Study of host–guest interaction between ß-cyclodextrin and alkyltrimethylammonium bromides in water

Petek, Anja; Krajnc, Majda; Petek, Aljana

doi:10.1007/s10847-016-0656-6

Cited by 13 publications

(10 citation statements)

References 42 publications

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“…This makes clear that the hydrocarbon chain length is the key structural surfactant feature determining the stability of the inclusion complexes investigated, which can be taken as evidence of the importance of the hydrophobic interactions contribution to the binding [10,31]. A similar result was found by other authors in the study of inclusion complexes formed between anionic, cationic and non-ionic surfactant homologs and cyclodextrins [10,37,38]. The presence of the aromatic rings at the end of the hydrophobic tail does not substantially affect K 1 , however, it does influence the location of the host and the guest in the inclusion complexes.…”

Section: S][cd] = [Sc] ([S T ] − [Scd])([cd T ] − [Scd]) = = X Scd (1supporting

confidence: 73%

“…The effects on the formation of the inclusion complexes of changing the size of the host cavity [10,[33][34][35][36]39], the hydrophobic chain length of the surfactant [10,37,38], the nature of the surfactant head group [10,39,40], and the number of hydrophobic chains and head groups of the surfactants [10,[41][42][43][44] have been examined. Nonetheless, to the authors´ knowledge, the influence of incorporating a functional group at the end of the hydrophobic surfactant chain on the formation of cyclodextrin-surfactant complexes has not been studied.…”

Section: Discussionmentioning

confidence: 99%

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Host-guest interactions between cyclodextrins and surfactants with functional groups at the end of the hydrophobic tail

Martı́n

Ostos

Angulo

et al. 2017

Journal of Colloid and Interface Science

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Graphical abstractIn this work the influence of the incorporation of aromatic substituents at the end of the hydrophobic tail on the binding of cationic surfactants to cyclodextrins was studied. 2 HOST-GUEST INTERACTIONS BETWEEN CYCLODEXTRINS AND SURFACTANTS WITH FUNCTIONAL GROUPS AT THE END AbstractThe aim of this work was to investigate the influence of the incorporation of substituents at the end of the hydrophobic tail on the binding of cationic surfactants to α-, β-, and -cyclodextrins. The equilibrium binding constants of the 1:1 inclusion complexes formed follow the trend K 1 (α-CD)>K 1 (β-CD)>>K 1 (-CD), which can be explained by considering the influence of the CD cavity volume on the host-guest interactions. From the comparison of the K 1 values obtained for dodecyltriethylammonium bromide, DTEAB, to those estimated for the surfactants with the substituents, it was found that the incorporation of a phenoxy group at the end of the hydrocarbon tail does not affect K 1 , and the inclusion of a naphthoxy group has some influence on the association process, slightly diminishing K 1 . This makes evident the importance of the contribution of hydrophobic interactions to the binding, the length of the hydrophobic chain being the key factor determining K 1 . However, the presence of the aromatic rings does influence the location of the host and the guest in the inclusion complexes. The observed NOE interactions between the aromatic protons and the CD protons indicate that the aromatic rings are partially inserted within the host cavity, with the cyclodextrin remaining close to the aromatic rings, which could be partially intercalated in the host cavity. To the authors´ knowledge this is the first study on the association of cyclodextrins with monomeric surfactants incorporating substituents at the end of the hydrophobic tail.

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Section: S][cd] = [Sc] ([S T ] − [Scd])([cd T ] − [Scd]) = = X Scd (1supporting

confidence: 73%

Section: Discussionmentioning

confidence: 99%

Host-guest interactions between cyclodextrins and surfactants with functional groups at the end of the hydrophobic tail

Martı́n

Ostos

Angulo

et al. 2017

Journal of Colloid and Interface Science

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“…With the alkyl chain length of dendrimer increasing from C 8 to C 16 , cmc values decrease from 8 × 10 −5 to 3 × 10 −6 mol/L, which are 2 orders of magnitude lower than that of alkyltrimethylammonium bromide (C n TAB, n = 8, 12, 16) as one branch of the corresponding dendrimer. 29 It suggests an excellent micelle-forming ability of the amphiphilic dendrimers. In addition, it is found that an increase in the alkyl chain length for G 1 C n brought in an efficient reduction in the surface tension, indicating that the dendrimers with longer chains tend to widely adsorb and pack tightly at the air−water interface due to the strong hydrophobic interaction.…”

Section: Resultsmentioning

confidence: 99%

PAMAM-Based Dendrimers with Different Alkyl Chains Self-Assemble on Silica Surfaces: Controllable Layer Structure and Molecular Aggregation

et al. 2018

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Amphiphilic poly(amidoamine) (PAMAM) dendrimers are a well-known dendritic family due to their remarkable ability to self-assemble on solid surface. However, the relationship between molecular conformation (or adsorption kinetics) of a self-assembled layer and molecular amphiphilicity of such kind of dendrimer is still lacking, which limits the development of modulating self-assembling structures and surface functionality. With this in mind, we synthesized a series of amphiphilic PAMAM-based dendrimers, denoted as GC , with different alkyl chains ( n = 8, 12, and 16), and investigated the molecular aggregation on silica surfaces by means of quartz crystal microbalance with dissipation, atomic force microscopy, and contact angle. After rinsing, remaining adsorption amounts of GC were higher than those of GC at high concentrations, suggesting that GC adlayers were more stable due to the stronger intermolecular hydrophobic interactions, whereas it preferred to adopt the intramolecular hydrophobic interactions for GC, with low adsorption amounts and unstable adlayers. Bilayer-like structures were inferred in GC and GC adlayers with loose conformation, whereas monolayer structures were likely to exist in the sparse adsorption film of GC. Our results provided more detailed understanding of the effect of molecular structure on the self-assembled structures of amphiphilic dendrimers on solid surfaces, shedding light on the controlled microstructure and wettability of functional surface by modulating the length of hydrophobic chains of dendrimers and a potential application of dendrimer-substrate combinations.

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“…Here we thoroughly discuss the standard molar Gibbs energy of micellization (Δ m G 0 ), standard molar enthalpy of micellization (Δ m H 0 ) and standard molar entropy of micellization (Δ m S 0 ). The obtained parameters are clearly arranged into tables and compared with those acquired by some other authors, and/or by other methods [18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60]. We did this because exact knowledge of parameters is inevitable for synthesis of the reliable in silico means of predicting bioavailability and the effects of the final drugs.…”

Section: Introductionmentioning

confidence: 99%

Effect of Molecular Composition of Head Group and Temperature on Micellar Properties of Ionic Surfactants with C12 Alkyl Chain

et al. 2019

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The paper analyses influences of the temperature and hydrophilic groups on micellar properties of ionic surfactants with 12-carbonic hydrophobic chains. The aim is to assess the impact of hydrophilic groups and temperature on thermodynamic parameters and micellization. This knowledge is indispensable for the formulation of new dosage forms. The method uses conductometric measurements. The following hydrophilic groups are analyzed: trimethylammonium bromide, trimethylammonium chloride, ethyldimethylammonium bromide, didodecyldimethylammonium bromide, pyridinium chloride, benzyldimethyl-ammonium chloride, methylephedrinium bromide, cis and trans-[(2-benzyloxy)-cyclohexyl-methyl]-N, N-dimethylammonium bromide, sodium sulphate and lithium sulphate. Except for a few cases, there is a good agreement between values of critical micellar concentrations (CMC) and critical vesicle concentration (CVC) obtained here and those which were obtained by other authors and/or by other physicochemical methods. Values of the CMC are compared with respect to the molar masses of hydrophilic groups. It was found that CMC values increased non-linearly with increasing system temperature. The degrees of counterion binding and thermodynamic parameters, like the standard molar Gibbs energy, enthalpy and entropy of micellization are determined and discussed in detail. The results obtained will be incorporated into in silico processes of modeling and design of optimal dosage forms, a current interdisciplinary research focus of the team.

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Study of host–guest interaction between ß-cyclodextrin and alkyltrimethylammonium bromides in water

Cited by 13 publications

References 42 publications

Host-guest interactions between cyclodextrins and surfactants with functional groups at the end of the hydrophobic tail

Host-guest interactions between cyclodextrins and surfactants with functional groups at the end of the hydrophobic tail

PAMAM-Based Dendrimers with Different Alkyl Chains Self-Assemble on Silica Surfaces: Controllable Layer Structure and Molecular Aggregation

Effect of Molecular Composition of Head Group and Temperature on Micellar Properties of Ionic Surfactants with C12 Alkyl Chain

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