Magnetic nanoparticle-supported lipid bilayers for drug delivery

Langmuir

Volumn 31, Issue 11, 2015, Pages 3326-3332

  Mattingly, Stephanie J ^a   Otoole, Martin G ^a   James, Kurtis T ^a   Clark, Geoffrey J ^b   Nantz, Michael H ^a  

^a University of Louisville   (United States)

^b University of Louisville School of Medicine   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DELIVERY; NANOMAGNETICS; NANOPARTICLES;

AMPHIPHILICS; ANTICANCER DRUG; LIPID PARTICLES; MAGNETIC NANO-PARTICLES; MCF-7 BREAST CANCER CELLS; OXIME ETHERS; POTENTIAL DRUG; SUPPORTED LIPID BILAYERS;

LIPID BILAYERS;

ANTINEOPLASTIC AGENT; DOXORUBICIN; LIPID BILAYER; MAGNETITE NANOPARTICLE;

CELL SURVIVAL; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG EFFECTS; HUMAN; LIPID BILAYER; MCF 7 CELL LINE; PROCEDURES;

ANTINEOPLASTIC AGENTS; CELL SURVIVAL; DOXORUBICIN; DRUG DELIVERY SYSTEMS; HUMANS; LIPID BILAYERS; MAGNETITE NANOPARTICLES; MCF-7 CELLS;

EID: 84925424290     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la504830z     Document Type: Article

References (49)

1. Bulte, J. W. M.; Kraitchman, D. L. Iron oxide MR contrast agents for molecular and cellular imaging NMR Biomed. 2004, 17, 484-499
2. Ma, H.-L.; Qi, X.-R.; Ding, W.-X.; Maitani, Y.; Nagai, T. Magnetic targeting after femoral artery administration and biocompatibility assessment of superparamagnetic iron oxide nanoparticles J. Biomed. Mater. Res., Part A 2008, 84 (3) 598-606
3. Thiesen, B.; Jordan, A. Clinical applications of magnetic nanoparticles for hyperthermia Int. J. Hyperthermia 2008, 24 (6) 467-474
4. Wei, H.; Insin, N.; Lee, J.; Han, H.-S.; Cordero, J.; Liu, W.; Bawendi, M. Compact zwitterion-coated iron oxide nanoparticles for biological applications Nano Lett. 2012, 12 (1) 22-25
5. Pastorino, F.; Marimpietri, D.; Brignole, C.; Paolo, D. D.; Pagnan, G.; Daga, A.; Piccardi, F.; Cilli, M.; Allen, T. M.; Ponzoni, M. Ligand-targeted liposomal therapies of neuroblastoma Curr. Med. Chem. 2007, 14, 3070-3078
6. Bothun, G.; Lelis, A.; Chen, Y.; Scully, K.; Anderson, L.; Stoner, M. Multicomponent folate-targeted magnetoliposomes: Design, characterization, and cellular uptake Nanomedicine 2011, 7 (6) 797-805
7. Wang, L.; Zhang, F.; Chen, J. Carbonyl sulfide derived from catalytic oxidation of carbon disulfide over atmospheric particles Environ. Sci. Technol. 2001, 35, 2543-2547
8. 2 over oxide catalysts of spinel type J. Res. Inst. Catal., Hokkaido Univ. 1953, 2 (2) 110-116
9. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. NMR chemical shifts of common laboratory solvents as trace impurities J. Org. Chem. 1997, 62 (21) 7512-7515
10. Li, C.; Ma, C.; Wang, F.; Xi, Z.; Wang, Z.; Deng, Y.; He, N. Preparation and biomedical applications of core-shell silica/magnetic nanoparticle composites J. Nanosci. Nanotechnol. 2012, 12 (4) 2964-2972
11. Malvindi, M. A.; De Matteis, V.; Galeone, A.; Brunetti, V.; Anyfantis, G. C.; Athanassiou, A.; Cingolani, R.; Pompa, P. P. Toxicity assessment of silica coated iron oxide nanoparticles and biocompatibility improvement by surface engineering PLoS One 2014, 9 (1 e85835
12. 2 nanoparticles by tweaking the silica coating thickness ACS Nano 2010, 4, 5339-5349
13. Villanueva, A.; Cañete, M.; Roca, A.; Calero, M.; Veintemillas-Verdaguer, S.; Serna, C.; Morales, M.; Miranda, R. The influence of surface functionalization on the enhanced internalization of magnetic nanoparticles in cancer cells Nanotechnology 2009, 20 (11) 115103
14. Zhang, Y.; Yang, M.; Portney, N.; Cui, D.; Budak, G.; Ozbay, E.; Ozkan, M.; Ozkan, C. Zeta potential: A surface electrical characteristic to probe the interaction of nanoparticles with normal and cancer human breast epithelial cells Biomed. Microdevices 2008, 10 (2) 321-328
15. De Cuyper, M.; Joniau, M. Magnetoliposomes Eur. Biophys. J. 1987, 15, 311-319
16. Rodrigues, A. R. O.; Gomes, I. T.; Almeida, B. G.; Araujo, J. P.; Castanheira, E. M. S.; Coutinho, P. J. G. Magnetoliposomes based on nickel/silica core/shell nanoparticles: Synthesis and characterization Mater. Chem. Phys. 2014, 148 (3) 978-987
17. Soenen, S.; Hodenius, M.; De Cuyper, M. Magnetoliposomes: Versatile innovative nanocolloids for use in biotechnology and biomedicine Nanomedicine 2009, 4 (2) 177-191
18. De Cuyper, M.; Soenen, S. J. H. Cationic magnetoliposomes Methods Mol. Biol. 2010, 605, 97-111
19. Soenen, S. J. H.; Brisson, A. R.; De Cuyper, M. Addressing the problem of cationic lipid-mediated toxicity: The magnetoliposome model Biomaterials 2009, 30 (22) 3691-3701
20. Soenen, S. J. H.; De Cuyper, M. How to assess cytotoxicity of (iron oxide-based) nanoparticles. A technical note using cationic magnetoliposomes Contrast Media Mol. Imaging 2011, 6 (3) 153-164
21. Soenen, S. J. H.; Vercauteren, D.; Braeckmans, K.; Noppe, W.; De Smedt, S.; De Cuyper, M. Stable long-term intracellular labeling with fluorescently tagged cationic magnetoliposomes ChemBioChem 2009, 10 (2) 257-267
22. Biswas, S.; Knipp, R. J.; Gordon, L. E.; Nandula, S. R.; Gorr, S.-U.; Clark, G. J.; Nantz, M. H. Hydrophobic oxime ethers: A versatile class of pDNA and siRNA transfection lipids ChemMedChem 2011, 6, 2063-2069
23. Junquera, E.; Aicart, E. Cationic lipids as transfecting agents of DNA in gene therapy Curr. Top. Med. Chem. 2014, 14 (5) 649-663
24. Biswas, S.; Gordon, L. E.; Clark, G. J.; Nantz, M. H. Click assembly of magnetic nanovectors for gene delivery Biomaterials 2011, 32, 2683-2688
25. Pan, X.; Guan, J.; Yoo, J.-W.; Epstein, A. J.; Lee, L. J.; Lee, R. J. Cationic lipid-coated magnetic nanoparticles associated with transferrin for gene delivery Int. J. Pharm. 2008, 358 (1-2) 263-270
26. Jiang, S.; Eltoukhy, A.; Love, K.; Langer, R.; Anderson, D. Lipidoid-coated iron oxide nanoparticles for efficient DNA and siRNA delivery Nano Lett. 2013, 13 (3) 1059-1064
27. Liu, J.; Jiang, X.; Ashley, C.; Brinker, C. J. Electrostatically mediated liposome fusion and lipid exchange with a nanoparticle-supported bilayer for control of surface charge, drug containment, and delivery J. Am. Chem. Soc. 2009, 131 (22) 7567-7569
28. Ashley, C. E.; Carnes, E. C.; Epler, K. E.; Padilla, D. P.; Phillips, G. K.; Castillo, R. E.; Wilkinson, D. C.; Wilkinson, B. S.; Burgard, C. A.; Kalinich, R. M.; Townson, J. L.; Chackerian, B.; Willman, C. L.; Peabody, D. S.; Wharton, W.; Brinker, C. J. Delivery of small interfering RNA by peptide-targeted mesoporous silica nanoparticle-supported lipid bilayers ACS Nano 2012, 6 (3) 2174-2188
29. Dengler, E. C.; Liu, J.; Kerwin, A.; Torres, S.; Olcott, C. M.; Bowman, B. N.; Armijo, L.; Gentry, K.; Wilkerson, J.; Wallace, J.; Jiang, X.; Carnes, E. C.; Brinker, C. J.; Milligan, E. D. Mesoporous silica-supported lipid bilayers (protocells) for DNA cargo delivery to the spinal cord J. Controlled Release 2013, 168 (2) 209-224
30. Li, S.-Z.; Ma, Y.; Yue, X.-L.; Cao, Z.; Dai, Z.-F. One-pot construction of doxorubicin conjugated magnetic silica nanoparticles New J. Chem. 2009, 33 (12) 2414-2418
31. Azizi, N.; Saidi, M. Highly chemoselective addition of amines to epoxides in water Org. Lett. 2005, 7 (17) 3649-3651
32. Kuwabe, S.; Torraca, K.; Buchwald, S. Palladium-catalyzed intramolecular C-O bond formation J. Am. Chem. Soc. 2001, 123 (49) 12202-12206
33. Effenberger, K.; Breyer, S.; Schobert, R. Modulation of doxorubicin activity in cancer cells by conjugation with fatty acyl and terpenyl hydrazones Eur. J. Med. Chem. 2010, 45 (5) 1947-1954
34. Dirksen, A.; Dawson, P. Rapid oxime and hydrazone ligations with aromatic aldehydes for biomolecular labeling Bioconjugate Chem. 2008, 19 (12) 2543-2548
35. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click chemistry: Diverse chemical function from a few good reactions Angew. Chem., Int. Ed. 2001, 40 (11) 2004-2021
36. Zhi, D.; Zhang, S.; Cui, S.; Zhao, Y.; Wang, Y.; Zhao, D. The headgroup evolution of cationic lipids for gene delivery Bioconjugate Chem. 2013, 24 (4) 487-519
37. Nantz, M. H.; Dicus, C. W.; Hilliard, B.; Yellayi, S.; Zou, S.; Hecker, J. G. The benefit of hydrophobic domain asymmetry on the efficacy of transfection as measured by in vivo imaging Mol. Pharmaceutics 2010, 7 (3) 786-794
38. Le Corre, S. S.; Berchel, M.; Le Gall, T.; Haelters, J.-P.; Lehn, P.; Montier, T.; Jaffres, P.-A. Cationic trialkylphosphates: Synthesis and transfection efficacies compared to phosphoramidate analogues Eur. J. Org. Chem. 2014, 2014 (36) 8041-8048
39. Tian Hu, S.; Brändle, E.; Zbinden, G. Inhibition of cardiotoxic, nephrotoxic and neurotoxic effects of doxorubicin by ICRF-159 Pharmacology 1983, 26 (4) 210-220
40. Carvalho, F. S.; Burgeiro, A.; Garcia, R.; Moreno, A. J.; Carvalho, R. A.; Oliveira, P. J. Doxorubicin-induced cardiotoxicity: From bioenergetic failure and cell death to cardiomyopathy Med. Res. Rev. 2014, 34 (1) 106-135
41. Kratz, F.; Beyer, U.; Roth, T.; Tarasova, N.; Collery, P.; Lechenault, F.; Cazabat, A.; Schumacher, P.; Unger, C.; Falken, U. Transferrin conjugates of doxorubicin: Synthesis, characterization, cellular uptake, and in vitro efficacy J. Pharm. Sci. 1998, 87 (3) 338-346
42. Rollas, S.; Küçükgüzel, Ş. Hydrazone, amide, carbamate, macromolecular and other prodrugs of doxorubicin Open Drug Delivery J. 2008, 2 (1) 77-85
43. Graeser, R.; Esser, N.; Unger, H.; Fichtner, I.; Zhu, A.; Unger, C.; Kratz, F. INNO-206, the (6-maleimidocaproyl hydrazone derivative of doxorubicin), shows superior antitumor efficacy compared to doxorubicin in different tumor xenograft models and in an orthotopic pancreas carcinoma model Invest. New Drugs 2010, 28 (1) 14-19
44. Krüger, M.; Beyer, U.; Schumacher, P.; Unger, C.; Zahn, H.; Kratz, F. Synthesis and stability of four maleimide derivatives of the anticancer drug doxorubicin for the preparation of chemoimmunoconjugates Chem. Pharm. Bull. 1997, 45, 399-401
45. Effenberger, K.; Breyer, S.; Ocker, M.; Schobert, R. New doxorubicin N-acyl hydrazones with improved efficacy and cell line specificity show modes of action different from the parent drug Int. J. Clin. Pharmacol. Ther. 2010, 48 (7) 485-486
46. Frézard, F.; Garnier-Suillerot, A. Permeability of lipid bilayer to anthracycline derivatives. Role of the bilayer composition and of the temperature Biochim. Biophys. Acta, Lipids Lipid Metab. 1998, 1389 (1) 13-22
47. Petralito, S.; Spera, R.; Memoli, A.; DInzeo, G.; Liberti, M.; Apollonio, F. Preparation and characterization of lipid vesicles entrapping iron oxide nanoparticles Asia-Pac. J. Chem. Eng. 2012, 7 (S3) S335-S341
48. Jain, T.; Morales, M.; Sahoo, S.; Leslie-Pelecky, D.; Labhasetwar, V. Iron oxide nanoparticles for sustained delivery of anticancer agents Mol. Pharmaceutics 2005, 2 (3) 194-205
49. Xu, Y.; Szoka, F. C., Jr. Mechanism of DNA release from cationic liposome/DNA complexes used in cell transfection Biochemistry 1996, 35 (18) 5616-5623