Influence of the protonation state on the binding mode of methyl orange with cucurbiturils

He, Suhang; Sun, Xuzhuo; Zhang, Hai Bo

doi:10.1016/j.molstruc.2015.11.039

Cited by 22 publications

(25 citation statements)

References 31 publications

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“…Host-guest binding between cationic pillararenes and MO has been studied also before in water 55 . The results presented here confirm binding between pillar [5]arene and MO in physiologically relevant media even though protonation stage of MO has been shown to have influence on the binding mode 56 . In the previously published study, inclusion complex is suggested to form in such a manner that the hydrophobic part of MO is inside the cavity and the sulfonated anionic head is outside the cavity.…”

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confidence: 75%

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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confidence: 75%

A supramolecular host–guest complex for heparin binding and sensing

et al. 2018

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“…CH···O interactions under acidic conditions. [11] In particular, the crystallization behavior of CB [8] can be tuned by hostguest chemistry, [12] which prompted us to develop an ovel chemical waste-free transient crystallization method fueled by TCA.…”

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confidence: 99%

Fuel‐Driven Transient Crystallization of a Cucurbit[8]uril‐Based Host–Guest Complex

et al. 2019

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Transient self‐assembling systems often suffer from accumulation of chemical wastes that interfere with the formation of pristine self‐assembled products in subsequent cycles. Herein, we report the transient crystallization of a cucurbit[8]uril‐based host‐guest complex, preventing the accumulation of chemical wastes. Base‐catalyzed thermal decarboxylation of trichloroacetic acid that chemically fuels the crystallization process dissolves the crystals, and produces volatile chemical wastes that are spontaneously removed from the solution. With such self‐clearance process, no significant damping in the formation of the crystals was observed. The morphology and structural integrity of the crystals was also maintained in subsequent cycles. The concept may be further extended to obtain other temporally functional materials, quasicrystals, etc., based on stimuli‐responsive guest molecules.

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“…The study of the interactions of fluorescent dyes with water-soluble macrocyclic host molecules has developed into an important area of supramolecular chemistry. − Upon complexation, the fluorescent dye frequently changes significantly, rarely dramatically, its fluorescence properties, such that both its complexation as well as its decomplexation can be followed with high sensitivity. This fluorescence response provides a robust method to (i) measure and compare the binding propensities of different macrocycles at low dye concentrations, − (ii) explore the physical properties of the inner cavities of macrocycles by means of solvatochromic effects, ,− (iii) develop refined fluorescent switches for advanced supramolecular architectures ,,,,− or molecular logic gates, ,− and (iv) monitor the reversible complexation of analytes to the macrocycles through indicator displacement strategies. − The latter method, because it can be both miniaturized and scaled up to high-throughput screening format, has enormous application potential in the environmental, biological, and food sciences.…”

Section: Introductionmentioning

confidence: 99%

Comparison of Complexation-Induced pK_a Shifts in the Ground and Excited States of Dyes as Well as Different Macrocyclic Hosts and Their Manifestation in Host-Retarded Excited-Dye Deprotonation

2017

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1-Aminopyrene and 1-naphthylamine-5-sulfonic acid were converted to the putrescine (1,4-diaminobutane)-substituted derivatives (dyes 1 and 2). The diaminobutyl anchor serves as a common binding motive for cation-receptor macrocycles such as cucurbit[n]urils (n = 6-8) and p-sulfonatocalix[4]arene. When protonated, they are prone to undergo a rapid deprotonation in their excited state to result in fluorescence from the unprotonated form (Förster cycle). The deprotonation can be suppressed by complexation with cation-receptor macrocycles, which allows the fluorescence of the locally excited (protonated) state to be dramatically enhanced (factor 12 for dye 1 and 83 for dye 2). This host-retarded excited-dye deprotonation is a direct consequence of the previously established complexation-induced pK shifts that dyes undergo upon binding to a macrocyclic host. The data set also allows a systematic comparison of complexation-induced pK shifts in the ground and excited state of a dye. The trends are comparable, which suggests that structural factors, that is, the geometry of the host-guest complexes, determine the magnitude of the shifts. In regard to the magnitude of the absolute pK shifts on the size of the macrocycles, we observe for dye 2 that the complexation-induced pK shifts decrease as the portals become larger along the cucurbit[n]uril series.

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Influence of the protonation state on the binding mode of methyl orange with cucurbiturils

Cited by 22 publications

References 31 publications

A supramolecular host–guest complex for heparin binding and sensing

A supramolecular host–guest complex for heparin binding and sensing

Fuel‐Driven Transient Crystallization of a Cucurbit[8]uril‐Based Host–Guest Complex

Comparison of Complexation-Induced pK_a Shifts in the Ground and Excited States of Dyes as Well as Different Macrocyclic Hosts and Their Manifestation in Host-Retarded Excited-Dye Deprotonation

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Influence of the protonation state on the binding mode of methyl orange with cucurbiturils

Cited by 22 publications

References 31 publications

A supramolecular host–guest complex for heparin binding and sensing

A supramolecular host–guest complex for heparin binding and sensing

Fuel‐Driven Transient Crystallization of a Cucurbit[8]uril‐Based Host–Guest Complex

Comparison of Complexation-Induced pKa Shifts in the Ground and Excited States of Dyes as Well as Different Macrocyclic Hosts and Their Manifestation in Host-Retarded Excited-Dye Deprotonation

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Comparison of Complexation-Induced pK_a Shifts in the Ground and Excited States of Dyes as Well as Different Macrocyclic Hosts and Their Manifestation in Host-Retarded Excited-Dye Deprotonation