Recognition of Viologen Derivatives in Water by <i>N</i>-Alkyl Ammonium Resorcinarene Chlorides

Beyeh, Ngong Kodiah; Jo, Hyun Hwa; Kolesnichenko, Igor V.; Pan, Fangfang; Kalenius, Elina; Anslyn, Eric V.; Ras, Robin H. A.

doi:10.1021/acs.joc.7b00449

Cited by 17 publications

(10 citation statements)

References 41 publications

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“…There are eight three-fold and six four-fold channels that span the cage and allow diffusion into the cavity. The cationic resorcin[4]arene hosts were synthesized by reacting the upper rim 2-position of the phenyl group with benzyloxycarbonyl (Boc)-protected amine in the presence of excess formaldehyde in a Mannich condensation reaction. , Finally, the Boc protection was removed using acid hydrolysis to achieve resorcin[4]arene hosts with 4, 8, and 16 amines (hosts R(4+) , R(8+) , and R(16+) , respectively). Additionally, a negatively charged control resorcinarene R(4−) was prepared.…”

Section: Resultsmentioning

confidence: 99%

Crystalline Cyclophane–Protein Cage Frameworks

et al. 2018

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Cyclophanes are macrocyclic supramolecular hosts famous for their ability to bind atomic or molecular guests via noncovalent interactions within their well-defined cavities. In a similar way, porous crystalline networks, such as metal–organic frameworks, can create microenvironments that enable controlled guest binding in the solid state. Both types of materials often consist of synthetic components, and they have been developed within separate research fields. Moreover, the use of biomolecules as their structural units has remained elusive. Here, we have synthesized a library of organic cyclophanes and studied their electrostatic self-assembly with biological metal-binding protein cages (ferritins) into ordered structures. We show that cationic pillar[5]arenes and ferritin cages form biohybrid cocrystals with an open protein network structure. Our cyclophane–protein cage frameworks bridge the gap between molecular frameworks and colloidal nanoparticle crystals and combine the versatility of synthetic supramolecular hosts with the highly selective recognition properties of biomolecules. Such host–guest materials are interesting for porous material applications, including water remediation and heterogeneous catalysis.

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Section: Resultsmentioning

confidence: 99%

Crystalline Cyclophane–Protein Cage Frameworks

et al. 2018

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“…The ability to detect a broad variety of analytes under a wide variety of real-world conditions is critical for a number of applications and in a wide range of scientific, medical, political, and security realms. Broadly speaking, chemists have been highly successful at developing detection methods for small organic molecules, , anions, , and cations; , biological macromolecules including peptides , and oligonucleotides; and whole cells , and organisms, including bacteria , and fungi. , Notable successes include the use of these systems for the detection of 2,4,6-trinitrotoluene (TNT) , in the air above land mines, for demarcation of tumor boundaries to enable highly effective tumor resection surgeries, and for the detection of bacteria in food, liquid, and the human body …”

Section: Introductionmentioning

confidence: 99%

Supramolecular Luminescent Sensors

2018

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There is great need for stand-alone luminescence-based chemosensors that exemplify selectivity, sensitivity, and applicability and that overcome the challenges that arise from complex, real-world media. Discussed herein are recent developments toward these goals in the field of supramolecular luminescent chemosensors, including macrocycles, polymers, and nanomaterials. Specific focus is placed on the development of new macrocycle hosts since 2010, coupled with considerations of the underlying principles of supramolecular chemistry as well as analytes of interest and common luminophores. State-of-the-art developments in the fields of polymer and nanomaterial sensors are also examined, and some remaining unsolved challenges in the area of chemosensors are discussed. CONTENTS 4.4. Explosives 4.5. Pharmaceutical Agents 4.6. Biologically Relevant 4.6.1. Adenosine Triphosphate (ATP)

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“…The resorcin [4]arenes used here exists in their C 4v crown conformation which is locked by intramolecular hydrogen bonds between adjacent hydroxyl groups at the upper rim. Further functionalization of the upper rim with amine containing moieties in a Mannich 38,39 condensation reaction with excess formaldehyde and subsequent ring opening with mineral acids 40 give the resorcin [4]arenes a cationic character that enables binding with anionic heparin. The pillar [5]arene used in this study has a characteristic pillar-like structure and cationic moieties on both upper and lower rim in addition to an electronrich internal cavity accessible from both sides.…”

Section: Introductionmentioning

confidence: 99%

A supramolecular host–guest complex for heparin binding and sensing

et al. 2018

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Heparin is an anionic polysaccharide widely used in clinics as an anticoagulant. However, heparin usage requires an antidote and sensors for safe operation during and after surgeries. In this study, a host-guest complex capable of selective heparin binding and sensing is presented. Heparin binding affinity was studied in solution with a variety of polycationic macrocyclic hosts, a pillar[5]arene and multiple resorcin[4]arenes, by dynamic light scattering, dye displacement assay, isothermal titration calorimetry, and anti-Xa assay. The measurements reveal the significant importance of multivalency in electrostatic host-heparin binding in competitive, application-relevant media. Additionally, to monitor the heparin concentration, a host-guest indicator displacement assay was performed by following the free and bound state of the methyl orange dye in UV-Vis spectroscopic experiments. Furthermore, this colorimetric sensing based on the tertiary host-guest-heparin supramolecular assembly was utilized in the construction of a calibration curve in a range of blood plasma concentrations.

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Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides

Cited by 17 publications

References 41 publications

Crystalline Cyclophane–Protein Cage Frameworks

Crystalline Cyclophane–Protein Cage Frameworks

Supramolecular Luminescent Sensors

A supramolecular host–guest complex for heparin binding and sensing

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