메뉴 건너뛰기




Volumn 20, Issue 10, 2008, Pages 1127-1133

Molecular dynamics study on the conformational flexibility and energetics in aqueous solution of methylated β-cyclodextrins

Author keywords

Cyclodextrins; Molecular dynamics; Molecular modeling; Solvent effects

Indexed keywords


EID: 75249106055     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20571     Document Type: Article
Times cited : (7)

References (47)
  • 3
    • 34548134519 scopus 로고    scopus 로고
    • Cyclodextrins as pharmaceutical solubilizers
    • Brewster ME, Loftsson T. Cyclodextrins as pharmaceutical solubilizers. Adv Drug Deliv Rev 2007;59:645-666.
    • (2007) Adv Drug Deliv Rev , vol.59 , pp. 645-666
    • Brewster, M.E.1    Loftsson, T.2
  • 5
    • 84911197734 scopus 로고    scopus 로고
    • Cyclodextrins-versatile pharmaceutical excipients
    • Chowdary KPR. Cyclodextrins-versatile pharmaceutical excipients. Int J Pharm Excip 2003;70-74.
    • (2003) Int J Pharm Excip , pp. 70-74
    • Chowdary, K.P.R.1
  • 6
    • 0037406527 scopus 로고    scopus 로고
    • When can cyclodextrins be considered for solubilization purposes?
    • Rao VM, Stella VJ. When can cyclodextrins be considered for solubilization purposes? J Pharm Sci 2003;92:927-932.
    • (2003) J Pharm Sci , vol.92 , pp. 927-932
    • Rao, V.M.1    Stella, V.J.2
  • 8
    • 33746970716 scopus 로고
    • Solubilization of cyclodextrins for analytical applications
    • Pharr DY, Fu ZS, Thuy K, Hinze WL. Solubilization of cyclodextrins for analytical applications. Anal Chem 1989;61:275-279.
    • (1989) Anal Chem , vol.61 , pp. 275-279
    • Pharr, D.Y.1    Fu, Z.S.2    Thuy, K.3    Hinze, W.L.4
  • 9
    • 0001822196 scopus 로고
    • Aqueous solubility behavior of three cyclodextrins
    • Jozwiakowski MJ, Connors KA. Aqueous solubility behavior of three cyclodextrins. Carbohydr Res 1985;143:51-59.
    • (1985) Carbohydr Res , vol.143 , pp. 51-59
    • Jozwiakowski, M.J.1    Connors, K.A.2
  • 11
    • 0016607907 scopus 로고
    • Complex formation between mycobacterial polysaccharides or cyclodextrins and palmitoyl coenzyme A
    • Bergeron R, Machida M. Complex formation between mycobacterial polysaccharides or cyclodextrins and palmitoyl coenzyme A. J Biol Chem 1975;250:1223-1230.
    • (1975) J Biol Chem , vol.250 , pp. 1223-1230
    • Bergeron, R.1    Machida, M.2
  • 12
    • 0001119930 scopus 로고    scopus 로고
    • Methods for selective modifications of cyclodextrins
    • Khan AR, Forgo P, Stine KJ, D'Souza VT. Methods for selective modifications of cyclodextrins. Chem Rev 1998;98:1977-1996.
    • (1998) Chem Rev , vol.98 , pp. 1977-1996
    • Khan, A.R.1    Forgo, P.2    Stine, K.J.3    D'Souza, V.T.4
  • 13
    • 0021221123 scopus 로고
    • Dimethyl-β-Cyclodextrin
    • Nigrádi M. Dimethyl-β-Cyclodextrin. Drug Fut 1984;9:577-578.
    • (1984) Drug Fut , vol.9 , pp. 577-578
    • Nigrádi, M.1
  • 14
    • 33847376972 scopus 로고
    • Dimethyl-β-cyclodextrin as parenteral drug carrier
    • Szejtli J. Dimethyl-β-cyclodextrin as parenteral drug carrier. J Inclus Phenom 1983;1:135-150.
    • (1983) J Inclus Phenom , vol.1 , pp. 135-150
    • Szejtli, J.1
  • 15
    • 84987210310 scopus 로고
    • Highly soluble b-cyclodextrin derivatives
    • Szejtli J. Highly soluble b-cyclodextrin derivatives. Starch 1984;36:429-432.
    • (1984) Starch , vol.36 , pp. 429-432
    • Szejtli, J.1
  • 16
    • 0021955115 scopus 로고
    • Pharmaceutical applications of methylated cyclodextrins
    • Uekama K. Pharmaceutical applications of methylated cyclodextrins. Pharm Int 1985;6:61-65.
    • (1985) Pharm Int , vol.6 , pp. 61-65
    • Uekama, K.1
  • 17
    • 84911070767 scopus 로고
    • version 5.0, Schrödinger, New York: LLC
    • MacroModel, version 5.0, Schrödinger, New York: LLC; 1995.
    • (1995) MacroModel
  • 19
    • 84988053694 scopus 로고
    • An all atom force field for simulations of proteins and nucleic acids
    • Weiner SJ, Kollman PA, Nguyen DT, Case DA. An all atom force field for simulations of proteins and nucleic acids. J Comput Chem 1986;7:230-252.
    • (1986) J Comput Chem , vol.7 , pp. 230-252
    • Weiner, S.J.1    Kollman, P.A.2    Nguyen, D.T.3    Case, D.A.4
  • 21
    • 84986492477 scopus 로고
    • Atomic charges derived from semiempirical methods
    • Besler BH, Merz KM, Kollman PA. Atomic charges derived from semiempirical methods. J Comp Chem 1990;11:431-439.
    • (1990) J Comp Chem , vol.11 , pp. 431-439
    • Besler, B.H.1    Merz, K.M.2    Kollman, P.A.3
  • 22
    • 84986468608 scopus 로고
    • An approach to computing electrostatic charges for molecules
    • Singh UC, Kollman PA. An approach to computing electrostatic charges for molecules. J Comp Chem 1984;5:129-145.
    • (1984) J Comp Chem , vol.5 , pp. 129-145
    • Singh, U.C.1    Kollman, P.A.2
  • 24
    • 84911214036 scopus 로고    scopus 로고
    • University of California, California
    • Amber 7, University of California, California, 2002.
    • (2002) Amber 7
  • 25
    • 0001398008 scopus 로고    scopus 로고
    • How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules?
    • Wang J, Cieplak P, Kollman PA. How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules? J Comput Chem 2000;21:1049-1074.
    • (2000) J Comput Chem , vol.21 , pp. 1049-1074
    • Wang, J.1    Cieplak, P.2    Kollman, P.A.3
  • 26
    • 33751155339 scopus 로고
    • Molecular mechanical and molecular dynamic simulations of glycoproteins and oligosacharides. 1. GLYCAM-93 parameter development
    • Woods RJ, Dwek RA, Edge CJ, Fraser-Reid B. Molecular mechanical and molecular dynamic simulations of glycoproteins and oligosacharides. 1. GLYCAM-93 parameter development. J Phys Chem 1995;99:3832-3846.
    • (1995) J Phys Chem , vol.99 , pp. 3832-3846
    • Woods, R.J.1    Dwek, R.A.2    Edge, C.J.3    Fraser-Reid, B.4
  • 29
    • 0000408363 scopus 로고    scopus 로고
    • Approximate atomic surfaces from linear combinations of pairwise overlaps (LCPO)
    • Weiser J, Shenkin PS, Still WC. Approximate atomic surfaces from linear combinations of pairwise overlaps (LCPO). J Comput Chem 1999;20:217-230.
    • (1999) J Comput Chem , vol.20 , pp. 217-230
    • Weiser, J.1    Shenkin, P.S.2    Still, W.C.3
  • 31
    • 0032560959 scopus 로고    scopus 로고
    • Continuum solvent studies of the stability of DNA, RNA, and phosphoramidate-DNA helixes
    • Srinivasan J, Cheatham TE III, Kollman PA, Case DA. Continuum solvent studies of the stability of DNA, RNA, and phosphoramidate-DNA helixes. J Am Chem Soc 1998;120:9401-9409.
    • (1998) J Am Chem Soc , vol.120 , pp. 9401-9409
    • Srinivasan, J.1    Cheatham, T.E.2    Kollman, P.A.3    Case, D.A.4
  • 33
    • 0344778061 scopus 로고
    • Semianalytical treatment of solvation for molecular mechanics and dynamics
    • Still WC, Tempczyk A, Hawley RC, Hendrickson TJ. Semianalytical treatment of solvation for molecular mechanics and dynamics. J Am Chem Soc 1990;112:6127-6129.
    • (1990) J Am Chem Soc , vol.112 , pp. 6127-6129
    • Still, W.C.1    Tempczyk, A.2    Hawley, R.C.3    Hendrickson, T.J.4
  • 34
    • 0034602373 scopus 로고    scopus 로고
    • Free energy calculations on dimer stability of the HIV protease using molecular dynamics and a continuum solvent model
    • Wang W, Kollman PA. Free energy calculations on dimer stability of the HIV protease using molecular dynamics and a continuum solvent model. J Mol Biol 2000;303:567-582.
    • (2000) J Mol Biol , vol.303 , pp. 567-582
    • Wang, W.1    Kollman, P.A.2
  • 35
    • 0034646574 scopus 로고    scopus 로고
    • Structure and thermodynamics of RNA-protein Binding: Using molecular dynamics and free energy analyses to calculate the free energies of binding and conformational change
    • Reyes C, Kollman PA. Structure and thermodynamics of RNA-protein Binding: using molecular dynamics and free energy analyses to calculate the free energies of binding and conformational change. J Mol Biol 2000;297:1145-1158.
    • (2000) J Mol Biol , vol.297 , pp. 1145-1158
    • Reyes, C.1    Kollman, P.A.2
  • 36
    • 0034212858 scopus 로고    scopus 로고
    • PA Use of MM-PB/SA in estimating the free energies of proteins: Application to native, intermediates, and unfolded villin headpiece
    • Lee MR, Duan Y, Kollman. PA Use of MM-PB/SA in estimating the free energies of proteins: application to native, intermediates, and unfolded villin headpiece. Proteins 2000;39:309-316.
    • (2000) Proteins , vol.39 , pp. 309-316
    • Lee, M.R.1    Duan, Y.2    Kollman3
  • 37
    • 0034811498 scopus 로고    scopus 로고
    • Kollman PA Use of MM-PBSA in reproducing the binding free energies to HIV-1 RT of TIBO derivatives and predicting the binding mode to HIV-1 RT of efavirenz by docking and MM-PBSA
    • Wang J, Morin P, Wang W, Kollman PA Use of MM-PBSA in reproducing the binding free energies to HIV-1 RT of TIBO derivatives and predicting the binding mode to HIV-1 RT of efavirenz by docking and MM-PBSA J Am Chem Soc 2001;123:5221-5230.
    • (2001) J Am Chem Soc , vol.123 , pp. 5221-5230
    • Wang, J.1    Morin, P.2    Wang, W.3
  • 38
    • 0037079570 scopus 로고    scopus 로고
    • Computational alanine scanning of the 1:1 human growth hormone-receptor complex
    • Huo S, Massova I, Kollman PA. Computational alanine scanning of the 1:1 human growth hormone-receptor complex. J Comput Chem 2002;23:15-27.
    • (2002) J Comput Chem , vol.23 , pp. 15-27
    • Huo, S.1    Massova, I.2    Kollman, P.A.3
  • 39
    • 11144290661 scopus 로고    scopus 로고
    • Double self-inclusion by rotating glucopyranose units in per-O-methylated b-cyclodextrin moieties attached to a porphyrin in aqueous solution
    • Nishiyabu R Kano K. Double self-inclusion by rotating glucopyranose units in per-O-methylated b-cyclodextrin moieties attached to a porphyrin in aqueous solution. Eur J Org Chem 2004; (24): 4985-4988.
    • (2004) Eur J Org Chem , Issue.24 , pp. 4985-4988
    • Kano, N.R.K.1
  • 40
    • 0034056857 scopus 로고    scopus 로고
    • Solid state and solution conformation of 6-{4-[N-tert-butoxycarbonyl-N-(N'-ethyl) propanamide]imidazolyl}-6-deoxycyclomaltoheptaose: Evidence of self-inclusion of the Boc group within the b-cyclodextrin cavity
    • Impellizzeri G, Pappelardo G, Dalessandro F, Rizzarelli E, Saviano M, Iacovino R, Benedetti E, Pedone C. Solid state and solution conformation of 6-{4-[N-tert-butoxycarbonyl-N-(N'-ethyl) propanamide]imidazolyl}-6-deoxycyclomaltoheptaose: evidence of self-inclusion of the Boc group within the b-cyclodextrin cavity. Eur J Org Chem 2000; (6): 1065-1076.
    • (2000) Eur J Org Chem , Issue.6 , pp. 1065-1076
    • Impellizzeri, G.1    Pappelardo, G.2    Dalessandro, F.3    Rizzarelli, E.4    Saviano, M.5    Iacovino, R.6    Benedetti, E.7    Pedone, C.8
  • 41
    • 0042762327 scopus 로고    scopus 로고
    • "Molecular magic". Formation of a self-inclusion complex from a dumbbell-shaped permethylated b-cyclodextrin derivative
    • Yamada T, Fukuhara G, Kaneda T. "Molecular magic". Formation of a self-inclusion complex from a dumbbell-shaped permethylated b-cyclodextrin derivative. Chem Lett 2003;32:534-535.
    • (2003) Chem Lett , vol.32 , pp. 534-535
    • Yamada, T.1    Fukuhara, G.2    Kaneda, T.3
  • 42
    • 0029739265 scopus 로고    scopus 로고
    • Investigation of the conformational behaviour of permethylated cyclodextrins by molecular modelling
    • Reinhardt R, Richter M, Mager P. Investigation of the conformational behaviour of permethylated cyclodextrins by molecular modelling. Carbohydr Res 1996;291:1-9.
    • (1996) Carbohydr Res , vol.291 , pp. 1-9
    • Reinhardt, R.1    Richter, M.2    Mager, P.3
  • 43
    • 84911044190 scopus 로고    scopus 로고
    • Ciclodextrines gegants, ciclodextrines modificades amb grups ancorats: Dimers i efecte en sistemes d'interes biologic
    • Doctoral Thesis. Bellaterra: Universitat Autonoma de Barcelona
    • Maestre I. Ciclodextrines gegants, ciclodextrines modificades amb grups ancorats: dimers i efecte en sistemes d'interes biologic. Estudis computacionals. Doctoral Thesis. Bellaterra: Universitat Autonoma de Barcelona; 2004.
    • (2004) Estudis Computacionals
    • Maestre, I.1
  • 44
    • 33751246763 scopus 로고    scopus 로고
    • Structural dynamics of some large-ring cyclodextrins. A molecular dynamics study: An analysis of force field performance
    • Maestre I, Bea I, Ivanov P, Jaime C. Structural dynamics of some large-ring cyclodextrins. A molecular dynamics study: an analysis of force field performance. Theor Chem Acc 2007;117:85-97.
    • (2007) Theor Chem Acc , vol.117 , pp. 85-97
    • Maestre, I.1    Bea, I.2    Ivanov, P.3    Jaime, C.4
  • 45
    • 0000021235 scopus 로고
    • The flip-flop hydrogen bonding phenomenon. Molecular dynamics simulation of crystalline b-cyclodextrin
    • Koehler JEH, Saenger W, Van Gunsteren WF. The flip-flop hydrogen bonding phenomenon. Molecular dynamics simulation of crystalline b-cyclodextrin. Eur Biophys J 1988;16:153-168.
    • (1988) Eur Biophys J , vol.16 , pp. 153-168
    • Koehler, J.E.H.1    Saenger, W.2    Van Gunsteren, W.F.3
  • 46
    • 0024301414 scopus 로고
    • Dynamics of hydrogen-bonding disorder in b-cyclodextrin undecahydrate
    • Steiner T, Saenger W, Kearley G, Lechner RE. Dynamics of hydrogen-bonding disorder in b-cyclodextrin undecahydrate. Phys B Condens Matter 1989;156-157:336-338.
    • (1989) Phys B Condens Matter , vol.156-157 , pp. 336-338
    • Steiner, T.1    Saenger, W.2    Kearley, G.3    Lechner, R.E.4
  • 47
    • 0001630204 scopus 로고
    • Topography of cyclodextrin inclusion complexes. 27. Disordered guest and water molecules, three-center and flip-flop O-H... O hydrogen bonds in crystalline b-cyclodextrin ethanol octahydrate at T = 295K a neutron and X-ray diffraction study
    • Steiner T, Mason SA Saenger WJ. Topography of cyclodextrin inclusion complexes. 27. Disordered guest and water molecules, three-center and flip-flop O-H... O hydrogen bonds in crystalline b-cyclodextrin ethanol octahydrate at T = 295K a neutron and X-ray diffraction study. J Am Chem Soc 1991;113:5676-5687.
    • (1991) J Am Chem Soc , vol.113 , pp. 5676-5687
    • Steiner, T.1    Mason, S.A.2    Saenger, W.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.