Development of a molecular mechanics force field for caffeine to investigate the interactions of caffeine in different solvent media

Sanjeewa, Rangana; Weerasinghe, Samantha

doi:10.1016/j.theochem.2009.12.027

Cited by 19 publications

(25 citation statements)

References 34 publications

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“…12,15 The effects of several co-solutes on the association properties of caffeine have also been studied in some detail, such as in the recent report of the change of the self-association constant in some salts of the Hofmeister series, increasing from NaClO 4 to NaSCN to Na 2 SO 4 to NaCl. 16 These data add to the previously reported effects on the solubility of caffeine in the presence of sucrose, 17 alcohol, 18 urea, 14,19 guanidinium chloride, 19 and KCl, 19 with substantial agreement on the change in the solvent properties affecting the homotactic caffeine aggregation.…”

Section: Introductionsupporting

confidence: 79%

“…By initially adopting the charge set for the simulation of stacking glucose against caffeine, it was found that the low partial charge values of this set promoted a strong hydrophobic behavior, underestimating the polar interactions. On the other hand, the unscaled charge set of Sanjeewa and Weeasinghe, 14 with high partial charges for O and N, was inappropriate for use with the chosen TIP3P and TIP4P water models. In this work, B3LYP and MP2 level quantum mechanical calculations were used to estimate electronic densities.…”

Section: Methodsmentioning

confidence: 99%

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Molecular Dynamics Simulation Studies of Caffeine Aggregation in Aqueous Solution

et al. 2011

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Molecular dynamics simulations were carried out on a system of eight independent caffeine molecules in a periodic box of water at 300 K, representing a solution near the solubility limit for caffeine at room temperature, using a newly-developed CHARMM-type force field for caffeine in water. Simulations were also conducted for single caffeine molecules in water using two different water models (TIP3P and TIP4P). Water was found to structure in a complex fashion around the planar caffeine molecules, which was not sensitive to the water model used. As expected, extensive aggregation of the caffeine molecules was observed, with the molecules stacking their flat faces against one another like coins, with their methylene groups staggered to avoid steric clashes. A dynamic equilibrum was observed between large n-mers, including stacks with all eight solute molecules, and smaller clusters, with the calculated osmotic coefficient being in acceptable agreement with the experimental value. The insensitivity of the results to water model and the congruence with experimental thermodynamic data suggest that the observed stacking interactions are a realistic representation of the actual association mechanism in aqueous caffeine solutions.

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Section: Introductionsupporting

confidence: 79%

Section: Methodsmentioning

confidence: 99%

Molecular Dynamics Simulation Studies of Caffeine Aggregation in Aqueous Solution

et al. 2011

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“…The comparison of τ cw c values in pure water and salt solution at a particular temperature is shown in Figure 6c,d. Consistent with previously reported values of τ cw c for caffeine−water binary system, 32 we also find that the value of the interaction parameter is positive for all systems studied here. Moreover, this finding suggests a greater preference of caffeine to the like molecules in salt solution suggesting salting-out behavior.…”

Section: Resultssupporting

confidence: 92%

Understanding the Role of Temperature Change and the Presence of NaCl Salts on Caffeine Aggregation in Aqueous Solution: From Structural and Thermodynamics Point of View

Sharma

Paul

2015

J. Phys. Chem. B

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To examine the molecular level understanding of temperature induced self-association of caffeine molecules in aqueous solution both in the presence and absence of salt NaCl, we have performed long MD simulations at a regime of temperatures ranging from 275 to 350 K with a temperature difference of 25 K. The calculations of different site-site radial distribution functions followed by coordination number analyses, the calculations of preferential interaction parameters, solvent accessible surface area, and cluster structure analyses show a depletion in the caffeine association propensity with increasing temperature. We have also observed the salting out effect of caffeine molecules in salt solution. The simultaneous presence of polar and nonpolar groups in a caffeine molecule leads to anisotropic hydration. Specifically, the hydration tendency of caffeine hydrophobic sites increases with increasing temperature, while hydrophilic sites tend to be less hydrated. This leads to a decrease in caffeine association. In accordance with some experimental studies on thermodynamics of caffeine association, we have also observed enthalpy driven association in pure water. But the presence of salt leads to entropy driven association specifically at higher temperature. This is due to the relatively stronger interactions of salt ions with caffeine at higher temperature.

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“…3D structures, force fields and partial charges of the molecules, were obtained from different sources. The DPPC structure was obtained from [33], caffeine from [34], and tetracaine was built using the online server PRODRG (available at http://davapc1.bioch.dundee.ac.uk/prodrg/) and SwissParam (http://swissparam.ch/). In Figure 6 a cubic interpolation of order 10 was used to smooth the energy surfaces.…”

Section: Methodsmentioning

confidence: 99%

The Influence of Non Polar and Polar Molecules in Mouse Motile Cells Membranes and Pure Lipid Bilayers

et al. 2013

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We report an experimental study of mouse sperm motility that shows chief aspects characteristic of neurons: the anesthetic (produced by tetracaine) and excitatory (produced by either caffeine or calcium) effects and their antagonic action. While tetracaine inhibits sperm motility and caffeine has an excitatory action, the combination of these two substances balance the effects, producing a motility quite similar to that of control cells. We also study the effects of these agents (anesthetic and excitatory) on the melting points of pure lipid liposomes constituted by 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and dipalmitoyl phosphatidic acid (DPPA). Tetracaine induces a large fluidization of the membrane, shifting the liposomes melting transition temperature to much lower values. The effect of caffeine is null, but its addition to tetracaine-doped liposomes greatly screen the fluidization effect. A high calcium concentration stiffens pure lipid membranes and strongly reduces the effect of tetracaine. Molecular Dynamics Simulations are performed to further understand our experimental findings at the molecular level. We find a strong correlation between the effect of antagonic molecules that could explain how the mechanical properties suitable for normal cell functioning are affected and recovered.

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Development of a molecular mechanics force field for caffeine to investigate the interactions of caffeine in different solvent media

Cited by 19 publications

References 34 publications

Molecular Dynamics Simulation Studies of Caffeine Aggregation in Aqueous Solution

Molecular Dynamics Simulation Studies of Caffeine Aggregation in Aqueous Solution

Understanding the Role of Temperature Change and the Presence of NaCl Salts on Caffeine Aggregation in Aqueous Solution: From Structural and Thermodynamics Point of View

The Influence of Non Polar and Polar Molecules in Mouse Motile Cells Membranes and Pure Lipid Bilayers

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