Artificial Receptors for Chemical Sensors E-Book

• Herausgeber: Wiley-VCH
• Kategorie: Fachliteratur
• Sprache: Englisch

Seitenzahl: 749

Veröffentlichungsjahr: 2010

Beschreibung

The first to provide systematically organized information on all three important aspects of artificial receptor design, this book brings together knowledge on an exceptionally hot and multidisciplinary field of research. Strong emphasis is placed on the methodology for discovering artificial receptors, with both definitions for chemosensitivity as well as experimental setups supplied. There follows coverage of numerous classes of artificial receptors, including synthesis, immobilization on surfaces, and quantitative data on properties. The third part of the book focuses on receptor arrays for artificial nose and tongue applications and the whole is rounded off with an outlook and an appendix with all relevant quantitative data on artificial receptors.

Leseprobe

Contents

Cover

Related Titles

Title Page

Copyright

Preface

List of Contributors

Chapter 1: Quantitative Characterization of Affinity Properties of Immobilized Receptors

1.1 Introduction

1.2 Measurements Under Equilibrium Conditions

1.3 Kinetic Measurements

1.4 Analysis of Temperature Dependencies

1.5 Experimental Techniques

References

Chapter 2: Selectivity of Chemical Receptors

2.1 Introduction

2.2 Some General Considerations on Selectivity

2.3 Correlation Between Selectivity and Affinity

2.4 Crown Ether and Cryptand Complexes: Hole Size Fitting and Other Effects

2.5 Recognition of Transition and Heavy Metal Ions

2.6 Recognition via Ion Pairing

2.7 Hydrogen Bonded Complexes and Solvent Effects

2.8 Lewis Acid Receptors

2.9 Complexes with Stacking and van der Waals Interactions

2.10 Multifunctional Receptors for Recognition of Complex Target Molecules

2.11 Conclusions

References

Chapter 3: Combinatorial Development of Sensing Materials

3.1 Introduction

3.2 General Principles of Combinatorial Materials Screening

3.3 Opportunities for Sensing Materials

3.4 Designs of Combinatorial Libraries of Sensing Materials

3.5 Discovery and Optimization of Sensing Materials Using Discrete Arrays

3.6 Optimization of Sensing Materials Using Gradient Arrays

3.7 Emerging Wireless Technologies for Combinatorial Screening of Sensing Materials

3.8 Summary and Outlook

Acknowledgments

References

Chapter 4: Fluorescent Cyclodextrins as Chemosensors for Molecule Detection in Water

4.1 Introduction

4.2 Pyrene-Appended Cyclodextrins

4.3 Fluorophore–Amino Acid–CD Triad Systems

4.4 Molecular Recognition by Regioisomers of Dansyl-Appended CDs

4.5 Turn-On Fluorescent Chemosensors

4.6 Effect of Protein Environment on Molecule Sensing

4.7 CD–Peptide Conjugates as Chemosensors

4.8 Immobilized Fluorescent CD on a Cellulose Membrane

4.9 Conclusion

References

Chapter 5: Cyclopeptide Derived Synthetic Receptors

5.1 Introduction

5.2 Receptors for Cations

5.3 Receptors for Ion Pairs

5.4 Receptors for Anions

5.5 Receptors for Neutral Substrates

5.6 Conclusion

References

Chapter 6: Boronic Acid-Based Receptors and Chemosensors

6.1 Introduction

6.2 De Novo Design

6.3 Combinatorial Approaches

6.4 Template-Directed Synthesis

Acknowledgment

References

Chapter 7: Artificial Receptor Compounds for Chiral Recognition

7.1 Introduction

7.2 Cyclodextrins

7.3 Crown Ethers

7.4 Calixarenes

7.5 Calix[4]resorcinarenes

7.6 Miscellaneous Receptor Compounds

7.7 Metal-Containing Receptor Compounds

References

Chapter 8: Fullerene Receptors Based on Calixarene Derivatives

8.1 Introduction

8.2 Calixarenes

8.3 Solid State Complexation by Calixarenes

8.4 Complexation in Solution

8.5 Calixarenes as Molecular Scaffolds

8.6 Outlook

References

Chapter 9: Guanidinium Based Anion Receptors

9.1 Introduction

9.2 Instructive Historical Examples

9.3 Recent Advances in Inorganic Anion Recognition

9.4 Organic and Biological Phosphates

9.5 Polycarboxylate Binding

9.6 Amino Acid Recognition

9.7 Dipeptides as Substrate

9.8 Polypeptide Recognition

9.9 Conclusion

References

Chapter 10: Artificial Receptors Based on Spreader-Bar Systems

References

Chapter 11: Potential of Aptamers as Artificial Receptors in Chemical Sensors

11.1 Introduction

11.2 Generation and Synthesis of Aptamers

11.3 Aptamer Arrays

11.4 Techniques for Readout of Ligand Binding to the Aptamer

11.5 Outlook/Summary

References

Chapter 12: Conducting Polymers as Artificial Receptors in Chemical Sensors

12.1 Introduction

12.2 Transducers for Artificial Receptors Based on Conducting Polymers

12.3 Intrinsic Sensitivity of Conducting Polymers

12.4 Conducting Polymers Modified with Receptor Groups

12.5 Conclusion

List of Abbreviations

References

Chapter 13: Molecularly Imprinted Polymers as Artificial Receptors

13.1 Introduction

13.2 Fundamentals of Molecular Imprinting

13.3 Polymer Formats and Polymerization Methods for MIPs

13.4 Evaluation of MIP Performance – Imprinting Efficiency

13.5 MIPs Mimicking Natural Receptors

13.6 Conclusions and Outlook

References

Chapter 14: Quantitative Affinity Data on Selected Artificial Receptors

14.1 Structures of Receptors

References

Index

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The Editors

Prof. Dr. Vladimir M. Mirsky

Lausitz University of Applied Sciences

Nanobiotechnology - BCV

Grossenhainer str. 57

01968 Senftenberg

Germany

Prof. Dr. Anatoly K. Yatsimirsky

Universidad Nacional Autónoma de México

Facultad de Química

04510 México D.F.

Mexico

Cover

Dr. N.V. Roznyatovskaya is acknowledged for her assistance in the design of the book cover.

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Library of Congress Card No.: applied for

British Library Cataloguing-in-Publication Data

A catalogue record for this book is available from the British Library.

Bibliographic information published by the Deutsche Nationalbibliothek

The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at http://dnb.d-nb.de.

© 2011 WILEY-VCH Verlag & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany

All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law.

ISBN: 978-3-527-32357-9

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Preface

One of the great achievements in modern chemistry is the development of artificial synthetic receptors, which are typically low molecular weight compounds that perform selective binding (recognition) of a compound of interest. Such compounds are used for the design and chemically addressed assembly of supramolecular structures. Another important application of these compounds is the development of chemical sensors. Over the past few few decades affinity assays have been based mainly on immunological techniques: antibodies are used routinely in clinical applications or in food analysis. However, they are expensive, unstable, and cannot be prepared for some types of analytes. For example, one cannot immunize animals with highly toxic compounds or with compounds that are present in all animals (such as glucose, sodium ion). The solution is to use artificial receptors. Recent years have seen intensive development in this field. Traditional approaches based on the chemical synthesis of small molecules with high affinity have been completed by molecularly imprinted polymerization and by biotechnological preparation and selection of natural macromolecules with such properties.

Syntheses, structures, and recognition properties of artificial receptors are touched on in many monographs in the field of supramolecular chemistry. The book Functional Synthetic Receptors edited by Thomas Schräder and Andrew D. Hamilton (Wiley-VCH Verlag GmbH, 2005) provides deep insight into fundamental aspects of the subject. There is little literature, however, discussing artificial receptors with the emphasis on their practical applications as components of chemical sensors and assays. This book intends to fill this gap.

The book starts with two chapters discussing the most relevant quantitative characteristics of receptors – binding affinity and selectivity. Chapter 3, on the combinatorial development of sensing materials, deals with an advanced technological approach to the discovery of new receptors. Chapters 4–9 discuss particular types of receptors (cyclodextrins, cyclopeptides, boronic acids, chiral receptors, calixarenes, and guanidinium derivatives) of significant current importance. Finally, Chapters 10–13 deal with receptors based on organized (spreader-bar approach) or polymeric (aptamers, conducting polymers, and molecular imprinting) structures. Chapter 14 provides an extensive compilation of the affinity properties of different receptors taken from current literature.

We hope that this book will be useful as a handbook for scientists (from universities and industry) and graduate and post-graduate students working in analytical and supramolecular chemistry, chemical sensors and biosensors, and in material science. It will also be of interest to experts and students working/studying surface chemistry, physical chemistry, and in some fields of organic chemistry, pharmacology, medical diagnostics, biotechnology, chemical technology, food, and environmental monitoring.

Finally, we express our gratitude to the authors of this book and hope that readers also find these contributions enjoyable, interesting, and useful.

February 2010

Vladimir M. Mirsky, Senftenberg

and

Anatoly K. Yatsimirsky, Mexico City

List of Contributors

Bettina Appel

Ernst-Moritz-Arndt Universität

Greifswald

Institut für Biochemie

Felix-Hausdorff-Str. 4

17487 Greifswald

Germany

Yunfeng Cheng

Georgia State University

Department of Chemistry and Center for Biotechnology and Drug Design

Atlanta, GA 30302-4098

USA

Qingli Hao

Nanjing University of Science and Technology

Key Laboratory of Soft Chemistry and Functional Materials

Ministry of Education

210094 Nanjing

China

Thomas Hirsch

University of Regensburg

Institute of Analytical Chemistry

Chemo- and Biosensors

Universitätsstraße 31

93040 Regensburg

Germany

Hiroshi Ikeda

Tokyo Institute of Technology

Graduate School of Bioscience and Biotechnology

Department of Bioengineering

4259-B-44 Nagatsuta-cho, Midori-ku

Yokohama 226-8501

Japan

Shan Jin

Georgia State University

Department of Chemistry and Center for Biotechnology and Drug Design

Atlanta, GA 30302-4098

USA

Stefan Kubik

Technische Universität Kaiserslautern

Fachbereich Chemie - Organische

Chemie

Erwin-Schrödinger-Strasse

67663 Kaiserslautern

Germany

Hannes Yacu Kuchelmeister

University of Duisburg-Essen

Institute for Organic Chemistry

Universitätsstraße 7

45141 Essen

Germany

Ondej Kundrát

Prague Institute of Chemical Technology

Department of Organic Chemistry

Technická 5

166 28 Prague 6

Czech Republic

Ulrich Lange

University of Regensburg

Institute of Analytical Chemistry, Chemo- and Biosensors

Universitätsstraße 31

93040 Regensburg

Germany

Pavel Lhoták

Prague Institute of Chemical Technology

Department of Organic Chemistry

Technická 5

166 28 Prague 6

Czech Republic

Florian Meier

University of Ulm

Institute of Analytical and Bioanalytical Chemistry

Albert-Einstein-Allee 11

89061 Ulm

Germany

Vladimir M. Mirsky

Lausitz University of Applied Sciences

Nanobiotechnology-BCV

Grossenhainer str. 57

01968 Senftenberg

Germany

Boris Mizaikoff

University of Ulm

Institute of Analytical and Bioanalytical

Chemistry

Albert-Einstein-Allee 11

89069 Ulm

Germany

Sabine Müller

Ernst-Moritz-Arndt Universität

Greifswald

Institut für Biochemie

Felix-Hausdorff-Str. 4

17487 Greifswald

Germany

Ngoc H. Pham

Bates College

Department of Chemistry

S. Andrews Road

Lewiston, ME 04240

USA

Radislav A. Potyrailo

General Electric Global Research

Chemical and Biological Sensing

Laboratory

Chemistry Technologies and Material

Characterization

1 Research Circle

Niskayuna, NY 12309

USA

Nataliya V. Roznyatovskaya

Fraunhofer Institute of Chemical Technology

Joseph-von-Fraunhofer-Straße 7

76327 Pfinztal-Berghausen

Germany

Carsten Schmuck

University of Duisburg-Essen

Institute for Organic Chemistry

Universitätsstraße 5

45141 Essen

Germany

Hans-Jörg Schneider

Universität des Saarlandes

FR Organische Chemie

66041 Saarbrücken

Germany

Sabine Stingel

Ernst-Moritz-Arndt Universität

Greifswald

Institut für Biochemie

Felix-Hausdorff-Str. 4

17487 Greifswald

Germany

Binghe Wang

Georgia State University

Department of Chemistry and Center for Biotechnology and Drug Design

Atlanta, GA 30302-4098

USA

Thomas J. Wenzel

Bates College

Department of Chemistry

S. Andrews Road

Lewiston, ME 04240

USA

Xiaochuan Yang

Georgia State University

Department of Chemistry and Center for Biotechnology and Drug Design

Atlanta, GA 30302-4098

USA

Anatoly K. Yatsimirsky

Universidad Nacional Autónoma de México

Facultad de Química

04510 México D.F.

México

Chapter 1

Quantitative Characterization of Affinity Properties of Immobilized Receptors

Vladimir M. Mirsky

1.1 Introduction

Affinity as a tendency of molecules (ligands) to associate with another type of molecules or polymers (receptor) can be described by a set of kinetic and thermodynamic parameters. These parameters include the adsorption (or binding, or association) constant, which can be recalculated as the free energy of binding, binding enthalpy and entropy, kinetic adsorption and desorption constants, and activation energies for binding and for dissociation.

There are several reasons for a quantitative characterization of affinity. The first is due to possible applications of these receptors in affinity sensors. The sensors are intended to measure volume concentrations of analytes. However, transducers of affinity sensors (refractometric, interferometric, mechano-acoustical, capacitive, and others) provide information on the surface concentration of analytes (ligands) on a layer of immobilized receptors (Figure 1.1). Therefore, it is important to obtain a calibration curve – the dependence between volume concentration of an analyte and its surface concentration. Such relations are named in physical chemistry as adsorption isotherms (the binding is usually performed at constant temperature). Several adsorption isotherms can be obtained from simple physical models. A mathematical description of these isotherms allows one not only a better understanding of binding process but also provides a mathematical basis for interpolation and extrapolation of the calibration curve, which is of importance for analytical applications.

Figure 1.1 Transducers of affinity sensors provide information on the surf ace concentration of bound analytes. For practical applications, information on the volume concentration is required.

The second reason includes material science aspects. Quantitative information can be used to make an appropriate choice of synthetic receptors for different applications and for prediction of the detection limit and selectivity of analytical devices based on these receptors. Additionally, these data can be used as descriptors for combinatorial optimization and for discovery of new sensing materials (the combinatorial approach is discussed in Chapter 3) [1–3].

The association can be investigated in the bulk phase (in the solution or suspension of the ligand and receptor molecules) or on a surface. Ligand–receptor interactions can be investigated in a bulk phase by titration and application of any analytical technique that is sensitive to the concentration of free or bound ligands or receptors. For example, the binding of dye molecules can be determined by colorimetry or fluorescence, while ions or redox-active species can be measured by potentiometric techniques. One of the most commonly used techniques that can be applied for various ligand–receptor systems is a NMR titration. Another general approach is based on isothermal calorimetry; in this case the heat produced during the ligand–receptor interaction is measured. This technique has the advantage of providing the enthalpy of binding in a single titration experiment. Analysis of ligand–receptor binding in bulk phases is well described in literature [4–7] and, therefore, is not covered in this chapter.

Applications of artificial receptors for chemical sensors require an immobilization of these receptors on a surface. In the 1980s to the beginning of 1990s there were many attempts to induce physical immobilization of chemoreceptors, for example, by using the Langmuir–Blodgett technique or electrostatically driven adsorption. Nowadays, receptor immobilization is performed mainly by formation of chemical bonds with some surface groups (e.g., peptide bond) or by introduction of surface anchoring groups into the receptor molecules. Chemical aspects of covalent receptor immobilization have been described [8–15]. The most widely used technology of chemical immobilization is based on the formation of an amide bond through activation by either EDC [1-ethyl-3-(3-dimethylaminopropyl)carbodiimide)] [14, 15] or an EDC–NHS (N-hydroxysuccinimide) mixture. The most widely used surface anchor group is the thiol group, which forms, spontaneously, an extremely strong bond with gold, silver, palladium, copper, and some other materials [13, 16–19].

Chemical immobilization of a receptor may influence its affinity properties. This chapter is focused on the characterization of affinity properties of immobilized receptors.

1.2 Measurements Under Equilibrium Conditions

Binding of a ligand (A) with a receptor (B) leading to the formation of a complex can be considered using a formal kinetic approach:

The rate of association (adsorption onto the receptor layer) is proportional to the ligand concentration (cL) and to the fraction of uncoated binding sites (1 − θ), where θ is the fraction of occupied binding sites. Therefore, the association rate is (1 − θ), where is the kinetic adsorption constant (also indicated as the kinetic association constant or kinetic binding constant). The rate of dissociation is where is the kinetic constant of desorption (also indicated as the kinetic constant of dissociation). At equilibrium conditions: