Glyceride lipid formulations: Molecular dynamics modeling of phase behavior during dispersion and molecular interactions between drugs and excipients

Pharmaceutical Research

Volumn 30, Issue 12, 2013, Pages 3238-3253

  Warren, Dallas B ^a   King, Dylan ^a   Benameur, Hassan ^b   Pouton, Colin W ^a   Chalmers, David K ^a  

^a MONASH UNIVERSITY   (Australia)

^b CAPSUGEL   (France)

Author keywords

drug microenvironment; lipid based formulations; microemulsions; molecular dynamics; phase behavior

Indexed keywords

ACICLOVIR; ACYLGLYCEROL; DANAZOL; DILAUROYL GLYCERIDE; DRUG; EXCIPIENT; HYDROCORTISONE; KETOPROFEN; LIPID; MONOLAUROYL GLYCERIDE; PROGESTERONE; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; COMPUTER PROGRAM; CONCENTRATION RESPONSE; DIFFUSION; DISPERSION; DRUG DISTRIBUTION; DRUG FORMULATION; DRUG MECHANISM; DRUG SOLUBILITY; DRUG STRUCTURE; HYDRATION; HYDROGEN BOND; HYDROPHOBICITY; MICELLE; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PHASE PARTITIONING; PHYSICAL CHEMISTRY; PRESSURE; PRIORITY JOURNAL; STRUCTURE ANALYSIS; TEMPERATURE; WATER CONTENT; WATER STRUCTURE;

EXCIPIENTS; GLYCERIDES; LIPIDS; MOLECULAR DYNAMICS SIMULATION; PHARMACEUTICAL PREPARATIONS; PHASE TRANSITION; SOLUBILITY;

EID: 84890443861     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-013-1206-1     Document Type: Article

References (66)

1. Warren DB, Chalmers DK, Pouton CW. Structure and dynamics of glyceride lipid formulations, with propylene glycol and water. Mol Pharm. 2009;6(2):604-14.
2. Turner DC, Yin F, Kindt JT, Zhang H. Molecular dynamics simulations of glycocholate/oleic acid mixed micelle assembly. Langmuir. 2010;26(7):4687-92.
3. Bogusz S, Venable RM, Pastor RW. Molecular dynamics simulations of octyl glucoside micelles: structural properties. J Phys Chem B. 2000;104:5462-70.
4. Rane SS, Anderson BD. Molecular dynamics simulations of functional group effects on solvation thermodynamics of model solutes in decane and tricaprylin. Mol Pharm. 2008;5:1023-36.
5. Marrink SJ, Tieleman DP. Molecular dynamics simulation of a lipid diamond cubic phase. J Am Chem Soc. 2001;123(49):12383-91.
6. Kasimova AO, Pavan GM, Danani A, Mondon K, Cristiani A, Scapozza L, et al. Validation of a novel molecular dynamics simulation approach for lipophilic drug incorporation into polymer micelles. J Phys Chem B. 2012;116(14):4338-45.
7. Pouton CW. Lipid formulations for oral administration of drugs: non-emulsifying, self-emulsifying and 'self-microemulsifying' drug delivery systems. Eur J Pharm Sci. 2000;11:S93-8.
8. Pouton CW. Formulation of poorly water-soluble drugs for oral administration: physicochemical and physiological issues and the lipid formulation classification system. Eur J Pharm Sci. 2006;29(3-4):278-87.
9. Mohsin K, Pouton CW. The influence of the ratio of lipid to surfactant and the presence of cosolvent on phase behaviour during aqueous dilution of lipid-based drug delivery systems. J Drug Del Sci Tech. 2012;22(6):531-40.
10. CRC Handbook of Chemistry and Physics. Boca Raton, Florida: CRC Press/Taylor and Francis; 2010. Available from: http://www.hbcpnetbase.com.
11. Zielenkiewicz W, Golankiewicz B, Perlovich G, KoÅbiał M. Aqueous solubilities, infinite dilution activity coefficients and octanol-water partition coefficients of tricyclic analogs of acyclovir. J Solution Chem. 1999;28(6):731-45.
12. Kristl A, Tukker JJ. Negative correlation of n-octanol/water partition coefficient and transport of some guanine derivatives through rat jejunum in vitro. Pharm Res. 1998;15(3):499-501.
13. Alsenz J, Meister E, Haenel E. Development of a partially automated solubility screening (PASS) assay for early drug development. J Pharm Sci. 2007;96(7):1748-62.
14. Erlich L, Yu D, Pallister DA, Levinson RS, Gole DG, Wilkinson PA, et al. Relative bioavailability of danazol in dogs from liquid-filled hard gelatin capsules. Int J Pharm. 1999;179(1):49-53.
15. Ying Hong Lu CBC. Physicochemical properties, binary and ternary phase diagrams of ketoprofen. Chirality. 2004;16(8):541-8.
16. Fujii M, Hori N, Shiozawa K, Wakabayashi K, Kawahara E, Matsumoto M. Effect of fatty acid Esters on permeation of ketoprofen through hairless rat skin. Int J Pharm. 2000;205(1-2):117-25.
17. La Rotonda MI, Amato G, Barbato F, Silipo C, Vittoria A. Relationships between octanol-water partition data, chromatographic indices and their dependence on pH in a set of nonsteroidal anti-inflammatory drugs. Quant Struct-Act Rel. 1983;2(4):168-73.
18. Hagen TA, Flynn GL. Solubility of hydrocortisone in organic and aqueous media: evidence for regular solution behavior in apolar solvents. J Pharm Sci. 1983;72(4):409-14.
19. Shoshtari SZ, Wen J, Alany RG. Octanol water partition coefficient determination for model steroids using an HPLC method. Lett Drugs Des Discov. 2008;5(6):394-400.
20. Nandi I, Bateson M, Bari M, Joshi HN. Synergistic effect of PEG-400 and cyclodextrin to enhance solubility of progesterone. AAPS PharmSciTech. 2003;4(1):E1.
21. Berendsen HJC, van der Spoel D, van Drunen R. GROMACS: a message-passing parallel molecular dynamics implementation. Comput Phys Commun. 1995;91(1-3):43-56.
22. Lindahl E, Hess B, van der Spoel D. GROMACS 3.0: a package for molecular simulation and trajectory analysis. J Mol Model. 2001;7:306-17.
23. van der Spoel D, van Buuren AR, Apol E, Meulenhoff PJ, Tieleman DP, Sijbers ALTM, et al. GROMACS user manual version 3.1.1. Groningen: Department of Biophysical Chemistry; 2002. p. 278.
24. Humphrey W, Dalke A, Schulten K. VMD: visual molecular dynamics. J Mol Graph. 1996;14(1):33-8.
25. Freudenberger C. g-sdf. 1.25 ed: Chemistry, University of Ulm; 2003.
26. Einstein A. The motion of elements suspended in static liquids as claimed in the molecular kinetic theory of heat. Ann Phys-Berlin. 1905;17(8):549-60. German.
27. van Gunsteren WF, Billeter SR, Eising AA, Hunenberger PH, Krueger P, Mark AE, et al. Biomolecular simulation: the GROMOS96 manual and user guide. Zurich: Hochschulverlag AG an der ETHC Zurich; 1996.
28. Daura X, Mark AE, Van Gunsteren WF. Parametrization of aliphatic CHn united atoms of GROMOS96 force field. J Comput Chem. 1998;19(5):535-47.
29. Berendsen HJC, Postma JPM, Gunsteren WF, Dinola A, Haak JR. Molecular dynamics with coupling to an external bath. J Chem Phys. 1984;81:3684-9.
30. Jorgensen WL, Jenson C. Temperature dependence of TIP3P, SPC, and TIP4P water from NPT Monte Carlo simulations: seeking temperatures of maximum density. J Comput Chem. 1998;19(10):1179-86.
31. Feenstra KA, Hess B, Berendsen HJC. Improving efficiency of large time-scale molecular dynamics simulations of hydrogen-rich systems. J Comput Chem. 1999;20(8):786-98.
32. Poger D, Mark AE. Lipid bilayers: the effect of force field on ordering and dynamics. J Chem Theory Comput. 2012;8(11):4807-17.
33. King DT, Warren DB, Pouton CW, Chalmers DK. Using molecular dynamics to study liquid phase behavior: simulations of the ternary sodium laurate/sodium oleate/water system. Langmuir. 2011;27(18):11381-93.
34. Paluch AS, Mobley DL, Maginn EJ. Small molecule solvation free energy: enhanced conformational sampling using expanded ensemble molecular dynamics simulation. J Chem Theory Comput. 2011;7(9):2910-8.
35. Anselmi M, Brunori M, Vallone B, Di Nola A. Molecular dynamics simulation of deoxy and carboxy murine neuroglobin in water. Biophys J. 2007;93(2):434-41.
36. Warren DB, Chalmers DK, Hutchison K, Dang W, Pouton CW. Molecular dynamics simulation of spontaneous bile salt aggregation. Colloids Surf A. 2006;280:182-93.
37. Tieleman DP, van der Spoel D, Berendsen HJC. Molecular dynamics simulations of dodecylphosphocholine micelles at three different aggregate sizes: micellar structure and chain relaxation. Biophys J. 2000;104:6380-8.
38. Marrink SJ, Mark AE. Molecular dynamics simulations of mixed micelles modelling human bile. Biochemistry. 2002;41:5375-82.
39. Bandyopadhyay S, Chanda J. Monolayer of monododecyl diethylene glycol surfactants adsorbed at the air/water interface: a molecular dynamics study. Langmuir. 2003;19:10443-8.
40. van der Spoel D, Lindahl E, Hess B, van Buuren AR, Apol E, Meulenhoff PJ, et al. GROMACS User Manual version 4.5.4 2010.
41. Anézo C, de Vries AH, Höltje H-D, Tieleman DP, Marrink S-J. Methodological issues in lipid bilayer simulations. J Phys Chem B. 2003;107(35):9424-33.
42. Miyamoto S, Kollman PA. SETTLE: an analytical version of the SHAKE and RATTLE algorithm for rigid water models. J Comput Chem. 1992;13:952-62.
43. Hess B, Bekker H, Berendsen HJC, Fraaije JGEM. LINCS: a linear constraint solver for molecular simulations. J Comput Chem. 1997;18:1463-72.
44. Essmann U, Perera L, Berkowitz ML, Darden T, Lee H, Pedersen LG. A smooth particle mesh ewald method. J Chem Phys. 1995;103(19):8577-93.
45. Bussi G, Donadio D, Parrinello M. Canonical sampling through velocity rescaling. J Chem Phys. 2007;126(1):014101.
46. Parrinello M, Rahman A. Polymorphic transitions in single-crystals - a new molecular-dynamics method. J Appl Phys. 1981;52(12):7182-90.
47. Nose S, Klein ML. Constant pressure molecular-dynamics for molecular-systems. Mol Phys. 1983;50(5):1055-76.
48. Harvey SC, Tan RKZ, Cheatham TE. The flying ice cube: velocity rescaling in molecular dynamics leads to violation of energy equipartition. J Comput Chem. 1998;19(7):726-40.
49. Chiu S-W, Clark M, Subramaniam S, Jakobsson E. Collective motion artifacts arising in long-duration molecular dynamics simulations. J Comput Chem. 2000;21(2):121-31.
50. Cheatham Iii TE, Brooks BR. Recent advances in molecular dynamics simulation towards the realistic representation of biomolecules in solution. Theor Chem Acc. 1998;99(5):279-88.
51. Lingenheil M, Denschlag R, Reichold R, Tavan P. The "Hot-solvent/ cold-solute" problem revisited. J Chem Theory Comput. 2008;4(8):1293-306.
52. Patel RY, Balaji PV. Effect of the choice of the pressure coupling method on the spontaneous aggregation of DPPC molecules. J Phys Chem B. 2005;109(30):14667-74.
53. Larsson K, Krog N. Structural properties of the lipid - water gel phase. Chem Phys Lipids. 1973;10(2):177-80.
54. Kanesaka I, Shimizu K. Infrared intensity and morphology of 1-monolaurin-water systems. Spectrochim Acta A. 2000;56(3):523-9.
55. Ljusberg-Wahren H, Gunnarsson T, Wannerberger L, Gustafsson J, Almgren M, Krog N. Micelles and liquid crystals in aqueous diglycerol monodecanoate systems. Prog Coll Pol Sci S. 1998;108:99-104.
56. Borné J, Nylander T, Khan A. Phase behavior and aggregate formation for the aqueous monoolein system mixed with sodium oleate and oleic acid. Langmuir. 2001;17(25):7742-51.
57. Pitzalis P, Monduzzi M, Krog N, Larsson H, Ljusberg-Wahren H, Nylander T. Characterization of the liquid - crystalline phases in the glycerol monooleate/diglycerol monooleate/water system. Langmuir. 2000;16(15):6358-65.
58. Levinger NE, Swafford LA. Ultrafast dynamics in reverse micelles. Annu Rev Phys Chem. 2009;60:385-406.
59. Geil B, Feiweier T, Pospiech EM, Eisenblatter J, Fujara F, Winter R. Relating structure and translational dynamics in aqueous dispersions of monoolein. Chem Phys Lipids. 2000;106(2):115-26.
60. Mahoney MW, Jorgensen WL. Diffusion constant of the TIP5P model of liquid water. J Chem Phys. 2001;114:363-6.
61. Holz M, Heil SR, Sacco A. Temperature-dependent self-diffusion coefficients of water and six selected molecular liquids for calibration in accurate 1H NMR PFG measurements. Phys Chem Chem Phys. 2000;2(20):4740-2.
62. Eriksson PO, Lindblom G. Lipid and water diffusion in bicontinuous cubic phases measured by Nmr. Biophys J. 1993;64(1):129-36.
63. Cuine JF, Charman WN, Pouton CW, Edwards GA, Porter CJ. Increasing the proportional content of surfactant (Cremophor EL) relative to lipid in self-emulsifying lipid-based formulations of danazol reduces oral bioavailability in beagle dogs. Pharm Res. 2007;24(4):748-57.
64. Anby MU, Williams HD, McIntosh M, Benameur H, Edwards GA, Pouton CW, et al. Lipid digestion as a trigger for supersaturation: evaluation of the impact of supersaturation stabilization on the in vitro and in vivo performance of self-emulsifying drug delivery systems. Mol Pharm. 2012;9(7):2063-79.
65. Williams HD, Anby MU, Sassene P, Kleberg K, Bakala-N'Goma J-C, Calderone M, et al. Toward the establishment of standardized in vitro tests for lipid-based formulations. 2. The effect of bile salt concentration and drug loading on the performance of type I, II, IIIA, IIIB, and IV formulations during in vitro digestion. Mol Pharm. 2012;9(11):3286-300.
66. Kaukonen A, Boyd B, Charman W, Porter C. Drug solubilization behavior during in vitro digestion of suspension formulations of poorly water-soluble drugs in triglyceride lipids. Pharm Res. 2004;21(2):254-60.