Delivery of drugs to cell membranes by encapsulation in PEG-PE micelles

Journal of Controlled Release

Volumn 160, Issue 3, 2012, Pages 637-651

  Wang, Jing ^a,b   Wang, Yiguang ^a   Liang, Wei ^a  

^a INSTITUTE OF BIOPHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Cell membranes; Drug delivery; FRET; Internalization; PEG PE micelles

Indexed keywords

AMPHIPHILIC PROPERTY; CULTURE MEDIUM; DRUG DELIVERY SYSTEM; ENDOPLASMIC RETICULUM; FLUORESCENCE TECHNIQUE; FRET; GOLGI APPARATUS; HYDROPHILIC DRUGS; IN-DEPTH UNDERSTANDING; INTERNALIZATION; INTRACELLULAR DISTRIBUTION; MEMBRANE FLUIDITY; POLYMER MICELLES; SITE-SPECIFIC;

CELL CULTURE; CELL MEMBRANES; DRUG DELIVERY; DRUG INTERACTIONS; MOLECULAR BIOLOGY; POLYETHYLENE GLYCOLS; POLYETHYLENE OXIDES;

MICELLES;

ADENOSINE TRIPHOSPHATE; MACROGOL; PHOSPHATIDYLETHANOLAMINE;

ARTICLE; CELL MEMBRANE; CELL VIABILITY; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; ENCAPSULATION; ENDOPLASMIC RETICULUM; GOLGI COMPLEX; HUMAN; HUMAN CELL; HYDROPHILICITY; HYDROPHOBICITY; MICELLE; PRIORITY JOURNAL;

CELL LINE, TUMOR; CELL MEMBRANE; ENDOPLASMIC RETICULUM; FLUORESCENT DYES; GOLGI APPARATUS; HUMANS; LIPOSOMES; MICELLES; PHARMACEUTICAL PREPARATIONS; PHOSPHATIDYLETHANOLAMINES; POLYETHYLENE GLYCOLS;

EID: 84862804927     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2012.02.021     Document Type: Article

References (53)

1. D. Peer, J.M. Karp, S. Hong, O.C. Farokhzad, R. Margalit, R. Langer, Nanocarriers as an emerging platform for cancer therapy, Nat. Nanotechnol. 2 (2007) 751-760.
2. O.C. Farokhzad, R. Langer, Impact of nanotechnology on drug delivery, ACS Nano 3 (2009) 16-20.
3. O. Harush-Frenkel, Y. Altschuler, S. Benita, Nanoparticle-cell interactions: drug delivery implications, Crit. Rev. Ther. Drug Carrier Syst. 25 (2008) 485-544.
4. G. Sahay, D.Y. Alakhova, A.V. Kabanov, Endocytosis of nanomedicines, J. Control. Release 145 (2010) 182-195.
5. H. Hillaireau, P. Couvreur, Nanocarrier's entry into the cell: relevance to drug delivery, Cell. Mol. Life Sci. 66 (2009) 2873-2896.
6. E. Gullotti, Y. Yeo, Extracellular activated nanocarriers: a new paradigm of tumor targeted drug delivery, Mol. Pharm. 6 (2009) 1041-1051.
7. H. Chen, S. Kim, L. Li, S. Wang, K. Park, J.X. Cheng, Release of hydrophobic molecules from polymer micelles into cell membranes revealed by Forster resonance energy transfer imaging, Proc. Natl. Acad. Sci. U. S. A. 105 (2008) 6596-6601.
8. S. Deshayes, M.C. Morris, G. Divita, F. Heitz, Cell-penetrating peptides: tools for intracellular delivery of therapeutics, Cell. Mol. Life Sci. 62 (2005) 1839-1849.
9. S. Deshayes, M. Morris, F. Heitz, G. Divita, Delivery of proteins and nucleic acids using a non-covalent peptide-based strategy, Adv. Drug Deliv. Rev. 60 (2008) 537-547.
10. R. Savic, L. Luo, A. Eisenberg, D. Maysinger, Micellar nanocontainers distribute to defined cytoplasmic organelles, Science 300 (2003) 615-618.
11. S.M. Moghimi, A.C. Hunter, J.C. Murray, A. Szewczyk, Cellular distribution of non-ionic micelles, Science 303 (2004) 626-628.
12. R. Duncan, Polymer conjugates as anticancer nanomedicines, Nat. Rev. Cancer 6 (2006) 688-701.
13. R. Haag, F. Kratz, Polymer therapeutics: concepts and applications, Angew. Chem. Int. Ed Engl. 45 (2006) 1198-1215.
14. L. Wasungu, D. Hoekstra, Cationic lipids, lipoplexes and intracellular delivery of genes, J. Control. Release 116 (2006) 255-264.
15. P.R. Leroueil, S. Hong, A. Mecke Jr., J.R. Baker, B.G. Orr, M.M. Banaszak Holl, Nanoparticle interaction with biological membranes: does nanotechnology present a Janus face? Acc. Chem. Res. 40 (2007) 335-342.
16. A.N. Lukyanov, V.P. Torchilin, Micelles from lipid derivatives of water-soluble polymers as delivery systems for poorly soluble drugs, Adv. Drug Deliv. Rev. 56 (2004) 1273-1289.
17. M.L. Adams, A. Lavasanifar, G.S. Kwon, Amphiphilic block copolymers for drug delivery, J. Pharm. Sci. 92 (2003) 1343-1355.
18. A.V. Kabanov, E.V. Batrakova, V.Y. Alakhov, Pluronic block copolymers as novel polymer therapeutics for drug and gene delivery, J. Control. Release 82 (2002) 189-212.
19. O.O. Krylova, N.S. Melik-Nubarov, G.A. Badun, A.L. Ksenofontov, F.M. Menger, A.A. Yaroslavov, Pluronic L61 accelerates flip-flop and transbilayer doxorubicin permeation, Chemistry 9 (2003) 3930-3936.
20. V.Y. Erukova, O.O. Krylova, Y.N. Antonenko, N.S. Melik-Nubarov, Effect of ethylene oxide and propylene oxide block copolymers on the permeability of bilayer lipid membranes to small solutes including doxorubicin, Biochim. Biophys. Acta 1468 (2000) 73-86.
21. T. Demina, I. Grozdova, O. Krylova, A. Zhirnov, V. Istratov, H. Frey, H. Kautz, N. Melik-Nubarov, Relationship between the structure of amphiphilic copolymers and their ability to disturb lipid bilayers, Biochemistry 44 (2005) 4042-4054.
22. A.N. Lukyanov, Z. Gao, V.P. Torchilin, Micelles from polyethylene glycol/phosphatidylethanolamine conjugates for tumor drug delivery, J. Control. Release 91 (2003) 97-102.
23. V.P. Torchilin, Targeted polymeric micelles for delivery of poorly soluble drugs, Cell. Mol. Life Sci. 61 (2004) 2549-2559.
24. N. Tang, G. Du, N. Wang, C. Liu, H. Hang, W. Liang, Improving penetration in tumors with nanoassemblies of phospholipids and doxorubicin, J. Natl. Cancer Inst. 99 (2007) 1004-1015.
25. J. Wang, H. Qu, L. Jin, W. Zeng, L. Qin, F. Zhang, X. Wei, W. Lu, C. Zhang, W. Liang, Pegylated phosphotidylethanolamine inhibiting P-glycoprotein expression and enhancing retention of doxorubicin in MCF7/ADR cells, J. Pharm. Sci. 100 (2011) 2267-2277.
26. Y. Wang, R. Wang, X. Lu, W. Lu, C. Zhang, W. Liang, Pegylated phospholipidsbased self-assembly with water-soluble drugs, Pharm. Res. 27 (2010) 361-370.
27. X. Lu, F. Zhang, L. Qin, F. Xiao, W. Liang, Polymeric micelles as a drug delivery system enhance cytotoxicity of vinorelbine through more intercellular accumulation, Drug Deliv. 17 (2010) 255-262.
28. W.M. Li, L. Xue, D.D. Mayer, M.B. Bally, Intermembrane transfer of polyethylene glycol-modified phosphatidylethanolamine as a means to reveal surface-associated binding ligands on liposomes, Biochim. Biophys. Acta 1513 (2001) 193-206.
29. U.S. Huth, R. Schubert, R. Peschka-Suss, Investigating the uptake and intracellular fate of pH-sensitive liposomes by flow cytometry and spectral bio-imaging, J. Control. Release 110 (2006) 490-504.
30. Zhao Baolu, Applications of electron spin resonance in biology and medicine, The Application of ESR in Cell Membrane Structure Study, 2009, pp. 158-160, Beijing.
31. P.P. Borbat, A.J. Costa-Filho, K.A. Earle, J.K. Moscicki, J.H. Freed, Electron spin resonance in studies of membranes and proteins, Science 12 (2001) 266-269.
32. W.K. Subczynski, A.Wisniewska, Physical properties of lipid bilayer membranes: relevance to membrane biological functions, Acta Biochim. Pol. 47 (2000) 613-625.
33. G.D. Eytan, Mechanism of multidrug resistance in relation to passive membrane permeation, Biomed. Pharmacother. 59 (2005) 90-97.
34. L. Gallois, M. Fiallo, A. Laigle, W. Priebe, A. Garnier-Suillerot, The overall partitioning of anthracyclines into phosphatidyl-containing model membranes depends neither on the drug charge nor the presence of anionic phospholipids, Eur. J. Biochem. 241 (1996) 879-887.
35. R. Regev, D. Yeheskely-Hayon, H. Katzir, G.D. Eytan, Transport of anthracyclines and mitoxantrone across membranes by a flip-flop mechanism, Biochem. Pharmacol. 70 (2005) 161-169.
36. H. Chen, S. Kim, W. He, H. Wang, P.S. Low, K. Park, J.X. Cheng, Fast release of lipophilic agents from circulating PEG-PDLLA micelles revealed by in vivo forster resonance energy transfer imaging, Langmuir 24 (2008) 5213-5217.
37. A.A. Yaroslavov, N.S. Melik-Nubarov, F.M. Menger, Polymer-induced flip-flop in biomembranes, Acc. Chem. Res. 39 (2006) 702-710.
38. J.D. Jones, T.E. Thompson, Mechanism of spontaneous, concentration- dependent phospholipid transfer between bilayers, Biochemistry 29 (1990) 1593-1600.
39. J.R. Silvius, M.J. Zuckermann, Interbilayer transfer of phospholipid-anchored macromolecules via monomer diffusion, Biochemistry 32 (1993) 3153-3161.
40. R. Regev, H. Katzir, D. Yeheskely-Hayon, G.D. Eytan, Modulation of Pglycoprotein-mediated multidrug resistance by acceleration of passive drug permeation across the plasma membrane, FEBS J. 274 (2007) 6204-6214.
41. B.R. Lentz, PEG as a tool to gain insight into membrane fusion, Eur. Biophys. J. 36 (2007) 315-326.
42. M. Companyo, A. Iborra, J. Villaverde, P. Martinez, A. Morros, Membrane fluidity changes in goat sperm induced by cholesterol depletion using betacyclodextrin, Biochim. Biophys. Acta 1768 (2007) 2246-2255.
43. A. Venne, S. Li, R. Mandeville, A. Kabanov, V. Alakhov, Hypersensitizing effect of pluronic L61 on cytotoxic activity, transport, and subcellular distribution of doxorubicin in multiple drug-resistant cells, Cancer Res. 56 (1996) 3626-3629.
44. A.V. Kabanov, E.V. Batrakova, V.Y. Alakhov, An essential relationship between ATP depletion and chemosensitizing activity of Pluronic block copolymers, J. Control. Release 91 (2003) 75-93.
45. H.M. Burt, X. Zhang, P. Toleikis, L. Embree, W.L. Hunter, Development of copolymers of poly(D, L-lactide) and methoxypolyethylene glycol as micellar carriers of paclitaxel, Colloid Surf. B: Biointerfaces 16 (1999) 161-171.
46. D.S. Dimitrov, Virus entry: molecular mechanisms and biomedical applications, Nat. Rev. Microbiol. 2 (2004) 109-122.
47. T. Musacchio, O. Vaze, G. D'Souza, V.P. Torchilin, Effective stabilization and delivery of siRNA: reversible siRNA-phospholipid conjugate in nanosized mixed polymeric micelles, Bioconjug. Chem. 21 (2010) 1530-1536.
48. D. Fischer, Y. Li, B. Ahlemeyer, J. Krieglstein, T. Kissel, In vitro cytotoxicity testing of polycations: influence of polymer structure on cell viability and hemolysis, Biomaterials 24 (2003) 1121-1131.
49. N. Singh, B. Manshian, G.J. Jenkins, S.M. Griffiths, P.M. Williams, T.G. Maffeis, C.J. Wright, S.H. Doak, NanoGenotoxicology: the DNA damaging potential of engineered nanomaterials, Biomaterials 30 (2009) 3891-3914.
50. A. Nel, T. Xia, L. Madler, N. Li, Toxic potential of materials at the nanolevel, Science 311 (2006) 622-627.
51. K.L. Aillon, Y. Xie, N. El-Gendy, C.J. Berkland, M.L. Forrest, Effects of nanomaterial physicochemical properties on in vivo toxicity, Adv. Drug Deliv. Rev. 61 (2009) 457-466.
52. O.C. Martin, R.E. Pagano, Transbilayer movement of fluorescent analogs of phosphatidylserine and phosphatidylethanolamine at the plasma membrane of cultured cells. Evidence for a protein-mediated and ATP-dependent process(es), J. Biol. Chem. 262 (1987) 5890-5898.
53. A.M. Grant, P.K. Hanson, L. Malone, J.W. Nichols, NBD-labeled phosphatidylcholine and phosphatidylethanolamine are internalized by transbilayer transport across the yeast plasma membrane, Traffic 2 (2001) 37-50.