Author: S. Maryamdokht Taimoory

Sharing the salt bowl: counterion identity drives N-alkyl resorcinarene affinity for pyrophosphate in water

2021

N-Alkyl ammonium resorcinarene chloride receptors, NARX4, have been shown to act as high-sensitivity detectors of pyrophosphate (PPi), a biomarker of disease, in aqueous media through the chloride-to-PPi exchange [NAR(Cl)4 to NARPPi]. The nature of the anion of the macrocyclic NARX4 (X = Cl−, Br−, triflate OTf−) receptor greatly influences the PPi-affinity in aqueous media. The binding affinity for [NAR (Cl)4] is 3.61 × 105 M−1, while the NAR (Br)4 and NAR (OTf)4 show stronger binding of 5.30 × 105 M−1, and 6.10 × 105 M−1, respectively. The effects of upper rim ammonium cation, –N+H2R substituents (R = 3-hydroxypropyl, cyclohexyl, benzyl, or napththalen-1-ylmethyl), of the macrocyclic resor…

kemialliset sidoksetChemistryfosfaatitliuoksetOrganic Chemistrysupramolekulaarinen kemiabiomarkkeritBiochemistry Biophysics and Structural Biology

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Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies

2018

Host–guest complexes of C-hexyl-2-bromoresorcinarene (BrC6) with twelve potential aromatic N-oxide guests were studied using single crystal X-ray diffraction analysis and 1H NMR spectroscopy. In the solid state, of the nine obtained X-ray crystal structures, eight were consistent with the formation of BrC6-N-oxide endo complexes. The lone exception was from the association between 4-phenylpyridine N-oxide and BrC6, in that case the host forms a self-inclusion complex. BrC6, as opposed to more rigid previously studied C-ethyl-2-bromoresorcinarene and C-propyl-2-bromoresorcinarene, undergoes remarkable cavity conformational changes to host different N-oxide guests through C–H···π(host) intera…

Solid-stateCrystal structure010402 general chemistry01 natural scienceslcsh:QD241-441lcsh:Organic chemistryPolarizabilitysupramolekulaarinen kemiaresorcinareneshost–guest chemistryHost–guest chemistrylcsh:Scienceta116Biochemistry Biophysics and Structural BiologyC–H···π Interactions010405 organic chemistryChemistryOrganic Chemistryendo/exo complexationSolution phaseditopic receptors0104 chemical sciencesaromatic N-oxidesChemistryCrystallographyProton NMRPolarlcsh:QSingle crystalBeilstein Journal of Organic Chemistry

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High-affinity and selective detection of pyrophosphate in water by a resorcinarene salt receptor

2017

N-Alkyl ammonium resorcinarenes selectively bind pyrophosphate in pure water with an exceptionally high binding constant of up to 1.60 × 107 M–1, three orders of magnitude higher than ATP.

pyrophosphatereceptors010402 general chemistryMass spectrometry01 natural sciencesPyrophosphateChloridemolecular diagnosticschemistry.chemical_compoundmedicineresorcinarenesta116Biochemistry Biophysics and Structural Biologyta114010405 organic chemistryIsothermal titration calorimetryGeneral ChemistryResorcinarenePhosphateCombinatorial chemistryOrders of magnitude (mass)0104 chemical sciencesChemistrychemistrySelectivitymedicine.drug

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Bringing a Molecular Plus One: Synergistic Binding Creates Guest-Mediated Three-Component Complexes

2020

Cethyl-2-methylresorcinarene (A), pyridine (B), and a set of 10 carboxylic acids (Cn) associate to form A·B·Cn ternary assemblies with 1:1:1 stoichiometry, representing a useful class of ternary systems where the guest mediates complex formation between the host and a third component. Although individually weak in solution, the combined strength of the multiple noncovalent interactions organizes the complexes even in a highly hydrogen-bond competing methanol solution, as explored by both experimental and computational methods. The interactions between A·B and Cn are dependent on the pKa values of carboxylic acids. The weak interactions between A and C further reinforce the interactions betw…

chemistry.chemical_classification010405 organic chemistryStereochemistryComponent (thermodynamics)Organic ChemistryComplex formationCarboxylic AcidsCooperative bindingHydrogen Bonding010402 general chemistry01 natural sciences0104 chemical sciencesChemistrychemistry.chemical_compoundMolecular recognitionchemistryPyridineNon-covalent interactionsTernary operationBiochemistry Biophysics and Structural BiologyStoichiometryThe Journal of Organic Chemistry

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Bringing a Molecular Plus One : Synergistic Binding Creates Guest-Mediated Three-Component Complexes

2020

C-Ethyl-2-Methylresorcinarene (A), pyridine (B), and a set of ten carboxylic acids (Cn) associate to form A·B·Cn ternary assemblies with 1:1:1 stoichiometry, representing a useful class of ternary systems where the guest mediates complex formation between the host and a third component. Although individually weak in solution, the combined strength of the multiple non-covalent interactions organizes the complexes even in a highly hydrogen-bond competing methanol solution as explored by both experimental and computational methods. The interactions be-tween A·B and Cn are dependent on the pKa values of carboxylic acids. The weak interactions between A and C further reinforce the interactions b…

carboxylic acidskarboksyylihapotsupramolekulaarinen kemiamolekyylitmolecular recognitionsupramolecular chemistrydiagnostic toolstunnistaminen

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