Molecular mechanism of cyclodextrin mediated cholesterol extraction

PLoS Computational Biology

Volumn 7, Issue 3, 2011, Pages

  López, Cesar A ^a   de Vries, Alex H ^a   Marrink, Siewert J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLODEXTRINS; DIMERS; EXTRACTION; FREE ENERGY; MOLECULAR DYNAMICS; MONOLAYERS;

ATOMIC-RESOLUTION; CHOLESTEROL MOLECULES; DYNAMICS SIMULATION; FREE-ENERGY CALCULATIONS; MEMBRANE SURFACE; MODEL MEMBRANES; MOLECULAR MECHANISM; NANOCARRIERS; NANOSECOND TIME SCALE; RATIONAL DESIGN;

CHOLESTEROL;

BETA CYCLODEXTRIN; CHOLESTEROL; CYCLODEXTRIN;

ARTICLE; BINDING AFFINITY; CARBOHYDRATE ANALYSIS; CELLULAR DISTRIBUTION; CHOLESTEROL EXTRACTION; CHOLESTEROL TRANSPORT; COMPLEX FORMATION; COMPUTER MODEL; CONTROLLED STUDY; DESORPTION; DIMERIZATION; ENERGY TRANSFER; EXTRACTION; HYDROPHOBICITY; LIPID COMPOSITION; LIPID MONOLAYER; MEMBRANE BINDING; MOLECULAR DYNAMICS; MOLECULAR MODEL; MOLECULAR STABILITY; NANOANALYSIS; SURFACE PROPERTY; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; THERMODYNAMICS;

CHOLESTEROL; CYCLODEXTRINS; KINETICS; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; THERMODYNAMICS;

EID: 79953649332     PISSN: 1553734X     EISSN: 15537358     Source Type: Journal    
DOI: 10.1371/journal.pcbi.1002020     Document Type: Article

References (48)

1. Valle ED, (2004) Cyclodextrins and their uses: a review. Process Biochem 39: 1033-1046.
2. Stella VJ, He Q, (2008) Cyclodextrins. Toxicol Pathol 36: 30-42.
3. Vyas A, Saraf S, Saraf S, (2008) Cyclodextrin based novel drug delivery systems. J Inclusion Phenom Macrocyclic Chem 62: 23-42.
4. Davis ME, Brewster ME, (2004) Cyclodextrin-based pharmaceutics: past, present and future. Nat Rev Drug Discov 3: 1023-1035.
5. Yu Y, Li J, Sun Y, Liang Q, Peng X, et al. (2008) Solubility of beta-cyclodextrin in different mixed solvents. Pet Sci 5: 263-268.
6. Ogoshi T, Harada A, (2008) Chemical sensors based on cyclodextrin derivatives. Sensors 8: 4961-4982.
7. van de Manakker F, Vermonden T, van Nostrum CF, Hennink WE, (2009) Cyclodextrin-based polymeric materials: synthesis, properties, and pharmaceutical/biomedical applications. Biomacromolecules 10: 3157-3175.
8. Harada A, Takashima Y, Yamaguchi H, (2009) Cyclodextrin-based supramolecular polymers. Chem Soc Rev 38: 875-882.
9. Bilensoy E, Hincal AA, (2009) Recent advances and future directions in amphiphilic cyclodextrin nanoparticles. Expert Opin Drug Deliv 6: 1161-1173.
10. Messner M, Kurkov SV, Jansook P, Loftsson T, (2010) Self-assembled cyclodextrin aggregates and nanoparticles. Int J Pharm 387: 199-208.
11. Zidovetzki R, Levitan I, (2007) Use of cyclodextrins to manipulate plasma membrane cholesterol content: evidence, misconceptions and control strategies. Biochim Biophys Acta 1768: 1311-1324.
12. Atger VM, de la Llera Moya M, Stoudt GW, Rodrigueza WV, Phillips MC, et al. (1997) Cyclodextrins as catalysts for the removal of cholesterol from macrophage foam cells. J Clin Invest 99: 773-780.
13. Leventis R, Silvius JR, (2001) Use of cyclodextrins to monitor transbilayer movement and differential lipid affinities of cholesterol. Biophys J 81: 2257-2267.
14. Mascetti J, Castano S, Cavagnat D, Desbat B, (2008) Organization of beta-cyclodextrin under pure cholesterol, dmpc, or dmpg and mixed cholesterol/phospholipid monolayers. Langmuir 24: 9616-9622.
15. Ohvo H, Slotte JP, (1996) Cyclodextrin-mediated removal of sterols from monolayers: effects of sterol structure and phospholipids on desorption rate. Biochemistry 35: 8018-8024.
16. Yancey PG, Rodrigueza WV, Kilsdonk EP, Stoudt GW, Johnson WJ, et al. (1996) Cellular cholesterol efflux mediated by cyclodextrins demonstration of kinetic pools and mechanism of efflux. J Biol Chem 271: 16026-16034.
17. Ohtani Y, Irie T, Uekama K, Fukunaga K, Pitha J, (1989) Differential effects of alpha-, beta- and gamma-cyclodextrins on human erythrocytes. Eur J Biochem 186: 17-22.
18. Ravichandran R, Divakar S, (1998) Inclusion of ring a of cholesterol inside the beta-cyclodextrin cavity: Evidence from oxidation reactions and structural studies. J Incl Phenom Macrocyclic Chem 30: 253-270.
19. Betzel C, Saenger W, Hingerty BE, Brown GM, (1984) Topography of cyclodextrin inclusion complexes, part 20 circular and ip-op hydrogen bonding in beta-cyclodextrin undecahydrate: a neutron diffraction study. J Am Chem Soc 106: 7545-7557.
20. Besenicar MP, Bavdek A, Kladnik A, Macek P, Anderluh G, (2008) Kinetics of cholesterol extraction from lipid membranes by methyl-beta-cyclodextrin-a surface plasmon resonance approach. Biochim Biophys Acta 1778: 175-184.
21. Ohvo-Rekilä H, Akerlund B, Slotte JP, (2000) Cyclodextrin-catalyzed extraction of unresent sterols from monolayer membranes and small unilamellar vesicles. Chem Phys Lipids 105: 167-178.
22. Castagne D, Fillet M, Delattre L, Evrard B, Nusgens B, et al. (2009) Study of the cholesterol extraction capacity of beta-cyclodextrin and its derivatives, relationships with their effects on endothelial cell viability and on membrane models. J Incl Phenom Macrocyclic Chem 63: 225-231.
23. Choi YH, Yang CH, Kim HW, Jung S, (2001) Molecular modeling studies of the beta-cyclodextrin in monomer and dimer form as hosts for the complexation of cholesterol. J Incl Phenom Macrocyclic Chem 39: 71-76.
24. Yu Y, Chipot C, Cai W, Shao X, (2006) Molecular dynamics study of the inclusion of cholesterol into cyclodextrins. J Phys Chem B 110: 6372-6378.
25. Hernández-Pascacio J, Garza C, Banquy X, Díaz-Vergara N, Amigo A, et al. (2007) Cyclodextrinbased self-assembled nanotubes at the water/air interface. J Phys Chem B 111: 12625-12630.
26. Weinzinger P, Weiss-Greiler P, Snor W, Viernstein H, Wolschann P, (2007) Molecular dynamics simulations and quantum chemical calculations on beta-cyclodextrin spironolactone complex. J Incl Phenom Macrocyclic Chem 57: 29-33.
27. Piñeiro A, Banquy X, Pérez-Casas S, Tovar E, García A, et al. (2007) On the characterization of host-guest complexes: surface tension, calorimetry, and molecular dynamics of cyclodextrins with a non-ionic surfactant. J Phys Chem B 111: 4383-4392.
28. Tsamaloukas A, Szadkowska H, Slotte PJ, Heerklotz H, (2005) Interactions of cholesterol with lipid membranes and cyclodextrin characterized by calorimetry. Biophys J 89: 1109-1119.
29. Williams RO, Mahaguna V, Sriwongjanya M, (1998) Characterization of an inclusion complex of cholesterol and hydroxypropyl-beta-cyclodextrin. Eur J Pharm Biopharm 46: 355-360.
30. Hernández-Pascacio J, Banquy X, Pérez-Casas S, Costas M, Amigo A, et al. (2008) A small molecular size system giving unexpected surface effects: alpha-cyclodextrin+sodium dodecyl sulfate in water. J Colloid Interface Sci 328: 391-395.
31. He Y, Fu P, Shen X, Gao H, (2008) Cyclodextrin-based aggregates and characterization by microscopy. Micron 39: 495-516.
32. Bonnet P, Jaime C, Morin-Allory L, (2002) Structure and thermodynamics of alpha-, beta-, and gamma-cyclodextrin dimers. molecular dynamics studies of the solvent effect and free binding energies. J Org Chem 67: 8602-8609.
33. Frijlink HW, Eissens AC, Hefting NR, Poelstra K, Lerk CF, et al. (1991) The effect of parenterally administered cyclodextrins on cholesterol levels in the rat. Pharm Res 8: 9-16.
34. Breslow R, Zhang B, (1996) Cholesterol recognition and binding by cyclodextrin dimers. J Am Chem Soc 118: 8495-8496.
35. Nishijo J, Moriyama S, Shiota S, (2003) Interactions of cholesterol with cyclodextrins in aqueous solution. Chem Pharm Bull (Tokyo) 51: 1253-1257.
36. Bennett WF, MacCallum JL, Hinner MJ, Marrink SJ, Tieleman DP, (2009) Molecular view of cholesterol ip-op and chemical potential in different membrane environments. J Am Chem Soc 131: 12714-12720.
37. Montiel PO, (2000) Soluble carbohydrates (trehalose in particular) and cryoprotection in polar biota. Cryo Letters 21: 83-90.
38. Hess B, Kutzner C, van der Spoel D, Lindahl E, (2008) Gromacs 4: Algorithms for highly efficient, load-balanced, and scalable molecular simulation. J Chem Theory Comput 4: 435-447.
39. Lins RD, Hünenberger PH, (2005) A new gromos force field for hexopyranose-based carbohydrates. J Comput Chem 26: 1400-1412.
40. Höltje M, Förster T, Brandt B, Engels T, von Rybinski W, et al. (2001) Molecular dynamics simulations of stratum corneum lipid models: fatty acids and cholesterol. Biochim Biophys Acta 1511: 156-167.
41. Berendsen HJC, Postma JPM, van Gunsteren WF, Hermans J, (1981) Interaction models for water in relation to protein hydration. pp. 331-342 Reidel: Dordrecht.
42. Hess B, Bekker H, Berendsen HJC, Fraaije J, (1997) Lincs: A linear constraint solver for molecular simulations. J Comput Chem 18: 1463-1472.
43. van Gunsteren WF, Berendsen HJC, (1990) Computer simulation of molecular dynamics: Methodology, applications, and perspectives in chemistry. Angew Chem Int Ed 29: 992-1023.
44. Tironi I, Sperb R, Smith P, van Gunsteren WF, (1995) A generalized reaction field method for molecular dynamics simulations. J Chem Phys 102: 5451-5459.
45. Berendsen HJC, Postma J, van Gunsteren WF, Dinola A, Haak J, (1984) Molecular dynamics with coupling to an external bath. J Chem Phys 81: 3684-3690.
46. Torrie G, Valleau J, (1977) Nonphysical sampling distributions in monte carlo free-energy estimation: Umbrella sampling. J Comput Phys 23: 187-199.
47. Kumar S, Rosenberg J, Bouzida D, Swendsen R, Kollman P, (1992) The weighted histogram analysis method for free-energy calculations on biomolecules. i. the method. J Comput Chem 13: 1011-1021.
48. Shoup D, Szabo A, (1982) Role of diffusion in ligand binding to macromolecules and cell-bound receptors. Biophys J 40: 33-39.