wonderful Target: VTPase and its Targeting
by Apicularen A, Salicylihalamide A and
Palmerolide A 59
9 Double Indemnity: Bistramide A 61
10 The Matrix: the Pladienolides and Splicing Factor
SF3b 62
11 The Unusual Suspects: (+ )-Avrainvillamide 65
12 Close Encounters of a Third Kind: Ammosamides,
Blebbestatin and Myosin 67
13 The End 69
References 69
Contents
Section 2 Sources of Compounds
Chapter 4 The Convention on Biological Diversity and its Impact on
Natural Product Research
Geoffrey A. Cor dell
1 Introduction 81
2 Historical Perspective 85
3 The Convention on Biological Diversity 87
4 Implementation and Regulatory Outcomes of the CBD 92
5 Assessment of Impact 95
5.1 An Overview and Some Examples 95
5.2 An Informal Survey 100
5.3 Survey Results 101
5.4 Survey Overview 116
6 The TRIPS Agreement and the CBD 116
7 Other Aspects and Outcomes 7.1 The International Cooperative Biodiversity 123
Group Programme 125
8 Some Recommendations 127
9 A Web of Interconnectedness 130
10 A Different World 131
11 Conclusions 133
Acl mowledgements 134
References 135
Chapter 5 Plants: Revamping the Oldest Source of Medicines with
Modern Science
Giovanni Appendino and Federica Pollastro
1 Introduction 140
2 Plant Secondary Metabolites vs. Secondary Metabolites
of Other Origin 143
3 Unnatural Sources of Plant Secondary Metabolites 146
4 Critical Issues in Plant-based Natural Product Drug
Discovery 149
4.1 Intellectual Property (IP) Issues 149
4.2 Pleiotropy and Synergy 151
4.3 Extract Libraries vs. Fraction (Peak) Libraries vs.
Compound Libraries 153
4.4 Removal of Interfering Compounds 155
5 Selection Strategies for Plant-Based Natural Product
Drug Discovery 156
5.1 Ethnopharmacology 156
xii Contents
5.2 Zoopharmacy and Animal Toxicology 157
5.3 Traditional Medicine 158
5.4 Dietary Plants and Spices 159
6 The Pharmaceutical Relevance of Plants 161
6.1 Plants as a Source of Lead Structures and Drugs 161
6.2 Plants as a Source of Standardised Extracts 163
7 Conclusions 167
References 168
Chapter 6 Macromarines: A Selective Account of the Potential of
Marine Sponges, Molluscs, Soft Corals and Tunicates as a
Source of Therapeutically Important Molecular Structures
Jennifer Carroll and Phillip Crews
1 Introduction 174
1.1 Macroorganisms: Outstanding Success in
Producing Viable Drug Leads 175
1.2 Setting that Ara A and Ara C Story Straight 175
1.3 The Potential Role of Invertebrate Associated
Microorganisms and Secondary Metabolite
Production 176
1.4 Macromarine Evolution 176
2 Sponges 177
2.1 Natural History of Sponges?a Primitive
Phylum with Remarkable Biosynthetic
Capabilities 177
3 Molluscs 186
3.1 Natural History of Molluscs?the Source of
Numerous Preclinical Drug Leads 186
4 Soft Corals 189
4.1 Natural History of Cnidarians?the Stinging
Nettle of the Sea 189
5 Tunicates 192
5.1 Natural History of Tunicates?Our Closest
Marine Invertebrate Relations 192
6 Conclusions 194
References 195
Chapter 7 Microorganisms: Their Role in the Discovery and
Development of Medicines
Cedric Pearce, Peter Eckard, Iris Gruen-Wollny and
Friedrich G. Hansske
1 Introduction 215
2 Bacteria 218
3 Fungi 220
4 Terrestrial and Marine Microorganisms 221
Contents xiii
5 Microbial Culture Collections 222
6 Evidence for Uncultivable Microbes 223
7 Metagenomic Approach to Access Uncultivable
Microbes 224
8 Culturing Techniques to Produce Secondary
Metabolites 225
9 Evidence for New Biosynthetic Pathways in Known
Microbes 227
10 Genetic Pathway Engineering and Modulation of
Post-translational Modification to Generate Novel
Compounds 227
11 Microbial Secondary Metabolites with Unique
Biological Activity and Chemical Diversity 228
12 Microbial Secondary Metabolites with Unique
Pharmacological Activity 231
13 Conclusions 232
Structures Discussed in Tables 7.2 and 7.3 233
References 236
Section 3 Advances in Technology
Chapter 8 Advances in Biological Screening for Lead Discovery
Christian N. Parker, Johannes Ottl, Daniela Gabriel and
Ji-Hu Zhang
1 Introduction 245
1.1 Natural Product Screening and the Development
ofHTS 247
1.2 Chapter Objectives 247
2 Types of HTS Assays 247
2.1 In vitro Biochemical Assays 248
2.2 Cell-based Assays 255
2.3 Modelling to Identify False Positives and
Negatives 261
3 Emerging Trends 262
3.1 New HTS Approaches 262
Acknowledgements 265
References 265
Chapter 9 Advances in Instrumentation, Automation, Dereplication and
Prefractionation
Tim S. Bugni, Mary Kay Harper, Malcolm W.B. McCulloch
and Emily L. Whitson
1 Introduction 272
2 Dereplication 274
Contents
3 Extraction 275
4 Prefractionation 276
5 Isolation and Purification 278
5.1 Automated Purification 279
6 HPLC Separation Technologies 279
7 Mass Spectrometry 282
8 NMR 285
8.1 Probe Technology 285
8.2 Structure Elucidation 287
8.3 Methods for Fast NMR 288
8.4 Automated Structure Elucidation 290
8.5 Configuration by NMR 291
8.6 Residual Dipolar Couplings 292
9 Conclusions 292
References 293
Chapter 10 Natural Product Combinatorial Biosynthesis: Promises and
Realities
Daniel W. Udwary
1 Introduction 299
2 A Brief History of Natural Product
Biosynthesis 300
3 Promises 304
4 Realities 307
5 Future Biotechnological Promises 312
References 314
Section 4 Natural Products in Clinical Development
Chapter 11 A Snapshot of Natural Product-Derived Compounds in Late
Stage Clinical Development at the End of 2008
Mark S. Butler
1 Introduction 321
2 NP-derived Drugs Launched in the Last
Five Years 324
3 Late Stage NDAs and Clinical Candidates 327
3.1 Antibacterial 327
3.2 Oncology 332
3.3 Other Therapeutic Areas 340
4 Conclusions and Outlook 342
References 343
Contents xv
Chapter 12 From Natural Product to Clinical Trials: NPI-0052
(Salinosporamide A), a Marine Actinomycete-Derived
Anticancer Agent
Kin S. Lam, G. Kenneth Lloyd, Saskia T. C. Neuteboom,
Michael A. Palladino, Kobi M. Sethna, Matthew A. Spear
and Barbara C. Potts
1 Introduction 355
1.1 Bioprospecting Marine Actinomycetes and the
Discovery of Salinispora and NPI-0052 355
1.2 The Ubiquitin-Proteasome System as a Target
for Drug Development 356
2 Mechanism of Action 358
3 Microbiology of Salinispora tropica, Fermentation
and Scale-up 359
4 Structural Biology and Structure-Activity Relation-
ship Studies 361
5 Translational Biology 363
6 IND-Enabling Studies of NPI-0052 364
7 API Manufacturing 365
8 Formulation Development and Drug Product
Manufacturing 366
9 Pharmacodynamics 367
10 Pharmacokinetics 368
11 Clinical Trials 368
12 Concluding Remarks 370
Acknowledgements 370
References 370
Chapter 13 From Natural Product to Clinical Trials: Bevirimat, a
Plant-Derived Anti-AIDS Drug
Keduo Qian, Theodore J. Nitz, Donglei Yu, Graham
P. Allaway, Susan L. Morris-Natschke and Kuo-Hsiung Lee
1 Introduction 374
2 Bioactivity-directed Fractionation and Isolation 375
3 Lead Identification 375
4 Lead Optimisation and SAR Study 377
4.1 Modification of the BA Triterpene Skeleton 377
4.2 Modification on C-3 Position of BA 378
4.3 Introduction of C-28 Side Chain into BA 382
4.4 Bifunctional BA Analogues?Potential for
Maturation Inhibitor Development 383
5 Mechanism of Action Studies of Bevirimat 384
Contents
6 Preclinical Studies of Bevirimat 385
7 Clinical Trials and Current Status of Bevirimat 387
8 Conclusions 388
Acknowledgements 388
References 388
Section 5 Case Studies of Marketed Natural Product-derived Drugs
Chapter 14 Daptomycin
Richard H. Baltz
1 Introduction 395
2 Discovery of A21987C and Daptomycin 396
2.1 Enzymatic Cleavage of the Fatty Acid Side Chain 396
2.2 Chemical Modifications of the A21978C Core
Peptide 397
3 Biosynthesis 3.1 Analysis of the Daptomycin Biosynthetic Gene 397
Cluster 397
3.2 Daptomycin Structure 398
4 Mechanism of Action Studies 399
4.1 Daptomycin Resistant Mutants 400
5 Antibacterial Activities 401
5.1 In vitro Activities 401
5.2 In vivo Activities in Animal Models 402
6 Clinical Studies 402
6.1 Eli Lilly and Company 402
6.2 The Passing of the Baton 403
6.3 Cubist Pharmaceuticals 403
7 Lessons Learned 404
8 Epilogue 405
References 405
Chapter 15 Micafungin
Akihiko Fujie, Shuichi Tawara and Seiji Hashimoto
1 Introduction 410
1.1 New Antifungal Compounds Discovered at
Fujisawa (a Predecessor of Astellas Pharma Inc.) 411
1.2 1,3-P-Glucan Synthase Inhibition and
Echinocandins 413
2 From the Discovery of FR901379 to Clinical Studies of
FK463 (Micafungin) 414
2.1 Discovery of FR901379 414
2.2 Generation of Lead Compound FR131535 418
Contents xvii
2.3 Lead Optimisation Leading to the Discovery of FK46312 13 421
2.4 Preclinical Studies of FK463 425
2.5 Industrial Manufacturing of Micafungin 2.6 Clinical Studies of FK463 426 426
3 Conclusions 427
Acknowledgements 427
References 427
Subject Index 429
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| spelling | Natural product chemistry for drug discovery ed. by Antony D. Buss ... Cambridge Royal Society of Chemistry 2010 XVII, 440 S. Ill., graph. Darst. 24 cm txt rdacontent n rdamedia nc rdacarrier RSC biomolecular sciences 18 Biological assay Natural products Pharmacognosy Buss, Antony D. Sonstige oth RSC biomolecular sciences 18 (DE-604)BV035847733 18 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=018705898&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Natural product chemistry for drug discovery RSC biomolecular sciences Biological assay Natural products Pharmacognosy |
| title | Natural product chemistry for drug discovery |
| title_auth | Natural product chemistry for drug discovery |
| title_exact_search | Natural product chemistry for drug discovery |
| title_full | Natural product chemistry for drug discovery ed. by Antony D. Buss ... |
| title_fullStr | Natural product chemistry for drug discovery ed. by Antony D. Buss ... |
| title_full_unstemmed | Natural product chemistry for drug discovery ed. by Antony D. Buss ... |
| title_short | Natural product chemistry for drug discovery |
| title_sort | natural product chemistry for drug discovery |
| topic | Biological assay Natural products Pharmacognosy |
| topic_facet | Biological assay Natural products Pharmacognosy |
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