Journal ArticleDOI
Ultrastable Host-Guest Complexes and Their Applications
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TLDR
These complexes with their exceptional affinity, chemical robustness, simple preparation, biocompatibility, and easy handling may replace the biotin–(strept)avidin system in diverse areas of research, including affinity chromatography, high throughput biochemical assays, imaging, and sensor technologies.Abstract:
This review describes monovalent synthetic receptor–ligand (or host–guest) pairs with extremely high binding affinity, comparable to that of the biotin–avidin pair, and their applications. Cucurbit[7]uril (CB[7]), a member of the host family cucurbit[n]uril (CB[n], n=5–8, 10), forms ultrastable host–guest complexes with ferrocene-, adamantane- or bicyclo[2.2.2]octane-based molecules having ammonium groups properly positioned to interact with the carbonyl oxygens at the portals of CB[7]. The extremely high affinity is achieved by a large enthalpic gain arising from the near perfect size/shape complementarity between the rigid CB cavity and the rigid core of the guest molecules, with the critical assistance of the positive entropy change due to the extensive dehydration of the host and guest. The high stability of the complexes allowed us and others to explore several biological applications such as immobilization of biomolecules on a solid surface, protein isolation, triggering intracellular events, and regulating enzymatic activities. These complexes with their exceptional affinity, chemical robustness, simple preparation, biocompatibility, and easy handling may replace the biotin–(strept)avidin system in diverse areas of research, including affinity chromatography, high throughput biochemical assays, imaging, and sensor technologies.read more
Citations
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Journal ArticleDOI
Cucurbiturils: from synthesis to high-affinity binding and catalysis
Khaleel I. Assaf,Werner M. Nau +1 more
TL;DR: The fundamental properties of CBn homologues and their cyclic derivatives are discussed with a focus on their synthesis and their applications in catalysis.
Journal ArticleDOI
The strategic use of supramolecular pKa shifts to enhance the bioavailability of drugs
Indrajit Ghosh,Werner M. Nau +1 more
TL;DR: Macrocyclic hosts of the cyclodextrin, sulfonatocalixarene, and cucurbituril type can be employed as discrete supramolecular drug delivery systems, thereby complementing existing supramolescular drug formulation strategies based on polymers, hydrogels, liposomes, and related microheterogeneous systems.
Journal ArticleDOI
Guest binding dynamics with cucurbit[7]uril in the presence of cations.
TL;DR: The kinetics results showed that formation of a complex between a positively charged guest with CB[n] can occur at a rate close to the diffusion-controlled limit with no detection of a stable exclusion complex.
Journal ArticleDOI
Templated Synthesis of Glycoluril Hexamer and Monofunctionalized Cucurbit[6]uril Derivatives
Derick Lucas,Tsuyoshi Minami,Greg Iannuzzi,Liping Cao,James B. Wittenberg,Pavel Anzenbacher,Lyle Isaacs +6 more
TL;DR: It is reported that the p-xylylenediammonium ion acts as a template in the cucurbit[n]uril forming reaction that biases the reaction toward the production of methylene bridged glycoluril hexamer (6C) and bis-nor-seco-CB[10].
Journal ArticleDOI
Nanomolar Binding of Peptides Containing Noncanonical Amino Acids by a Synthetic Receptor
Leigh A. Logsdon,Christopher L. Schardon,Vijayakumar Ramalingam,Sharon K. Kwee,Adam R. Urbach +4 more
TL;DR: Q7 binds to N-terminal AMPhe several orders of magnitude more tightly than any of the canonical amino acid residues, which makes it attractive for the development of minimal affinity tags.
References
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Journal ArticleDOI
Complexation Thermodynamics of Cyclodextrins.
Journal ArticleDOI
The cucurbit[n]uril family
TL;DR: In 1981, the macrocyclic methylene-bridged glycoluril hexamer (CB[6]) was dubbed "cucurbituril" by Mock and co-workers because of its resemblance to the most prominent member of the cucurbitaceae family of plants--the pumpkin.
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Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry.
TL;DR: This Account is a compilation of recent literature covering the syntheses of the homologues and derivatives, and their supramolecular chemistry of cucurbituril, a synthetic receptor.
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New Cucurbituril Homologues: Syntheses, Isolation, Characterization, and X-ray Crystal Structures of Cucurbit[n]uril (n = 5, 7, and 8)
Jaheon Kim,In-Sun Jung,Soo Young Kim,Eunsung Lee,Jin-Koo Kang,Shigeru Sakamoto,and Kentaro Yamaguchi,Kimoon Kim +7 more
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Protein S-nitrosylation: a physiological signal for neuronal nitric oxide.
Samie R. Jaffrey,Hediye Erdjument-Bromage,Christopher D. Ferris,Paul Tempst,Solomon H. Snyder +4 more
TL;DR: Protein S-nitrosylation is established as a physiological signalling mechanism for neuronally generated NO in mice harbouring a genomic deletion of neuronal NO synthase (nNOS).