Effect of interfacial molecular recognition of non-surface-active species on the main characteristics of monolayers

Vollhardt, D.

doi:10.1016/j.cis.2005.03.008

Cited by 16 publications

(9 citation statements)

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“…To summarize, spontaneous clusterization of 2C n H 2 n +1 -melamine at the interface can take place if the alkyl chain length is 10 and more carbon atoms, in agreement with the experimental data reported in ref . The clusterization process involves the formation of stacked dimers (see Figure ), which then arrange into more complicated stacked clusters.…”

Section: Resultssupporting

confidence: 91%

“…The use of two-dimensional arrangements at the air−solution interface turned out to be an interesting approach to regulate the recognition process by incorporating strong directional interactions of hydrogen bonds with a dissolved component for the manufacture of thin films. , Correspondingly, amphiphilic melamine derivatives have been synthesized and used as host-component in monolayers and bilayers for interfacial molecular recognition of barbiturates. − It has been shown that systems consisting of an amphiphilic melamine-type monolayer and a pyrimidine derivative dissolved in the aqueous subphase are good candidates for the formation of interfacial supramolecular entities by hydrogen-bond-based molecular recognition of nonsurface-active substrates. The molecular recognition of nonsurface-active pyrimidine derivatives dissolved in the aqueous subphase changes drastically and in specific way the characteristic features (π− A isotherms, morphology of the condensed phase domains) of these special melamine-type monolayers. − …”

Section: Introductionmentioning

confidence: 99%

“…It is interesting to note that the striking differences in the main characteristics between the supramolecular assemblies can be related to their different chemical structures depending on the chemical structure of the pyrimidine derivatives. − , The headgroup of 2,4-di( n -alkylamino)-6-amino-1,3,5-triazine (2C n H 2 n +1 -melamine) has two binding faces on both sides. The binding faces of the studied pyrimidine derivatives are different.…”

Section: Introductionmentioning

confidence: 99%

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Quantum-Chemical Description of the Thermodynamic Characteristics of Clusterization of Melamine-type Amphiphiles at the Air/Water Interface

et al. 2009

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The semiempiric PM3 method is used to calculate the thermodynamic parameters of the formation of monomers, dimers, trimers, and tetramers of the amphiphilic melamine-type series of 2,4-di(n-alkylamino)-6-amino-1,3,5-triazine (2C(n)H(2n+1)-melamine) with n = 9-16. The most stable conformations are determined, which then are used to construct the clusters. The peculiar feature of these structures is the existence of a bend at one of the alkyl chains. Thus, the formation of infinite films becomes possible because of their spatial arrangement. From the calculation of the relative amount of various conformers in the mixture, it follows that, if the alkyl chain length is lower than 11-12 carbon atoms, the mixture is composed mainly of the monomers that do not contain any intramolecular interactions, whereas for higher alkyl chain lengths the monomers that involve such interactions prevail in the mixture. For all clusters thus considered, the thermodynamic parameters (enthalpies, entropies, and Gibbs' energies) of clusterization are calculated. It is shown that the dependencies of these parameters on the alkyl chain length either exhibit stepwise shape or are represented by the combination of a linear and stepwise function. This depends on the different number of hydrogen-hydrogen interactions in the structures considered. Five types of clusters that are capable of the formation of infinite 2D films are considered in detail. For each of these types, the dependencies of the clusterization enthalpy, entropy, and Gibbs' energy on the alkyl chain length in the constituting monomers are derived. Using these dependencies, it becomes possible to calculate these thermodynamic characteristics for clusters of any size, and also for infinite 2D films. It is shown that the spontaneous clusterization of 2C(n)H(2n+1)-melamine becomes possible if the alkyl chain length exceeds 9 carbon atoms.

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Section: Resultssupporting

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quantum-Chemical Description of the Thermodynamic Characteristics of Clusterization of Melamine-type Amphiphiles at the Air/Water Interface

et al. 2009

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“…An analogous mechanism of tuning of lipid layer structure via weak non-covalent interactions with non-surface active agents was already reported by Vollhardt in 2005. 7 The proposed mechanism agrees with the assumption that HA is capable of participating in energetically favorable interaction with polar lipid headgroups which might ensure uniform distribution of the phospholipid surfactant layer in the lungs in vivo. 63,64 Two major hypotheses are suggested to explain the interaction between HA and the lipid headgroups.…”

Section: Discussionsupporting

confidence: 79%

“…via hydrogen bonding to the lipid headgroups. 7,8 Thus the rst aim of our work was to study the interaction of high molecular weight HA with lms of meibomian lipids at the air/water interface. Meibomian lipids are secreted by specialized meibomian glands located in the eyelid margin.…”

Section: Introductionmentioning

confidence: 99%

Surface chemistry study of the interactions of hyaluronic acid and benzalkonium chloride with meibomian and corneal cell lipids

et al. 2013

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Hyaluronic acid (HA) is a non-surface active water soluble anionic polyelectrolyte found in sub-nanomolar levels in human tears and implemented in substitutes of human tears' aqueous layer. In the current work we studied the interactions of high molecular weight (M w 1 Â 10 6 Da) HA with films of ocular surface lipids and investigated the potential of HA to modify the interactions of the lipid films with the low M w cationic surfactant dodecyldimethylbenzylammonium chloride (C12-BAC) known for its adverse effects on tear film compounds. The interactions of HA and/or C12-BAC with meibomian and corneal lipid films were examined using a Langmuir surface balance. The film morphology was monitored by Brewster Angle Microscopy. The HA/C12-BAC interactions at the air/water interface and in the solution bulk were also examined. HA interacted with meibomian lipids and enhanced the structure and the rheological properties of the meibum films. HA bound C12-BAC in bulky polymer/surfactant complexes and at $0.1% HA neutralized the capability of C12-BAC to penetrate the lipid layers and to disrupt their integrity and viscoelasticity. The results were correlated with the capability of HA to maintain the viability of C12-BAC treated corneal cells. Our study suggests a possible novel implementation of high M w anionic polyelectrolytes like HA: the polymers can be instilled on the ocular surface together with cationic surfactant containing drugs, and increase the biocompatibility of the ophthalmic formulations.A molecular scale mechanism is proposed for the interactions of HA with tear lipids and cationic surfactants.

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Applications of Brewster angle microscopy from biological materials to biological systems

Daear¹,

Mahadeo²,

Prenner³

2017

Biochimica et Biophysica Acta (BBA) - Biomembranes

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Brewster angle microscopy (BAM) is a powerful technique that allows for real-time visualization of Langmuir monolayers. The lateral organization of these films can be investigated, including phase separation and the formation of domains, which may be of different sizes and shapes depending on the properties of the monolayer. Different molecules or small changes within a molecule such as the molecule's length or presence of a double bond can alter the monolayer's lateral organization that is usually undetected using surface pressure-area isotherms. The effect of such changes can be clearly observed using BAM in real-time, under full hydration, which is an experimental advantage in many cases. While previous BAM reviews focused more on selected compounds or compared the impact of structural variations on the lateral domain formation, this review provided a broader overview of BAM application using biological materials and systems including the visualization of amphiphilic molecules, proteins, drugs, extracts, DNA, and nanoparticles at the air-water interface.

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Effect of interfacial molecular recognition of non-surface-active species on the main characteristics of monolayers

Cited by 16 publications

References 44 publications

Quantum-Chemical Description of the Thermodynamic Characteristics of Clusterization of Melamine-type Amphiphiles at the Air/Water Interface

Quantum-Chemical Description of the Thermodynamic Characteristics of Clusterization of Melamine-type Amphiphiles at the Air/Water Interface

Surface chemistry study of the interactions of hyaluronic acid and benzalkonium chloride with meibomian and corneal cell lipids

Applications of Brewster angle microscopy from biological materials to biological systems

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