Scrutinizing ITC-study on the formation of inclusion complexes of nonionic surfactant Triton X-100 and cyclodextrins

Müller, Bernd-Kristof; Ritter, Helmut

doi:10.1007/s10847-011-9955-0

Cited by 15 publications

(11 citation statements)

References 21 publications

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“…The ITC method has been widely used for characterization of drug inclusion complexes with natural CDs [9][10][11][12][13][14][15][16], but none of the experiments have dealt with the investigated drugs.…”

Section: Introductionmentioning

confidence: 99%

Isothermal titration calorimetry (ITC) study of natural cyclodextrins inclusion complexes with tropane alkaloids

Wszelaka‐Rylik

Gierycz

2015

J Therm Anal Calorim

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Isothermal titration calorimetry (ITC) has been used to characterize inclusion complex formation of natural cyclodextrins (a-and b-cyclodextrin) with three tropane alkaloids (scopolamine, homatropine hydrobromide and atropine sulfate) in aqueous solutions. ITC measurements were taken at 298.15 K on a MicroCal OMEGA ultrasensitive titration calorimeter (MicroCal Inc.). The experimental data were analyzed on the basis of the model of a single set of identical sites (ITC Tutorial Guide). b-CD forms inclusion complexes of stoichiometry 1:2 with homatropine hydrobromide and 1:1 with scopolamine and atropine sulfate. The smaller molecule of a-CD forms very weak inclusion complexes with the tropane alkaloids. So, only one complex of the same stoichiometry 1:2 with homatropine hydrobromide has been detected by the ITC experiment. Based on the experimental values of equilibrium constant (K) and enthalpy of complex formation (DH), the Gibbs energy of complex formation (DG) and the entropy of complex formation (DS) have been calculated, for all the investigated systems. Obtained results showed that complex formation of both a-and b-CD with all the investigated tropane alkaloids is entropy driven. This indicated that the difference in the cavity dimensions is not reflected in different driving forces of complex formation and binding modes which resulted in the same stoichiometry of the obtained inclusion complexes.

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Section: Introductionmentioning

confidence: 99%

Isothermal titration calorimetry (ITC) study of natural cyclodextrins inclusion complexes with tropane alkaloids

Wszelaka‐Rylik

Gierycz

2015

J Therm Anal Calorim

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“…With increasing amount of RAMEB-CD, the signals of the aromatic protons d and e also shifted from 7.16 and 6.78 ppm to 7.34 and 6.93 ppm. Assumingly, the hydrophobic tert -octyl group is complexed first; secondly the aryl group is complexed by RAMEB-CD [12]. …”

Section: Resultsmentioning

confidence: 99%

“…Different methods, e.g., surface tension, isothermal titration calorimetric, and fluorescence studies, were used to determine the equilibrium constant [4–12]. The results also differ in the stoichiometry of the formed complexes [4,7,9–11].…”

Section: Introductionmentioning

confidence: 99%

“…Host/guest ratios of 1:1 [4,7], 2:1 [9] and the coexistence of 1:1 and 2:1 [10–11] complexes of β-CD and Triton ® X-100 are reported in literature. In our previous paper, the coexistence of a 1:1 and 2:1 complex with an extraordinary high ( K 1 = 1.71 × 10 5 M −1 ) and a lower equilibrium constant ( K 2 = 260 M −1 ) was described [12]. Due to the fact that the tert -octyl group represents the preferred binding site of the molecule it can be assumed that complexation takes place at this position first.…”

Section: Introductionmentioning

confidence: 99%

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Influence of cyclodextrin on the solubility and the polymerization of (meth)acrylated Triton^® X-100

Kemnitz¹,

Ritter

2012

Beilstein J. Org. Chem.

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SummaryTriton® X-100 (poly(ethylene glycol) tert-octylphenyl ether) was (meth)acrylated and polymerized in the absence and presence of randomly methylated β-cyclodextrin (RAMEB-CD). Triton®-polymers that were polymerized with RAMEB-CD in water were compared with polymers that were synthesized in organic solvents after the addition of RAMEB-CD. The polymers were characterized by 1H NMR and FTIR spectroscopy, matrix-assisted laser desorption ionization mass spectrometry (MALDI-TOF MS), dynamic light scattering (DLS), gel-permeation chromatography (GPC) and turbidity measurements. Additionally, the viscosity change of the methacrylic homopolymer with RAMEB-CD was evaluated.

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“…Since 4-alkylphenyl moieties are good guests for ß-cyclodextrin [37–38], we were encouraged to use 4- tert -butylphenol as well as 4- tert -octylphenol and modify them with mercapto groups. By doing so, well-defined PDEAAm end-group labeled polymers can be obtained by using classical free-radical chain transfer polymerization techniques.…”

Section: Introductionmentioning

confidence: 99%

End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water

Reinelt

Steinke

Ritter

2014

Beilstein J. Org. Chem.

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SummaryIn this work we report the synthesis of thermo-, oxidation- and cyclodextrin- (CD) responsive end-group-functionalized polymers, based on N,N-diethylacrylamide (DEAAm). In a classical free-radical chain transfer polymerization, using thiol-functionalized 4-alkylphenols, namely 3-(4-(1,1-dimethylethan-1-yl)phenoxy)propane-1-thiol and 3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propane-1-thiol, poly(N,N-diethylacrylamide) (PDEAAm) with well-defined hydrophobic end-groups is obtained. These end-group-functionalized polymers show different cloud point values, depending on the degree of polymerization and the presence of randomly methylated β-cyclodextrin (RAMEB-CD). Additionally, the influence of the oxidation of the incorporated thioether linkages on the cloud point is investigated. The resulting hydrophilic sulfoxides show higher cloud point values for the lower critical solution temperature (LCST). A high degree of functionalization is supported by 1H NMR-, SEC-, FTIR- and MALDI–TOF measurements.

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Scrutinizing ITC-study on the formation of inclusion complexes of nonionic surfactant Triton X-100 and cyclodextrins

Cited by 15 publications

References 21 publications

Isothermal titration calorimetry (ITC) study of natural cyclodextrins inclusion complexes with tropane alkaloids

Isothermal titration calorimetry (ITC) study of natural cyclodextrins inclusion complexes with tropane alkaloids

Influence of cyclodextrin on the solubility and the polymerization of (meth)acrylated Triton^® X-100

End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water

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Scrutinizing ITC-study on the formation of inclusion complexes of nonionic surfactant Triton X-100 and cyclodextrins

Cited by 15 publications

References 21 publications

Isothermal titration calorimetry (ITC) study of natural cyclodextrins inclusion complexes with tropane alkaloids

Isothermal titration calorimetry (ITC) study of natural cyclodextrins inclusion complexes with tropane alkaloids

Influence of cyclodextrin on the solubility and the polymerization of (meth)acrylated Triton® X-100

End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water

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Influence of cyclodextrin on the solubility and the polymerization of (meth)acrylated Triton^® X-100