Monomeric fullerenes in lipid membranes: Effects of molecular shape and polarity

Langmuir

Volumn 27, Issue 20, 2011, Pages 12560-12568

  Bortolus, Marco ^a   Parisio, Giulia ^a   Maniero, Anna Lisa ^a   Ferrarini, Alberta ^a  

^a UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BI-LAYER; BICELLES; DERIVATIZATIONS; DISPERSION INTERACTION; EXPERIMENTAL STUDIES; FULLERENE CAGES; FULLEROPYRROLIDINES; HYDROCARBON CHAINS; HYDROPHOBIC SOLUTES; LIPID MEMBRANES; LOW CONCENTRATIONS; MOLECULAR DYNAMICS SIMULATIONS; MOLECULAR SHAPES; NITROXIDES; PERMEABILITY MODEL; PHOSPHOLIPID MEMBRANE; PREFERENTIAL ORIENTATION; SINGLE-MOLECULE; SPHERICAL SHAPE; SPIN-LABELED LIPIDS; THEORETICAL PREDICTION;

COMPUTER SIMULATION; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROCARBONS; LIPID BILAYERS; MOLECULAR DYNAMICS; PARAMAGNETIC MATERIALS; PARAMAGNETIC RESONANCE; PARAMAGNETISM; PHOSPHOLIPIDS;

FULLERENES;

FULLERENE DERIVATIVE; MEMBRANE LIPID;

ARTICLE; BIOLOGICAL MODEL; CHEMISTRY;

FULLERENES; MEMBRANE LIPIDS; MODELS, BIOLOGICAL;

EID: 80053990322     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la202524r     Document Type: Article

References (61)

1. Jensen, A. W.; Wilson, S. R.; Schuster, D. I. Biological Applications of Fullerenes Bioorg. Med. Chem. 1996, 4, 767-779 (Pubitemid 26202375)
2. Bosi, S.; Da Ros, T.; Spalluto, G.; Prato, M. Fullerene derivatives: An attractive tool for biological application Eur. J. Med. Chem. 2003, 38, 913-923 (Pubitemid 37455402)
3. Andreev, I.; Petrukhina, A.; Garmanova, A.; Babakhin, A.; Andreev, S.; Romanova, V.; Troshin, P.; Troshina, O.; DuBuske, L. Penetration of Fullerene C60 Derivatives through Biological Membranes Fullerenes Nanotubes Carbon Nanostruct. 2008, 16, 89-102 (Pubitemid 351357221)
4. Johnston, H. J.; Hutchison, G. R.; Christensen, F. M.; Aschberger, K.; Stone, V. The biological mechanisms and physicochemical characteristics responsible for driving fullerene toxicity Toxicol. Sci. 2010, 114, 162-182
5. Ke, P. C.; Lamm, M. H. A biophysical perspective of understanding nanoparticles at large Phys. Chem. Chem. Phys. 2011, 13, 7273-7283
6. Anilkumar, P.; Lu, F.; Cao, L.; Luo, P. G.; Liu, J.-H.; Sahu, S.; Tackett, K. N., II; Wang, Y.; Sun, Y.-P. Fullerenes for Applications in Biology and Medicine Curr. Med. Chem. 2011, 18, 2045-2059
7. Colvin, V. L. The potential environmental impact of engineered nanomaterials Nat. Biotechnol. 2003, 21, 1166-1170 (Pubitemid 37203347)
8. 60 cytotoxicity is due to lipid peroxidation Biomaterials 2005, 26, 7587-7595 (Pubitemid 41187558)
9. Sayes, C. M.; Fortner, J. D.; Guo, W.; Lyon, D.; Boyd, A. M.; Ausman, K. D.; Tao, Y. J.; Sitharaman, B.; Wilson, L. J.; Hughes, J. B.; West, J. L.; Colvin, V. L. The Differential Cytotoxicity of Water-Soluble Fullerenes Nano Lett. 2004, 4, 1881-1887
10. Monticelli, L.; Salonen, E.; Ke, P. C.; Vattulainen, I. Effects of carbon nanoparticles on lipid membranes: A molecular simulation perspective Soft Matter 2009, 5, 4433-4445
11. Ke, P. C.; Qiao, R. Carbon nanomaterials in biological systems J. Phys.: Condens. Matter 2007, 19, 373101:1-25
12. 60 Langmuir 2009, 25 (9) 4875-4879
13. Gasbarri, C.; Guernelli, S.; Boncompagni, S.; Angelini, G.; Siani, G.; De Maria, P.; Fontana, A. Fine-tuning of POPC liposomal leakage by the use of β-cyclodextrin and several hydrophobic guests J. Liposome Res. 2010, 20, 202-210
14. Zhan, W.; Jiang, K.; Smith, M. D.; Bostic, H. E.; Best, M. D.; L, M.; Ruppel, J. V.; Kim, C.; Zhang, X. P. Photocurrent generation from porphyrin/fullerene complexes assembled in a tethered lipid bilayer Langmuir 2010, 26, 15671-15679
15. 60 into Artificial Lipid Membranes J. Am. Chem. Soc. 1993, 115, 3386-3387
16. 60 in biological systems. A visible-UV absorption study of solvent-dependent parameters and solute aggregation J. Phys. Chem. 1994, 98, 3492-3500
17. 60 adducts in micellar and vesicular supramolecular assemblies; introductory flash photolysis and photoredox experiments in micelles Recl. Trav. Chim. Pays-Bas 1996, 115, 72-76 (Pubitemid 126797606)
18. De Maria, P.; Fontana, A.; Gasbarri, C.; Velluto, D. Effects of fullerene guests on the stability of 1-palmitoyl-2-oleoylphosphatidylcholine liposomes Soft Matter 2006, 2, 595-602 (Pubitemid 43938475)
19. 60 and its derivatives across a lipid bilayer Nano Lett. 2007, 7, 614-619 (Pubitemid 46516035)
20. 60 Fullerenes in a Dimyristolyphosphatidylcholine Lipid Bilayer J. Phys. Chem. B 2007, 111, 4067-4072 (Pubitemid 46732954)
21. 60 Fullerenes through a Lipid Membrane: A Molecular Dynamics Simulation Study J. Phys. Chem. B 2008, 112, 2078-2084 (Pubitemid 351316332)
22. Wong-Ekkabut, J.; Baoukina, S.; Triampo, W.; Tang, I. M.; Tieleman, D. P.; Monticelli, L. Computer simulation study of fullerene translocation through lipid membranes Nat. Nanotechnol. 2008, 3, 363-368 (Pubitemid 351809610)
23. 60 and its derivatives with a lipid bilayer via molecular dynamics simulations Nanotechnology 2009, 20, 115102
24. Redmill, P. S.; McCabe, C. Molecular Dynamics Study of the Behavior of Selected Nanoscale Building Blocks in a Gel-Phase Lipid Bilayer J. Phys. Chem. B 2010, 114, 9165-9172
25. Fiedler, S. L.; Violi, A. Simulation of Nanoparticle Permeation through a Lipid Membrane Biophys. J. 2010, 99, 144-152
26. DeVane, R.; Jusufi, A.; Shinoda, W.; Chiu, C.; Nielsen, S. O.; Moore, P. B.; Klein, M. L. Parametrization and Application of a Coarse Grained Force Field for Benzene/Fullerene Interactions with Lipids J. Phys. Chem. B 2010, 114, 16364-16372
27. 60: Synthesis, characterization, and functionalization of fullerene pyrrolidines J. Am. Chem. Soc. 1993, 115, 9798-9799
28. Mazzoni, M.; Franco, L.; Corvaja, C.; Zordan, G.; Menna, E.; Scorrano, G.; Maggini, M. Synthesis, EPR and ENDOR of [60]Fulleropyrrolidine Bisadducts with Nitroxide Addends: Magnitude and Sign of the Exchange Interaction ChemPhysChem 2002, 6, 527-531
29. 3-Symmetry J. Am. Chem. Soc. 1999, 121, 3246-3247 (Pubitemid 29189784)
30. Spin Labeling: The Next Millennium; Berliner, L., Ed.; Biological Magnetic Resonance; Plenum Press: New York, 1998; Vol. 14.
31. Cardon, T. B.; Tiburu, E. K.; Lorigan, G. A. Magnetically aligned phospholipid bilayers in weak magnetic fields: Optimization, mechanism, and advantages for X-band EPR studies J. Magn. Reson. 2003, 161, 77-90
32. Chen, J.; Brooks, C. L.; Khandogin, J. Recent advances in implicit solvent-based methods for biomolecular simulations Curr. Opin. Struct. Biol. 2008, 18, 140-148
33. Grossfield, A. Implicit Modeling of Membranes Curr. Top. Membr. 2008, 60, 131-157
34. Parisio, G.; Ferrarini, A. Solute Partitioning into Lipid Bilayers: An Implicit Model for Nonuniform and Ordered Environment J. Chem. Theory Comput. 2010, 6, 2267-2280
35. Budil, D. E.; Lee, S.; Saxena, S.; Freed, J. H. Nonlinear-Least-Squares Analysis of Slow-Motion EPR Spectra in One and Two Dimensions Using a Modified Levenberg-Marquardt Algorithm J. Magn. Reson. 1996, 120, 155-189 (Pubitemid 126751752)
36. Mazzoni, M.; Franco, L.; Ferrarini, A.; Corvaja, C.; Zordan, G.; Scorrano, G.; Maggini, M. Unexpected High Ordering of a [60]Fullerene Nitroxide in the Nematic Phase of 4,4′-Azoxyanisole Liq. Cryst. 2002, 29, 203-208
37. Ollila, O. H. S.; Róg, T.; Karttunen, M.; Vattulainen, I. Role of sterol type on lateral pressure profiles of lipid membranes affecting membrane protein functionality: Comparison between cholesterol, desmosterol, 7-dehydrocholesterol and ketosterol J. Struct. Biol. 2007, 159, 311-323 (Pubitemid 47095396)
38. Kupiainen, M.; Falck, E.; Ollila, O. H. S.; Niemelä, P.; Gurtovenko, A. A. Free Volume Properties of Sphingomyelin, DMPC, DPPC, and PLPC Bilayers J. Comput. Theor. Nanosci. 2005, 2, 401-413 (Pubitemid 41556048)
39. Falk, E.; Patra, M.; Karttunen, M.; Hyvönen, M. T.; Vattulainen, I. Lessons of Slicing Membranes: Interplay of Packing, Free Area, and Lateral Diffusion in Phospholipid/Cholesterol Bilayers Biophys. J. 2004, 87, 1076-1091 (Pubitemid 39095086)
40. Tanizaki, S.; Feig, M. J. A generalized Born formalism for heterogeneous dielectric environments: Application to the implicit modeling of biological membranes J. Chem. Phys. 2005, 122, 124706:1-13
41. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford CT, 2004.
42. CRC Handbook of Chemistry and Physics, 87 th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 2007.
43. Sanner, M. F.; Olson, A.; Spehner, J.-C. Reduced surface: An efficient way to compute molecular surfaces Biopolymers 1996, 38, 305-320
44. Bondi, A. van der Waals Volumes and Radi J. Phys. Chem. 1964, 68, 441-451
45. Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids J. Am. Chem. Soc. 1996, 118, 11225-11236 (Pubitemid 26399746)
46. Murzyn, K.; Rog, T.; Blicharski, W.; Dutka, M.; Pyka, J.; Szytula, S.; Froncisz, W. Influence of the disulfide bond configuration on the dynamics of the spin label attached to cytochrome c Proteins 2006, 62, 1088-1100 (Pubitemid 43364171)
47. Nieh, M.-P.; Glinka, C. J.; Krueger, S.; Prosser, R. S.; Katsaras, J. SANS study of the structural phase of magnetically alignable phospholipid mixtures Langmuir 2001, 17, 2629-2638 (Pubitemid 35330513)
48. Ramos, J.; Imaz, A.; Callejas-Fernández, J.; Barbosa-Barros, L.; Estelrich, J.; Quesada-Pérez, M.; Forcada, J. Soft nanoparticles (thermo-responsive nanogels and bicelles) with biotechnological applications: From synthesis to simulation through colloidal characterization Soft Matter 2011, 7, 5067-5082
49. Hauser, H.; Hinckley, C. C.; Krebs, J.; Levine, B. A.; Philips, M. C.; Williams, R. J. P. The interaction of ions with phosphatidylcholine Biochim. Biophys. Acta 1977, 468, 364-377
50. Conti, J.; Halladay, H. N.; Petersheim, M. An ionotropic phase transition in phosphatidylcholine: Cation and anion cooperativity Biochim. Biophys. Acta 1987, 902, 53-64
51. Altenbach, C.; Greenhalgh, D. A.; Khorana, H. G.; Hubbell, W. L. A collision gradient method to determine the immersion depth of nitroxides in lipid bilayers: Application to spin-labeled mutants of bacteriorhodopsin Proc. Natl. Acad. Sci. U.S.A. 1994, 91 (5) 1667-1671 (Pubitemid 24080266)
52. Dave, P. C.; Nusair, N. A.; Inbaraj, J. J.; Lorigan, G. A. Electron paramagnetic resonance studies of magnetically aligned phospholipid bilayers utilizing a phospholipid spin label: The effect of cholesterol Biochim. Biophys. Acta 2005, 1714, 141-151 (Pubitemid 41133616)
53. Cantor, R. S. Lateral pressures in cell membranes: A mechanism for modulation of protein function J. Phys. Chem. 1997, 101, 1723-1725 (Pubitemid 127578327)
54. Gallicchio, E.; Levy, R. M. AGBNP: An analytic implicit solvent model suitable for molecular dynamics simulations and high-resolution modeling J. Comput. Chem. 2004, 25, 479-499
55. Seelig, J. Deuterium magnetic resonance: Theory and application to lipid membranes Q. Rev. Biophys. 1977, 10, 353-418 (Pubitemid 8203096)
56. Ferrarini, A.; Moro, G. J.; Nordio, P. L.; Luckhurst, G. R. A shape model for molecular ordering in nematics Mol. Phys. 1992, 77, 1-15
57. 60 Simulated by Using Classical Potentials J. Phys. Chem. B 2009, 113, 7045-7048
58. Diamond, J. M.; Katz, Y. Interpretation of nonelectrolyte partition coefficients between dimyristoyl lecithin and water J. Membr. Biol. 1974, 17, 121-154
59. Xiang, T. -X.; Anderson, B. D. Liposomal Drug Transport: A Molecular Perspective from Molecular Dynamics Simulations in Lipid Bilayers Adv. Drug Delivery Rev. 2006, 58, 1357-1378 (Pubitemid 44781393)
60. Orsi, M.; Essex, J. W. Permeability of drugs and hormones through a lipid bilayer: Insights from dual-resolution molecular dynamics Soft Matter 2010, 6, 3797-3808
61. Mayer, P. T.; Xiang, T.-X.; Anderson, B. D. Independence of Substituent Contributions to the Transport of Small Molecule Permeants in Lipid Bilayers AAPS PharmSci 2000, 2, 14:1-13