Synthesis of Macrocyclic Lanthanide Chelates for Anion Sensing and Magnetic Resonance Imaging Applications PDF Download
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Author: Christopher G. Gulgas
Publisher:
ISBN:
Category :
Languages : en
Pages : 133
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Book Description
Novel Eu3-containing macrocyclic complexes were synthesized and studied as anion sensing probe molecules. Several of these macrocycles exhibited unique luminescence responses to hydrogen-bond accepting anions (fluoride, acetate, and dihydrogen phosphate) in DMSO, even in the presence of a chloride ion background. The first series of compounds highlighted a high-yielding synthetic route for highly functional macrocycles that incorporate a Eu3 chelate, aromatic antennae, thiourea groups as anion-binding units, and a variable linker that tunes the size and rigidity of the pocket. These macrocycles exhibited Eu3 luminescence where emission intensity ([lambda]exc = 272 nm, [lambda]em = 614 nm) was correlated to the linker length. Anion-induced changes in emission intensity were dependent on the basicity of the anion, and emission enhancements were observed up to 77% upon titration with fluoride in one case. Through luminescence lifetime studies of the Eu3+ macrocycles and the study of a newly synthesized series of organic model compounds, it was determined that the luminescence response to anions was the result of interaction with the thiourea moieties and no evidence was observed for anion coordination to Eu3+. Additionally, two second-generation macrocycles were synthesized, incorporating an amine unit for stronger binding affinity. One of these macrocycles, featuring a pendant naphthalene antenna, responded to several anions in aqueous solution by means of a luminescence decrease of up to 30%. This general macrocyclic design shows promise for the development of Eu3+-based anion sensors that function in competitive solvents. In continuing work with lanthanide complexes, a new targeted Gd3+-based magnetic resonance imaging contrast agent was designed and synthesized for specific binding to the dopamine receptor protein. A relaxivity of 7.1 mM−1s−1 was measured for this complex at 400 mHz and 310 K.A Eu3+ analogue was also synthesized and structurally characterized. Luminescence lifetime measurements revealed the presence of 2 coordinated water molecules in aqueous solution, consistent with the observed relaxivity of the Gd3+ complex. The synthetic scheme described herein can be extended to the synthesis of a series of targeted complexes for enhanced dopamine receptor binding and imaging studies.
Author: Christopher G. Gulgas
Publisher:
ISBN:
Category :
Languages : en
Pages : 133
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Book Description
Novel Eu3-containing macrocyclic complexes were synthesized and studied as anion sensing probe molecules. Several of these macrocycles exhibited unique luminescence responses to hydrogen-bond accepting anions (fluoride, acetate, and dihydrogen phosphate) in DMSO, even in the presence of a chloride ion background. The first series of compounds highlighted a high-yielding synthetic route for highly functional macrocycles that incorporate a Eu3 chelate, aromatic antennae, thiourea groups as anion-binding units, and a variable linker that tunes the size and rigidity of the pocket. These macrocycles exhibited Eu3 luminescence where emission intensity ([lambda]exc = 272 nm, [lambda]em = 614 nm) was correlated to the linker length. Anion-induced changes in emission intensity were dependent on the basicity of the anion, and emission enhancements were observed up to 77% upon titration with fluoride in one case. Through luminescence lifetime studies of the Eu3+ macrocycles and the study of a newly synthesized series of organic model compounds, it was determined that the luminescence response to anions was the result of interaction with the thiourea moieties and no evidence was observed for anion coordination to Eu3+. Additionally, two second-generation macrocycles were synthesized, incorporating an amine unit for stronger binding affinity. One of these macrocycles, featuring a pendant naphthalene antenna, responded to several anions in aqueous solution by means of a luminescence decrease of up to 30%. This general macrocyclic design shows promise for the development of Eu3+-based anion sensors that function in competitive solvents. In continuing work with lanthanide complexes, a new targeted Gd3+-based magnetic resonance imaging contrast agent was designed and synthesized for specific binding to the dopamine receptor protein. A relaxivity of 7.1 mM−1s−1 was measured for this complex at 400 mHz and 310 K.A Eu3+ analogue was also synthesized and structurally characterized. Luminescence lifetime measurements revealed the presence of 2 coordinated water molecules in aqueous solution, consistent with the observed relaxivity of the Gd3+ complex. The synthetic scheme described herein can be extended to the synthesis of a series of targeted complexes for enhanced dopamine receptor binding and imaging studies.
Author: Graeme James Stasiuk
Publisher:
ISBN:
Category :
Languages : en
Pages :
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Book Description
This thesis reports a series of novel Ln-DO3A based complexes, modulation of emission intensity (Eu and Tb) has been achieved and relaxivity, r1, (Gd) has been shown. Propargyl-appended lanthanide complexes derived from DO3A, has a hydration state, q = 2. They undergo Cu(I) catalysed cycloaddition reactions with azides to form 1,2,3-triazole appended complexes: coordination of one of the triazole nitrogen atoms to the metal centre changes the local coordination environment and luminescence studies indicate a hydration state of q = 1. Propargyl-appended Ln(III) complexes show unanticipated reactivity towards NaN3 in the Cu(I) catalysed 'click' reaction yielding an unsubstituted 1,2,3-triazole. The resulting Eu(III) complex exhibits pH-responsive 1H NMR and Ln(III) luminescence behaviour in the physiological pH range, consistent with deprotonation of the NH-acidic bound triazole. The coordination mode of the NH-triazole switches from NH-triazole bound in a pyridinic manner to bound in an anionic manner as a triazolide, while retaining a q = 1. This was demonstrated in luminescent studies of Eu(III) and Tb(III) complexes with a pKa ~ 7.5. Relaxation measurements on the Gd(III) analogue show a q =1 throughout the pH range, i.e. no change in hydration state. To overcome the unanticipated reactivity of NaN3 with propargyl-appended Ln(III) complexes, p-ethynylbenzyl-appended Ln(III) complexes were synthesised. These show promise as precursors for multimeric, self-associating and d-f hybrid complexes, via the Cu(I) catalysed cycloaddition or 'click' reaction. Luminescent studies show evidence of the formation of 1,2,3-triazoles that do not bind to the Ln(III) metal centre, with a hydration state q =1. These complexes have been applied in the synthesis of multimeric, self-associating and d-f hybrid compounds. Uridine was attached to a EuDO3A chelate via four different linkers. These complexes are precursors for an accumulation and activation strategy, developed as enzyme activated contrast agents. Neutral q = 1 Eu(III) uridine-DO3A based complexes were successfully synthesised and linked via a propyl, amide or 1,2,3-triazole unit.
Author:
Publisher:
ISBN:
Category : Dissertations, Academic
Languages : en
Pages : 994
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Book Description
Author: Jonathan L Sessler
Publisher: Royal Society of Chemistry
ISBN: 1847552471
Category : Science
Languages : en
Pages : 431
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Book Description
Anion recognition plays a critical role in a range of biological processes, and a variety of receptors and carriers can be found throughout the natural world. Chemists working in the area of supramolecular chemistry have created a range of anion receptors, drawing inspiration from nature as well as their own inventive processes. This book traces the origins of anion recognition chemistry as a unique sub-field in supramolecular chemistry while illustrating the basic approaches currently being used to effect receptor design. The combination of biological overview and summary of current synthetic approaches provides a coverage that is both comprehensive and comprehensible. First, the authors detail the key design motifs that have been used to generate synthetic receptors and which are likely to provide the basis for further developments. They also highlight briefly some of the features that are present in naturally occurring anion recognition and transport systems and summarise the applications of anion recognition chemistry. Providing as it does a detailed review for practitioners in the field and a concise introduction to the topic for newcomers, Anion Receptor Chemistry reflects the current state of the art. Fully referenced and illustrated in colour, it is a welcome addition to the literature.
Author: Michel M.J. Modo
Publisher: CRC Press
ISBN: 1420004093
Category : Medical
Languages : en
Pages : 440
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Book Description
The ability of molecular and cellular imaging to track the survival, migration, and differentiation of cells in vivo as well as monitor particular gene expression in living subjects is rapidly moving from the research laboratory into daily clinical settings. The interdisciplinary nature of the field mandates a constant dialogue among molecular and
Author: Jinkui Tang
Publisher: Springer
ISBN: 3662469995
Category : Science
Languages : en
Pages : 219
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Book Description
This book begins by providing basic information on single-molecule magnets (SMMs), covering the magnetism of lanthanide, the characterization and relaxation dynamics of SMMs and advanced means of studying lanthanide SMMs. It then systematically introduces lanthanide SMMs ranging from mononuclear and dinuclear to polynuclear complexes, classifying them and highlighting those SMMs with high barrier and blocking temperatures – an approach that provides some very valuable indicators for the structural features needed to optimize the contribution of an Ising type spin to a molecular magnet. The final chapter presents some of the newest developments in the lanthanide SMM field, such as the design of multifunctional and stimuli-responsive magnetic materials as well as the anchoring and organization of the SMMs on surfaces. In addition, the crystal structure and magnetic data are clearly presented with a wealth of illustrations in each chapter, helping newcomers and experts alike to better grasp ongoing trends and explore new directions. Jinkui Tang is a professor at Changchun Institute of Applied Chemistry, Chinese Academy of Sciences. Peng Zhang is currently pursuing his PhD at Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, with a specific focus on the molecular magnetism of lanthanide compounds under the supervision of Prof. Jinkui Tang.
Author: Kristin Bowman-James
Publisher: John Wiley & Sons
ISBN: 3527639519
Category : Science
Languages : en
Pages : 644
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Book Description
Building on the pioneering work in supramolecular chemistry from the last 20 years or so, this monograph addresses new and recent approaches to anion coordination chemistry. Synthesis of receptors, biological receptors and metallareceptors, the energetics of anion binding, molecular structures of anion complexes, sensing devices are presented and computational studies addressed to aid with the understanding of the different driving forces responsible for anion complexation. The reader is promised an actual picture of the state of the art for this exciting and constantly evolving field of supramolecular anion coordination chemistry. The topics range from ion channels to selective sensors, making it attractive to all researchers and PhD students with an interest in supramolecular chemistry.
Author: Andre S. Merbach
Publisher: John Wiley & Sons
ISBN: 1118503678
Category : Science
Languages : en
Pages : 514
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Book Description
Magnetic Resonance Imaging (MRI) is one of the most important tools in clinical diagnostics and biomedical research. The number of MRI scanners operating around the world is estimated to be approximately 20,000, and the development of contrast agents, currently used in about a third of the 50 million clinical MRI examinations performed every year, has largely contributed to this significant achievement. This completely revised and extended second edition: Includes new chapters on targeted, responsive, PARACEST and nanoparticle MRI contrast agents. Covers the basic chemistries, MR physics and the most important techniques used by chemists in the characterization of MRI agents from every angle from synthesis to safety considerations. Is written for all of those involved in the development and application of contrast agents in MRI. Presented in colour, it provides readers with true representation and easy interpretation of the images. A word from the Authors: Twelve years after the first edition published, we are convinced that the chemistry of MRI agents has a bright future. By assembling all important information on the design principles and functioning of magnetic resonance imaging probes, this book intends to be a useful tool for both experts and newcomers in the field. We hope that it helps inspire further work in order to create more efficient and specific imaging probes that will allow materializing the dream of seeing even deeper and better inside the living organisms. Reviews of the First Edition: "...attempts, for the first time, to review the whole spectrum of involved chemical disciplines in this technique..."—Journal of the American Chemical Society "...well balanced in its scope and attention to detail...a valuable addition to the library of MR scientists..."—NMR in Biomedicine
Author: Mario Berberan-Santos
Publisher: Mdpi AG
ISBN: 9783036516332
Category : Science
Languages : en
Pages : 198
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Book Description
A growing interest has been devoted to the development of host systems for ionic and neutral species based on calixarenes. These cyclic oligomers show important host-guest properties, which has led to numerous applications in a broad range of fields, including organocatalysis, sensing, extraction and separation, and, more recently, biomedical applications. The relative ease of the functionalization of their upper and lower rims and the presence of a pre-organized cavity that is available in different sizes and conformations make calixarenes attractive building blocks for the construction of supramolecular assemblies. This book presents the most recent developments on the host-guest properties of calixarenes, as well as the new synthetic methods and applications.
Author: Pekka Hänninen
Publisher: Springer Science & Business Media
ISBN: 3642210236
Category : Science
Languages : en
Pages : 392
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Book Description
Lanthanides have fascinated scientists for more than two centuries now, and since efficient separation techniques were established roughly 50 years ago, they have increasingly found their way into industrial exploitation and our everyday lives. Numerous applications are based on their unique luminescent properties, which are highlighted in this volume. It presents established knowledge about the photophysical basics, relevant lanthanide probes or materials, and describes instrumentation-related aspects including chemical and physical sensors. The uses of lanthanides in bioanalysis and medicine are outlined, such as assays for in vitro diagnostics and research. All chapters were compiled by renowned scientists with a broad audience in mind, providing both beginners in the field and advanced researchers with comprehensive information on on the given subject.
