Molecular Dynamics Simulation of Palmitate Ester Self-Assembly with Diclofenac
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
4. Conclusions
Acknowledgment
References
- Drakulic, B.J.; Juranic, I.O.; Eric, S.; Zloh, M. Role of complexes formation between drugs and penetration enhancers in transdermal delivery. Int. J. Pharm 2008, 363, 40–49. [Google Scholar]
- Tadros, T.; Izquierdo, P.; Esquena, J.; Solans, C. Formulation and stability of nano-emulsions. Adv. Colloid Interface Sci 2004, 109, 303–318. [Google Scholar]
- Devarajan, V.; Ravichandran, V. Nanoemulsions: As modified drug delivery tool. Int. J. Compr. Pharm 2011, 2, 1–6. [Google Scholar]
- Solans, C.; Izquierdo, P.; Nolla, J.; Azemar, N.; Garcia-Celma, M.J. Nano-emulsions. Curr. Opin. Colloid Interface Sci 2005, 10, 102–110. [Google Scholar]
- Sulaiman, A.; Basri, M.; Salleh, A.B.; Rahman, R.N.Z.; Ahmad, R.S. Phase behavior of oleyl oleate with nonionic surfactants. J. Dispersion Sci. Technol 2005, 26, 1–3. [Google Scholar]
- Gunawan, E.R.; Basri, M.; Rahman, M.B.A.; Salleh, A.B.; Rahman, R.N.Z. Study on response surface methodology (RSM) of lipase-catalyzed synthesis of palm-based wax ester. Enzym. Microb. Technol 2005, 37, 739–744. [Google Scholar] [Green Version]
- Peltola, S.; Saarinen-Savolainen, P.; Kiesvaara, J.; Suhonen, T.M.; Urtti, A. Microemulsions for topical delivery of estradiol. Int. J. Pharm 2003, 254, 99–107. [Google Scholar]
- El-Sabbagh, H.; Ghanem, A.H.; Abdel-Alim, H.M. Solubilization of indometacin. Pharmazie 1978, 33, 529–531. [Google Scholar]
- Rowe, R.C.; Sheskey, P.J.; Owen, A.J. Handbook of Pharmaceutical Excipients; American Pharmaceutical Association: Washington, DC, USA, 2005. [Google Scholar]
- Puvvada, S.; Blankschtein, D. Theoretical and experimental investigations of micellar properties of aqueous solutions containing binary mixtures of nonionic surfactants. J. Phys. Chem 1992, 96, 5567–5579. [Google Scholar]
- Van Gunsteren, W.S.; Bakowies, D.; Baron, R.; Chandrasekhar, I.; Christen, M.; Daura, X.; Gee, P.; Geerke, D.P.; Glattli, A.; Hunenberger, P.H.; et al. Biomolecular modeling: Goals, problems, perspectives. Angew. Chem. Int. Ed 2006, 45, 4064–4092. [Google Scholar]
- Bogusz, S.; Venable, R.M.; Pastor, R.W. Molecular dynamics simulations of Octyl Glucoside Micelles: Structural properties. J. Phys. Chem. B 2000, 104, 5462–5470. [Google Scholar]
- Bogusz, S.; Venable, R.M.; Pastor, R.W. Molecular dynamics simulations of Octyl Glucoside Micelles: Dynamic properties. J. Phys. Chem. B 2001, 105, 8312–8321. [Google Scholar]
- Cunha-Silva, L.; Teixeira-Dias, J.J.C. Aqueous solution inclusion of the nonionic surfactant C12E4 in β-cyclodextrin: Implications of micellization in stoichiometry determination and model calculations. J. Incl. Phenom. Macrocycl. Chem 2002, 43, 127–131. [Google Scholar]
- Tieleman, D.P.; van der Spoel, D.; Berendsen, H.J.C. Molecular dynamics simulations of dodecylphosphocholine micelles at three different aggregate sizes: Micellar structure and chain relaxation. J. Phys. Chem. B 2000, 104, 6380–6388. [Google Scholar]
- Marrink, S.J.; Tieleman, D.P.; Mark, A.E. Molecular dynamics simulation of the kinetics of spontaneous micelle formation. J. Phys. Chem. B 2000, 104, 12165–12173. [Google Scholar]
- Lazaridis, T.; Mallik, B.; Yong, C. Implicit solvent simulations of DPC micelle formation. J. Phys. Chem. B 2005, 109, 15098–15106. [Google Scholar]
- Bruce, C.D.; Berkowitz, M.L.; Perera, L.; Forbes, M.D.E. Molecular dynamics simulation of sodium dodecyl sulfate micelle in water: Micellar structural characteristics and counterion distribution. J. Phys. Chem. B 2002, 106, 3788–3793. [Google Scholar]
- De Moura, A.F.; Freitas, L.C.G. Molecular dynamics Simulation of the sodium octanoate micelle in aqueous solution: Comparison of force field parameters and molecular topology effects on the micellar structure. Braz. J. Phys 2004, 34, 64–72. [Google Scholar]
- De Moura, A.F.; Freitas, L.C.G. Molecular dynamics simulation of the sodium octanoate micelle in aqueous solution. Chem. Phys. Lett 2005, 411, 474–478. [Google Scholar]
- Abdul Rahman, M.B.; Huan, Q.-Y.; Tejo, B.A.; Basri, M.; Salleh, A.B.; Abdul Rahman, R.N.Z. Self-assembly formation of palm-based esters nano-emulsion: A molecular dynamics study. Chem. Phys. Lett 2009, 480, 220–224. [Google Scholar]
- Abdul Rahman, M.B.; Latif, M.A.M.; Basri, M.; Salleh, A.B.; Abdul Rahman, R.N.Z. Molecular dynamics simulation of oleyl oleate swollen micelles system. Mol. Simul 2010, 36, 403–407. [Google Scholar]
- Manconi, M.; Mura, S.; Sinico, C.; Fadda, A.M.; Vila, A.O.; Molina, F. Development and characterization of liposomes containing glycols as carriers for diclofenac. Colloids Surf. A 2009, 342, 53–58. [Google Scholar]
- Lindahl, E.; Hess, B.; van der Spoel, D. GROMACS 3.0: A package for molecular simulation and trajectory analysis. J. Mol. Model 2001, 7, 306–317. [Google Scholar]
- Van der Spoel, D.; Lindahl, E.; Hess, B.; Groenhof, G.; Mark, A.E.; Berendsen, H.J.C. GROMACS: Fast, flexible and free. J. Comput. Chem 2005, 26, 1701–1718. [Google Scholar]
- Israelachvili, J.; Ladyzhinski, I. The Physico-Chemical Basis of Self-Assembling Structures. In Forces, Growth and form in Soft Condensed Matter: At the Interface between Physics and Biology; Springer: Dordrecht, The Netherlands, 2005; pp. 1–28. [Google Scholar]
- Ratke, L.; Voorhees, P.W. Growth and Coarsening: Ostwald Ripening in Material Processing; Springer: Dordrecht, The Netherlands, 2002; pp. 117–118. [Google Scholar]
- Bogusz, S.; Venable, R.M.; Pastor, R.W. Molecular dynamics simulations of octyl glucoside micelles: Structural properties. J. Phys. Chem. B 2000, 104, 5462–5470. [Google Scholar]
- De Smet, Y.; Deriemaeker, L.; Finsy, R. Ostwald ripening of alkane emulsions in the presence of surfactant micelle. Langmuir 1999, 15, 6745–6754. [Google Scholar]
- Maillet, J.B.; Lachet, V.; Coveney, P.V. Large scale molecular dynamics simulation of self-assembly processes in short and long chain cationic surfactants. Phys. Chem. Chem. Physics 1999, 1, 5277–5290. [Google Scholar]
- Salinal, S.; Cui, S.; Cochran, H.; Cummings, P. Molecular simulation of a dichain surfactant/water/carbon dioxide system.1: Structural properties of aggregates. Langmuir 2001, 17, 1773–1783. [Google Scholar]
- Konidala, P.; He, L.; Niemeyer, B. Molecular dynamics characterization of n-octyl-β-d-glucopyranoside micelle structure in aqueous solution. J. Mol. Graph. Model 2006, 25, 77–86. [Google Scholar]
- Nokhodchi, A.; Sharabiani, K.; Rashidi, M.R.; Ghafourian, T. The effect of terpene concentrations on the skin penetration of diclofenac sodium. Int. J. Pharm 2007, 335, 97–105. [Google Scholar]
- Fini, A.; Fazio, G.; Gonzalez-Rodriguez, M.; Cavallari, C.; Passerini, N.; Rodriguez, L. Formation of ion-pairs in aqueous solutions of diclofenac salts. Int. J. Pharm 1999, 187, 163–173. [Google Scholar]
- Sintov, A.C.; Botner, S.H. Transdermal drug delivery using microemulsion and aqueous systems: Influence of skin storage conditions on the in vitro permeability of diclofenac from aqueous vehicle systems. Int. J. Pharm 2006, 311, 55–62. [Google Scholar]
- Long, C.; Zhang, L.; Qian, Y. Dissipative Particle Dynamics Simulation of Ibuprofen Molecules Distribution in the Matrix Of solid Lipid Microparticles (SLM). Proceedings of 16th European Symposium on Computer Aided Process Engineering and 9th International Symposium on Process Systems Engineering, Garmisch-Partenkirchen, Germany, 9–13 July 2006; pp. 1649–1654.
- Jorgensen, W.L.; Maxwell, D.S.; Tirado-Rives, J. Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids. J. Am. Chem. Soc 1996, 118, 11225–11236. [Google Scholar]
- Schmidt, M.W.; Baldridge, K.K.; Boatz, J.A.; Elbert, S.T.; Gordon, M.S.; Jensen, J.H.; Koseki, S.; Matsunaga, N.; Nguyen, K.A.; Su, S.J.; et al. General atomic and molecular electronic structure system. J. Comput. Chem 1993, 14, 1347–1363. [Google Scholar]
- Bayly, C.I.; Cieplak, P.; Cornell, W.; Kollman, P.A. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: The RESP model. J. Phys. Chem 1993, 97, 10269–10280. [Google Scholar]
- Ferguson, D.M. Parameterization and evaluation of a flexible water model. J. Comput. Chem 1995, 16, 501–511. [Google Scholar]
- Hess, B.; Bekker, H.; Berendsen, H.J.C.; Fraaije, J.G.E.M. LINCS: A linear constraint solver for molecular simulation. J. Comput. Chem 1998, 18, 1463–1472. [Google Scholar]
- Miyamoto, S.; Kollman, P.A. SETTLE: An analytical version of the SHAKE and RATTLE algorithm for rigid water models. J. Comput. Chem 1992, 13, 952–962. [Google Scholar]
- Berendsen, H.J.C.; Postma, J.P.M.; van Gunsteren, W.F.; DiNola, A.; Haak, J.R. Molecular dynamics with coupling to an external bath. J. Chem. Phys 1984, 81, 3684–3690. [Google Scholar]
- Essman, U.; Perera, L.; Berkowitz, M.; Darden, T.; Lee, H.; Pedersen, L.G. A smooth particle mesh Ewald method. J. Chem. Phys 1995, 103, 8577–8593. [Google Scholar]
- Parrinello, M.; Rahman, A. Polymorphic transitions in single crystals: A new molecular dynamics method. J. Appl. Phys 1981, 52, 7182–7190. [Google Scholar]
- Matazmi, I.D. Formation and Characterization of Oleyl Esters nanoemulasion system. In M.Sc. Thesis; Universiti Putra Malaysia: Kuala Lumpur, Malaysia, December 2009. [Google Scholar]
- Martinez, J.M.; Martinez, L. Packing optimization for automated generation of complex system’s initial configurations for molecular dynamics and docking. J. Comput. Chem 2003, 24, 819–825. [Google Scholar]
Model system | <Rg> (nm) | Rs (nm) | <I1> (104 amu nm2) | <I2> (104 amu nm2) | <I3> (104 amu nm2) | I1:I2:I3 | e | Droplet size (Exp.) (nm) |
---|---|---|---|---|---|---|---|---|
OP/T80 | 5.10 (±0.006) | 6.58 | 60.22 (±1.24) | 55.80 (±1.10) | 39.94 (±1.96) | 1.5:1.4:1 | 0.6 | 5.87 |
OP/T80/DIF | 2.07 (±0.002) | 2.67 | 10.43 (±0.31) | 8.75 (±0.15) | 7.86 (±0.25) | 1.3:1.1:1 | 0.5 | - |
Model system | Hydrophobic (nm2) | Hydrophilic (nm2) | Total (nm2) |
---|---|---|---|
OP/T80 | 192.58 (±4.65) | 28.94 (±0.93) | 221.52 (±5.33) |
OP/T80/DIF | 132.41 (±2.23) | 21.24 (±0.91) | 153.65 (±2.57) |
Model | Number of molecules | # SPC | Box edge (nm) | Average density (g/cm3) | Concentration (w%) | Average total energy (kJ/mol) |
---|---|---|---|---|---|---|
T80 | 1 | 5368 | 5 | 1.01 ± 0.00 | 1.4 | −1.69 × 105 ± 305 |
OP | 1 | 2145 | 4 | 1.01 ± 0.00 | 1.3 | −6.76 × 104 ± 191 |
DIF | 1 | 1391 | 3.5 | 1.01 ± 0.00 | 1.2 | −4.41 × 104 ± 142 |
OP/T80 | 20;8 | 49133 | 11.5 | - | 3.0;0.5 | −1.52 × 106 ± 1140 |
OP/T80/DIF | 20;8;4 | 55837 | 12 | - | 2.6;0.4;0.1 | −1.74 × 106 ± 1038 |
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Abedi Karjiban, R.; Basri, M.; Abdul Rahman, M.B.; Salleh, A.B. Molecular Dynamics Simulation of Palmitate Ester Self-Assembly with Diclofenac. Int. J. Mol. Sci. 2012, 13, 9572-9583. https://doi.org/10.3390/ijms13089572
Abedi Karjiban R, Basri M, Abdul Rahman MB, Salleh AB. Molecular Dynamics Simulation of Palmitate Ester Self-Assembly with Diclofenac. International Journal of Molecular Sciences. 2012; 13(8):9572-9583. https://doi.org/10.3390/ijms13089572
Chicago/Turabian StyleAbedi Karjiban, Roghayeh, Mahiran Basri, Mohd Basyaruddin Abdul Rahman, and Abu Bakar Salleh. 2012. "Molecular Dynamics Simulation of Palmitate Ester Self-Assembly with Diclofenac" International Journal of Molecular Sciences 13, no. 8: 9572-9583. https://doi.org/10.3390/ijms13089572