Guanosine and its derivatives have a high potential for self-recognition and self-assembly, as well as the recognition ability for other biologically important molecules. This book explores in detail these properties with the goal of increasing knowledge of the basic principles of guanosine-assembly, synthesis of new optimised materials and exploration of their electronic and optical properties. Following the work of COST Action MP0802, the aim is to design novel reproducible and well ordered supramolecular structures to serve as molecular-scale architectures for new hybrid molecular electronics. Coverage includes synthesis, characterisation and optimisation, theoretical modelling and prediction, biochemical and biorecognition properties and applications in nanotechnology especially in molecular electronics. Appealing to researchers working in the field ranging from chemists, biologists and material scientists, this title will be a welcome addition to the inter-disciplinary literature providing direction for future research and ideas for industrial applications.
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Guanosine and its derivatives have a high potential for self-recognition and self-assembly, as well as the recognition ability for other biologically important molecules. This book explores in detail these properties with the goal of increasing knowledge of the basic principles of guanosine-assembly, synthesis of new optimised materials and exploration of their electronic and optical properties. Following the work of COST Action MP0802, the aim is to design novel reproducible and well ordered supramolecular structures to serve as molecular-scale architectures for new hybrid molecular electronics. Coverage includes synthesis, characterisation and optimisation, theoretical modelling and prediction, biochemical and biorecognition properties and applications in nanotechnology especially in molecular electronics. Appealing to researchers working in the field ranging from chemists, biologists and material scientists, this title will be a welcome addition to the inter-disciplinary literature providing direction for future research and ideas for industrial applications.
Chapter 1,
Introduction: From G-Quartet to G-Quadruplex and its Nanoarchitectures Lea Spindler, 1,
Guanylic acid Self-Assembly: 100 years on Gang Wu, 3,
Functional Assemblies made from Supramolecular G-Quadruplexes J.M Rivera, 15,
Self-Assembly of Lipophilic Guanosines: Switching between different Assemblies Stefano Masiero, Silvia Pieraccini and, 28,
Nanopatterning the Surface with ordered Supramolecular Architectures: Controlling the Self-Assembly of Guanine-based Hydrogen-Bonded Motifs Artur Ciesielski, Mathieu Surin, Gian Piero Spada and Paolo Samor, 40,
Morphological Heterogeneity of Supramolecular G-DNA Polymers derived from Guanine Rich Oligonucleotides T.C. Marsh, Z.M. Henseler and M.A. Klimstra, 48,
Thermondynamics of G-Quadruplexes C Giancola, 63,
G-Quadruplex Nanostructures Probed at the Single Molecular Level by Force-Based Methods Soma Dhakal, Hanbin Mao, Arivazhagan Rajendran, Masayuki Endo, and Hiroshi Sugiyama, 73,
Chapter 2,
Introduction: Synthesis and Characterization Gian Piero Spada, 87,
Synthesis and Properties of Oligonucleotides Forming G-Quadruplexes A. Aviño, andR. Eritja, 89,
Electrochemical Characterization of Guanine Quadruplexes A. — M. Chiorcea — Paquim, P. Santos, V.C. Diculescu, R. Eritja and A.M. Oliveira-Brett, 100,
AFM of Guanine Rich Oligonucleotide Surface Structures James Vesenka, 110,
Solution Dynamics and Structure of G-Quadruplexes Studied by Dynamic Light Scattering Lea Spindler, 121,
GMP-Quadruplex Structures in Dilute Solutions and in Condensed Phases: An X-Ray Scattering Analysis E. Jr. Baldassarri, M. G. Ortore, A. Gonnelli, M. Marcinekova, S. Mazzoni, M. L. Travaglini and P. Mariani, 135,
Temperature-Gradient Gel Electrophoresis: Unfolding of G-Quadruplexes Viktor Viglaský, Katarina Tlucková, Petra Tóthová and L'ubos Bauer, 147,
Specific Behaviour of Guanosine in Liponucleoside Thin Films L. Coga, M. Devetak, S. Masiero, G.P. Spada and I. Drevensek-Olenik, 154,
Chapter 3,
Theoretical Modelling, Analysis and Prediction Shozeb Haider, 165,
Fundamentals and Applications of the Geometric Formalism of Quadruplex Folding Mateus Webba da Silva and Andreas Ioannis Karsisiotis, 167,
Guanine, Xanthine and Uric Acid Assemblies: Comparative Theoretical and Experimental Studies Gábor Paragi, János Szolomájer, Zoltán Kupihár, Gyula Batta, Zoltán Kele, Petra Pádár, Botond Penke, Hester Zijlstra, Celia Fonseca Guerra, F. Matthias Bickelhaup, and Lajos Kovács, 179,
Computational Methods for Studying G-Quadruplex Nuceic Acids B. Islam, V. D'Atri, M. Sgobba, J. Husby and S. Haider, 194,
Chapter 4,
Introduction: Recognition of Quadruplexes Mateus Webba da Silva, 213,
Biological Functions of G-Quadruplexes Nancy Maizels, 215,
Regulation of Gene Transcription by DNA G-Quadruplexes Michael Fry, 223,
The Reality of Quadruplex Nucleic Acids as a Therapeutic Target G. N. Parkinson, 237,
Screening for Quadruplex Binding Ligands: A Game of Chance? E. Largy and M.-P. Teulade-Fichou, 248,
Recognition of G-Quadruplexes by Metal Complexes Kogularamanan Suntharalingam and Ramon Vilar, 263,
Chapter 5,
Introduction: Applications in Bioanalytics, Therapy and Molecular Electronics Wolfgang Fritzsche, 275,
Catalytic G-Quadruplexes Dipankar Sen, 277,
Catalytic G-Quadruplexes for the Detection of Telomerase Activity Joanna Kosman, Bernard Juskowiak, 285,
G-Quadruplex forming Oligonucleotides with Tailor-made Modifications as effective aptamers for Potential Therapeutic Applications Domenica Musumeci and Daniela Montesarchio, 292,
Dep-Based Integration of G-Quadruplex Structures Christian Leiterer, Andreas Kopielski, Irit Lubitz, Alexander Kotlyar, Antti-Pekka Eskelinen, Päivi Törmä and Wolfgang Fritzsche, 306,
Conductive Behaviour of G4-DNA-Silver Nanoparticle Structures T. Parviainen, G. Eidelshten, A. Kotlyar, and J. J. Toppari, 314,
Novel Materials for Molecular Electronics – Synthese and Characterization of Long G4-DNA Dvir Rotem, Gennady Eidelshtein, Alexander Kotlyar and Danny Porath, 324,
Subject Index, 337,
From G-Quartet to G-Quadruplex and its Nanoarchitectures
Chapter Editor: Lea Spindler
In 1910 Ivar Bang reported that concentrated solutions of guanylic acid formed a gel. It took half a century before Gellert et al. in 1962 discovered the structural motif, a guanine-quartet, to be the basis for guanylic acid gelation. This chapter starts with a historical overview and gives credit to Ivar Bang and several other pioneers in the field. Then the basic principles of guanine self-assembly are explored, either for individual molecules like guanosine and its derivatives, or for guanine-rich oligonucleotides and G-rich DNA-sequences. Finally, we show how these guanine-based nanoarchitectures are visualised by surface techniques like scanning tunnelling microscopy or atomic force microscopy.
GUANYLIC ACID SELF-ASSEMBLY: 100 YEARS LATER
Gang Wu
Department of Chemistry, Queen's University, Kingston, Ontario, Canada K7L 3N6
1 INTRODUCTION
It is commonly accepted that the work of Gellert, Lipsett, and Davies published in 1962 marks the beginning of modern research on G-quartet related molecular systems. Interestingly, the opening sentence of this seminal paper stated, "In 1910, Bang reported that concentrated solutions of guanylic acid formed a gel." This referred to a paper published half of a century earlier. They then described two structural models used to explain the experimental X-ray diffraction patterns obtained for guanylic acid fibers. The fibers were drawn from two different types of guanylic acid gels: one from concentrated aqueous solutions of guanosine 3'-monophosphate (3'-GMP) under an acidic condition (pH 5) and the other from the 5' isomer, 5'-GMP, under a similar condition. The central structural building block proposed for the 3'-GMP gel consists of four hydrogen bonded guanine bases in a planar fashion, which is now known as a G-quartet or G-tetrad. The structural model proposed for the 5'-GMP gel was initially ambiguous, due to the limited quality of the X-ray data. Later, Davies and co-workers showed that the correct structural model for 5'-GMP gels obtained at pH 5 consists of hydrogen bonded guanine bases that form a continuous helix similar to the shape of a lock-washer. These two models are illustrated in Figure 1.
In the past 20 years, research activities in the field of G-quartet related molecular systems have grown exponentially. Recent discoveries of the existence of the G-quartet motif in many biologically important systems such as telomeres, promoters of many genes, and sequences related to various human diseases have triggered tremendous research interest in this unusual type of nucleic acid structures. Now G-quartet structures can be found in such diverse areas as molecular biology, medicinal chemistry, supramolecular chemistry, and nanotechnology. It is interesting to note that, as the field of G-quartet research expands in recent years, one can also find increasingly more references to the aforementioned 1910 article by Bang....
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