Metal induced folding: synthesis and conformational analysis of the lanthanide complexes of two 44-membered hydrazone macrocycles

Klein, Jörg M.; Clegg, Jack K.; Saggiomo, Vittorio; Reck, Lisa; Lüning, Ulrich; Sanders, Jeremy K. M.

doi:10.1039/c2dt11861k

Cited by 19 publications

(8 citation statements)

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“…Integrating the bis-hydrazone moiety into macrocycles converts the local shape changes upon coordination into overall conformational switching of the macrocyles. 43 The ''S''-shaped 44-membered [2 + 2] macrocycles 27 and 28 each consist of two bis-acylhydrazone units connected by flexible linkers. Upon coordination with La 3+ , Eu 3+ and Dy 3+ , 27 and 28 twist from their ''S'' conformation to accommodate the metal cations with their two NNNOO-binding units (Fig.…”

Section: Dynamic Shape Adaptationmentioning

confidence: 99%

Hydrazone-based switches, metallo-assemblies and sensors

2014

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The hydrazone functional group has been extensively studied and used in the context of supramolecular chemistry. Its pervasiveness and versatility can be attributed to its ease of synthesis, modularity, and most importantly unique structural properties, which enable its integration in different applications. This review provides an overview of the utilization of hydrazones in three supramolecular chemistry related areas: molecular switches, metallo-assemblies and sensors. These topics were chosen because they highlight the diversity of hydrazones, and emphasize their uniqueness vis-à-vis the imine functional group. Discussion entails (i) chemical and light activated switching of hydrazones, and how this can be used in controlling the properties of self-assembled systems, (ii) the use of hydrazones in the formation of dynamic and stimuli responsive metallogrids, and (iii) the use of hydrazones in detecting metal cations (Zn(2+), Cu(2+), Hg(2+), etc.), anions (F(-), CN(-), P2O7(4-), etc.) and neutral molecules (amines, water, Cys, etc.).

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Section: Dynamic Shape Adaptationmentioning

confidence: 99%

Hydrazone-based switches, metallo-assemblies and sensors

2014

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“…[8] Although randomly functionalized nanoparticles or nanoparticles functionalized with as ingle ligand have found applications in nanomedicine, [9] imaging, [10] sensing, [11] and as building blocks in controlled self-assembly, [12] the efficient and selective multivalent binding of biomacromolecules requires ac omplementary pattern of small recognition units on the surface of the nanoparticle. [11a, 13] Ap romising approach to obtain ar eceptor complementary to its target is to synthesize it under thermodynamic control in the presence of the target that acts as at emplate.T his approach has been successfully utilized in dynamic combinatorial chemistry (DCC) [14] to make receptors for small molecules, [15] ligands binding to pockets of biomacromolecules, [16] and multivalent polymers. [14n,17] We reasoned that the same approach may be utilized to achieve the selective functionalization of nanoparticle surfaces.D CC involving nanoparticles and small building blocks is so far unexplored, but should lead to multivalent receptors for biomacromolecules ( Figure 1A)i f certain criteria are met.…”

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confidence: 99%

Localized Template‐Driven Functionalization of Nanoparticles by Dynamic Combinatorial Chemistry

et al. 2015

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We have developed a method for the localized functionalization of gold nanoparticles using imine-based dynamic combinatorial chemistry. By using DNA templates, amines were grafted on the aldehyde-functionalized nanoparticles only if and where the nanoparticles interacted with the template molecules. Functionalization of the nanoparticles was controlled solely by the DNA template; only amines capable of interacting with DNA were bound to the surface. Interestingly, even though our libraries contained only a handful of simple amines, the DNA sequence influenced their attachment to the surface. Our method opens up new opportunities for the synthesis of multivalent, nanoparticle-based receptors for biomacromolecules.

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“…44-Membered hydrazone macrocycles such as L 69 have been prepared and their lanthanide(III) complexes studied. 112 Single crystal X-ray studies show that upon complexation there are significant changes in conformation from a stacked to a twisted helical structure. Love and co-workers have developed a range of heteroditopic This journal is © The Royal Society of Chemistry 2013 Schiff-base pyrrole macrocycles including L 70 .…”

Section: Compartmental Ligandsmentioning

confidence: 99%

Macrocyclic coordination chemistry

Burke

Archibald

2013

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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This chapter reviews the literature published on macrocyclic coordination chemistry during 2012. The aim is to describe the key advances, focusing on complexes formed with transition metal and lanthanide ions. Porphyrin ligands and supramolecular chemistry are not covered. New chelator design, coordination complex formation and characterisation are presented along with details on the most common applications including luminescent compound formation, MRI contrast agents and radiopharmaceuticals. HighlightsIn 2012, some elegant studies and new tools for radiopharmaceutical imaging were reported. Cooper and co-workers carried out a comparative study of bifunctional chelators for 64 Cu giving a definitive answer to which had the most favourable properties for in vivo imaging use. 1 This is extremely important when chemists are creating tools for use by biologists and medics. Denat and co-workers reported a new bifunctional chelator; a glutaric acid anhydride derivative of DOTA that will have high impact as a tool for labelling proteins and peptides. 2,3 Caravan and co-workers advanced MRI contrast agent technology by developing an amino acid derivative of DOTA that allows high rigidity and improved high field relaxivity properties when incorporated into a peptide. 4 These optimised tools will allow molecular imaging applications to reach their full potential.Catalysis is also an important area for macrocyclic chelator and metal complex design with the role of the zirconium(IV) cyclam complex in polylactide formation particularly interesting. 5 A key advance was made in the work of Williams and Kember, where they generated a highly active catalyst for copolymerisation of epoxides and carbon dioxide, offering a non-toxic and cost effective alternative to current processes. 6

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Metal induced folding: synthesis and conformational analysis of the lanthanide complexes of two 44-membered hydrazone macrocycles

Cited by 19 publications

References 50 publications

Hydrazone-based switches, metallo-assemblies and sensors

Hydrazone-based switches, metallo-assemblies and sensors

Localized Template‐Driven Functionalization of Nanoparticles by Dynamic Combinatorial Chemistry

Macrocyclic coordination chemistry

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