Chemistry And Biology of Heparin And Heparan Sulfate

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ISBN: 9780080448596 | 0080448593
Cover: Hardcover
Copyright: 12/28/2005

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The chemistry, biochemistry and pharmacology of heparin and heparan sulfate have been and continue to be a major scientific undertaking - heparin and its derivative remain important drugs in clinical practice. Chemistry and Biology of Heparin and Heparan Sulfate provides readers with an insight into the chemistry, biology and clinical applications of heparin and heparan sulfate and examines their function in various physiological and pathological conditions. Providing a wealth of useful information, no other tome covers the diversity of topics in the field. Students, doctors, chemists, biochemists, and research scientists will find this book an invaluable source for updating their current knowledge of developments in this area. * Comprehensively reviews all aspects of heparin and heparan sulfate research * Uniquely describes the chemistry, biology and clinical application of heparins and heparan sulfates in one work * Provides an invaluable source of knowledge of current developments for chemists, biochemists, medical doctors, researchers, students and practitioners

Preface

vii

Contributors

Structure and Active Domains of Heparin

(28)

Benito Casu

Introduction

(1)

Heparin Components

(7)

Molecular Conformation of Heparin Residues and Sequences

(2)

Heparin Domains Involved in Biological Interactions

(6)

Molecular Conformation of Active Domains

(2)

Conclusions

(10)

Structure and Function of Cell Associated and Pericellular Heparan Sulfate Proteoglycans

(26)

Sandra G. Velleman

Caini Liu

Introduction

(1)

Heparan Sulfate Synthesis

(1)

Molecular Structure of Heparan Sulfate and Binding Ligands

(3)

Types of Heparan Sulfate Proteoglycans

(1)

Syndecans

(2)

Role of Syndecan in Development

(2)

Glypicans

(2)

Roles of Glypican in Tissue Development

(1)

Betaglycan and CD44

(1)

Pericellular Heparan Sulfate Proteoglycans

(2)

Role in Disease Pathogenesis

(2)

Summary

(10)

Methods for Structural Analysis of Heparin and Heparan Sulfate

(24)

Ishan Capila

Nur Sibel Gunay

Zachary Shriver

Ganesh Venkataraman

Introduction

(1)

Structure of Heparin and Heparan Sulfate

(1)

Separation-Based Analysis of Heparin and Heparan Sulfate

(5)

Mass Spectrometric Analysis of Heparin and Heparan Sulfate

(5)

Nuclear Magnetic Resonance Analysis of Heparin and Heparan Sulfate

(3)

New Methodologies for Structural Analysis of Heparin and Heparan Sulfate

(1)

Summary and Conclusions

(8)

Synthetic Approach to Define Structure-Activity Relationship of Heparin and Heparan Sulfate

(64)

Christian Noti

Peter H. Seeberger

Introduction

(1)

Biosynthesis

(2)

Structure of Heparin/Heparan Sulfate

(2)

Chemical Synthesis of Defined Heparin Oligosaccharides

(45)

Summary and Outlook

129

(14)

Biochemical and Pharmacological Rationale for Synthetic Heparin Polysaccharides

143

(36)

Jeanine M. Walenga

Walter P. Jeske

Jawed Fareed

Introduction

143

(1)

Biological Activities and Mechanisms of Action of Heparin

144

(3)

Fractionation and Fragmentation of Heparin

147

(5)

Elucidation of the Minimum Heparin Sequence for Binding to AT

152

(2)

Synthesis of the Pentasaccharide Representing the Critical Binding Site of Heparin to AT

154

(1)

Pre-Clinical Pharmacology of Fondaparinux

155

(4)

Clinical Trials of Fondaparinux

159

(1)

Derivatives of Pentasaccharide

160

(3)

Summary

163

(16)

Separation and Sequencing of Heparin and Heparan Sulphate Saccharides

179

(24)

Mark A. Skidmore

Jeremy E. Turnbull

Introduction

179

(2)

Seperation of Heparin and Heparan Sulphate Oligosaccharides

181

(11)

Heparin and Heparan Sulphate Sequencing

192

(6)

Discussion

198

(5)

Biosynthesis of Heparin and Heparan Sulfate

203

(42)

Shuji Mizumoto

Hiroshi Kitagawa

Kazuyuki Sugahara

Introduction

203

(2)

Biosynthetic Enzymes and Transporters of Uridine Diphosphate-Sugars and 3'-Phosphoadenosine 5'-Phosphosulfate

205

(3)

Biosynthesis of Heparin and Heparan Sulfate Backbones

208

(12)

Modification of the Sugar Backbones of Heparin and Heparan Sulfate

220

(6)

Conclusions

226

(19)

Remodeling of Heparan Sulfation by Extracellular Endosulfatases

245

(14)

Xingbin Ai

Marion Kusche-Gulberg

Ulf Lindahl

Charles Emerson, Jr.

Introduction

245

(1)

Identification of Sulf Enzymes

246

(2)

Expression and Enzymatic Activity of Sulf Enzymes

248

(1)

Signaling Regulatory Functions of Extracellular Sulfatases

249

(4)

Sulf Function in Tumor and Angiogenesis

253

(2)

Conclusions

255

(4)

Heparan Sulfate Degradation by Heparanases

259

(26)

Karen J. Bame

Heparanase Proteins

259

(2)

Synthesis of Heparanase 1

261

(8)

Heparanase 1 Catalytic Activity

269

(6)

Biological Functions of Heparanase 1

275

(10)

Lysosomal Degradation of Heparin and Heparan Sulfate

285

(28)

Peter J. Meikle

Maria Fuller

John J. Hopwood

Introduction

285

(1)

Transport of Heparin and Heparan Sulfate to the Lysosome

286

(1)

endo-Degradation of Heparin and Heparan Sulfate

286

(5)

exo-Degradation of Heparin and Heparan Sulfate

291

(7)

Transport of Degradation Products out of the Lysosome

298

(1)

Diagnostic and Clinical Aspects of the Mucopolysaccharides

299

(4)

Summary and Future Challenges in the Field

303

(10)

Heparin Regulation of the Complement System

313

(32)

Haining Yu

Eva M. Munoz

R. Erik Edens

Robert J. Linhardt

Introduction

313

(1)

Background and History

314

(4)

Heparin Regulation of the Complement System

318

(12)

The Effects of Heparin on the Alternative Pathway

330

(7)

Conclusions

337

(8)

Surface-Based Studies of Heparin/Heparan Sulfate-Protein Interactions: Considerations for Surface Immobilisation of HS/Heparin Saccharides and Monitoring Their Interactions with Binding Proteins

345

(22)

Tim Rudd

Mark A. Skidmore

Edwin A. Yates

Introduction

345

(2)

Attachment

347

(7)

Methods of Attachment to Surfaces

354

(2)

Detection of Binding Partners

356

(11)

Heparin Activation of Serpins

367

(32)

James A. Huntington

Introduction

367

(1)

General Features of Heparin Binding Serpins

368

(5)

Antithrombin

373

(6)

Heparin Cofactor II

379

(3)

The Others

382

(6)

Conclusions

388

(11)

Role of Heparan Sulfate in Fibroblast Growth Factor Signaling

399

(36)

Nicholas J. Harmer

Introduction and Perspective

399

(1)

Fibroblast Growth Factors

400

(2)

FGF receptors

402

(3)

Interactions of the FGFs and FGFRs with Heparin

405

(9)

Structural Studies of FGF, FGFR and Heparin Complexes

414

(12)

Conclusions and Future Perspectives

426

(9)

Role of Anticoagulant Heparan Sulfate in Mammalian Reproduction

435

(26)

Ariane I. de Agostini

Ghamartaj Hosseini

Marc Princivalle

Ji-Cui Dong

Introduction

435

(1)

Anticoagulant Heparan Sulfate Proteoglycans

435

(2)

Anticoagulant Heparan Sulfate Proteoglycans in the Reproductive Tract

437

(14)

Reproduction in Mice Deficient in Anticoagulant Heparan Sulfate Proteoglycans

451

(2)

Perspectives

453

(8)

Glycol-Splilting as a Device for Modulating Inhibition of Growth Factors and Heparanase by Heparin and Heparin Derivatives

461

(22)

Annamaria Naggi

Introduction

461

(1)

Glycol-Split Heparins

462

(5)

Protein-Binding and Associated Biological Properties of Glycol-Split Heparins

467

(7)

Conformational Implications of Glycol-Splitting

474

(2)

Conclusions

476

(7)

Antithrombin Activation and Designing Novel Heparin Mimies

483

(30)

Umesh R. Desai

Introduction

483

(3)

Antithrombin Inhibition of Procoagulant Proteinases

486

(1)

Structure of Heparin and Heparin Pentasaccharide

487

(1)

Mechanism of Heparin Activation of Antithrombin

488

(3)

The Heparin Binding Site in Antithrombin

491

(2)

The Heparin Binding Site in Factor Xa and Thrombin

493

(1)

Thermodynamics and Kinetics of Heparin Binding to Antithrombin

494

(2)

Rationale for Designing Functional Mimies of Heparin

496

(1)

Heparin Mimies

497

(7)

Conclusions

504

(9)

Influence of Heparin Chemical Modifications on Its Antiproliferative Properties

513

(20)

Hari G. Garg

Robert J. Linhardt

Charles A. Hales

Introduction

513

(1)

Background and Significance of Chemical Modification of Heparin

514

(1)

Mechanisms Contributing to Heparin Inhibition of Smooth Muscle Cell Growth

515

(1)

Importance of 3-O-Sulfo Group on the Internal Giueosamine Residue of Pentasaccharide for Antiproliferative Activity

516

(1)

Minimal Heparin Oligosaccharide Size Necessary for Antiproliferative Activity

517

(2)

Effect of Chemical Modification of Heparin on Its Antiproliferative Activity

519

(5)

Effect of the Type of Serum on Antiproliferative Activity

524

(9)

Mechanisms of Cell Growth Regulation by Heparin and Heparan Sulfate

533

(38)

Matthew A. Nugent

Kimberly Forsten-Williams

Morris J. Karnovsky

Elazer R. Edelman

Introduction

533

(1)

Modulation of Growth Factor Action

534

(10)

Direct Regulation of Cell Growth

544

(2)

Growth Control in Disease

546

(7)

Conclusions

553

(18)

Heparin and Low Molecular Weight Heparin in Thrombosis and Inflammation: Emerging Link

571

(12)

Shaker A. Mousa

Introduction

571

(1)

Emerging Links Between Thrombosis and Inflammation: Potential Role of Heparin

572

(3)

Heparin versus Low Molecular Weight Heparin

575

(2)

Heparin as an Anti-Inflammatory Molecule: Potential Mechanisms

577

(1)

Conclusions

578

(5)

Basic and Clinical Difference of Heparin and Low Molecular Weight Heparin Treatment

583

(24)

Debra Hoppensteadt

Omer Iqbal

Jawed Fareed

Introduction

583

(1)

Unfractionated Heparin and Newer Anticoagulant and Antithrombotic Drugs

584

(5)

Low Molecular Weight Heparins and Their Impact on the Management of Thrombotic and Vascular Disorders

589

(5)

Monitoring of Heparin and Low Molecular Weight Heparins

594

(3)

Clinical Trials with Low Molecular Weight Heparins

597

(1)

Generic Low Molecular Weight Heparins

598

(2)

American College of Chest Physicians Consensus Recommendations

600

(3)

Summary

603

(4)

Perlecan: An Extracellular Matrix Heparan Sulfate Proteoglycan that Regulates Key Events in Vascular Development and Disease

607

(30)

Michael G. Kinsella

Thomas N. Wight

Introduction

607

(1)

Perlecan--The Gene, the Protein Core, and the Glycosaminoglycans

607

(3)

Perlecan is a Key Extracellular Matrix Component in Basement Membranes and in the Development of the Vascular System

610

(1)

Phenotypic Regulation of Vascular Cells by Perlecan

611

(4)

Perlecan in Intimal Hyperplasia

615

(3)

Perlecan in Atherosclerosis

618

(3)

Perlecan and Angiogenesis

621

(2)

Conclusions

623

(14)

Heparin and Low Molecular Weight Heparins in Clinical Cardiology

637

(36)

Mehmet E. Korkmaz

Introduction

637

(1)

Overview of Pharmacology

637

(4)

Clinical Experience

641

(21)

Conclusions

662

(11)

Heparin-Induced Thrombocytopenia

673

(26)

Theodore E. Warkentin

William E. Dager

Introduction

673

(1)

Pathogenesis

673

(4)

Clinical Picture

677

(2)

Laboratory Testing for Heparin-Induced Thrombocytopenia Antibodies

679

(1)

Treatment

680

(19)

Role of Heparan Sulfate in Cancer

699

(28)

Dongfang Liu

Ram Sasisekharan

Introduction

699

(1)

Structure Features of Glycosaminoglycans

699

(3)

Biosynthesis and Degradation of Heparan Sulfate Glycosaminoglycans

702

(1)

Biological Functions of Heparan Sulfate Glycosaminoglycans

703

(3)

Heparan Sulfate Glycosaminoglycans in Cancer

706

(21)

Use of Heparin Preparations in Older Patients

727

(18)

Antonella Tufano

Matteo Nicola Dario Di Minno

Introduction

727

(1)

Aging and the Haemostatic System

728

(1)

Unfractionated Heparin, Low Molecular Weight Heparins, and Fondaparinux: Pharmacological Properties

729

(2)

Unfractionated Heparin, Low Molecular Weight Heparins, and Fondaparinux: Clinical Use in Elderly

731

(3)

Heparin and Low Molecular Weight Heparins: Risk of Bleeding in the Elderly

734

(3)

Conclusions and Perspectives

737

(8)

Advances in Low Molecular Weight Heparin Use in Pregnancy

745

(24)

Andrew J. Thomson

Ian A. Greer

Introduction

745

(1)

Pharmacology and Pharmacokineties of Low Molecular Weight Heparin in Pregnancy

745

(3)

Indications for the Use of Low Molecular Weight Heparin in Pregnancy

748

(11)

Safety of Low Molecular Weight Heparin in Pregnancy

759

(2)

Conclusions

761

(8)

Subject Index

769

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Chemistry And Biology of Heparin And Heparan Sulfate

Summary

Table of Contents

Supplemental Materials

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Chemistry And Biology of Heparin And Heparan Sulfate

Summary

Table of Contents

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