Nanoparticles from renewable polymers

Frontiers in Chemistry

Volumn 2, Issue JUL, 2014, Pages

  Wurm, Frederik R ^a   Weiss, Clemens K ^b  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b UNIVERSITY OF APPLIED SCIENCES BINGEN   (Germany)

Author keywords

Biodegradation; Formulation of nanoparticles; Nanoparticles; Polymers

Indexed keywords

EID: 84987621233     PISSN: None     EISSN: 22962646     Source Type: Journal    
DOI: 10.3389/fchem.2014.00049     Document Type: Review

References (161)

1. Alexandrino, E. M., Ritz, S., Marsico, F., Baier, G., Mailander, V., Landfester, K., et al. (2014). Paclitaxel-loaded polyphosphate nanoparticles: a potential strategy for bone cancer treatment. J. Mater. Chem. B 2, 1298-1306. doi: 10.1039/c3tb21295e
2. Andrieu, J., Kotman, N., Maier, M., Mailänder, V., Strauss, W. S. L., Weiss, C. K., et al. (2012). Live monitoring of cargo release from peptide-based hybrid nanocapsules induced by enzyme cleavage. Macromol. Rapid Commun. 33, 248-253. doi: 10.1002/marc.201100729
3. Andrieux, K., and Couvreur, P. (2009). Polyalkylcyanoacrylate nanoparticles for delivery of drugs across the blood-brain barrier. Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol. 1, 463-474. doi: 10.1002/wnan.5
4. Anton, N., Benoit, J.-P., and Saulnier, P. (2008). Design and production of nanoparticles formulated from nano-emulsion templates-a review. J. Control. Release 128, 185-199. doi: 10.1016/j.jconrel.2008.02.007
5. Aschenbrenner, E., Bley, K., Koynov, K., Makowski, M., Kappl, M., Landfester, K., et al. (2013). Using the polymeric ouzo effect for the preparation of polysaccharide-based nanoparticles. Langmuir 29, 8845-8855. doi: 10.1021/la4017867
6. Astruc, D., Lu, F., and Aranzaes, J. R. (2005). Nanoparticles as recyclable catalysts: the frontier between homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed. Engl. 44, 7852-7872. doi: 10.1002/anie.200500766
7. Asua, J. M. (2002). Miniemulsion polymerization. Prog. Polym. Sci. 27, 1283-1346. doi: 10.1016/S0079-6700(02)00010-2
8. Asua, J. M. (2004). Emulsion polymerization: from fundamental mechanisms to process developments. J. Polym. Sci. A Polym. Chem. 42, 1025-1041. doi: 10.1002/pola.11096
9. Aubry, J., Ganachaud, F., Addad, J. P. C., and Cabane, B. (2009). Nanoprecipitation of polymethylmethacrylate by solvent shifting: 1. Boundaries. Langmuir 25, 1970-1979. doi: 10.1021/la803000e
10. Auvergne, R., Caillol, S., David, G., Boutevin, B., and Pascault, J.-P. (2014). Biobased thermosetting epoxy: present and future. Chem. Rev. 114, 1082-1115. doi: 10.1021/cr3001274
11. Baier, G., Baki, A., Tomcin, S., Mailänder, V., Alexandrino, E., Wurm, F., et al. (2014). Stabilization of nanoparticles synthesized by miniemulsion polymerization using "green" amino-acid based surfactants. Macromol. Symp. 337, 9-17. doi: 10.1002/masy.201450301
12. Baier, G., Baumann, D., Siebert, J. M., Musyanovych, A., Mailänder, V., and Landfester, K. (2012). Suppressing unspecific cell uptake for targeted delivery using hydroxyethyl starch nanocapsules. Biomacromolecules 13, 2704-2715. doi: 10.1021/bm300653v
13. Baier, G., Cavallaro, A., Vasilev, K., Mailänder, V., Musyanovych, A., and Landfester, K. (2013). Enzyme responsive hyaluronic acid nanocapsules containing polyhexanide and their exposure to bacteria to prevent infection. Biomacromolecules 14, 1103-1112. doi: 10.1021/bm302003m
14. Balthasar, S., Michaelis, K., Dinauer, N., Von Briesen, H., Kreuter, J., and Langer, K. (2005). Preparation and characterization of antibody modified gelatin nanoparticles as drug carrier system for uptake in lymphocytes. Biomater 26, 2723-2732. doi: 10.1016/j.biomaterials.2004.07.047
15. Barrère, M., and Landfester, K. (2003). High molecular weight polyurethane and polymer hybrid particles in aqueous miniemulsion. Macromolecules 36, 5119-5125. doi: 10.1021/ma025981+
16. Bazile, D., Prud'homme, C., Bassoullet, M.-T., Marlard, M., Spenlehauer, G., and Veillard, M. (1995). Stealth me.PEG-PLA nanoparticles avoid uptake by the mononuclear phagocytes system. J. Pharm. Sci. 84, 493-498. doi: 10.1002/jps.2600840420
17. Beck-Broichsitter, M., Rytting, E., Lebhardt, T., Wang, X. Y., and Kissel, T. (2010). Preparation of nanoparticles by solvent displacement for drug delivery: a shift in the "ouzo region" upon drug loading. Eur. J. Pharm. Sci. 41, 244-253. doi: 10.1016/j.ejps.2010.06.007
18. Becker, J., Trugler, A., Jakab, A., Hohenester, U., and Sonnichsen, C. (2010). The optimal aspect ratio of gold nanorods for plasmonic bio-sensing. Plasmonics 5, 161-167. doi: 10.1007/s11468-010-9130-2
19. Biermann, U., Bornscheuer, U., Meier, M. A., Metzger, J. O., and Schäfer, H. J. (2011). Oils and fats as renewable raw materials in chemistry. Angew. Chem. Int. Ed. Engl. 50, 3854-3871. doi: 10.1002/anie.201002767
20. Bodnar, M., Hartmann, J. F., and Borbely, J. (2005). Preparation and characterization of chitosan-based nanoparticles. Biomacromolecules 6, 2521-2527. doi: 10.1021/bm0502258
21. Bombalski, L., Min, K., Dong, H., Tang, C., and Matyjaszewski, K. (2007). Preparation of well-defined hybrid materials by atrp in miniemulsion. Macromolecules 40, 7429-7432. doi: 10.1021/ma071408k
22. Bourges, J. L. (2003). Ocular drug delivery targeting the retina and retinal pigment epithelium using polylactide nanoparticles. Invest. Ophthalmol. Vis. Sci. 44, 3562-3569. doi: 10.1167/iovs.02-1068
23. Brick, M. C., Palmer, H. J., and Whitesides, T. H. (2003). Formation of colloidal dispersions of organic materials in aqueous media by solvent shifting. Langmuir 19, 6367-6380. doi: 10.1021/la034173o
24. Calvo-Flores, F. G., and Dobado, J. A. (2010). Lignin as renewable raw material. ChemSusChem 3, 1227-1235. doi: 10.1002/cssc.201000157
25. Cardoso, P. B., Araújo, P. H. H., and Sayer, C. (2013). Encapsulation of jojoba and andiroba oils by miniemulsion polymerization. effect on molar mass distribution. Macromol. Symp. 324, 114-123. doi: 10.1002/masy.201200075
26. Cardoso, P. B., Musyanovych, A., Landfester, K., Sayer, C., De Araújo, P. H. H., and Meier, M. A. R. (2014). ADMET reactions in miniemulsion. J. Polym. Sci. A Polym. Chem. 52, 1300-1305. doi: 10.1002/pola.27118
27. Cauvin, S., and Ganachaud, F. (2004). On the preparation and polymerization of p-methoxystyrene miniemulsions in the presence of excess ytterbium triflate. Macromol. Symp. 215, 179-190. doi: 10.1002/masy.200451115
28. Chen, Q., Schönherr, H., and Vancso, G. J. (2009). Mechanical properties of block copolymer vesicle membranes by atomic force microscopy. Soft Matter 5, 4944. doi: 10.1039/b903110c
29. Crespy, D., and Landfester, K. (2010). Miniemulsion polymerization as a versatile tool for the synthesis of functionalized polymers. Beilstein J. Org. Chem. 6, 1132-1148. doi: 10.3762/bjoc.6.130
30. Crespy, D., and Landfester, K. (2011). Making dry fertile: a practical tour of non-aqueous emulsions and miniemulsions, their preparation and some applications. Soft Matter 7, 11054-11064. doi: 10.1039/c1sm06156a
31. Crespy, D., Musyanovych, A., and Landfester, K. (2006). Synthesis of polymer particles and nanocapsules stabilized with PEO/PPO containing polymerizable surfactants in miniemulsion. Colloid Polym. Sci. 284, 780-787. doi: 10.1007/s00396-005-1446-7
32. Daniel, M. C., and Astruc, D. (2004). Gold nanoparticles: assembly, supramolecular chemistry, quantum-size-related properties, and applications toward biology, catalysis, and nanotechnology. Chem. Rev. 104, 293-346. doi: 10.1021/cr030698+
33. De Lima, A. P. D., Aschenbrenner, E. M., Oliveira, S. D. N., Doucet, J.-B., Weiss, C. K., Ziener, U., et al. (2013). Towards regioselective enzymatic hydrolysis and glycerolysis of tricaprylin in miniemulsion and the direct preparation of polyurethane from the hydrolysis products. J. Mol. Catal. B Enzym. 98, 127-137. doi: 10.1016/j.molcatb.2013.10.013
34. Eldem, T., Speiser, P., and Hincal, A. (1991). Optimization of spray-dried and-congealed lipid micropellets and characterization of their surface morphology by scanning electron microscopy. Pharm. Res. 8, 47-54. doi: 10.1023/A:1015874121860
35. Esteves, A. C. C., Bombalski, L., Trindade, T., Matyjaszewski, K., and Barros-Timmons, A. (2007). Polymer grafting from Cds quantum dots via AGET ATRP in miniemulsion. Small 3, 1230-1236. doi: 10.1002/smll.200600510
36. Ethirajan, A., Schoeller, K., Musyanovych, A., Ziener, U., and Landfester, K. (2008a). Synthesis and optimization of gelatin nanoparticles using the miniemulsion process. Biomacromolecules 9, 2383-2389. doi: 10.1021/bm800377w
37. Ethirajan, A., Ziener, U., Chuvilin, A., Kaiser, U., Colfen, H., and Landfester, K. (2008b). Biomimetic hydroxyapatite crystallization in gelatin nanoparticles synthesized using a miniemulsion process. Adv. Funct. Mater. 18, 2221-2227. doi: 10.1002/adfm.200800048
38. Faria, F. A. C., Evtuguin, D. V., Rudnitskaya, A., Gomes, M. T. S. R., Oliveira, J. A. B. P., and Costa, L. C. (2012). Lignin-based polyurethane doped with carbon nanotubes for sensor applications. Polym. Int. 61, 788-794. doi: 10.1002/pi.4140
39. Fernandes, E. M., Pires, R. A., Mano, J. F., and Reis, R. L. (2013). Bionanocomposites from lignocellulosic resources: properties, applications and future trends for their use in the biomedical field. Prog. Polym. Sci. 38, 1415-1441. doi: 10.1016/j.progpolymsci.2013.05.013
40. Fuchs, A. V., Kotman, N., Andrieu, J., Mailänder, V., Weiss, C. K., and Landfester, K. (2013). Enzyme cleavable nanoparticles from peptide based triblock copolymers. Nanoscale 5, 4829-4839. doi: 10.1039/c3nr00706e
41. Gan, Z., Zhang, T., Liu, Y., and Wu, D. (2012). Temperature-triggered enzyme immobilization and release based on cross-linked gelatin nanoparticles. PLoS ONE 7:e47154. doi: 10.1371/journal.pone.0047154
42. Ganachaud, F., and Katz, J. L. (2005). Nanoparticles and nanocapsules created using the ouzo effect: spontaneous emulsification as an alternative to ultrasonic and high-shear devices. Chemphyschem 6, 209-216. doi: 10.1002/cphc.200400527
43. Gandini, A. (2008). Polymers from renewable resources: a challenge for the future of macromolecular materials. Macromolecules 41, 9491-9504. doi: 10.1021/ma801735u
44. Gandini, A. (2011). The irruption of polymers from renewable resources on the scene of macromolecular science and technology. Green Chem. 13, 1061-1083. doi: 10.1039/c0gc00789g
45. Gandini, A., and Belgacem, M. N. (1997). Furans in polymer chemistry. Prog. Polym. Sci. 22, 1203-1379. doi: 10.1016/S0079-6700(97)00004-X
46. Gandini, A., Silvestre, A. J. D., Neto, C. P., Sousa, A. F., and Gomes, M. (2009). The furan counterpart of poly(ethylene terephthalate): an alternative material based on renewable resources. J. Polym. Sci. A Polym. Chem. 47, 295-298. doi: 10.1002/pola.23130
47. Gao, G., Dallmeyer, J. I., and Kadla, J. F. (2012). Synthesis of lignin nanofibers with ionic-responsive shells: water-expandable lignin-based nanofibrous mats. Biomacromolecules 13, 3602-3610. doi: 10.1021/bm301039f
48. Gauthier, M. A., and Klok, H.-A. (2008). Peptide/protein-polymer conjugates: synthetic strategies and design concepts. Chem. Commun. 2591-2611. doi: 10.1039/b719689j
49. Good, I. L., Kenoyer, J. M., and Meadow, R. H. (2009). New evidence for early silk in the indus civilization. Archaeometry 51, 457-466. doi: 10.1111/j.1475-4754.2008.00454.x
50. Goodwin, J. W., Hearn, J., Ho, C. C., and Ottewill, R. H. (1974). Studies on the preparation and characterisation of monodisperse polystyrene laticee. Colloid Polym. Sci. 252, 464-471. doi: 10.1007/BF01554752
51. Guilmanov, V., Ballistreri, A., Impallomeni, G., and Gross, R. A. (2002). Oxygen transfer rate and sophorose lipid production by Candida bombicola. Biotechnol. Bioeng. 77, 489-494. doi: 10.1002/bit.10177
52. Gupta, A. P., and Kumar, V. (2007). New emerging trends in synthetic biodegradable polymers-polylactide: a critique. Eur. Polym. J. 43, 4053-4074. doi: 10.1016/j.eurpolymj.2007.06.045
53. Guterres, S. S., Fessi, H., Barratt, G., Devissaguet, J. P., and Puisieux, F. (1995). Poly(DL-lactide) nanocapsules containing diclofenac: I. Formulation and stability study. Int. J. Pharm. 113, 57-63. doi: 10.1016/0378-5173(94)00177-7
54. Harkins, W. D. (1947). A general theory of the mechanism of emulsion polymerization1. J. Am. Chem. Soc. 69, 1428-1444. doi: 10.1021/ja01198a053
55. Hatakeyama, H., and Hatakeyama, T. (2010). "Lignin, proteins, bioactive nanocomposites, " in Biopolymers, eds. A. Abe, K. Dusek, and S. Kobayashi. (Berlin: Springer Verlag), 1-63.
56. Hawkins, M. J., Soon-Shiong, P., and Desai, N. (2008). Protein nanoparticles as drug carriers in clinical medicine. Adv. Drug Deliv. Rev. 60, 876-885. doi: 10.1016/j.addr.2007.08.044
57. Horn, D., and Rieger, J. (2001). Organic nanoparticles in the aqueous phase-theory, experiment, and use. Angew. Chem.Int. Ed.Engl. 40, 4331-4361. doi: 10.1002/1521-3773(20011203)40:23<4330::AID-ANIE4330>3.0.CO;2-W
58. Hornig, S., Biskup, C., Gräfe, A., Wotschadlo, J., Liebert, T., Mohr, G. J., et al. (2008). Biocompatible fluorescent nanoparticles for pH-sensoring. Soft Matter 4, 1169-1172. doi: 10.1039/b800276b
59. Hornig, S., and Heinze, T. (2007). Nanoscale structures of dextran esters. Carbohydr. Polym. 68, 280-286. doi: 10.1016/j.carbpol.2006.12.007
60. Hornig, S., and Heinze, T. (2008). Efficient approach to design stable water-dispersible nanoparticles of hydrophobic cellulose esters. Biomacromolecules 9, 1487-1492. doi: 10.1021/bm8000155
61. Hornig, S., Heinze, T., Becer, C. R., and Schubert, U. S. (2009). Synthetic polymeric nanoparticles by nanoprecipitation. J. Mater. Chem. 19, 3838-3840. doi: 10.1039/b906556n
62. Hosler, D. (1999). Prehistoric polymers: rubber processing in ancient mesoamerica. Science 284, 1988-1991. doi: 10.1126/science.284.5422.1988
63. Janes, K. A., Calvo, P., and Alonso, M. J. (2001). Polysaccharide colloidal particles as delivery systems for macromolecules. Adv. Drug Deliv. Rev. 47, 83-97. doi: 10.1016/S0169-409X(00)00123-X
64. Jang, Y.-S., Kim, B., Shin, J. H., Choi, Y. J., Choi, S., Song, C. W., et al. (2012). Bio-based production of C2-C6 platform chemicals. Biotechnol. Bioeng. 109, 2437-2459. doi: 10.1002/bit.24599
65. Jenning, V., Gysler, A., Schäfer-Korting, M., and Gohla, S. H. (2000). Vitamin A loaded solid lipid nanoparticles for topical use: occlusive properties and drug targeting to the upper skin. Eur. J. Pharm. Biopharm. 49, 211-218. doi: 10.1016/S0939-6411(99)00075-2
66. Jeong, Y.-I., Choi, K.-C., and Song, C.-E. (2006a). Doxorubicin release from core-shell type nanoparticles of poly(DL-lactide-co-glycolide)-grafted dextran. Arch. Pharm. Res. 29, 712-719. doi: 10.1007/BF02968257
67. Jeong, Y.-I., Na, H.-S., Oh, J.-S., Choi, K.-C., Song, C.-E., and Lee, H.-C. (2006b). Adriamycin release from self-assembling nanospheres of poly(dl-lactide-co-glycolide)-grafted pullulan. Int. J. Pharm. 322, 154-160. doi: 10.1016/j.ijpharm.2006.05.020
68. Jönsson, J. B., Müllner, M., Piculell, L., and Karlsson, O. J. (2013). Emulsion condensation polymerization in dispersed aqueous media. interfacial reactions and nanoparticle formation. Macromolecules 46, 9104-9113. doi: 10.1021/ma401799g
69. Kamat, P. V. (2007). Meeting the clean energy demand: nanostructure architectures for solar energy conversion. J. Phys. Chem. C 111, 2834-2860. doi: 10.1021/jp066952u
70. Kfoury, G., Raquez, J.-M., Hassouna, F., Odent, J., Toniazzo, V., Ruch, D., et al. (2013). Recent advances in high performance poly(lactide): from "green" plasticization to super-tough materials via (reactive) compounding. Front. Chem. 1:32 doi: 10.3389/fchem.2013.00032
71. Khan, S. A., and Schneider, M. (2013). Improvement of nanoprecipitation technique for preparation of gelatin nanoparticles and potential macromolecular drug loading. Macromol. Biosci. 13, 455-463. doi: 10.1002/mabi.201200382
72. Kim, I.-Y., Seo, S.-J., Moon, H.-S., Yoo, M.-K., Park, I.-Y., Kim, B.-C., et al. (2008). Chitosan and its derivatives for tissue engineering applications. Biotechnol. Adv. 26, 1-21. doi: 10.1016/j.biotechadv.2007.07.009
73. Klinger, D., Aschenbrenner, E. M., Weiss, C. K., and Landfester, K. (2012). Enzymatically degradable nanogels by inverse miniemulsion copolymerization of acrylamide with dextran methacrylates as crosslinkers. Polym. Chem. 3, 204-216. doi: 10.1039/c1py00415h
74. Kommareddy, S., and Amiji, M. (2007). Poly(Ethylene Glycol)-Modified thiolated gelatin nanoparticles for glutathione-responsive intracellular DNA delivery. Nanomedicine 3, 32-42. doi: 10.1016/j.nano.2006.11.005
75. Krishna, O. D., and Kiick, K. L. (2010). Protein-and peptide-modified synthetic polymeric biomaterials. Biopolymers 94, 32-48. doi: 10.1002/bip.21333
76. Kvavadze, E., Bar-Yosef, O., Belfer-Cohen, A., Boaretto, E., Jakeli, N., Matskevich, Z., et al. (2009). 30, 000-year-old wild flax fibers. Science 325, 1359-1359. doi: 10.1126/science.1175404
77. Landfester, K. (2000). Recent developments in miniemlsions-formation and stability mechanisms. Macromol. Symp. 150, 171-178. doi: 10.1002/1521-3900(200002)150:1<171::AID-MASY171>3.0.CO;2-D
78. Landfester, K. (2009). Miniemulsion polymerization and the structure of polymer and hybrid nanoparticles13. Angew. Chem. Int. Ed. Engl. 48, 4488-4507. doi: 10.1002/anie.200900723
79. Landfester, K., Bechthold, N., Tiarks, F., and Antonietti, M. (1999a). Formulation and stability mechanisms of polymerizable miniemulsions. Macromolecules 32, 5222-5228. doi: 10.1021/ma990299+
80. Landfester, K., Bechthold, N., Tiarks, F., and Antonietti, M. (1999b). Miniemulsion polymerization with cationic and nonionic surfactants: a very efficient use of surfactants for heterophase polymerization. Macromolecules 32, 2679-2683. doi: 10.1021/ma9819438
81. Landfester, K., Rothe, R., and Antonietti, M. (2002). Convenient synthesis of fluorinated latexes and core-shell structures by miniemulsion polymerization. Macromolecules 35, 1658-1662. doi: 10.1021/ma011608a
82. Landfester, K., Tiarks, F., Hentze, H.-P., and Antonietti, M. (2000). Polyaddition in miniemulsions: a new route to polymer dispersions. Macromol. Chem. Phys. 201, 1-5. doi: 10.1002/(SICI)1521-3935(20000101)201:1<1::AID-MACP1>3.0.CO;2-N
83. Landfester, K., and Weiss, C. K. (2010). Encapsulation by miniemulsion polymerization. Adv. Polym. Sci. 229, 1-49. doi: 10.1007/12_2009_43
84. Liebert, T., Hornig, S., Hesse, S., and Heinze, T. (2005). Nanoparticles on the basis of highly functionalized dextrans. J. Am. Chem. Soc. 127, 10484-10485. doi: 10.1021/ja052594h
85. Liebner, R., Mathaes, R., Meyer, M., Hey, T., Winter, G., and Besheer, A. (2014). Protein HESylation for half-life extension: synthesis, characterization and pharmacokinetics of HESylated anakinra. Eur. J. Pharm. Biopharm. 87, 378-385. doi: 10.1016/j.ejpb.2014.03.010
86. Limouzin, C., Caviggia, A., Ganachaud, F., and Hémery, P. (2003). Anionic polymerization of n-butyl cyanoacrylate in emulsion and miniemulsion. Macromolecules 36, 667-674. doi: 10.1021/ma0257402
87. Liu, Z., Jiao, Y., Wang, Y., Zhou, C., and Zhang, Z. (2008). Polysaccharides-based nanoparticles as drug delivery systems. Adv. Drug Deliv. Rev. 60, 1650-1662. doi: 10.1016/j.addr.2008.09.001
88. Lligadas, G., Ronda, J. C., Galià, M., and Cádiz, V. (2013). Renewable polymeric materials from vegetable oils: a perspective. Mater. Today 16, 337-343. doi: 10.1016/j.mattod.2013.08.016
89. Lora, J. H., and Glasser, W. G. (2002). Recent industrial applications of lignin: a sustainable alternative to nonrenewable materials. J. Polym. Environ. 10, 39-48. doi: 10.1023/A:1021070006895
90. Luengo, J. M., Garcí A. B., Sandoval, A., Naharro, G., and Olivera, E. A. R. (2003). Bioplastics from microorganisms. Curr. Opin. Microbiol. 6, 251-260. doi: 10.1016/S1369-5274(03)00040-7
91. Lutz, J.-F., and Börner, H. G. (2008). Modern trends in polymer bioconjugates design. Prog. Polym. Sci. 33, 1-39. doi: 10.1016/j.progpolymsci.2007.07.005
92. Madhavan Nampoothiri, K., Nair, N. R., and John, R. P. (2010). An overview of the recent developments in polylactide (PLA) research. Bioresour. Technol. 101, 8493-8501. doi: 10.1016/j.biortech.2010.05.092
93. Maier, M., Kotman, N., Friedrichs, C., Andrieu, J., Wagner, M., Graf, R., et al. (2011). Highly site specific, protease cleavable, hydrophobic peptide-polymer nanoparticles. Macromolecules 44, 6258-6267. doi: 10.1021/ma201149b
94. Mailander, V., and Landfester, K. (2009). Interaction of nanoparticles with cells. Biomacromolecules 10, 2379-2400. doi: 10.1021/bm900266r
95. Malzahn, K., Jamieson, W. D., Dröge, M., Mailänder, V., Jenkins, A. T. A., Weiss, C. K., et al. (2014a). Advanced dextran based nanogels for fighting Staphylococcus aureus infections by sustained zinc release. J. Mater. Chem. B 2, 2175-2183. doi: 10.1039/c3tb21335h
96. Malzahn, K., Marsico, F., Koynov, K., Landfester, K., Weiss, C. K., and Wurm, F. R. (2014b). Selective interfacial olefin cross metathesis for the preparation of hollow nanocapsules. ACS Macro Lett. 3, 40-43. doi: 10.1021/mz400578e
97. Mao, H. Q., and Leong, K. W. (2005). "Design of polyphosphoester-DNA nanoparticles for non-viral gene delivery, " in Advances in Genetics, eds M.-C. H. Leaf Huang and W. Ernst (San Diego, CA; London: Academic Press), 275-306.
98. McClements, D. J. (2012). Nanoemulsions versus microemulsions: terminology, differences, and similarities. Soft Matter 8, 1719. doi: 10.1039/c2sm06903b
99. Miao, S., Wang, P., Su, Z., and Zhang, S. (2014). Vegetable-oil-based polymers as future polymeric biomaterials. Acta Biomater. 10, 1692-1704. doi: 10.1016/j.actbio.2013.08.040
100. Miller, C. A. (2006). "Spontaneous emulsification: recent developments with emphasis on self-emulsification, " in Emulsion and Emulsion Stability, Surfactant Science Series, Vol. 61, ed J. Sjöblom (Boca Raton, FL: CRC Press; Taylor & Francis).
101. Montero de Espinosa, L., and Meier, M. A. R. (2011). Plant oils: the perfect renewable resource for polymer science?! Eur. Polym. J. 47, 837-852. doi: 10.1016/j.eurpolymj.2010.11.020
102. Mora-Huertas, C. E., Fessi, H., and Elaissari, A. (2010). Polymer-based nanocapsules for drug delivery. Int. J. Pharm. 385, 113-142. doi: 10.1016/j.ijpharm.2009.10.018
103. Mora-Huertas, C. E., Fessi, H., and Elaissari, A. (2011). Influence of process and formulation parameters on the formation of submicron particles by solvent displacement and emulsification-diffusion methods Critical comparison. Adv. Colloid Interface Sci. 163, 90-122. doi: 10.1016/j.cis.2011.02.005
104. Mosiewicki, M. A., and Aranguren, M. I. (2013). A short review on novel biocomposites based on plant oil precursors. Eur. Polym. J. 49, 1243-1256. doi: 10.1016/j.eurpolymj.2013.02.034
105. Müller, R. H., Mäder, K., and Gohla, S. (2000). Solid lipid nanoparticles (SLN) for controlled drug delivery-a review of the state of the art. Eur. J. Pharm. Biopharm. 50, 161-177. doi: 10.1016/S0939-6411(00)00087-4
106. Muñoz-Espí, R., Weiss, C. K., and Landfester, K. (2012). Inorganic nanoparticles prepared in miniemulsion. Curr. Opin. Colloid Interface Sci. 17, 212-224. doi: 10.1016/j.cocis.2012.04.002
107. Musto, P. (2013). Grand challenges in polymer chemistry: energy, environment, health. Front. Chem. 1:31. doi: 10.3389/fchem.2013.00031
108. Musyanovych, A., Schmitz-Wienke, J., Mailänder, V., Walther, P., and Landfester, K. (2008). Preparation of biodegradable polymer nanoparticles by miniemulsion technique and their cell interactions. Macromol. Biosci. 8, 127-139. doi: 10.1002/mabi.200700241
109. Mutlu, H., and Meier, M. A. R. (2010). Castor oil as a renewable resource for the chemical industry. Eur. J. Lipid Sci. Technol. 112, 10-30. doi: 10.1002/ejlt.200900138
110. Na, H. B., Song, I. C., and Hyeon, T. (2009). Inorganic nanoparticles for MRI contrast agents. Adv. Mater. 21, 2133-2148. doi: 10.1002/adma.200802366
111. Niwa, T., Takeuchi, H., Hino, T., Kunou, N., and Kawashima, Y. (1993). Preparations of biodegradable nanospheres of water-soluble and insoluble drugs with D, L-lactide/glycolide copolymer by a novel spontaneous emulsification solvent diffusion method, and the drug release behavior. J. Control. Release 25, 89-98. doi: 10.1016/0168-3659(93)90097-O
112. Noga, M., Edinger, D., Rödl, W., Wagner, E., Winter, G., and Besheer, A. (2012). Controlled shielding and deshielding of gene delivery polyplexes using hydroxyethyl starch (HES) and alpha-amylase. J. Control. Release 159, 92-103. doi: 10.1016/j.jconrel.2012.01.006
113. Nouvel, C., Raynaud, J., Marie, E., Dellacherie, E., Six, J. L., and Durand, A. (2009). Biodegradable nanoparticles made from polylactide-grafted dextran copolymers. J. Colloid Interface Sci. 330, 337-343. doi: 10.1016/j.jcis.2008.10.069
114. Oh, J. K., Siegwart, D. J., Lee, H. I., Sherwood, G., Peteanu, L., Hollinger, J. O., et al. (2007). Biodegradable nanogels prepared by atom transfer radical polymerization as potential drug delivery carriers: synthesis, biodegradation, in vitro release, and bioconjugation. J. Am. Chem. Soc. 129, 5939-5945. doi: 10.1021/ja069150l
115. Owens, D. E. III., and Peppas, N. A. (2006). Opsonization, biodistribution, and pharmacokinetics of polymeric nanoparticles. Int. J. Pharm. 307, 93-102. doi: 10.1016/j.ijpharm.2005.10.010
116. Paiphansiri, U., Dausend, J., Musyanovych, A., Mailänder, V., and Landfester, K. (2009). Fluorescent polyurethane nanocapsules prepared via inverse miniemulsion: surface functionalization for use as biocarriers. Macromol. Biosci. 9, 575-584. doi: 10.1002/mabi.200800293
117. Pavel, F. M. (2004). Microemulsion polymerization. J. Disper. Sci. Technol. 25, 1-16. doi: 10.1081/DIS-120027662
118. Peracchia, M. T., Fattal, E., Desmaële, D., Besnard, M., Noel, J.-P., Gomis, J. M., et al. (1999a). Stealth PEGylated polycyanoacrylate nanoparticles for intravenous administratio and splenic targeting. J. Control. Release 60, 121-128. doi: 10.1016/S0168-3659(99)00063-2
119. Peracchia, M. T., Harnisch, S., Pinto-Alphandary, H., Gulik, A., Dedieu, J.-C., Desmaële, D., et al. (1999b). Visualization of in vitro protein-rejecting properties of PEGylated stealth(R) polycyanoacrylate nanoparticles. Biomaterials 20, 1269-1275. doi: 10.1016/S0142-9612(99)00021-6
120. Perez, C., Sanchez, A., Putnam, D., Ting, D., Langer, R., and Alonso, M. J. (2001). Poly (lactic acid)-poly (ethylene glycol) nanoparticles as new carriers for the delivery of plasmid DNA. J. Control. Release 75, 211-224. doi: 10.1016/S0168-3659(01)00397-2
121. Pillay, V., Tomar, T., Kumar, M., Kumar, P., Singh, H., and Choonara, Y. E. (2013). In vivo evaluation of a conjugated poly(lactide-ethylene glycol) nanoparticle depot formulation for prolonged insulin delivery in the diabetic rabbit model. Int. J. Nanomedicine. 8, 505-520. doi: 10.2147/IJN.S38011
122. Prabaharan, M., and Mano, J. F. (2005). Chitosan-based particles as controlled drug delivery systems. Drug Deliv. 12, 41-57. doi: 10.1080/10717540590889781
123. Pranger, L., and Tannenbaum, R. (2008). Biobased nanocomposites prepared by in situ polymerization of furfuryl alcohol with cellulose whiskers or montmorillonite clay. Macromolecules 41, 8682-8687. doi: 10.1021/ma8020213
124. Raquez, J. M., Deléglise, M., Lacrampe, M. F., and Krawczak, P. (2010). Thermosetting (bio)materials derived from renewable resources: a critical review. Prog. Polym. Sci. 35, 487-509. doi: 10.1016/j.progpolymsci.2010.01.001
125. Raquez, J.-M., Habibi, Y., Murariu, M., and Dubois, P. (2013). Polylactide (PLA)-based nanocomposites. Prog. Polym. Sci. 38, 1504-1542. doi: 10.1016/j.progpolymsci.2013.05.014
126. Sahil, H., Tapon-Bretaudière, J., Fischer, A.-M., Sternberg, C., Spenlehauer, G., Verrecchia, T., et al. (1997). Interactions of poly(lactic acid) and poly(lactic acid-co-ethylene oxide) nanoparticles with the plasma factors of the coagulation system. Biomaterials 18, 281-288. doi: 10.1016/S0142-9612(96)00146-9
127. Schork, F. J., Luo, Y., Smulders, W., Russum, J. P., Butté, A., and Fontenot, K. (2005). Miniemulsion polymerization. Adv. Polym. Sci. 175, 129-255. doi: 10.1007/b100115
128. Schubert, S., Delaney, J. J. T., and Schubert, U. S. (2011). Nanoprecipitation and nanoformulation of polymers: from history to powerful possibilities beyond poly(lactic acid). Soft Matter 7, 1581-1588. doi: 10.1039/c0sm00862a
129. Schwarz, C., Mehnert, W., Lucks, J. S., and Müller, R. H. (1994). Solid lipid nanoparticles (SLN) for controlled drug delivery. I. Production, characterization and sterilization. J. Control. Release 30, 83-96. doi: 10.1016/0168-3659(94)90047-7
130. Scott, C., Wu, D., Ho, C. C., and Co, C. C. (2005). Liquid-core capsules via interfacial polymerization: a free-radical analogy of the nylon rope trick. J. Am. Chem. Soc. 127, 4160-4161. doi: 10.1021/ja044532h
131. Sharma, V., and Kundu, P. P. (2008). Condensation polymers from natural oils. Prog. Polym. Sci. 33, 1199-1215. doi: 10.1016/j.progpolymsci.2008.07.004
132. Shen, Y., Zhang, S., Zhang, F., Loftis, A., Pavía-Sanders, A., Zou, J., et al. (2013). Polyphosphoester-based cationic nanoparticles serendipitously release integral biologically-active components to serve as novel degradable inducible nitric oxide synthase inhibitors. Adv. Mater. 25, 5609-5614. doi: 10.1002/adma.201302842
133. Siegwart, D. J., Srinivasan, A., Bencherif, S. A., Karunanidhi, A., Oh, J. K., Vaidya, S., et al. (2009). Cellular uptake of functional nanogels prepared by inverse miniemulsion atrp with encapsulated proteins, carbohydrates, and gold nanoparticles. Biomacromolecules 10, 2300-2309. doi: 10.1021/bm9004904
134. Staff, R. H., Landfester, K., and Crespy, D. (2013). Recent advances in the emulsion solvent evaporation technique for the preparation of nanoparticles and nanocapsules. Adv. Polym. Sci. 262, 329-344. doi: 10.1007/12_2013_233
135. Steinbach, T., Alexandrino, E. M., and Wurm, F. R. (2013). Unsaturated poly(phosphoester)s via ring-opening metathesis polymerization. Polym. Chem. 4, 3800-3806. doi: 10.1039/c3py00437f
136. Thioune, O., Fessi, H., Devissaguet, J. P., and Puisieux, F. (1997). Preparation of pseudolatex by nanoprecipitation: influence of the solvent nature on intrinsic viscosity and interaction constant. Int. J. Pharm. 146, 233-238. doi: 10.1016/S0378-5173(96)04830-2
137. Tiarks, F., Landfester, K., and Antonietti, M. (2001). One-step preparation of polyurethane dispersions by miniemulsion polyaddition. J. Polym. Sci. A: Polym. Chem. 39, 2520-2524. doi: 10.1002/pola.1228
138. Torchilin, V. P., and Trubetskoy, V. S. (1995). Which polymers can make nanoparticulate drug carriers long-circulating? Adv. Drug Deliv. Rev. 16, 141-155. doi: 10.1016/0169-409X(95)00022-Y
139. Torza, S., and Mason, S. G. (1970). Three-phase interactions in shear and electrical fields. J. Colloid Interface Sci. 33, 67-83. doi: 10.1016/0021-9797(70)90073-1
140. Urban, M., Musyanovych, A., and Landfester, K. (2009). Fluorescent superparamagnetic polylactide nanoparticles by combination of miniemulsion and emulsion/solvent evaporation techniques. Macromol. Chem. Phys. 210, 961-970. doi: 10.1002/macp.200900071
141. Vallet-Regi, M., Balas, F., and Arcos, D. (2007). Mesoporous materials for drug delivery. Angew. Chem. Int. Ed. Engl. 46, 7548-7558. doi: 10.1002/anie.200604488
142. Van Keuren, E., Bone, A., and Ma, C. B. (2008). Phthalocyanine nanoparticle formation in supersaturated solutions. Langmuir 24, 6079-6084. doi: 10.1021/la800290s
143. Van Keuren, E., Georgieva, E., and Durst, M. (2003). Kinetics of the growth of anthracene nanoparticles. J. Disper. Sci. Technol. 24, 721-729. doi: 10.1081/DIS-120023819
144. Vemula, P. K., and John, G. (2008). Crops: a green approach toward self-assembled soft materials. Acc. Chem. Res. 41, 769-782. doi: 10.1021/ar7002682
145. Vitale, S. A., and Katz, J. L. (2003). Liquid droplet dispersions formed by homogeneous liquid-liquid nucleation: "The Ouzo Effect." Langmuir 19, 4105-4110. doi: 10.1021/la026842o
146. Weiss, C. K., and Landfester, K. (2010). Miniemulsion polymerization as a means to encapsulate organic and inorganic materials. Adv. Polym. Sci. 233, 185-236. doi: 10.1007/12_2010_61
147. Weiss, C. K., Lorenz, M. R., Mailänder, V., and Landfester, K. (2007a). Cellular uptake behavior of unfunctionalized and functionalized pbca particles prepared in a miniemulsion. Macromol. Biosci. 7, 883-896. doi: 10.1002/mabi.200700046
148. Weiss, C. K., Ziener, U., and Landfester, K. (2007b). A route to non-functionalized and functionalized poly (n-butylcyanoacrylate) nanoparticles: preparation in miniemulsion. Macromolecules 40, 928-938. doi: 10.1021/ma061865l
149. Westesen, K., Bunjes, H., and Koch, M. H. J. (1997). Physicochemical characterization of lipid nanoparticles and evaluation of their drug loading capacity and sustained release potential. J. Control. Release 48, 223-236. doi: 10.1016/S0168-3659(97)00046-1
150. Wilbon, P. A., Chu, F., and Tang, C. (2013). Progress in renewable polymers from natural terpenes, terpenoids, and rosin. Macromol. Rapid Commun. 34, 8-37. doi: 10.1002/marc.201200513
151. Wu, D., Scott, C., Ho, C. C., and Co, C. C. (2006). Aqueous-core capsules via interfacial free radical alternating copolymerization. Macromolecules 39, 5848-5853. doi: 10.1021/ma060951i
152. Xu, C., Miranda-Nieves, D., Ankrum, J. A., Matthiesen, M. E., Phillips, J. A., Roes, I., et al. (2012). Tracking mesenchymal stem cells with iron oxide nanoparticle loaded poly(lactide-co-glycolide) microparticles. Nano Lett. 12, 4131-4139. doi: 10.1021/nl301658q
153. Xu, J., Singh, A., and Amiji, M. M. (2014). Redox-responsive targeted gelatin nanoparticles for delivery of combination wt-p53 expressing plasmid DNA and gemcitabine in the treatment of pancreatic cancer. BMC Cancer 14:75. doi: 10.1186/1471-2407-14-75
154. Yiamsawas, D., Baier, G., Thines, E., Landfester, K., and Wurm, F. R. (2014). Biodegradable lignin nanocontainers. RSC Adv. 4, 11661-11663. doi: 10.1039/c3ra47971d
155. Yoo, H. S., Choi, H.-K., and Park, T. G. (2001). Protein-fatty acid complex for enhanced loading and stability within biodegradable nanoparticles. J. Pharm. Sci. 90, 194-201. doi: 10.1002/1520-6017(200102)90:2<194::AID-JPS10>3.0.CO;2-Q
156. Yu, L., Dean, K., and Li, L. (2006). Polymer blends and composites from renewable resources. Prog. Polym. Sci. 31, 576-602. doi: 10.1016/j.progpolymsci.2006.03.002
157. Zaric, M., Lyubomska, O., Touzelet, O., Poux, C., Al-Zahrani, S., Fay, F., et al. (2013). Skin dendritic cell targeting via microneedle arrays laden with antigen-encapsulated polyL-lactide-co-glycolide nanoparticles induces efficient antitumor and antiviral immune responses. ACS Nano 7, 2042-2055. doi: 10.1021/nn304235j
158. Zhang, S., Zou, J., Zhang, F., Elsabahy, M., Felder, S. E., Zhu, J., et al. (2012). Rapid and versatile construction of diverse and functional nanostructures derived from a polyphosphoester-based biomimetic block copolymer system. J. Am. Chem. Soc. 134, 18467-18474. doi: 10.1021/ja309037m
159. Zhi, J., Wang, Y., and Luo, G. (2005). Adsorption of diuretic furosemide onto chitosan nanoparticles prepared with a water-in-oil nanoemulsion system. React. Funct. Polym. 65, 249-257. doi: 10.1016/j.reactfunctpolym.2005.06.009
160. Zini, E., Gazzano, M., Scandola, M., Wallner, S. R., and Gross, R. A. (2008). Glycolipid biomaterials: solid-state properties of a poly(sophorolipid). Macromolecules 41, 7463-7468. doi: 10.1021/ma800496f
161. Zur Mühlen, A., and Mehnert, W. (1998). Drug release and release mechanisms of prednisolone loaded solid lipid nanoparticles. Pharmazie 2, 552-555.