Molecular insights on the cyclic peptide nanotube-mediated transportation of antitumor drug 5-fluorouracil

Molecular Pharmaceutics

Volumn 7, Issue 6, 2010, Pages 1985-1994

  Liu, Huifang ^a   Chen, Jian ^a   Shen, Qing ^a   Fu, Wei ^a   Wu, Wei ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CYCLOPEPTIDE; DIMYRISTOYLPHOSPHATIDYLCHOLINE; FLUOROURACIL; GLUTAMINE; GRAMICIDIN A; LEUCINE; NANOTUBE; TRYPTOPHAN;

ARTICLE; DIFFUSION COEFFICIENT; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG TRANSPORT; ENERGY; HYDROPHOBICITY; LIPID BILAYER; LIPOSOMAL DELIVERY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PRIORITY JOURNAL;

ANTINEOPLASTIC AGENTS; FLUOROURACIL; LIPOSOMES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR DYNAMICS SIMULATION; NANOTUBES; PEPTIDES, CYCLIC;

EID: 78649915651     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp100274f     Document Type: Article

References (37)

1. Adson, A.; Burton, P. S.; Raub, T. J.; Barsuhn, C. L.; Audus, K. L.; Ho, N. F. Passive diffusion of weak organic electrolytes across Caco-2 cell monolayers: uncoupling the contributions of hydrodynamic, transcellular, and paracellular barriers J. Pharm. Sci. 1995, 84 (10) 1197-1204
2. Ghadiri, M. R. Self-assembled nanoscale tubular ensembles Adv. Mater. 1995, 7 (7) 675-677
3. Buriak, J. M.; Ghadiri, M. R. Self-assembly of peptide based nanotubes Mater. Sci. Eng.: C 1997, 4 (4) 207-212
4. Karlstrom, A.; Unden, A. Association of cyclic peptides in aqueous solution measured by fluorescence quenching Biopolymers 1997, 41 (1) 1-4
5. Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. Self-assembling peptide nanotubes J. Am. Chem. Soc. 1996, 118 (1) 43-50
6. Ghadiri, M. R.; Granja, J. R.; Buehler, L. K. Artificial Transmembrane Ion Channels from Self-Assembling Peptide Nanotubes Nature 1994, 369 (6478) 301-304
7. Desantis, P.; Morosett, S.; Rizzo, R. Conformational-Analysis of Regular Enantiomeric Sequences Macromolecules 1974, 7 (1) 52-58
8. + permeation across the gramicidin a channel J. Phys. Chem. B 2006, 110 (25) 12789-12795
9. n] (n = 3-6) J. Phys. Chem. B 2002, 106 (7) 1570-1575
10. m =1-4] J. Phys. Chem. B 1997, 101 (49) 10576-10583
11. Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.; Khazanovich, N. Self-Assembling Organic Nanotubes Based on a Cyclic Peptide Architecture Nature 1993, 366 (6453) 324-327
12. Polaskova, M. E.; Ede, N. J.; Lambert, J. N. Synthesis of nanotubule-forming cyclic octapeptides via an Fmoc strategy Aust. J. Chem. 1998, 51 (7) 535-540
13. Kim, H. S.; Hartgerink, J. D.; Ghadiri, M. R. Oriented self-assembly of cyclic peptide nanotubes in lipid membranes J. Am. Chem. Soc. 1998, 120 (18) 4417-4424
14. Sanchez-Quesada, J.; Ghadiri, M. R.; Bayley, H.; Braha, O. Cyclic peptides as molecular adapters for a pore-forming protein J. Am. Chem. Soc. 2000, 122 (48) 11757-11766
15. Ashkenasy, G.; Ghadiri, M. R. Boolean logic functions of a synthetic peptide network J. Am. Chem. Soc. 2004, 126 (36) 11140-11141
16. Granja, J. R.; Ghadiri, M. R. Channel-Mediated Transport of Glucose across Lipid Bilayers J. Am. Chem. Soc. 1994, 116 (23) 10785-10786
17. Engels, M.; Bashford, D.; Ghadiri, M. R. Structure and Dynamics of Self-Assembling Peptide Nanotubes and the Channel-Mediated Water Organization and Self-Diffusion-A Molecular-Dynamics Study J. Am. Chem. Soc. 1995, 117 (36) 9151-9158
18. Asthagiri, D.; Pratt, L. R.; Ashbaugh, H. S. Absolute hydration free energies of ions, ion-water clusters, and quasichemical theory J. Chem. Phys. 2003, 119 (5) 2702-2708
19. Tarek, M.; Maigret, B.; Chipot, C. Molecular dynamics investigation of an oriented cyclic peptide nanotube in DMPC bilayers Biophys. J. 2003, 85 (4) 2287-2298
20. + ion in a cyclic peptide nanotube J. Phys. Chem. B 2006, 110 (51) 26448-26460
21. Chen, J.; Zhang, B.; Xie, C.; Lu, Y.; Wu, W. Synthesis of a highly hydrophobic cyclic decapeptide by solid-phase synthesis of linear peptide and cyclization in solution Chin. Chem. Lett. 2010, 21 (4) 391-394
22. Zhu, J. C.; Cheng, J.; Liao, Z. X.; Lai, Z. H.; Liu, B. Investigation of structures and properties of cyclic peptide nanotubes by experiment and molecular dynamics J. Comput.-Aided Mol. Des. 2008, 22 (11) 773-781
23. Fu, W.; Shen, J. H.; Luo, X. M.; Zhu, W. L.; Cheng, J. G.; Yu, K. Q.; Briggs, J. M.; Jin, G. Z.; Chen, K. X.; Jiang, H. L. Dopamine D1 receptor agonist and D2 receptor antagonist effects of the natural product (-)-stepholidine: Molecular Modeling and dynamics Simulations Biophys. J. 2007, 93 (5) 1431-1441
24. Vandrunen, R.; Vanderspoel, D.; Berendsen, H. J. C. GROMACS-a software package and parallel computer for molecular dynamics. In Abstracts of Papers, 209th National Meeting of the American Chemical Society; American Chemical Society: Washington, DC; 1995; p 49-COMP.
25. Daura, X.; Mark, A. E.; van Gunsteren, W. F. Parametrization of aliphatic CHn united atoms of GROMOS96 force field J. Comput. Chem. 1998, 19 (5) 535-547
26. Berendsen, H. J. C.; Postma, J. P. M.; Vangunsteren, W. F.; Dinola, A.; Haak, J. R. Molecular dynamics with coupling to an external bath J. Chem. Phys. 1984, 81 (8) 3684-3690
27. Hess, B.; Bekker, H.; Berendsen, H. J. C.; Fraaije, J. LINCS: A linear constraint solver for molecular simulations J. Comput. Chem. 1997, 18 (12) 1463-1472
28. Darden, T.; York, D.; Pedersen, L. Particle Mesh Ewald-an N.Log(N) Method for Ewald Sums in Large Systems J. Chem. Phys. 1993, 98 (12) 10089-10092
29. Schuettelkopf, A. W.; van Aalten, D. M. F. PRODRG-a tool for high-throughput crystallography of protein-ligand complexes Acta Crystallogr. 2004, D60, 1355-1363
30. Bode, B. M.; Gordon, M. S. MacMolPlt: A graphical user interface for GAMESS J. Mol. Graphics Modell. 1998, 16 (3) 133
31. Jingchuan, Z.; Jie, C.; Zhouxiong, L.; Zhonghong, L.; Bo, L. Investigation of structures and properties of cyclic peptide nanotubes by experiment and molecular dynamics J. Comput.-Aided Mol. Des. 2008, 22, 773-781
32. Jillian, M.; Buriak, M.; Reza, G. Self-assembly of peptide based nanotubes Mater. Sci. Eng.: C 1997, 4, 207-212
33. Stout, D. G.; Steponkus, P. L.; Bustard, L. D.; Cotts, R. M. Water permeability of Chlorella cell membranes by nuclear magnetic resonance: Measured diffusion coefficients and relaxation times Plant Physiol. 1978, 62 (1) 146-151
34. Woolf, T. B.; Roux, B. Molecular dynamics simulation of the Gramicidin channel in a phospholipid bilayer Proc. Natl. Acad. Sci. U.S.A. 1994, 91 (24) 11631-11635
35. Roux, B. Computational studies of the gramicidin channel Acc. Chem. Res. 2002, 35 (6) 366-375
36. Roux, B.; Prodhom, B.; Karplus, M. Ion transport in the gramicidin channel-molecular dynamics study of single and double occupancy Biophys. J. 1995, 68 (3) 876-892
37. Asthagiri, D.; Bashford, D. Continuum and atomistic modeling of ion partitioning into a peptide nanotube Biophys. J. 2002, 82 (3) 1176-1189