{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,10]],"date-time":"2026-03-10T01:33:39Z","timestamp":1773106419278,"version":"3.50.1"},"reference-count":48,"publisher":"Public Library of Science (PLoS)","issue":"3","license":[{"start":{"date-parts":[[2011,3,24]],"date-time":"2011-03-24T00:00:00Z","timestamp":1300924800000},"content-version":"unspecified","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["www.ploscompbiol.org"],"crossmark-restriction":false},"short-container-title":["PLoS Comput Biol"],"DOI":"10.1371\/journal.pcbi.1002020","type":"journal-article","created":{"date-parts":[[2011,3,24]],"date-time":"2011-03-24T20:53:54Z","timestamp":1301000034000},"page":"e1002020","update-policy":"https:\/\/doi.org\/10.1371\/journal.pcbi.corrections_policy","source":"Crossref","is-referenced-by-count":191,"title":["Molecular Mechanism of Cyclodextrin Mediated Cholesterol Extraction"],"prefix":"10.1371","volume":"7","author":[{"given":"Cesar A.","family":"L\u00f3pez","sequence":"first","affiliation":[]},{"given":"Alex H.","family":"de Vries","sequence":"additional","affiliation":[]},{"given":"Siewert J.","family":"Marrink","sequence":"additional","affiliation":[]}],"member":"340","published-online":{"date-parts":[[2011,3,24]]},"reference":[{"key":"ref1","doi-asserted-by":"crossref","first-page":"1033","DOI":"10.1016\/S0032-9592(03)00258-9","article-title":"Cyclodextrins and their uses: a review.","volume":"39","author":"ED Valle","year":"2004","journal-title":"Process Biochem"},{"key":"ref2","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1177\/0192623307310945","article-title":"Cyclodextrins.","volume":"36","author":"VJ Stella","year":"2008","journal-title":"Toxicol Pathol"},{"key":"ref3","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1007\/s10847-008-9456-y","article-title":"Cyclodextrin based novel drug delivery systems.","volume":"62","author":"A Vyas","year":"2008","journal-title":"J Inclusion Phenom Macrocyclic Chem"},{"key":"ref4","doi-asserted-by":"crossref","first-page":"1023","DOI":"10.1038\/nrd1576","article-title":"Cyclodextrin-based pharmaceutics: past, present and future.","volume":"3","author":"ME Davis","year":"2004","journal-title":"Nat Rev Drug Discov"},{"key":"ref5","doi-asserted-by":"crossref","first-page":"263","DOI":"10.1007\/s12182-008-0044-y","article-title":"Solubility of beta-cyclodextrin in different mixed solvents.","volume":"5","author":"Y Yu","year":"2008","journal-title":"Pet Sci"},{"key":"ref6","doi-asserted-by":"crossref","first-page":"4961","DOI":"10.3390\/s8084961","article-title":"Chemical sensors based on cyclodextrin derivatives.","volume":"8","author":"T Ogoshi","year":"2008","journal-title":"Sensors"},{"key":"ref7","doi-asserted-by":"crossref","first-page":"3157","DOI":"10.1021\/bm901065f","article-title":"Cyclodextrin-based polymeric materials: synthesis, properties, and pharmaceutical\/biomedical applications.","volume":"10","author":"F van de Manakker","year":"2009","journal-title":"Biomacromolecules"},{"key":"ref8","doi-asserted-by":"crossref","first-page":"875","DOI":"10.1039\/b705458k","article-title":"Cyclodextrin-based supramolecular polymers.","volume":"38","author":"A Harada","year":"2009","journal-title":"Chem Soc Rev"},{"key":"ref9","doi-asserted-by":"crossref","first-page":"1161","DOI":"10.1517\/17425240903222218","article-title":"Recent advances and future directions in amphiphilic cyclodextrin nanoparticles.","volume":"6","author":"E Bilensoy","year":"2009","journal-title":"Expert Opin Drug Deliv"},{"key":"ref10","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1016\/j.ijpharm.2009.11.035","article-title":"Self-assembled cyclodextrin aggregates and nanoparticles.","volume":"387","author":"M Messner","year":"2010","journal-title":"Int J Pharm"},{"key":"ref11","doi-asserted-by":"crossref","first-page":"1311","DOI":"10.1016\/j.bbamem.2007.03.026","article-title":"Use of cyclodextrins to manipulate plasma membrane cholesterol content: evidence, misconceptions and control strategies.","volume":"1768","author":"R Zidovetzki","year":"2007","journal-title":"Biochim Biophys Acta"},{"key":"ref12","doi-asserted-by":"crossref","first-page":"773","DOI":"10.1172\/JCI119223","article-title":"Cyclodextrins as catalysts for the removal of cholesterol from macrophage foam cells.","volume":"99","author":"VM Atger","year":"1997","journal-title":"J Clin Invest"},{"key":"ref13","doi-asserted-by":"crossref","first-page":"2257","DOI":"10.1016\/S0006-3495(01)75873-0","article-title":"Use of cyclodextrins to monitor transbilayer movement and differential lipid affinities of cholesterol.","volume":"81","author":"R Leventis","year":"2001","journal-title":"Biophys J"},{"key":"ref14","doi-asserted-by":"crossref","first-page":"9616","DOI":"10.1021\/la8004294","article-title":"Organization of beta-cyclodextrin under pure cholesterol, dmpc, or dmpg and mixed cholesterol\/phospholipid monolayers.","volume":"24","author":"J Mascetti","year":"2008","journal-title":"Langmuir"},{"key":"ref15","doi-asserted-by":"crossref","first-page":"8018","DOI":"10.1021\/bi9528816","article-title":"Cyclodextrin-mediated removal of sterols from monolayers: effects of sterol structure and phospholipids on desorption rate.","volume":"35","author":"H Ohvo","year":"1996","journal-title":"Biochemistry"},{"key":"ref16","doi-asserted-by":"crossref","first-page":"16026","DOI":"10.1074\/jbc.271.27.16026","article-title":"Cellular cholesterol efflux mediated by cyclodextrins demonstration of kinetic pools and mechanism of efflux.","volume":"271","author":"PG Yancey","year":"1996","journal-title":"J Biol Chem"},{"key":"ref17","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1111\/j.1432-1033.1989.tb15171.x","article-title":"Differential effects of alpha-, beta- and gamma-cyclodextrins on human erythrocytes.","volume":"186","author":"Y Ohtani","year":"1989","journal-title":"Eur J Biochem"},{"key":"ref18","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1023\/A:1007912809965","article-title":"Inclusion of ring a of cholesterol inside the beta-cyclodextrin cavity: Evidence from oxidation reactions and structural studies.","volume":"30","author":"R Ravichandran","year":"1998","journal-title":"J Incl Phenom Macrocyclic Chem"},{"key":"ref19","doi-asserted-by":"crossref","first-page":"7545","DOI":"10.1021\/ja00336a039","article-title":"Topography of cyclodextrin inclusion complexes, part 20 circular and ip-op hydrogen bonding in beta-cyclodextrin undecahydrate: a neutron diffraction study.","volume":"106","author":"C Betzel","year":"1984","journal-title":"J Am Chem Soc"},{"key":"ref20","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1016\/j.bbamem.2007.09.022","article-title":"Kinetics of cholesterol extraction from lipid membranes by methyl-beta-cyclodextrin-a surface plasmon resonance approach.","volume":"1778","author":"MP Besenicar","year":"2008","journal-title":"Biochim Biophys Acta"},{"key":"ref21","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/S0009-3084(00)00122-5","article-title":"Cyclodextrin-catalyzed extraction of unresent sterols from monolayer membranes and small unilamellar vesicles.","volume":"105","author":"H Ohvo-Rekil\u00e4","year":"2000","journal-title":"Chem Phys Lipids"},{"key":"ref22","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1007\/s10847-008-9510-9","article-title":"Study of the cholesterol extraction capacity of beta-cyclodextrin and its derivatives, relationships with their effects on endothelial cell viability and on membrane models.","volume":"63","author":"D Castagne","year":"2009","journal-title":"J Incl Phenom Macrocyclic Chem"},{"key":"ref23","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1023\/A:1008196029391","article-title":"Molecular modeling studies of the beta-cyclodextrin in monomer and dimer form as hosts for the complexation of cholesterol.","volume":"39","author":"YH Choi","year":"2001","journal-title":"J Incl Phenom Macrocyclic Chem"},{"key":"ref24","doi-asserted-by":"crossref","first-page":"6372","DOI":"10.1021\/jp056751a","article-title":"Molecular dynamics study of the inclusion of cholesterol into cyclodextrins.","volume":"110","author":"Y Yu","year":"2006","journal-title":"J Phys Chem B"},{"key":"ref25","doi-asserted-by":"crossref","first-page":"12625","DOI":"10.1021\/jp076576t","article-title":"Cyclodextrinbased self-assembled nanotubes at the water\/air interface.","volume":"111","author":"J Hern\u00e1ndez-Pascacio","year":"2007","journal-title":"J Phys Chem B"},{"key":"ref26","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1007\/s10847-006-9165-3","article-title":"Molecular dynamics simulations and quantum chemical calculations on beta-cyclodextrin spironolactone complex.","volume":"57","author":"P Weinzinger","year":"2007","journal-title":"J Incl Phenom Macrocyclic Chem"},{"key":"ref27","doi-asserted-by":"crossref","first-page":"4383","DOI":"10.1021\/jp0688815","article-title":"On the characterization of host-guest complexes: surface tension, calorimetry, and molecular dynamics of cyclodextrins with a non-ionic surfactant.","volume":"111","author":"A Pi\u00f1eiro","year":"2007","journal-title":"J Phys Chem B"},{"key":"ref28","doi-asserted-by":"crossref","first-page":"1109","DOI":"10.1529\/biophysj.105.061846","article-title":"Interactions of cholesterol with lipid membranes and cyclodextrin characterized by calorimetry.","volume":"89","author":"A Tsamaloukas","year":"2005","journal-title":"Biophys J"},{"key":"ref29","doi-asserted-by":"crossref","first-page":"355","DOI":"10.1016\/S0939-6411(98)00033-2","article-title":"Characterization of an inclusion complex of cholesterol and hydroxypropyl-beta-cyclodextrin.","volume":"46","author":"RO Williams","year":"1998","journal-title":"Eur J Pharm Biopharm"},{"key":"ref30","doi-asserted-by":"crossref","first-page":"391","DOI":"10.1016\/j.jcis.2008.09.002","article-title":"A small molecular size system giving unexpected surface effects: alpha-cyclodextrin+sodium dodecyl sulfate in water.","volume":"328","author":"J Hern\u00e1ndez-Pascacio","year":"2008","journal-title":"J Colloid Interface Sci"},{"key":"ref31","doi-asserted-by":"crossref","first-page":"495","DOI":"10.1016\/j.micron.2007.06.017","article-title":"Cyclodextrin-based aggregates and characterization by microscopy.","volume":"39","author":"Y He","year":"2008","journal-title":"Micron"},{"key":"ref32","doi-asserted-by":"crossref","first-page":"8602","DOI":"10.1021\/jo026166v","article-title":"Structure and thermodynamics of alpha-, beta-, and gamma-cyclodextrin dimers. molecular dynamics studies of the solvent effect and free binding energies.","volume":"67","author":"P Bonnet","year":"2002","journal-title":"J Org Chem"},{"key":"ref33","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1023\/A:1015861719134","article-title":"The effect of parenterally administered cyclodextrins on cholesterol levels in the rat.","volume":"8","author":"HW Frijlink","year":"1991","journal-title":"Pharm Res"},{"key":"ref34","doi-asserted-by":"crossref","first-page":"8495","DOI":"10.1021\/ja961567b","article-title":"Cholesterol recognition and binding by cyclodextrin dimers.","volume":"118","author":"R Breslow","year":"1996","journal-title":"J Am Chem Soc"},{"key":"ref35","doi-asserted-by":"crossref","first-page":"1253","DOI":"10.1248\/cpb.51.1253","article-title":"Interactions of cholesterol with cyclodextrins in aqueous solution.","volume":"51","author":"J Nishijo","year":"2003","journal-title":"Chem Pharm Bull (Tokyo)"},{"key":"ref36","doi-asserted-by":"crossref","first-page":"12714","DOI":"10.1021\/ja903529f","article-title":"Molecular view of cholesterol ip-op and chemical potential in different membrane environments.","volume":"131","author":"WF Bennett","year":"2009","journal-title":"J Am Chem Soc"},{"key":"ref37","first-page":"83","article-title":"Soluble carbohydrates (trehalose in particular) and cryoprotection in polar biota.","volume":"21","author":"PO Montiel","year":"2000","journal-title":"Cryo Letters"},{"key":"ref38","doi-asserted-by":"crossref","first-page":"435","DOI":"10.1021\/ct700301q","article-title":"Gromacs 4: Algorithms for highly efficient, load-balanced, and scalable molecular simulation.","volume":"4","author":"B Hess","year":"2008","journal-title":"J Chem Theory Comput"},{"key":"ref39","doi-asserted-by":"crossref","first-page":"1400","DOI":"10.1002\/jcc.20275","article-title":"A new gromos force field for hexopyranose-based carbohydrates.","volume":"26","author":"RD Lins","year":"2005","journal-title":"J Comput Chem"},{"key":"ref40","doi-asserted-by":"crossref","first-page":"156","DOI":"10.1016\/S0005-2736(01)00270-X","article-title":"Molecular dynamics simulations of stratum corneum lipid models: fatty acids and cholesterol.","volume":"1511","author":"M H\u00f6ltje","year":"2001","journal-title":"Biochim Biophys Acta"},{"key":"ref41","first-page":"331","article-title":"Interaction models for water in relation to protein hydration.","author":"HJC Berendsen","year":"1981"},{"key":"ref42","doi-asserted-by":"crossref","first-page":"1463","DOI":"10.1002\/(SICI)1096-987X(199709)18:12<1463::AID-JCC4>3.0.CO;2-H","article-title":"Lincs: A linear constraint solver for molecular simulations.","volume":"18","author":"B Hess","year":"1997","journal-title":"J Comput Chem"},{"key":"ref43","doi-asserted-by":"crossref","first-page":"992","DOI":"10.1002\/anie.199009921","article-title":"Computer simulation of molecular dynamics: Methodology, applications, and perspectives in chemistry.","volume":"29","author":"WF van Gunsteren","year":"1990","journal-title":"Angew Chem Int Ed"},{"key":"ref44","doi-asserted-by":"crossref","first-page":"5451","DOI":"10.1063\/1.469273","article-title":"A generalized reaction field method for molecular dynamics simulations.","volume":"102","author":"I Tironi","year":"1995","journal-title":"J Chem Phys"},{"key":"ref45","doi-asserted-by":"crossref","first-page":"3684","DOI":"10.1063\/1.448118","article-title":"Molecular dynamics with coupling to an external bath.","volume":"81","author":"HJC Berendsen","year":"1984","journal-title":"J Chem Phys"},{"key":"ref46","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1016\/0021-9991(77)90121-8","article-title":"Nonphysical sampling distributions in monte carlo free-energy estimation: Umbrella sampling.","volume":"23","author":"G Torrie","year":"1977","journal-title":"J Comput Phys"},{"key":"ref47","doi-asserted-by":"crossref","first-page":"1011","DOI":"10.1002\/jcc.540130812","article-title":"The weighted histogram analysis method for free-energy calculations on biomolecules. i. the method.","volume":"13","author":"S Kumar","year":"1992","journal-title":"J Comput Chem"},{"key":"ref48","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/S0006-3495(82)84455-X","article-title":"Role of diffusion in ligand binding to macromolecules and cell-bound receptors.","volume":"40","author":"D Shoup","year":"1982","journal-title":"Biophys J"}],"container-title":["PLoS Computational Biology"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/dx.plos.org\/10.1371\/journal.pcbi.1002020","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2020,5,8]],"date-time":"2020-05-08T18:49:01Z","timestamp":1588963741000},"score":1,"resource":{"primary":{"URL":"https:\/\/dx.plos.org\/10.1371\/journal.pcbi.1002020"}},"subtitle":[],"editor":[{"given":"Max","family":"Berkowitz","sequence":"first","affiliation":[]}],"short-title":[],"issued":{"date-parts":[[2011,3,24]]},"references-count":48,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2011,3,24]]}},"URL":"https:\/\/doi.org\/10.1371\/journal.pcbi.1002020","relation":{},"ISSN":["1553-7358"],"issn-type":[{"value":"1553-7358","type":"electronic"}],"subject":[],"published":{"date-parts":[[2011,3,24]]}}}