Interaction Between Cucurbit[8]uril and HCl Salts of 3,4,7,8-Tetramethyl-1,10-phenanthroline

Cong, Hongliang; Zhu, Qian‐Jiang; Hou, Hongbo; Xue, Sai‐Feng; Tao, Zhu

doi:10.1080/10610270600837181

Cited by 10 publications

(6 citation statements)

References 31 publications

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“…[10,11] The combination of high affinity and selectivity, including enantioselective binding, has remained a constant challenge in host-guest chemistry, in which macrocycles have remained inferior to biological receptors, such as enzymes and antibodies. [12][13][14][15] Cucurbiturils have recently emerged as an interesting class of macrocycles with a high affinity for neutral and cationic organic guests, [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33] and in a few exemplary instances, with host-guest binding constants approaching that of biotin-avidin. [25,26,29] However, cucurbiturils, for example, cu-curbit [7]uril (CB7, composed of 7 glycoluril units), suffer from the same shortcoming of other macrocycles in that their overall selectivity is mediocre in the context of biomimetic applications.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Tandem Enzyme Assays for Multiparameter Sensor Arrays and Enantiomeric Excess Determination of Amino Acids

Bailey

Hennig

Uzunova

et al. 2008

Chemistry A European J

176

158

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The coupling of an enzymatic transformation with dynamic host-guest exchange allows the unselective binding of macrocycles to be used for highly selective analyte sensing. The resulting supramolecular tandem enzyme assays require the enzymatic substrate and its corresponding product to differ significantly in their affinity for macrocycles, for example, cation receptors, and to show a differential propensity to displace a fluorescent dye from its host-guest complex. The enzymatic transformation results in a concomitant dye displacement that can be accurately followed by optical spectroscopy, specifically fluorescence. By exploiting this label-free continuous enzyme assay principle with the fluorescent dye Dapoxyl and the macrocyclic host cucurbit[7]uril, a multiparameter sensor array has been designed, which is capable of detecting the presence of amino acids (e.g. histidine, arginine, lysine, and tyrosine) and their decarboxylases. Only in the presence of both, the particular amino acid and the corresponding decarboxylase, is the amine or diamine product formed. These products are more highly positively charged than the substrate, have a higher affinity for the macrocycle and, therefore, displace the dye from the complex. The extension of the high selectivity and muM sensitivity of the tandem assay principle has also allowed for the accurate measurement of D-lysine enantiomeric excesses of up to 99.98 %, as only the L-enantiomer is accepted by the enzyme as a substrate and is converted to the product that is responsible for the observed fluorescence signal.

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Section: Introductionmentioning

confidence: 99%

Supramolecular Tandem Enzyme Assays for Multiparameter Sensor Arrays and Enantiomeric Excess Determination of Amino Acids

Bailey

Hennig

Uzunova

et al. 2008

Chemistry A European J

176

158

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“…Q [8], which has a larger cavity than Q [6] and Q [7], can include stoichiometric guests to form 1:2 or 1:1:1 ternary complexes [47][48][49]. For example, the seminal investigation on the electrochemistry of the inclusion of the methylviologen dication 8 within Q [8] showed that the cation radical 9 of the guest upon reduction resided simultaneously in the cavity of Q [8], forming the inclusion complex in a ratio of 1:2 (Scheme 10) [49].…”

Section: Cucurbit[8]uril-induced Chemical Controlmentioning

confidence: 99%

Host-induced Chemical Control: Supramolecular Catalysis Based on the Host – Guest Interaction of Cucurbit[n]urils

Cong¹,

Tao

Xue³

et al. 2011

COC

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The controllable functional encapsulation of cucurbit[n]urils (Q[n]s) to form supramolecular catalysts is reviewed. The relationship of the supramolecular catalytic activity with the structure of included guests and cucurbit[n]urils is documented and discussed. The controllable functional encapsulation is attributed to overall interactions of hydrophobic, ion-dipole and size effects of the cucurbit[n]urils. The accelerated and stereochemical aspects of chemical reactions result from overcoming the hindrance of decreased entropy, the hydrophobic effect and the encapsulation model induced by hosts. The stability of drugs and chemical intermediates of the inclusion complexes depends on the environment within the hydrophobic cavity; the enhanced charge-transfer process of the included electron donor and acceptor guests depends on the compressed distance between guests, the electron donors, and acceptors within the limited space.

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“…Becke's three-parameter hybrid functional with the correlation functional of Lee, Yang and Parr (B3LYP) 14 was used for full geometry optimization, solvent effect, and BSSEcorrected 15 (Basis Set Superposition Error corrected) binding energy with STO-3G basis set. 16 The Onsager model 17 was used to calculate the solvent effect, as part of this computing package.…”

Section: Theoretical Calculationsmentioning

confidence: 99%

“…Generally, INH as a sort of weak basic drug can be absorbed in the intestine where the pH value is kept in neutrality (pH = 6-8), and the pH of a solution can influence on the interaction in a host-guest system. 16 In Fig. 3, the curves A, B and C show the absorbance vs. pH for INH and its host-guest complexes with Q[6] and Q [7] at a ratio of 1 : 1, respectively.…”

Section: Acidity Effect On Interaction Of Q[6 7] With Inh Guestmentioning

confidence: 99%

Cucurbituril-resisted acylation of the anti-tuberculosis drug isoniazidvia a supramolecular strategy

Cong

Xue

et al. 2011

Org. Biomol. Chem.

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A chemical investigation reveals that the resistance to acylation of an anti-tuberculosis drug, isoniazid is a consequent result of the inclusion or exclusion of cucurbit[n]urils (n = 6 or 7). The (1)H NMR spectra analysis shows that the different interaction models of the isoniazid with the two cucurbiturils are dependent on the cavity size of the hosts. Quantum chemistry calculations with density functional theory method indicate that the interaction of the isoniazid with both cucurbiturils is through thermodynamic stabilization in both the gas phase and aqueous solution through hydrogen bonding on the portal carbonyls of the cucurbiturils. Electronic absorption titration spectra suggest the hosts and guest interact in a ratio of 1 : 1 with moderate binding constants. Acylation kinetics of isoniazid with various acylating agents in the presence of the cucurbiturils revealed that resistance is only dependent on the host-isoniazid ratio, and independent on the size of the cucurbiturils and the species of acylating agents.

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Interaction Between Cucurbit[8]uril and HCl Salts of 3,4,7,8-Tetramethyl-1,10-phenanthroline

Cited by 10 publications

References 31 publications

Supramolecular Tandem Enzyme Assays for Multiparameter Sensor Arrays and Enantiomeric Excess Determination of Amino Acids

Supramolecular Tandem Enzyme Assays for Multiparameter Sensor Arrays and Enantiomeric Excess Determination of Amino Acids

Host-induced Chemical Control: Supramolecular Catalysis Based on the Host – Guest Interaction of Cucurbit[n]urils

Cucurbituril-resisted acylation of the anti-tuberculosis drug isoniazidvia a supramolecular strategy

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