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Volumn 3, Issue 5, 2006, Pages 589-600

Molecular dynamics simulations and experimental studies of binding and mobility of 7-tert-butyldimethylsilyl-10-hydroxycamptothecin and its 20(S)-4-aminobutyrate ester in DMPC membranes

Author keywords

Anticancer drugs; Camptothecins; DB 67; DMPC; Fluorescence; Lactone hydrolysis; Lipid bilayers; Liposomes; Membrane binding; Molecular dynamics simulation; Prodrugs

Indexed keywords

4 AMINOBUTYRATE ESTER; 7 TERT BUTYLDIMETHYLSILYL 10 HYDROXYCAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; DNA TOPOISOMERASE INHIBITOR; ESTER DERIVATIVE; LACTONE; LIPID; LIPOSOME; PHOSPHATE; SOLVENT; SURFACE WATER; UNCLASSIFIED DRUG;

EID: 33750401902     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp0600081     Document Type: Article
Times cited : (13)

References (40)
  • 1
    • 0027096415 scopus 로고
    • A kinetic and mechanistic study of the hydrolysis of camptothecin and some analogues
    • Fassberg, J.; Stella, V. J. A kinetic and mechanistic study of the hydrolysis of camptothecin and some analogues. J. Pharm. Sci. 1992, 81 (7), 676-684.
    • (1992) J. Pharm. Sci. , vol.81 , Issue.7 , pp. 676-684
    • Fassberg, J.1    Stella, V.J.2
  • 2
    • 0027276081 scopus 로고
    • Lipid bilayer partitioning and stability of camptothecin drugs
    • Burke, T. G.; Mishra, A. K.; Wani, M. C.; Wall, M. E. Lipid bilayer partitioning and stability of camptothecin drugs. Biochemistry 1993, 32 (20), 5352-5364.
    • (1993) Biochemistry , vol.32 , Issue.20 , pp. 5352-5364
    • Burke, T.G.1    Mishra, A.K.2    Wani, M.C.3    Wall, M.E.4
  • 3
    • 0028012774 scopus 로고
    • The structural basis of camptothecin interactions with human serum albumin: Impact on drug stability
    • Burke, T. G.; Mi, Z. The structural basis of camptothecin interactions with human serum albumin: impact on drug stability. J. Med. Chem. 1994, 37 (1), 40-46.
    • (1994) J. Med. Chem. , vol.37 , Issue.1 , pp. 40-46
    • Burke, T.G.1    Mi, Z.2
  • 5
    • 0035816198 scopus 로고    scopus 로고
    • The highly lipophilic DNA topoisomerase I inhibitor DB-67 displays elevated lactone levels in human blood and potent anticancer activity
    • Bom, D.; Curran, D. P.; Zhang, J.; Zimmer, S. G.; Bevins, R.; Kruszewski, S.; Howe, J. N.; Bingcang, A.; Latus, L. J.; Burke, T. G. The highly lipophilic DNA topoisomerase I inhibitor DB-67 displays elevated lactone levels in human blood and potent anticancer activity. J Controlled Release 2001, 74 (1-3), 325-333.
    • (2001) J Controlled Release , vol.74 , Issue.1-3 , pp. 325-333
    • Bom, D.1    Curran, D.P.2    Zhang, J.3    Zimmer, S.G.4    Bevins, R.5    Kruszewski, S.6    Howe, J.N.7    Bingcang, A.8    Latus, L.J.9    Burke, T.G.10
  • 6
    • 0036689443 scopus 로고    scopus 로고
    • Stable supersaturated aqueous solutions of silatecan 7-t- butyldimethylsilyl-10-hydroxycamptothecin via chemical conversion in the presence of a chemical modified b-cyclodextrin
    • Xiang, T. X.; Anderson, B. D. Stable supersaturated aqueous solutions of silatecan 7-t-butyldimethylsilyl-10-hydroxycamptothecin via chemical conversion in the presence of a chemical modified b-cyclodextrin. Pharm. Res. 2002, 19 (8), 1215-1222.
    • (2002) Pharm. Res. , vol.19 , Issue.8 , pp. 1215-1222
    • Xiang, T.X.1    Anderson, B.D.2
  • 8
    • 0034213232 scopus 로고    scopus 로고
    • Liposomal delivery of camptothecins
    • Emerson, D. L. Liposomal delivery of camptothecins. Pharm. Sci. Technol. Today 2000, 3 (6), 205-209.
    • (2000) Pharm. Sci. Technol. Today , vol.3 , Issue.6 , pp. 205-209
    • Emerson, D.L.1
  • 9
    • 5144225469 scopus 로고    scopus 로고
    • Liposomal irinotecan: Formulation development and therapeutic assessment in murine xenograft models of colorectal cancer
    • Messerer, C. L.; Ramsay, E. C.; Waterhouse, D.; Ng, R.; Simms, E.-M.; Harasym, N.; Tardi, P.; Mayer, L. D.; Bally, M. B. Liposomal irinotecan: formulation development and therapeutic assessment in murine xenograft models of colorectal cancer. Clin. Cancer Res. 2004, 10 (19), 6638-6649.
    • (2004) Clin. Cancer Res. , vol.10 , Issue.19 , pp. 6638-6649
    • Messerer, C.L.1    Ramsay, E.C.2    Waterhouse, D.3    Ng, R.4    Simms, E.-M.5    Harasym, N.6    Tardi, P.7    Mayer, L.D.8    Bally, M.B.9
  • 10
    • 0034234238 scopus 로고    scopus 로고
    • Liposomal encapsulation of topotecan enhances anticancer efficacy in murine and human xenograft models
    • Tardi, P.; Choice, E.; Masin, D.; Redelmeier, T.; Bally, M.; Madden, T. D. Liposomal encapsulation of topotecan enhances anticancer efficacy in murine and human xenograft models. Cancer Res. 2000, 60 (13), 3389-3393.
    • (2000) Cancer Res. , vol.60 , Issue.13 , pp. 3389-3393
    • Tardi, P.1    Choice, E.2    Masin, D.3    Redelmeier, T.4    Bally, M.5    Madden, T.D.6
  • 11
    • 0037014697 scopus 로고    scopus 로고
    • A versatile prodrug approach for liposomal core-loading of water-insoluble camptothecin anticancer drugs
    • Liu, X.; Lynn, B. C.; Zhang, J.; Song, L.; Bom, D.; Du, W.; Curran, D. P.; Burke, T. G. A versatile prodrug approach for liposomal core-loading of water-insoluble camptothecin anticancer drugs. J. Am. Chem. Soc. 2002, 124 (26), 7650-7651.
    • (2002) J. Am. Chem. Soc. , vol.124 , Issue.26 , pp. 7650-7651
    • Liu, X.1    Lynn, B.C.2    Zhang, J.3    Song, L.4    Bom, D.5    Du, W.6    Curran, D.P.7    Burke, T.G.8
  • 12
    • 4344600433 scopus 로고    scopus 로고
    • Degradation of camptothecin-20(S)-glycinate ester prodrug under physiological conditions
    • Liu, X.; Zhang, J.; Song, L.; Lynn, B. C.; Burke, T. G. Degradation of camptothecin-20(S)-glycinate ester prodrug under physiological conditions. J. Pharm. Biomed. Anal. 2004, 35 (5), 1113-1125.
    • (2004) J. Pharm. Biomed. Anal. , vol.35 , Issue.5 , pp. 1113-1125
    • Liu, X.1    Zhang, J.2    Song, L.3    Lynn, B.C.4    Burke, T.G.5
  • 13
    • 0032738066 scopus 로고    scopus 로고
    • Simulation studies of the interaction of antimicrobial peptides and lipid bilayers
    • La Rocca, P.; Biggin, P. C.; Tieleman, D. P.; Sansom, M. S. P. Simulation studies of the interaction of antimicrobial peptides and lipid bilayers. Biochim. Biophys. Acta 1999, 1462, 185-200.
    • (1999) Biochim. Biophys. Acta , vol.1462 , pp. 185-200
    • La Rocca, P.1    Biggin, P.C.2    Tieleman, D.P.3    Sansom, M.S.P.4
  • 14
    • 0033758069 scopus 로고    scopus 로고
    • Molecular dynamics simulations of lipid bilayers
    • Feller, S. E. Molecular dynamics simulations of lipid bilayers. Curr. Opin. Colloid Interface Sci. 2000, 5, 217-223.
    • (2000) Curr. Opin. Colloid Interface Sci. , vol.5 , pp. 217-223
    • Feller, S.E.1
  • 17
    • 3042524904 scopus 로고
    • A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: The RESP model
    • Bayly, C. I.; Cieplak, P.; Cornell, W. D.; 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.
    • (1993) J. Phys. Chem. , vol.97 , pp. 10269-10280
    • Bayly, C.I.1    Cieplak, P.2    Cornell, W.D.3    Kollman, P.A.4
  • 18
    • 0029099308 scopus 로고
    • Incorporation of surface tension into molecular dynamics simulation of an interface: A fluid phase lipid bilayer membrane
    • Chiu, S.-W.; Clark, M.; Balaji, V.; Subramaniam, S.; Scott, H. L.; Jakobsson, E. Incorporation of surface tension into molecular dynamics simulation of an interface: A fluid phase lipid bilayer membrane. Biophys. J. 1995, 69, 1230-1245.
    • (1995) Biophys. J. , vol.69 , pp. 1230-1245
    • Chiu, S.-W.1    Clark, M.2    Balaji, V.3    Subramaniam, S.4    Scott, H.L.5    Jakobsson, E.6
  • 19
    • 20544433165 scopus 로고
    • Van der Waals volumes and radii
    • Bondi, A. van der Waals volumes and radii. J. Phys. Chem. 1964, 68 (3), 441-451.
    • (1964) J. Phys. Chem. , vol.68 , Issue.3 , pp. 441-451
    • Bondi, A.1
  • 20
    • 0842346274 scopus 로고    scopus 로고
    • Quantum chemical study of the Si-C bond photodissociation in benzylsilane derivatives: A specific excited-state' silicon effect
    • Budyka, M. F.; Zyubina, T. S.; Zarkadis, A. K. Quantum chemical study of the Si-C bond photodissociation in benzylsilane derivatives: a specific excited-state' silicon effect. Theochem 2004, 668 (1), 1-11.
    • (2004) Theochem , vol.668 , Issue.1 , pp. 1-11
    • Budyka, M.F.1    Zyubina, T.S.2    Zarkadis, A.K.3
  • 21
    • 0001398008 scopus 로고    scopus 로고
    • How well does a restrained electrostatic potential (RESP) model perform in calculation conformational energies of organic and biological molecules?
    • Wang, J. M.; Cieplak, P.; Kollman, P. A. How well does a restrained electrostatic potential (RESP) model perform in calculation conformational energies of organic and biological molecules? J. Comput. Chem. 2000, 12, 1049-1074.
    • (2000) J. Comput. Chem. , vol.12 , pp. 1049-1074
    • Wang, J.M.1    Cieplak, P.2    Kollman, P.A.3
  • 23
    • 33750425158 scopus 로고    scopus 로고
    • Preparation and formulation of highly lipophilic camptothecin prodrugs for therapeutic use in the treatment of cancer and AIDS
    • WO 2002062340 A1 20020815
    • Bom, D. C.; Burke, T. G. Preparation and formulation of highly lipophilic camptothecin prodrugs for therapeutic use in the treatment of cancer and AIDS. WO 2002062340 A1 20020815. 2002.
    • (2002)
    • Bom, D.C.1    Burke, T.G.2
  • 24
    • 33750388955 scopus 로고    scopus 로고
    • Engineered liposomal particles containing core-loaded prodrugs for the controlled release of camptothecins
    • WO 2003043584 A2 20030530
    • Burke, T. G.; Bom, D. C. Engineered liposomal particles containing core-loaded prodrugs for the controlled release of camptothecins. WO 2003043584 A2 20030530, 2003.
    • (2003)
    • Burke, T.G.1    Bom, D.C.2
  • 26
    • 0016168286 scopus 로고
    • Interpretation of nonelectrolyte partition coefficients between dimyristoyl lecithin and water
    • Diamond, J. M.; Katz, Y. Interpretation of nonelectrolyte partition coefficients between dimyristoyl lecithin and water. J. Membr. Biol. 1974, 17, 121-154.
    • (1974) J. Membr. Biol. , vol.17 , pp. 121-154
    • Diamond, J.M.1    Katz, Y.2
  • 27
    • 0032474434 scopus 로고    scopus 로고
    • Location of diphenylhexatriene (DPH) and its derivatives within membranes: Comparison of different fluorescence quenching analyses and membrane depth
    • Kaiser, R. D.; London, E. Location of diphenylhexatriene (DPH) and its derivatives within membranes: comparison of different fluorescence quenching analyses and membrane depth. Biochemistry 1998, 37, 8180-8190.
    • (1998) Biochemistry , vol.37 , pp. 8180-8190
    • Kaiser, R.D.1    London, E.2
  • 28
    • 0026787997 scopus 로고
    • Polarity of lipid bilayers. A fluorescence investigation
    • Perochon, E.; Lopez, A.; Tocanne, J. F. Polarity of lipid bilayers. A fluorescence investigation. Biochemistry 1992, 31, 7672-7682.
    • (1992) Biochemistry , vol.31 , pp. 7672-7682
    • Perochon, E.1    Lopez, A.2    Tocanne, J.F.3
  • 29
    • 2942650543 scopus 로고    scopus 로고
    • Distribution of ethanol in a model membrane: A computer simulation study
    • Chanda, J.; Bandyopadhyay, S. Distribution of ethanol in a model membrane: a computer simulation study. Chem. Phys. Lett. 2004, 392 (1-3), 249-254.
    • (2004) Chem. Phys. Lett. , vol.392 , Issue.1-3 , pp. 249-254
    • Chanda, J.1    Bandyopadhyay, S.2
  • 31
    • 22144486884 scopus 로고    scopus 로고
    • Structure of fully hydrated fluid phase DMPC and DLPC lipid bilayers using X-ray scattering from oriented multilamellar arrays and from unilamellar vesicles
    • Kucerka, N.; Liu, Y.; Chu, N.; Petrache, H. I.; Tristram-Nagle, S.; Nagle, J. F. Structure of fully hydrated fluid phase DMPC and DLPC lipid bilayers using X-ray scattering from oriented multilamellar arrays and from unilamellar vesicles. Biophys. J. 2005, 88 (4), 2626-2637.
    • (2005) Biophys. J. , vol.88 , Issue.4 , pp. 2626-2637
    • Kucerka, N.1    Liu, Y.2    Chu, N.3    Petrache, H.I.4    Tristram-Nagle, S.5    Nagle, J.F.6
  • 32
    • 0018786933 scopus 로고
    • Temperature and compositional dependence of the structure of hydrated dimyristoyl lecithin
    • Janiak, M. J.; Small, D. M.; Shipley, G. G. Temperature and compositional dependence of the structure of hydrated dimyristoyl lecithin. J. Biol. Chem. 1979, 254 (13), 6068-6078.
    • (1979) J. Biol. Chem. , vol.254 , Issue.13 , pp. 6068-6078
    • Janiak, M.J.1    Small, D.M.2    Shipley, G.G.3
  • 33
    • 0026343796 scopus 로고
    • Iodide penetration into lipid bilayers as a probe of membrane lipid organization
    • Langner, M.; Hui, S. W. Iodide penetration into lipid bilayers as a probe of membrane lipid organization. Chem. Phys. Lipids 1991, 60, 127-132.
    • (1991) Chem. Phys. Lipids , vol.60 , pp. 127-132
    • Langner, M.1    Hui, S.W.2
  • 34
    • 2342505916 scopus 로고    scopus 로고
    • Permeation of small molecules through a lipid bilayer: A computer simulation
    • Bemporad, D.; Essex, J. W.; Luttmann, C. Permeation of small molecules through a lipid bilayer: A computer simulation. J. Phys. Chem. 2004, 108, 4875-4884.
    • (2004) J. Phys. Chem. , vol.108 , pp. 4875-4884
    • Bemporad, D.1    Essex, J.W.2    Luttmann, C.3
  • 35
    • 0019886580 scopus 로고
    • Values for and significance of order parameters and "cone angles" of fluorophore rotation in lipid bilayers
    • Engel, L. W.; Prendergast, F. G. Values for and significance of order parameters and "cone angles" of fluorophore rotation in lipid bilayers. Biochemistry 1981, 20, 7338-7345.
    • (1981) Biochemistry , vol.20 , pp. 7338-7345
    • Engel, L.W.1    Prendergast, F.G.2
  • 36
    • 33750394416 scopus 로고    scopus 로고
    • Photophysical properties of camptothecin: Excited-state tautomerization in aqueous solution
    • New Orleans, LA, March 24-28; American Chemical Society: Washington, DC; ANYL-062
    • Dey, J.; Warner, I. M., Photophysical properties of camptothecin: Excited-state tautomerization in aqueous solution. In Book of Abstracts, 211th National Meeting of the American Chemical Society, New Orleans, LA, March 24-28; American Chemical Society: Washington, DC, 1996; ANYL-062.
    • (1996) Book of Abstracts, 211th National Meeting of the American Chemical Society
    • Dey, J.1    Warner, I.M.2
  • 37
    • 0023051112 scopus 로고
    • Steady-state fluorescence polarization data in membranes. Resolution into physical parameters by an extended Perrin equation for restricted rotation of fluorophores
    • van der Meer, B. W.; van Hoeven, R. P.; van Bliterswijk, W. J. Steady-state fluorescence polarization data in membranes. Resolution into physical parameters by an extended Perrin equation for restricted rotation of fluorophores. Biochim. Biophys. Acta 1986, 854, 38-44.
    • (1986) Biochim. Biophys. Acta , vol.854 , pp. 38-44
    • Van Der Meer, B.W.1    Van Hoeven, R.P.2    Van Bliterswijk, W.J.3
  • 38
    • 0018706325 scopus 로고
    • Studies of the effect of chloramphenicol, ethidium bromide and camptothecin on the reproduction of Rous sarcoma virus in infected chick embryo cells
    • Leblond-Larouche, L.; Morais, R.; Zollinger, M. Studies of the effect of chloramphenicol, ethidium bromide and camptothecin on the reproduction of Rous sarcoma virus in infected chick embryo cells. J. Gen. Virol. 1979, 44 (2), 323-331.
    • (1979) J. Gen. Virol. , vol.44 , Issue.2 , pp. 323-331
    • Leblond-Larouche, L.1    Morais, R.2    Zollinger, M.3
  • 39
    • 0000043930 scopus 로고    scopus 로고
    • Solvation free energy of biomacromolecules: Parameters for a modified generalized Born model consistent with the AMBER force field
    • Jayaram, B.; Sprous, D.; Beveridge, D. L. Solvation free energy of biomacromolecules: Parameters for a modified generalized Born model consistent with the AMBER force field. J. Phys. Chem. 1998, 10, 9571-9576.
    • (1998) J. Phys. Chem. , vol.10 , pp. 9571-9576
    • Jayaram, B.1    Sprous, D.2    Beveridge, D.L.3
  • 40
    • 0026641763 scopus 로고
    • Liposomal stabilization of camptothecin's lactone ring
    • Burke, T. G.; Staubus, A. E.; Mishra, A. K. Liposomal Stabilization of Camptothecin's Lactone Ring. J. Am. Chem. Soc. 1992, 114, 8318-8319.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 8318-8319
    • Burke, T.G.1    Staubus, A.E.2    Mishra, A.K.3


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