- SERS multiplexing of methylxanthine drug isomersviahost-guest size matching and machine learning
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Multiplexed detection and quantification of structurally similar drug molecules, methylxanthine MeX, incl. theobromine TBR, theophylline TPH and caffeine CAF, have been demonstratedviasolution-based surface-enhanced Raman spectroscopy (SERS), achieving highly reproducible SERS signals with detection limits down to ～50 nM for TBR and TPH, and ～1 μM for CAF. Our SERS substrates are formed by aqueous self-assembly of gold nanoparticles (Au NPs) and supramolecular host molecules, cucurbit[n]urils (CBn,n= 7, 8). We demonstrate that the binding constants can be significantly increased using a host-guest size matching approach, which enables effective enrichment of analyte molecules in close proximity to the plasmonic hotspots. The dynamic range and the robustness of the sensing scheme can be extended using machine learning algorithms, which shows promise for potential applications in therapeutic drug monitoring, food processing, forensics and veterinary science.
- Chio, Weng-I Katherine,Dinish, U. S.,Jones, Tabitha,Lee, Tung-Chun,Liu, Jia,Olivo, Malini,Parkin, Ivan P.,Perumal, Jayakumar
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supporting information
p. 12624 - 12632
(2021/10/06)
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- Supramolecular assembly of poly(ionic liquid) nanogel driven by host-stabilized charge transfer interaction
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Poly(ionic liquid) (PIL)-based nanogels, functionalized by naphthyl (Np), are fabricated via a facile one-step ternary crosslinking copolymerization in selective solvent. The size of PIL nanogels can be conveniently regulated through the feed ratio of IL monomer to crosslinker. The presence of Np groups in PIL nanogel is confirmed by using ultraviolet–visible (UV–vis), Fourier transform infrared, and X-ray photoelectron spectroscopy measurements. Through introducing cucurbit[8]uril (CB[8]) and bisviologen compound (DEDV) as the host molecule and electron acceptor, respectively, host-stabilized charge transfer (HSCT) interaction is achieved through utilizing Np containing PIL nanogel as the building block. The studies reveal that PIL nanogels can form schistose aggregates in the scale of micrometer via HSCT interaction. The aggregates will be broken in the presence a competitive guest molecule (amantadine) and can recover by adding another host molecule (CB[7]). HSCT interaction among CB[8], DEDV and PIL nanogel is investigated by dynamic light scattering, UV–vis, and Proton nuclear magnetic resonance. Our studies thus provided an applicable strategy for constructing dynamic polymer nanoparticles through noncovalent interaction.
- Tang, Yuntao,Wang, Ke,Zuo, Yong,Chen, Xi,Xiong, Yubing,Yuan, Yumin
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p. 2251 - 2259
(2019/11/13)
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- PROCESS FOR THE PREPARATION OF CUCURBITURIL DERIVATIVES
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This invention relates to cucurbituril and/or one or more derivatives thereof with low formaldehyde content, to a process of manufacturing said cucurbituril and/or one or more derivatives thereof and to the use of said cucurbituril and/or one or more derivatives thereof, in particular in consumer and industrial products, and in industrial processes.
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Page/Page column 16
(2018/07/22)
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- Orthogonal switching of self-sorting processes in a stimuli-responsive library of cucurbit[8]uril complexes
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The self-sorting processes in dynamic libraries of cucurbit[8]uril complexes can be switched in an orthogonal way by external stimuli. Protonated phenylpyridine guests form a 2:1 homoternary π-donor-π-acceptor complex, while deprotonation makes it a partner for ethylviologen in a 1:1:1 heteroternary complex. Reduction of the viologen instead generates a 2:1 homoternary complex of viologen radical-cations.
- Schoder, Stefan,Schalley, Christoph A.
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supporting information
p. 9546 - 9549
(2017/09/01)
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- Cucurbit[n]uril formation proceeds by step-growth cyclo-oligomerization
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In contrast to the high yield formation of cucurbit[n]uril (CB[n]) from a 1:2 ratio of glycoluril to formaldehyde, the condensation of glycoluril with less than 2 equiv of formaldehyde delivers a reaction mixture that contains glycoluril oligomers (2-6) and CB[n] compounds that lack one or more methylene bridges known as nor-seco-cucurbit[n]urils (ns-CB[n]). In this paper we report the chromatographic purification of C-shaped glycoluril oligomers (dimer-hexamer), their characterization in solution, and their X-ray crystal structures. Quite interestingly, despite being acyclic glycoluril pentamer 5 and hexamer 6 retain the ability to bind to guests typical of CB[6] but are also able to expand their cavity to accommodate larger guests like cationic adamantane derivatives. We performed product resubmission experiments with glycoluril oligomers 2-6 and found preferences for the formation of specific ring sizes during CB[n] formation. A comprehensive mechanistic scheme is proposed that accounts for the observed formation of 2-6 and ns-CB[n]. Overall, the experiments establish that a step-growth cyclo-oligomerization process operates during CB[n] formation.
- Huang, Wei-Hao,Zavalij, Peter Y.,Isaacs, Lyle
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supporting information; scheme or table
p. 8446 - 8454
(2009/02/02)
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- Controlling factors in the synthesis of cucurbituril and its homologues
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The acid-catalyzed synthesis of cucurbit[n]urils from formaldehyde and glycoluril is poorly understood. In this paper, we examine a wide range of reaction conditions that include the effects of acid type, acid concentration, reactant concentrations, and temperature to both probe the mechanism and optimize the yields of isolated cucurbit[n]urils, where n = 5-10. A mechanism for the formation of these cucurbit[n]urils is presented. Individual cucurbit[n]urils were unambiguously identified in reaction mixtures using ESMS and 13C NMR.
- Day, Anthony,Arnold, Alan P.,Blanch, Rodney J.,Snushall, Barry
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p. 8094 - 8100
(2007/10/03)
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