Details

Multivalency


Multivalency

Concepts, Research and Applications
1. Aufl.

von: Jurriaan Huskens, Leonard J. Prins, Rainer Haag, Bart Jan Ravoo

104,99 €

Verlag: Wiley
Format: PDF
Veröffentl.: 16.11.2017
ISBN/EAN: 9781119143475
Sprache: englisch
Anzahl Seiten: 416

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Beschreibungen

<p><b>Connects fundamental knowledge of multivalent interactions with current practice and state-of-the-art applications</b> </p> <p>Multivalency is a widespread phenomenon, with applications spanning supramolecular chemistry, materials chemistry, pharmaceutical chemistry and biochemistry. This advanced textbook provides students and junior scientists with an excellent introduction to the fundamentals of multivalent interactions, whilst expanding the knowledge of experienced researchers in the field.</p> <p><i>Multivalency: Concepts, Research & Applications</i> is divided into three parts. Part one provides background knowledge on various aspects of multivalency and cooperativity and presents practical methods for their study. Fundamental aspects such as thermodynamics, kinetics and the principle of effective molarity are described, and characterisation methods, experimental methodologies and data treatment methods are also discussed. Parts two and three provide an overview of current systems in which multivalency plays an important role in chemistry and biology, with a focus on the design rules, underlying chemistry and the fundamental principles of multivalency. The systems covered range from chemical/materials-based ones such as dendrimers and sensors, to biological systems including cell recognition and protein binding. Examples and case studies from biochemistry/bioorganic chemistry as well as synthetic systems feature throughout the book.</p> <ul> <li>Introduces students and young scientists to the field of multivalent interactions and assists experienced researchers utilising the methodologies in their work</li> <li>Features examples and case studies from biochemistry/bioorganic chemistry, as well as synthetic systems throughout the book</li> <li>Edited by leading experts in the field with contributions from established scientists</li> </ul> <p><i>Multivalency: Concepts, Research & Applications</i> is recommended for graduate students and junior scientists in supramolecular chemistry and related fields, looking for an introduction to multivalent interactions. It is also highly useful to experienced academics and scientists in industry working on research relating to multivalent and cooperative systems in supramolecular chemistry, organic chemistry, pharmaceutical chemistry, chemical biology, biochemistry, materials science and nanotechnology.</p>
<p>List of Contributors xi</p> <p>Foreword xv</p> <p>Preface xvii</p> <p><b>Part I General Introduction to Multivalent Interactions 1</b></p> <p><b>1 Additivity of Energy Contributions in Multivalent Complexes 3<br /></b><i>Hans?-Jorg Schneider</i></p> <p>1.1 Introduction 3</p> <p>1.2 Additivity of Single Interactions – Examples 3</p> <p>1.3 Limitations of Additivity 7</p> <p>1.3.1 Free Energy Values ΔG Instead of Enthalpic and Entropic Values ΔH, TΔS 7</p> <p>1.3.2 Mismatch as Limitation of Additivity 9</p> <p>1.3.3 Medium Effects as Limiting Factor 12</p> <p>1.3.4 Strain and Induced Fit 12</p> <p>1.4 Cooperativity 13</p> <p>1.5 Allostery 14</p> <p>1.6 Conclusions 17</p> <p>References 18</p> <p><b>2 Models and Methods in Multivalent Systems 23<br /></b><i>Jurriaan Huskens</i></p> <p>2.1 Introduction 23</p> <p>2.1.1 General Introduction 23</p> <p>2.1.2 Multivalent versus Cooperative Interactions 24</p> <p>2.2 Numerical Data Analysis 25</p> <p>2.2.1 Model Simulations Using a Spreadsheet Approach 26</p> <p>2.2.2 Setting Up and Assessing Titrations 30</p> <p>2.2.3 Using Spreadsheet Simulations to Fit Experimental Data to a Model 36</p> <p>2.3 Models for Multivalent Systems 41</p> <p>2.3.1 The Simplest Multivalent System: A 1:1 Complex with Two Interaction Sites 41</p> <p>2.3.2 Multivalent Binding at Surfaces 46</p> <p>2.4 Special Multivalent Systems 53</p> <p>2.4.1 Increasing the Valency of Interfacial Assemblies: Dendrimers, Oligomers, and Polymers  53</p> <p>2.4.2 Heterotropic Interactions 58</p> <p>2.4.3 Kinetics and Dynamics 63</p> <p>2.5 Conclusions 68</p> <p>Acknowledgments 68</p> <p>References 68</p> <p><b>3 Design Principles for Super Selectivity using Multivalent Interactions 75<br /></b><i>Tine Curk, Jure Dobnikar, and Daan Frenkel</i></p> <p>3.1 Introduction 75</p> <p>3.1.1 Background: Ultra?-sensitive Response 75</p> <p>3.2 Super Selectivity: An Emergent Property of Multivalency 78</p> <p>3.3 Multivalent Polymer Adsorption 84</p> <p>3.4 Which Systems are Super Selective? 86</p> <p>3.4.1 Rigid Geometry Interactions 86</p> <p>3.4.2 Disordered Multivalency 87</p> <p>3.5 Design Principles for Super?-Selective Targeting 90</p> <p>3.6 Summary: It is interesting, but is it useful? 93</p> <p>Appendix 3.A: What Is Effective Molarity? 95</p> <p>Acknowledgements 98</p> <p>References 98</p> <p><b>4 Multivalency in Biosystems 103<br /></b><i>Jens Dernedde</i></p> <p>4.1 Introduction 103</p> <p>4.2 Cell–Cell Adhesion 104</p> <p>4.2.1 Homotypic Interactions, Cadherins Keep Cells Together 105</p> <p>4.2.2 Selectins, Heterotypic Cell Adhesion to Fight Infections 106</p> <p>4.2.3 Bacterial Adhesion by FimH 108</p> <p>4.3 Phase Transition, Multivalent Intracellular Assemblies 109</p> <p>4.4 Multivalency in the Fluid Phase, Pathogen Opsonization 111</p> <p>4.5 Conclusion 113</p> <p>Acknowledgment 113</p> <p>References 114</p> <p><b>Part II Multivalent Systems in Chemistry 121</b></p> <p><b>5 Multivalency in Cyclodextrin/Polymer Systems 123<br /></b><i>Akihito Hashidzume and Akira Harada</i></p> <p>5.1 Introduction 123</p> <p>5.2 General Perspectives of Multivalency in Cyclodextrin/Polymer Systems 125</p> <p>5.3 Typical Examples of Multivalency in Cyclodextrin/Polymer Systems 126</p> <p>5.3.1 Formation of Polymer Aggregates from Cyclodextrin?-Polymers and Guest?-Polymers 126</p> <p>5.3.2 Selectivity of Interaction Enhanced by Multivalency 127</p> <p>5.3.3 Self?-Healable Hydrogels Based on Multivalency 134</p> <p>5.4 Summary and Outlook 136</p> <p>Acknowledgments 136</p> <p>References 138</p> <p><b>6 Cucurbit[n-uril?-Mediated Multiple Interactions 143<br /></b><i>Zehuan Huang and Xi Zhang</i></p> <p>6.1 Introduction to Cucurbit[n-uril Chemistry 143</p> <p>6.2 Heteroternary Complexes 143</p> <p>6.3 Homoternary Complexes 146</p> <p>6.4 Conclusions 150</p> <p>References 150</p> <p><b>7 Multivalency as a Design Criterion in Catalyst Development 153<br /></b><i>Paolo Scrimin, Maria A. Cardona, Carlos M. Leon Prieto, and Leonard J. Prins</i></p> <p>7.1 Introduction 153</p> <p>7.2 Formation of Enzyme?-Like Catalytic Pockets 154</p> <p>7.3 Cooperativity Between Functional Groups 157</p> <p>7.4 Mechanistic Effects 161</p> <p>7.5 The Dendritic Effect in Multivalent Nanozymes 164</p> <p>7.5.1 Peptide?-Based Dendrimers for the Cleavage of Phosphodiesters 166</p> <p>7.5.2 Catalytic 3D SAMs on Au NPs 168</p> <p>7.6 Multivalent Catalysts and Multivalent Substrates 170</p> <p>7.7 Conclusions 172</p> <p>Acknowledgements 174</p> <p>References 174</p> <p><b>8 Multivalent Molecular Recognition on the Surface of Bilayer Vesicles 177<br /></b><i>Jens Voskuhl, Ulrike Kauscher, and Bart Jan Ravoo</i></p> <p>8.1 Introduction 177</p> <p>8.2 Molecular Recognition of Vesicles 179</p> <p>8.2.1 Metal Coordination 180</p> <p>8.2.2 Light Responsive Interactions 184</p> <p>8.2.3 Hydrogen Bonding and Electrostatic Interactions 185</p> <p>8.3 Biomimetic Vesicles 188</p> <p>8.3.1 Vesicles as Multivalent Platforms 188</p> <p>8.3.2 Membrane Fusion 193</p> <p>8.4 Vesicle?-based Supramolecular Materials 196</p> <p>8.4.1 Hydrogels 196</p> <p>8.4.2 Immobilization of Vesicles 198</p> <p>8.4.3 Nanoparticles and Nanocontainers 198</p> <p>8.5 Conclusion 201</p> <p>Acknowledgment 201</p> <p>References 201</p> <p><b>Part III Multivalent Systems in Biology 205</b></p> <p><b>9 Blocking Pathogens by Multivalent Inhibitors 207<br /></b><i>Sumati Bhatia, Benjamin Ziem, and Rainer Haag</i></p> <p>9.1 Introduction 207</p> <p>9.2 Design of Multivalent Ligand Architectures 209</p> <p>9.3 Multivalent Carbohydrate Ligands 212</p> <p>9.4 Scaffold Architecture 215</p> <p>9.4.1 Linear and Dendritic Scaffolds 215</p> <p>9.4.2 Multivalent Gold Nanoparticles 218</p> <p>9.4.3 2D Platforms 220</p> <p>9.5 Nano?-and Microgels for Pathogen Inhibition 222</p> <p>9.6 Conclusion 223</p> <p>Acknowledgments 224</p> <p>References 224</p> <p><b>10 Multivalent Protein Recognition Using Synthetic Receptors 229<br /></b><i>Akash Gupta, Moumita Ray, and Vincent M. Rotello</i></p> <p>10.1 Introduction 229</p> <p>10.2 Structural Properties of Protein Surfaces 229</p> <p>10.2.1 Protein–Protein Interfacial Areas 229</p> <p>10.2.2 Chemical Nature of the Protein–Protein Interface 230</p> <p>10.2.3 “Hot Spots” 230</p> <p>10.2.4 O?-Ring Structure 232</p> <p>10.3 Synthetic Receptors for Protein Surface Recognition 232</p> <p>10.3.1 Porphyrin Scaffolds for Protein Surface Recognition 232</p> <p>10.3.2 Protein Surface Recognition Using Molecular Tweezers 238</p> <p>10.3.3 Calixarene Scaffolds for Protein Surface Recognition 240</p> <p>10.3.4 Recognition of Protein Surfaces Using Nanoparticles 243</p> <p>10.3.4.1 Nanoparticles as Protein Mimics 244</p> <p>10.3.4.2 Regulating the Structure and Function of Proteins Using Nanoparticles 246</p> <p>10.3.4.3 Nanoparticle?-based Protein Sensors 250</p> <p>10.4 Future Perspective and Challenges 254</p> <p>Acknowledgment 257</p> <p>References 257</p> <p><b>11 Multivalent Calixarenes for the Targeting of Biomacromolecules 263<br /></b><i>Francesco Sansone and Alessandro Casnati</i></p> <p>11.1 Introduction 263</p> <p>11.2 Binding to Proteins and Enzymes 266</p> <p>11.3 Recognition of Carbohydrate Binding Proteins (Lectins) 273</p> <p>11.4 Binding Polyphosphates, Oligonucleotides and Nucleic Acids 279</p> <p>11.5 Conclusions 284</p> <p>Acknowledgements 285</p> <p>References 285</p> <p><b>12 Cucurbit[n]uril Assemblies for Biomolecular Applications 291<br /></b><i>Emanuela Cavatorta, Luc Brunsveld, Jurriaan Huskens, and Pascal Jonkheijm</i></p> <p>12.1 Introduction 291</p> <p>12.2 Molecular Recognition Properties of CB[n- 293</p> <p>12.2.1 Interactions with the Carbonyl Portals of CB[n- 293</p> <p>12.2.2 Release of High Energy Water Molecules from the CB[n- Cavity 295</p> <p>12.2.3 Enthalpy?-driven Hydrophobic Effect for CB[n- 295</p> <p>12.2.4 Enthalpy?-driven Hydrophobic Effect for CB[8- Heteroternary Complexes 297</p> <p>12.3 Control Over the Binding Affinity with CB[n- 299</p> <p>12.4 CB[n] Recognition of Amino Acids, Peptides, and Proteins 301</p> <p>12.5 CB[n] for Bioanalytical and Biomedical Applications 305</p> <p>12.5.1 CB[n]-mediated Assembly of Bioactive Polymers and Hydrogels 305</p> <p>12.5.2 CB[n]-mediated Assembly of Bioactive Nanoparticles 307</p> <p>12.5.3 CB[n]?-mediated Assembly on Bioactive Surfaces 313</p> <p>12.6 Conclusions and Outlook 317</p> <p>Acknowledgment 319</p> <p>References 319</p> <p><b>13 Multivalent Lectin–Glycan Interactions in the Immune System 325<br /></b><i>Joao T. Monteiro and Bernd Lepenies</i></p> <p>13.1 Introduction 325</p> <p>13.2 Targeting Innate Immunity to Shape Adaptive Immunity 327</p> <p>13.3 C?-type Lectin Receptors 328</p> <p>13.3.1 Multivalent Glycoconjugates Targeting DC?-SIGN 331</p> <p>13.3.2 Multivalent Glycoconjugates Targeting Other CLRs 331</p> <p>13.4 Galectins 332</p> <p>13.5 Siglecs 334</p> <p>13.6 Conclusions 335</p> <p>Acknowledgment 335</p> <p>References 335<br /><br /></p> <p><b>14 Blocking Disease Linked Lectins with Multivalent Carbohydrates 345<br /></b><i>Marjon Stel and Roland J. Pieters</i></p> <p>14.1 Introduction 345</p> <p>14.2 Haemagglutinin 347</p> <p>14.3 LecA 349</p> <p>14.4 LecB 354</p> <p>14.5 Galectins 358</p> <p>14.6 Concanavalin A 362</p> <p>14.7 Cholera Toxin 366</p> <p>14.8 Propeller Lectins 367</p> <p>14.9 Conclusion 371</p> <p>Acknowledgements 371</p> <p>References 371</p> <p>Index 381</p>
<p><b>Jurriaan Huskens, PhD</b> (1968) is full professor of "Molecular Nanofabrication" at the University of Twente, Netherlands. Present research interests encompass: supramolecular chemistry at interfaces, supramolecular materials, multivalency, nanofabrication, and solar fuels. <p><b>Leonard J. Prins, PhD</b> is a professor in Organic Chemistry at the University of Padova, Italy. His current research interests include network reactivity in complex chemical systems and the origin of cooperativity in multivalent catalysts. <p><b>Rainer Haag, PhD</b> joined the Freie Universität Berlin as full Professor of Organic and Macromolecular Chemistry in 2004. Currently he serves on the Editorial Board of the Angewandte Chemistry and is the spokesperson of the collaborative research center 765 on "multivalency." <p><b>Bart Jan Ravoo, PhD</b> (1970) is full professor at the Westfälische Wilhelms-Universität Münster, Germany, where he is in charge of the "Synthesis of Nanoscale Systems" group. Since 2016 he is co-director of the Center for Soft Nanoscience (SoN). His main research interest are soft materials made by self-assembly, functional nanoparticles, and self-assembled monolayers.
<p><b>Connects fundamental knowledge of multivalent interactions with current practice and state-of-the-art applications</b> <p>M<i>ultivalency: Concepts, Research & Applications</i> is divided into three parts. Part one provides background knowledge on various aspects of multivalency and cooperativity and presents practical methods for their study. Fundamental aspects such as thermodynamics, kinetics and the principle of effective molarity are described, and characterisation methods, experimental methodologies and data treatment methods are also discussed. Parts two and three provide an overview of current systems in which multivalency plays an important role in chemistry and biology, with a focus on the design rules, underlying chemistry and the fundamental principles of multivalency. The systems covered range from chemical/materials-based ones such as dendrimers and sensors, to biological systems including cell recognition and protein binding. Examples and case studies from biochemistry/bioorganic chemistry as well as synthetic systems feature throughout the book. <ul> <li>Introduces students and young scientists to the field of multivalent interactions and assists experienced researchers utilising the methodologies in their work</li> <li>Features examples and case studies from biochemistry/bioorganic chemistry, as well as synthetic systems throughout the book</li> <li>Edited by leading experts in the field with contributions from established scientists</li> </ul> <p><i>Multivalency: Concepts, Research & Applications</i> is recommended for graduate students and junior scientists in supramolecular chemistry and related fields. It is also highly useful to those working on research relating to multivalent and cooperative systems in supramolecular chemistry, organic chemistry, pharmaceutical chemistry, chemical biology, biochemistry, materials science and nanotechnology.

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