Abstract
Recent developments in controlled/living radical polymerization methods (CLRP) have created the opportunity to prepare polymeric based systems with site specific functionality that has significantly expanded the range of physical and chemical properties that can be generated in materials prepared by these systems. For example, CLRP prepared block copolymers can self-assemble into nanoparticles that can be used in drug delivery applications. The development of synthetic procedures for preparation of materials targeting new and more efficient drug delivery systems (DDS) is of great interest since ultimately they can mimic most of the properties of biological systems.
This chapter will initially discuss the key aspects of the development of nanotechnology for drug delivery. The cell internalization process will be described and related with the relevant properties required for the “nanocarrier systems”. Afterwards, a summary of the polymeric systems that can be used for DDS will be provided and the importance of CLRP methods in the preparation of polymer-based systems will be discussed. Finally, mechanisms of block copolymers self-assembly will be discussed and supported with some examples of CLRP-based self-assembly systems for drug delivery applications.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
References
Alonso MJ (2004) Nanomedicines for overcoming biological barriers. Biomed Pharmacother 58:168–172
Freichels H, Jerome R, Jerome C (2011) Sugar-labeled and PEGylated (bio)degradable polymers intended for targeted drug delivery systems. Carbohydr Polym 86:1093–1106
Bajpai AK, Shukla SK, Bhanu S, Kanjane S (2008) Responsive polymers in controlled drug delivery. Prog Polym Sci 33:1088–1118
Yoo JW, Doshi N, Mitragotri S (2011) Adaptive micro and nanoparticles: temporal control over carrier properties to facilitate drug delivery. Adv Drug Deliv Rev 63:1247–1256
Canelas DA, Herlihy KP, DeSimone JM (2009) Top-down particle fabrication: control of size and shape for diagnostic imaging and drug delivery. Wiley Interdiscip Rev Nanomed Nanobiotechnol 1:391–404
Sahay G, Alakhova DY, Kabanov AV (2010) Endocytosis of nanomedicines. J Control Release 145:182–195
Wang J, Byrne JD, Napier ME, DeSimone JM (2011) More effective nanomedicines through particle design. Small 7:1919–1931
Aderem A, Underhill DM (1999) Mechanisms of phagocytosis in macrophages. Annu Rev Immunol 17:593–623
Petros RA, DeSimone JM (2010) Strategies in the design of nanoparticles for therapeutic applications. Nat Rev Drug Discov 9:615–627
Hillaireau H, Couvreur P (2009) Nanocarriers’ entry into the cell: relevance to drug delivery. Cell Mol Life Sci 66:2873–2896
Champion JA, Walker A, Mitragotri S (2008) Role of particle size in phagocytosis of polymeric microspheres. Pharm Res 25:1815–1821
Mayor S, Pagano RE (2007) Pathways of clathrin-independent endocytosis. Nat Rev Mol Cell Biol 8:603–612
Bareford LM, Swaan PW (2007) Endocytic mechanisms for targeted drug delivery. Adv Drug Deliv Rev 59:748–758
Swanson JA, Watts C (1995) Macropinocytosis. Trends Cell Biol 5:424–428
Sharma P, Varma R, Sarasij RC, Ira, Gousset K, Krishnamoorthy G, Rao M, Mayor S (2004) Nanoscale organization of multiple GPI-anchored proteins in living cell membranes. Cell 116:577–589
Kalia M, Kumari S, Chadda R, Hill MM, Parton RG, Mayor S (2006) Arf6-independent GPI-anchored protein-enriched early endosomal compartments fuse with sorting endosomes via a Rab5/phosphatidylinositol-3′-kinase-dependent machinery. Mol Biol Cell 17:3689–3704
Howes MT, Kirkham M, Riches J, Cortese K, Walser PJ, Simpson F, Hill MM, Jones A, Lundmark R, Lindsay MR, Hernandez-Deviez DJ, Hadzic G, McCluskey A, Bashir R, Liu L, Pilch P, McMahon H, Robinson PJ, Hancock JF, Mayor S, Parton RG (2010) Clathrin-independent carriers form a high capacity endocytic sorting system at the leading edge of migrating cells. J Cell Biol 190:675–691
Ferrari M (2008) Nanogeometry: beyond drug delivery. Nat Nanotechnol 3:131–132
Mitragotri S, Lahann J (2009) Physical approaches to biomaterial design. Nat Mater 8:15–23
Matsumura Y, Maeda H (1986) A new concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs. Cancer Res 46:6387–6392
Beningo KA, Wang YL (2002) Fc-receptor-mediated phagocytosis is regulated by mechanical properties of the target. J Cell Sci 115:849–856
Verma A, Stellacci F (2010) Effect of surface properties on nanoparticle-cell interactions. Small 6:12–21
Doshi N, Mitragotri S (2010) Macrophages recognize size and shape of their targets. PLoS One 5:e10051
Decuzzi P, Pasqualini R, Arap W, Ferrari M (2009) Intravascular delivery of particulate systems: does geometry really matter? Pharm Res 26:235–243
Yoo JW, Doshi N, Mitragotri S (2010) Endocytosis and intracellular distribution of PLGA particles in endothelial cells: effect of particle geometry. Macromol Rapid Commun 31:142–148
Frojmovic MM, Milton JG (1982) Human platelet size, shape, and related functions in health and disease. Physiol Rev 62:185–261
Haghgooie R, Toner M, Doyle PS (2010) Squishy non-spherical hydrogel microparticles. Macromol Rapid Commun 31:128–134
Doshi N, Zahr AS, Bhaskar S, Lahann J, Mitragotri S (2009) Red blood cell-mimicking synthetic biomaterial particles. Proc Natl Acad Sci U S A 106:21495–21499
Geng Y, Dalhaimer P, Cai S, Tsai R, Tewari M, Minko T, Discher DE (2007) Shape effects of filaments versus spherical particles in flow and drug delivery. Nat Nanotechnol 2:249–255
Merdan T, Kopecek J, Kissel T (2002) Prospects for cationic polymers in gene and oligonucleotide therapy against cancer. Adv Drug Deliv Rev 54:715–758
Pack DW, Hoffman AS, Pun S, Stayton PS (2005) Design and development of polymers for gene delivery. Nat Rev Drug Discov 4:581–593
He C, Hu Y, Yin L, Tang C, Yin C (2010) Effects of particle size and surface charge on cellular uptake and biodistribution of polymeric nanoparticles. Biomaterials 31:3657–3666
Xiao K, Li Y, Luo J, Lee JS, Xiao W, Gonik AM, Agarwal RG, Lam KS (2011) The effect of surface charge on in vivo biodistribution of PEG-oligocholic acid based micellar nanoparticles. Biomaterials 32:3435–3446
Venkataraman S, Ong WL, Ong ZY, Joachim Loo SC, Ee PL, Yang YY (2011) The role of PEG architecture and molecular weight in the gene transfection performance of PEGylated poly(dimethylaminoethyl methacrylate) based cationic polymers. Biomaterials 32:2369–2378
Cruz LJ, Tacken PJ, Fokkink R, Figdor CG (2011) The influence of PEG chain length and targeting moiety on antibody-mediated delivery of nanoparticle vaccines to human dendritic cells. Biomaterials 32:6791–6803
Blit PH, McClung WG, Brash JL, Woodhouse KA, Santerre JP (2011) Platelet inhibition and endothelial cell adhesion on elastin-like polypeptide surface modified materials. Biomaterials 32:5790–5800
Wang J, Tian S, Petros RA, Napier ME, Desimone JM (2010) The complex role of multivalency in nanoparticles targeting the transferrin receptor for cancer therapies. J Am Chem Soc 132:11306–11313
Spain SG, Cameron NR (2011) A spoonful of sugar: the application of glycopolymers in therapeutics. Polymer Chem 2:60–68
Chen CK, Shiang YC, Huang CC, Chang HT (2011) Using self-assembled aptamers and fibrinogen-conjugated gold nanoparticles to detect DNA based on controlled thrombin activity. Biosens Bioelectron 26:3464–3468
Vogelson CT (2001) Advances in drug delivery systems. Mod Drug Discov 4:49–50
Nair LS, Laurencin CT (2007) Biodegradable polymers as biomaterials. Prog Polym Sci 32:762–798
Grund S, Bauer M, Fischer D (2011) Polymers in drug delivery – state of the art and future trends. Adv Eng Mater 13:B61–B87
Ulery BD, Nair LS, Laurencin CT (2011) Biomedical applications of biodegradable polymers. J Polym Sci, Part B: Polym Phys 49:832–864
Maham A, Tang Z, Wu H, Wang J, Lin Y (2009) Protein-based nanomedicine platforms for drug delivery. Small 5:1706–1721
Pastorino L, Erokhina S, Soumetz FC, Bianchini P, Konovalov O, Diaspro A, Ruggiero C, Erokhin V (2011) Collagen containing microcapsules: smart containers for disease controlled therapy. J Colloid Interface Sci 357:56–62
Kanematsu A, Yamamoto S, Ozeki M, Noguchi T, Kanatani I, Ogawa O, Tabata Y (2004) Collagenous matrices as release carriers of exogenous growth factors. Biomaterials 25:4513–4520
Nagai N, Kumasaka N, Kawashima T, Kaji H, Nishizawa M, Abe T (2010) Preparation and characterization of collagen microspheres for sustained release of VEGF. J Mater Sci Mater Med 21:1891–1898
Holladay C, Keeney M, Greiser U, Murphy M, O’Brien T, Pandit A (2009) A matrix reservoir for improved control of non-viral gene delivery. J Control Release 136:220–225
Viñas-Castells R, Holladay C, di Luca A, Díaz VM, Pandit A (2009) Snail1 down-regulation using small interfering RNA complexes delivered through collagen scaffolds. Bioconjug Chem 20:2262–2269
Krebs MD, Jeon O, Alsberg E (2009) Localized and sustained delivery of silencing RNA from macroscopic biopolymer hydrogels. J Am Chem Soc 131:9204–9206
Naidu BVK, Paulson AT (2011) A new method for the preparation of gelatin nanoparticles: encapsulation and drug release characteristics. J Appl Polym Sci 121:3495–3500
GuhaSarkar S, Banerjee R (2010) Intravesical drug delivery: challenges, current status, opportunities and novel strategies. J Control Release 148:147–159
Guo R, Cheng Y, Ding D, Li X, Zhang L, Jiang X, Liu B (2011) Synthesis and antitumoral activity of gelatin/polyoxometalate hybrid nanoparticles. Macromol Biosci 11:839–847
Kumari A, Yadav SK, Yadav SC (2010) Biodegradable polymeric nanoparticles based drug delivery systems. Colloids Surf B Biointerfaces 75:1–18
Yadav SC, Kumari A, Yadav R (2011) Development of peptide and protein nanotherapeutics by nanoencapsulation and nanobioconjugation. Peptides 32:173–187
Kuijpers AJ, van Wachem PB, van Luyn MJ, Engbers GH, Krijgsveld J, Zaat SA, Dankert J, Feijen J (2000) In vivo and in vitro release of lysozyme from cross-linked gelatin hydrogels: a model system for the delivery of antibacterial proteins from prosthetic heart valves. J Control Release 67:323–336
Huang S, Fu XB (2010) Naturally derived materials-based cell and drug delivery systems in skin regeneration. J Control Release 142:149–159
Kim MS, Shin YM, Lee JH, Kim SI, Nam YS, Shin CS, Shin H (2011) Release kinetics and in vitro bioactivity of basic fibroblast growth factor: effect of the thickness of fibrous matrices. Macromol Biosci 11:122–130
Kratz F (2008) Albumin as a drug carrier: design of prodrugs, drug conjugates and nanoparticles. J Control Release 132:171–183
Sebak S, Mirzaei M, Malhotra M, Kulamarva A, Prakash S (2011) Human serum albumin nanoparticles as an efficient noscapine drug delivery system for potential use in breast cancer: preparation and in vitro analysis. Int J Nanomedicine 5:525–532
Zhao D, Zhao X, Zu Y, Li J, Zhang Y, Jiang R, Zhang Z (2011) Preparation, characterization, and in vitro targeted delivery of folate-decorated paclitaxel-loaded bovine serum albumin nanoparticles. Int J Nanomedicine 5:669–677
Zöphel L, Eisele K, Gropeanu R, Rouhanipour A, Koynov K, Lieberwirth I, Müllen K, Weil T (2010) Preparation of defined albumin–polymer hybrids for efficient cell transfection. Macromol Chem Phys 211:146–153
Baldwin AD, Kiick KL (2010) Polysaccharide-modified synthetic polymeric biomaterials. Peptide Sci 94:128–140
Nagpal K, Singh SK, Mishra DN (2010) Chitosan nanoparticles: a promising system in novel drug delivery. Chem Pharm Bull(Tokyo) 58:1423–1430
Dash M, Chiellini F, Ottenbrite RM, Chiellini E (2011) Chitosan-a versatile semi-synthetic polymer in biomedical applications. Prog Polym Sci 36:981–1014
Peniche H, Peniche C (2011) Chitosan nanoparticles: a contribution to nanomedicine. Polym Int 60:883–889
Wang JJ, Zeng ZW, Xiao RZ, Xie T, Zhou GL, Zhan XR, Wang SL (2011) Recent advances of chitosan nanoparticles as drug carriers. Int J Nanomedicine 6:765–774
de la Fuente M, Raviña M, Paolicelli P, Sanchez A, Seijo B, Alonso MJ (2010) Chitosan-based nanostructures: a delivery platform for ocular therapeutics. Adv Drug Deliv Rev 62:100–117
Ta HT, Dass CR, Dunstan DE (2008) Injectable chitosan hydrogels for localised cancer therapy. J Control Release 126:205–216
Bhattarai N, Gunn J, Zhang MQ (2010) Chitosan-based hydrogels for controlled, localized drug delivery. Adv Drug Deliv Rev 62:83–99
Gaspar VM, Sousa F, Queiroz JA, Correia IJ (2011) Formulation of chitosan-TPP-pDNA nanocapsules for gene therapy applications. Nanotechnology 22:015101
Rudzinski WE, Aminabhavi TM (2010) Chitosan as a carrier for targeted delivery of small interfering RNA. Int J Pharm 399:1–11
Nair LS, Laurencin CT (2006) Polymers as biomaterials for tissue engineering and controlled drug delivery. Adv Biochem Eng Biotechnol 102:47–90
Augst AD, Kong HJ, Mooney DJ (2006) Alginate hydrogels as biomaterials. Macromol Biosci 6:623–633
Séchoy O, Tissié G, Sébastian C, Maurin F, Driot JY, Trinquand C (2000) A new long acting ophthalmic formulation of Carteolol containing alginic acid. Int J Pharm 207:109–116
Hassan MA (2007) A long acting ophthalmic gel formulations of atenolol. Drug Dev Ind Pharm 33:1192–1198
Azhdarinia A, Yang DJ, Yu DF, Mendez R, Oh C, Kohanim S, Bryant J, Kim EE (2005) Regional radiochemotherapy using in situ hydrogel. Pharm Res 22:776–783
Hori Y, Stern PJ, Hynes RO, Irvine DJ (2009) Engulfing tumors with synthetic extracellular matrices for cancer immunotherapy. Biomaterials 30:6757–6767
Hori Y, Winans AM, Huang CC, Horrigan EM, Irvine DJ (2008) Injectable dendritic cell-carrying alginate gels for immunization and immunotherapy. Biomaterials 29:3671–3682
Freeman I, Cohen S (2009) The influence of the sequential delivery of angiogenic factors from affinity-binding alginate scaffolds on vascularization. Biomaterials 30:2122–2131
Han YF, Han YQ, Pan YG, Chen YL, Chai JK (2010) Transplantation of microencapsulated cells expressing VEGF improves angiogenesis in implanted xenogeneic acellular dermis on wound. Transplant Proc 42:1935–1943
Silva EA, Mooney DJ (2010) Effects of VEGF temporal and spatial presentation on angiogenesis. Biomaterials 31:1235–1241
Tian JY, Sun XQ, Chen XG (2008) Formation and oral administration of alginate microspheres loaded with pDNA coding for lymphocystis disease virus (LCDV) to Japanese flounder. Fish Shellfish Immunol 24:592–599
Krebs MD, Salter E, Chen E, Sutter KA, Alsberg E (2010) Calcium phosphate-DNA nanoparticle gene delivery from alginate hydrogels induces in vivo osteogenesis. J Biomed Mater Res A 92:1131–1138
Hornig S, Bunjes H, Heinze T (2009) Preparation and characterization of nanoparticles based on dextran-drug conjugates. J Colloid Interface Sci 338:56–62
Coviello T, Matricardi P, Marianecci C, Alhaique F (2007) Polysaccharide hydrogels for modified release formulations. J Control Release 119:5–24
Shrivastava PK, Shrivastava SK (2009) Dextran polysaccharides: successful macromolecular carrier for drug delivery. Int J Pharm Sci 1:353–368
Shrivastava PK, Shrivastava SK (2010) Dextran carrier macromolecule for colon specific delivery of celecoxib. Curr Drug Deliv 7:144–151
Acharya S, Sahoo SK (2011) PLGA nanoparticles containing various anticancer agents and tumour delivery by EPR effect. Adv Drug Deliv Rev 63:170–183
Kumari A, Yadav SK, Pakade YB, Kumar V, Singh B, Chaudhary A, Yadav SC (2011) Nanoencapsulation and characterization of Albizia chinensis isolated antioxidant quercitrin on PLA nanoparticles. Colloids Surf B Biointerfaces 82:224–232
Mundargi RC, Babu VR, Rangaswamy V, Patel P, Aminabhavi TM (2008) Nano/micro technologies for delivering macromolecular therapeutics using poly(D, L-lactide-co-glycolide) and its derivatives. J Control Release 125:193–209
Sinha VR, Bansal K, Kaushik R, Kumria R, Trehan A (2004) Poly-epsilon-caprolactone microspheres and nanospheres: an overview. Int J Pharm 278:1–23
Natu MV, Gaspar MN, Ribeiro CA, Correia IJ, Silva D, de Sousa HC, Gil MH (2011) A poly(epsilon-caprolactone) device for sustained release of an anti-glaucoma drug. Biomed Mater 6:025003
Wei X, Gong C, Gou M, Fu S, Guo Q, Shi S, Luo F, Guo G, Qiu L, Qian Z (2009) Biodegradable poly(epsilon-caprolactone)-poly(ethylene glycol) copolymers as drug delivery system. Int J Pharm 381:1–18
Sun TM, Du JZ, Yao YD, Mao CQ, Dou S, Huang SY, Zhang PZ, Leong KW, Song EW, Wang J (2011) Simultaneous delivery of siRNA and Paclitaxel via a ‘two-in-one’ micelleplex promotes synergistic tumor suppression. ACS Nano 5:1483–1494
Xiong XB, Lavasanifar A (2011) Traceable multifunctional micellar nanocarriers for cancer-targeted co-delivery of MDR-1 siRNA and Doxorubicin. ACS Nano 5:5202–5213
Heller J, Barr J (2004) Poly(ortho esters)—from concept to reality. Biomacromolecules 5:1625–1632
Heller J, Barr J, Ng SY, Abdellauoi KS, Gurny R (2002) Poly(ortho esters): synthesis, characterization, properties and uses. Adv Drug Deliv Rev 54:1015–1039
Vauthier C, Dubernet C, Chauvierre C, Brigger I, Couvreur P (2003) Drug delivery to resistant tumors: the potential of poly(alkyl cyanoacrylate) nanoparticles. J Control Release 93:151–160
Vauthier C, Labarre D, Ponchel G (2007) Design aspects of poly(alkylcyanoacrylate) nanoparticles for drug delivery. J Drug Target 15:641–663
Anguita-Alonso P, Giacometti A, Cirioni O, Ghiselli R, Orlando F, Saba V, Scalise G, Sevo M, Tuzova M, Patel R, Balaban N (2007) RNAIII-inhibiting-peptide-loaded in vivo Polymethylmethacrylate prevents in vivo Staphylococcus aureus biofilm formation. Antimicrob Agents Chemother 51:2594–2596
Tao SL, Lubeley MW, Desai TA (2003) Bioadhesive poly(methyl methacrylate) microdevices for controlled drug delivery. J Control Release 88:215–228
Yuksel N, Baykara M, Shirinzade H, Suzen S (2011) Investigation of triacetin effect on indomethacin release from poly(methyl methacrylate) microspheres: evaluation of interactions using FT-IR and NMR spectroscopies. Int J Pharm 404:102–109
Dalmoro A, Lamberti G, Titomanlio G, Barba AA, d’Amore M (2010) Enteric micro-particles for targeted oral drug delivery. AAPS PharmSciTech 11:1500–1507
Anderson EM, Noble ML, Garty S, Ma H, Bryers JD, Shen TT, Ratner BD (2009) Sustained release of antibiotic from poly(2-hydroxyethyl methacrylate) to prevent blinding infections after cataract surgery. Biomaterials 30:5675–5681
Nyangoga H, Zecheru T, Filmon R, Baslé MF, Cincu C, Chappard D (2009) Synthesis and use of pHEMA microbeads with human EA.hy 926 endothelial cells. J Biomed Mater Res B Appl Biomater 89:501–507
Minoo-Rabeeh-Hobabi, Hassanzadeh D, Azarmi S, Entezami AA (2007) Effect of synthesis method and buffer composition on the LCST of a smart copolymer of N-isopropylacrylamide and acrylic acid. Polym Adv Technol 18:986–992
Braunecker WA, Matyjaszewski K (2007) Controlled/living radical polymerization: features, developments, and perspectives. Prog Polym Sci 32:93–146
Matyjaszewski K, Tsarevsky NV (2009) Nanostructured functional materials prepared by atom transfer radical polymerization. Nat Chem 1:276–288
Qiu J, Charleux B, Matyjaszewski K (2001) Controlled/living radical polymerization in aqueous media: homogeneous and heterogeneous systems. Prog Polym Sci 26:2083–2134
Matyjaszewski K (1996) Controlled radical polymerization. Curr Opin Solid State Mater Sci 1:769–776
Zetterlund PB, Kagawa Y, Okubo M (2008) Controlled/living radical polymerization in dispersed systems. Chem Rev 108:3747–3794
Matyjaszewski K (1995) Introduction to living polymerization. Living and/or controlled polymerization. J Phys Org Chem 8:197–207
Matyjaszewski K, Gaynor S, Greszta D, Mardare D, Shigemoto T (1995) ‘Living’ and controlled radical polymerization. J Phys Org Chem 8:306–315
Matyjaszewski K, Gaynor S, Wang JS (1995) Controlled radical polymerizations – the use of akyl iodides in degenerative transfer. Macromolecules 28:2093–2095
Moad G, Rizzardo E, Thang SH (2008) Radical addition-fragmentation chemistry in polymer synthesis. Polymer 49:1079–1131
Matyjaszewski K, Xia JH (2001) Atom transfer radical polymerization. Chem Rev 101:2921–2990
Tsarevsky NV, Matyjaszewski K (2007) “Green” atom transfer radical polymerization: from process design to preparation of well-defined environmentally friendly polymeric materials. Chem Rev 107:2270–2299
Wang JS, Matyjaszewski K (1995) Controlled/“living” radical polymerization. atom transfer radical polymerization in the presence of transition-metal complexes. J Am Chem Soc 117:5614–5615
di Lena F, Matyjaszewski K (2010) Transition metal catalysts for controlled radical polymerization. Prog Polym Sci 35:959–1021
Kamigaito M, Ando T, Sawamoto M (2001) Metal-catalyzed living radical polymerization. Chem Rev 101:3689–3745
Davis KA, Matyjaszewski K (2002) Statistical, gradient, block, and graft copolymers by controlled/living radical polymerizations. Adv Polym Sci 159:1–13
Matyjaszewski K, Ziegler MJ, Arehart SV, Greszta D, Pakula T (2000) Gradient copolymers by atom transfer radical copolymerization. J Phys Org Chem 13:775–786
Hadjichristidis N, Iatrou H, Pitsikalis M, Mays J (2006) Macromolecular architectures by living and controlled/living polymerizations. Prog Polym Sci 31:1068–1132
Gao H, Matyjaszewski K (2009) Synthesis of functional polymers with controlled architecture by CRP of monomers in the presence of cross-linkers: from stars to gels. Prog Polym Sci 34:317–350
Coessens V, Pintauer T, Matyjaszewski K (2001) Functional polymers by atom transfer radical polymerization. Prog Polym Sci 26:337–377
Gauthier MA, Gibson MI, Klok HA (2009) Synthesis of functional polymers by post-polymerization modification. Angew Chem Int Ed Engl 48:48–58
Lutz JF, Boerner HG (2008) Modern trends in polymer bioconjugates design. Prog Polym Sci 33:1–39
Boyer C, Bulmus V, Davis TP, Ladmiral V, Liu J, Perrier S (2009) Bioapplications of RAFT polymerization. Chem Rev 109:5402–5436
Fournier D, Hoogenboom R, Schubert US (2007) Clicking polymers: a straightforward approach to novel macromolecular architectures. Chem Soc Rev 36:1369–1380
Huisgen R (1963) 1.3-Dipolare cycloadditionen – Ruckschau und ausblick. Angew Chem Int Ed Engl 75:604–637
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew Chem Int Ed Engl 41:2596–2599
Golas PL, Tsarevsky NV, Sumerlin BS, Walker LM, Matyjaszewski K (2007) Multisegmented block copolymers by ‘click’ coupling of polymers prepared by ATRP. Aust J Chem 60:400–404
Golas PL, Matyjaszewski K (2010) Marrying click chemistry with polymerization: expanding the scope of polymeric materials. Chem Soc Rev 39:1338–1354
Sumerlin BS, Tsarevsky NV, Louche G, Lee RY, Matyjaszewski K (2005) Highly efficient \“click\” functionalization of Poly(3-azidopropyl methacrylate) prepared by ATRP. Macromolecules 38:7540–7545
Tsarevsky NV, Sumerlin BS, Matyjaszewski K (2005) Step-growth “click” coupling of telechelic polymers prepared by atom transfer radical polymerization. Macromolecules 38:3558–3561
Yan L, Ding J, Qi R, Yang L, Hu X, Huang Y, Jing X (2010) Versatile synthesis of functional biodegradable polymers by combining ring-opening polymerization and postpolymerization modification via Michael-type addition reaction. Macromolecules 43:201–207
Schuewer N, Klok HA (2011) Tuning the pH sensitivity of poly(methacrylic acid) brushes. Langmuir 27:4789–4796
Whitesides GM, Mathias JP, Seto CT (1991) Molecular self-assembly and nanochemistry – a chemical strategy for the synthesis of nanostructures. Science 254:1312–1319
Rodriguez-Hernandez J, Chécot F, Gnanou Y, Lecommandoux S (2005) Toward ‘smart’ nano-objects by self-assembly of block copolymers in solution. Prog Polym Sci 30:691–724
Lynd NA, Meuler AJ, Hillmyer MA (2008) Polydispersity and block copolymer self-assembly. Prog Polym Sci 33:875–893
Listak J, Jakubowski W, Mueller L, Plichta A, Matyjaszewski K, Bockstaller MR (2008) Effect of symmetry of molecular weight distribution in block copolymers on formation of “metastable” morphologies. Macromolecules 41:5919–5927
Kim JK, Yang SY, Lee Y, Kim Y (2010) Functional nanomaterials based on block copolymer self-assembly. Prog Polym Sci 35:1325–1349
Allen C, Maysinger D, Eisenberg A (1999) Nano-engineering block copolymer aggregates for drug delivery. Colloids Surf B Biointerfaces 16:3–27
Forster S, Antonietti M (1998) Amphiphilic block copolymers in structure-controlled nanomaterial hybrids. Adv Mater 10:195–217
Israelachvili JN (1992) Intermolecular and surface forces, 2nd edn. Academic, London
Tsitsilianis C, Roiter Y, Katsampas I, Minko S (2008) Diversity of nanostructured self-assemblies from a pH-responsive ABC terpolymer in aqueous media. Macromolecules 41:925–934
Xiong D, He Z, An Y, Li Z, Wang H, Chen X, Shi L (2008) Temperature-responsive multilayered micelles formed from the complexation of PNIPAM-b-P4VP block-copolymer and PS-b-PAA core-shell micelles. Polymer 49:2548–2552
Lee HI, Wu W, Oh JK, Mueller L, Sherwood G, Peteanu L, Kowalewski T, Matyjaszewski K (2007) Light-induced reversible formation of polymeric micelles. Angew Chem Int Ed Engl 46:2453–2457
De Clercq B, Laperre J, Ruys L (2005) The controlled radical polymerisation process as an instrument for tailor-made coating applications. Prog Org Coat 53:195–206
Zeng J, Shi K, Zhang Y, Sun X, Zhang B (2008) Construction and micellization of a noncovalent double hydrophilic block copolymer. Chem Commun (Camb) 32:3753–3755
Shenhar R, Norsten TB, Rotello VM (2005) Polymer-mediated nanoparticle assembly: structural control and applications. Adv Mater 17:657–669
Tyrrell ZL, Shen YQ, Radosz M (2010) Fabrication of micellar nanoparticles for drug delivery through the self-assembly of block copolymers. Prog Polym Sci 35:1128–1143
Forster S, Zisenis M, Wenz E, Antonietti M (1996) Micellization of strongly segregated block copolymers. J Chem Phys 104:9956–9970
Azzam T, Bronstein L, Eisenberg A (2008) Water-soluble surface-anchored gold and palladium nanoparticles stabilized by exchange of low molecular weight ligands with biamphiphilic triblock copolymers. Langmuir 24:6521–6529
Yu S, Azzam T, Rouiller I, Eisenberg A (2009) “Breathing” vesicles. J Am Chem Soc 131:10557–10566
du Sart GG, Rachmawati R, Voet V, Alberda van Ekenstein G, Polushkin E, ten Brinke G, Loos K (2008) Poly(tert-butyl methacrylate-b-styrene-b-4-vinylpyridine) triblock copolymers: synthesis, interactions, and self-assembly. Macromolecules 41:6393–6399
Bivigou-Koumba AM, Kristen J, Laschewsky A, Müller-Buschbaum P, Papadakis CM (2009) Synthesis of symmetrical triblock copolymers of styrene and n-isopropylacrylamide using bifunctional bis(trithiocarbonate)s as RAFT agents. Macromol Chem Phys 210:565–578
Nottelet B, Vert M, Coudane J (2008) Novel amphiphilic degradable poly(epsilon-caprolactone)-graft-poly (4-vinyl pyridine), poly (epsilon-caprolactone)-graft-poly (dimethylaminoethyl methacrylate) and water-soluble derivatives. Macromol Rapid Commun 29:743–750
You YZ, Hong C, Wang W, Lu W, Pan C (2004) Preparation and characterization of thermally responsive and biodegradable block copolymer comprised of PNIPAAM and PLA by combination of ROP and RAFT methods. Macromolecules 37:9761–9767
Bockstaller MR, Mickiewicz RA, Thomas EL (2005) Block copolymer nanocomposites: perspectives for tailored functional materials. Adv Mater 17:1331–1349
Fahmi A, Pietsch T, Mendoza C, Cheval N (2009) Functional hybrid materials. Mater Today 12:44–50
Oh JK, Park JM (2011) Iron oxide-based superparamagnetic polymeric nanomaterials: design, preparation, and biomedical application. Prog Polym Sci 36:168–189
Khandare J, Minko T (2006) Polymer-drug conjugates: progress in polymeric prodrugs. Prog Polym Sci 31:359–397
Read ES, Armes SP (2007) Recent advances in shell cross-linked micelles. Chem Commun 29:3021–3035
Smith AE, Xu X, McCormick CL (2010) Stimuli-responsive amphiphilic (co)polymers via RAFT polymerization. Prog Polym Sci 35:45–93
Siegwart DJ, Oh JK, Matyjaszewski K (2012) ATRP in the design of functional materials for biomedical applications. Prog Polym Sci 37:18–37
Oh JK, Bencherif SA, Matyjaszewski K (2009) Atom transfer radical polymerization in inverse miniemulsion: a versatile route toward preparation and functionalization of microgels/nanogels for targeted drug delivery applications. Polymer 50:4407–4423
Oh JK, Drumright R, Siegwart DJ, Matyjaszewski K (2008) The development of microgels/nanogels for drug delivery applications. Prog Polym Sci 33:448–477
Oh JK, Siegwart DJ, Lee HI, Sherwood G, Peteanu L, Hollinger JO, Kataoka K, Matyjaszewski K (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
Roy D, Cambre JN, Sumerlin BS (2010) Future perspectives and recent advances in stimuli-responsive materials. Prog Polym Sci 35:278–301
Bajpai AK, Bajpai J, Saini R, Gupta R (2011) Responsive polymers in biology and technology. Polym Rev 51:53–97
Pasparakis G, Vamvakaki M (2011) Multiresponsive polymers: nano-sized assemblies, stimuli-sensitive gels and smart surfaces. Polym Chem 2:1234–1248
Mano JF (2008) Stimuli-responsive polymeric systems for biomedical applications. Adv Eng Mater 10:515–527
Schmaljohann D (2006) Thermo- and pH-responsive polymers in drug delivery. Adv Drug Deliv Rev 58:1655–1670
Liechty WB, Kryscio DR, Slaughter BV, Peppas NA (2010) Polymers for drug delivery systems. Ann Rev Chem Biomol Eng 1:149–173
Ma Y, Tang Y, Billingham NC, Armes SP, Lewis AL (2003) Synthesis of biocompatible, stimuli-responsive, physical gels based on ABA triblock copolymers. Biomacromolecules 4:864–868
Schild HG (1992) Poly(N-isopropylacrylamide): experiment, theory and application. Prog Polym Sci 17:63–249
Cho SH, Jhon MS, Yuk SH, Lee HB (1997) Temperature-induced phase transition of poly(N, N-dimethylaminoethyl methacrylate-co-acrylamide). J Polym Sci, Part B: Polym Phys 35:595–598
Yamamoto SI, Pietrasik J, Matyjaszewski K (2008) Temperature- and pH-responsive dense copolymer brushes prepared by ATRP. Macromolecules 41:7013–7020
Yamamoto SI, Pietrasik J, Matyjaszewski K (2007) ATRP synthesis of thermally responsive molecular brushes from Oligo(ethylene oxide) Methacrylates. Macromolecules 40:9348–9353
Dong H, Matyjaszewski K (2010) Thermally responsive P(M(EO)2MA-co-OEOMA) copolymers via AGET ATRP in miniemulsion. Macromolecules 43:4623–4628
Dong H, Mantha V, Matyjaszewski K (2009) Thermally responsive PM(EO)2MA magnetic microgels via activators generated by electron transfer atom transfer radical polymerization in miniemulsion. Chem Mater 21:3965–3972
Filipcsei G, Fehér J, Zrínyi M (2000) Electric field sensitive neutral polymer gels. J Mol Struct 554:109–117
George PM, LaVan DA, Burdick JA, Chen CY, Liang E, Langer R (2006) Electrically controlled drug delivery from biotin-doped conductive polypyrrole. Adv Mater 18:577–581
Jeon G, Yang SY, Byun J, Kim JK (2011) Electrically actuatable smart nanoporous membrane for pulsatile drug release. Nano Lett 11:1284–1288
Katz JS, Burdick JA (2010) Light-responsive biomaterials: development and applications. Macromol Biosci 10:339–348
Narayana Reddy N, Murali Mohan Y, Varaprasad K, Ravindra S, Joy PA, Mohana Raju K (2011) Magnetic and electric responsive hydrogel–magnetic nanocomposites for drug-delivery application. J App Polym Sci 122:1364–1375
Filipcsei G, Csetneki I, Szilagyi A, Zrinyi M (2007) Magnetic field-responsive smart polymer composites. In: Oligomers—polymer composites—molecular imprinting. Springer, Berlin/Heidelberg
Kang H, Liu H, Zhang X, Yan J, Zhu Z, Peng L, Yang H, Kim Y, Tan W (2011) Photoresponsive DNA-cross-linked hydrogels for controllable release and cancer therapy. Langmuir 27:399–408
Bousguet A, Ibarboure E, Papon E, Labrugère C, Rodríguez-Hernández J (2010) Structured multistimuli-responsive functional polymer surfaces obtained by interfacial diffusion of Amphiphilic block copolymers. J Polym Sci A Polym Chem 48:1952–1961
Roy D, Cambre JN, Sumerlin BS (2009) Triply-responsive boronic acid block copolymers: solution self-assembly induced by changes in temperature, pH, or sugar concentration. Chem Commun 16:2106–2108
Weiss J, Laschewsky A (2011) Temperature-induced self-assembly of triple-responsive triblock copolymers in aqueous solutions. Langmuir 27:4465–4473
Butun V, Billingham NC, Armes SP (1998) Unusual aggregation behavior of a novel tertiary amine methacrylate-based diblock copolymer: formation of micelles and reverse micelles in aqueous solution. J Am Chem Soc 120:11818–11819
Butun V, Liu S, Weaver JVM, Bories-Azeau X, Cai Y, Armes SP (2006) A brief review of ‘schizophrenic’ block copolymers. React Funct Polym 66:157–165
Liu SY, Billingham NC, Armes SP (2001) A schizophrenic water-soluble diblock copolymer. Angew Chem Int Ed Engl 40:2328–2331
Naik SS, Ray JG, Savin DA (2011) Temperature- and pH-responsive self-assembly of poly(propylene oxide)-b-poly(lysine) block copolymers in aqueous solution. Langmuir 27:7231–7240
Jiang X, Zhao B (2008) Tuning micellization and dissociation transitions of thermo- and ph-sensitive poly(ethylene oxide)-b-poly(methoxydi(ethylene glycol) methacrylate-co-methacrylic acid) in aqueous solution by combining temperature and ph triggers. Macromolecules 41:9366–9375
Xiong DA, Shi L, Jiang X, An Y, Chen X, Lü J (2007) Composite worm-like aggregates formed from a pair of block-copolymers containing hydrogen-bonding donor and acceptor. Macromol Rapid Commun 28:194–199
Liu SY, Armes SP (2002) Polymeric surfactants for the new millennium: a pH-responsive, zwitterionic, schizophrenic diblock copolymer. Angew Chem Int Ed Eng 41:1413–1416
Du J, O’Reilly RK (2010) pH-Responsive vesicles from a schizophrenic diblock copolymer. Macromol Chem Phys 211:1530–1537
Wang L, Liu M, Gao C, Ma L, Cui D (2010) A pH-, thermo-, and glucose-, triple-responsive hydrogels: synthesis and controlled drug delivery. React Funct Polym 70:159–167
Timko BP, Dvir T, Kohane DS (2010) Remotely triggerable drug delivery systems. Adv Mater 22:4925–4943
Wiradharma N, Zhang Y, Venkataraman S, Hedrick JL, Yanga YY (2009) Self-assembled polymer nanostructures for delivery of anticancer therapeutics. Nano Today 4:302–317
Branco MC, Schneider JP (2009) Self-assembling materials for therapeutic delivery. Acta Biomater 5:817–831
Onaca O, Enea R, Hughes DW, Meier W (2009) Stimuli-responsive polymersomes as nanocarriers for drug and gene delivery. Macromol Biosci 9:129–139
Alarcon CDH, Pennadam S, Alexander C (2005) Stimuli responsive polymers for biomedical applications. Chem Soc Rev 34:276–285
Calderón M, Quadir MA, Strumia M, Haag R (2010) Functional dendritic polymer architectures as stimuli-responsive nanocarriers. Biochimie 92:1242–1251
Motornov M, Roiter Y, Tokarev I, Minko S (2010) Stimuli-responsive nanoparticles, nanogels and capsules for integrated multifunctional intelligent systems. Prog Polym Sci 35:174–211
York AW, Kirkland SE, McCormick CL (2008) Advances in the synthesis of amphiphilic block copolymers via RAFT polymerization: stimuli-responsive drug and gene delivery. Adv Drug Deliv Rev 60:1018–1036
Nishiyama N, Kataoka K (2006) Current state, achievements, and future prospects of polymeric micelles as nanocarriers for drug and gene delivery. Pharmacol Ther 112:630–648
Fu R, Fu GD (2011) Polymeric nanomaterials from combined click chemistry and controlled radical polymerization. Polym Chem 2:465–475
Kataoka K, Harada A, Nagasaki Y (2001) Block copolymer micelles for drug delivery: design, characterization and biological significance. Adv Drug Deliv Rev 47:113–131
Sant V, Smith D, Leroux J (2004) Novel pH-sensitive supramolecular assemblies for oral delivery of poorly water soluble drugs: preparation and characterization. J Control Release 97:301–312
Yuan W, Yuan J, Zheng S, Hong X (2007) Synthesis, characterization, and controllable drug release of dendritic star-block copolymer by ring-opening polymerization and atom transfer radical polymerization. Polymer 48:2585–2594
Licciardi M, Tang Y, Billingham NC, Armes SP, Lewis AL (2005) Synthesis of novel folic acid-functionalized biocompatible block copolymers by atom transfer radical polymerization for gene delivery and encapsulation of hydrophobic drugs. Biomacromolecules 6:1085–1096
Karanikolopoulos N, Pitsikalis M, Hadjichristidis N, Georgikopoulou K, Calogeropoulou T, Dunlap JR (2007) pH-responsive aggregates from double hydrophilic block copolymers carrying zwitterionic groups. Encapsulation of antiparasitic compounds for the treatment of Leishmaniasis. Langmuir 23:4214–4224
Tang Y, Liu SY, Armes SP, Billingham NC (2003) Solubilization and controlled release of a hydrophobic drug using novel micelle-forming ABC triblock copolymers. Biomacromolecules 4:1636–1645
Ahmed F, Pakunlu RI, Brannan A, Bates F, Minko T, Discher DE (2006) Biodegradable polymersomes loaded with both paclitaxel and doxorubicin permeate and shrink tumors, inducing apoptosis in proportion to accumulated drug. J Control Release 116:150–158
Du J, O’Reilly RK (2009) Advances and challenges in smart and functional polymer vesicles. Soft Matter 5:3544–3561
Qin S, Geng Y, Discher DE, Yang S (2006) Temperature-controlled assembly and release from polymer vesicles of poly(ethylene oxide)-block-poly(N-isopropylacrylamide). Adv Mater 18:2905–2909
Tian L, Hammond PT (2006) Comb-dendritic block copolymers as tree-shaped macromolecular amphiphiles for nanoparticle self-assembly. Chem Mater 18:3976–3984
Tian L, Nguyen P, Hammond PT (2006) Vesicular self-assembly of comb-dendritic block copolymers. Chem Commun 33:3489–3491
Yu WY, Zhang N (2009) Surface modification of nanocarriers for cancer therapy. Curr Nanosci 5:123–134
Veronese FM, Mero A (2008) The impact of PEGylation on biological therapies. BioDrugs 22:315–329
Reichelt S, Elsner C, Pender A, Buchmeiser MR (2011) Tailoring the surface of magnetic microparticles for protein immobilization. J Appl Polym Sci 121:3628–3634
Lu AH, Salabas EL, Schuth F (2007) Magnetic nanoparticles: synthesis, protection, functionalization, and application. Angew Chem Int Ed Engl 46:1222–1244
Lin PC, Ueng SH, Yu SC, Jan MD, Adak AK, Yu CC, Lin CC (2007) Surface modification of magnetic nanoparticle via Cu(I)-Catalyzed alkyne-azide 2+3 cycloaddition. Org Lett 9:2131–2134
Shim M, Wong Shi Kam N, Chen RJ, Li Y, Dai H (2002) Functionalization of carbon nanotubes for biocompatibility and biomolecular recognition. Nano Lett 2:285–288
Liu Z, Sun X, Nakayama-Ratchford N, Dai H (2007) Supramolecular chemistry on water-soluble carbon nanotubes for drug loading and delivery. ACS Nano 1:50–56
Prencipe G, Tabakman SM, Welsher K, Liu Z, Goodwin AP, Zhang L, Henry J, Dai H (2009) PEG branched polymer for functionalization of nanomaterials with ultralong blood circulation. J Am Chem Soc 131:4783–4787
Jiang X, Lok MC, Hennink WE (2007) Degradable-brushed pHEMA–pDMAEMA synthesized via ATRP and click chemistry for gene delivery. Bioconjug Chem 18:2077–2084
Du JZ, Tang LY, Song WJ, Shi Y, Wang J (2009) Evaluation of polymeric micelles from brush polymer with poly(epsilon-caprolactone)-b-poly(ethylene glycol) side chains as drug carrier. Biomacromolecules 10:2169–2174
Ma YH, Tang Y, Billingham NC, Armes SP, Lewis AL, Lloyd AW, Salvage JP (2003) Well-defined biocompatible block copolymers via atom transfer radical polymerization of 2-methacryloyloxyethyl phosphorylcholine in protic media. Macromolecules 36:3475–3484
Hu YQ, Kim MS, Kim BS, Lee DS (2007) Synthesis and pH-dependent micellization of 2-(diisopropylamino)ethyl methacrylate based amphiphilic diblock copolymers via RAFT polymerization. Polymer 48:3437–3443
Licciardi M, Giammona G, Du J, Armes SP, Tang Y, Lewis AL (2006) New folate-functionalized biocompatible block copolymer micelles as potential anti-cancer drug delivery systems. Polymer 47:2946–2955
Lee SM, Chen H, Dettmer CM, O’Halloran TV, Nguyen ST (2007) Polymer-caged lipsomes: a pH-Responsive delivery system with high stability. J Am Chem Soc 129:15096–15097
Haag R, Kratz F (2006) Polymer therapeutics: concepts and applications. Angew Chem Int Ed Engl 45:1198–1215
Tong R, Cheng J (2008) Paclitaxel-initiated, controlled polymerization of lactide for the formulation of polymeric nanoparticulate delivery vehicles. Angew Chem Int Ed Engl 47:4830–4834
Rettig H, Krause E, Borner HG (2004) Atom transfer radical polymerization with polypeptide initiators: a general approach to block copolymers of sequence-defined polypeptides and synthetic polymers. Macromol Rapid Commun 25:1251–1256
Nicolas J, Mantovani G, Haddleton DM (2007) Living radical polymerization as a tool for the synthesis of polymer-protein/peptide bioconjugates. Macromol Rapid Commun 28:1083–1111
Lele BS, Murata H, Matyjaszewski K, Russell AJ (2005) Synthesis of uniform protein-polymer conjugates. Biomacromolecules 6:3380–3387
Averick S, Simakova A, Park S, Konkolewicz D, Magenau AJD, Mehl RA, Matyjaszewski K (2012) ATRP under biologically relevant conditions: grafting from a protein. ACS Macro Lett 1:6–10
Peeler JC, Woodman BF, Averick S, Miyake-Stoner SJ, Stokes AL, Hess KR, Matyjaszewski K, Mehl RA (2010) Genetically encoded initiator for polymer growth from proteins. J Am Chem Soc 132:13575–13577
Averick SE, Magenau AJD, Simakova A, Woodman BF, Seong A, Mehl RA, Matyjaszewski K (2011) Covalently incorporated protein-nanogels using AGET ATRP in an inverse miniemulsion. Polym Chem 2:1476–1478
Averick S, Paredes E, Li W, Matyjaszewski K, Das SR (2011) Direct DNA conjugation to star polymers for controlled reversible assemblies. Bioconjug Chem 22:2030–2037
Shakya AK, Sami H, Srivastava A, Kumar A (2010) Stability of responsive polymer-protein bioconjugates. Prog Polym Sci 35:459–486
Acknowledgements
The authors gratefully acknowledge FP7-Health-2009-2.4.4-2-Project RdCVF for financial support.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Rocha, N. et al. (2013). The Importance of Controlled/Living Radical Polymerization Techniques in the Design of Tailor Made Nanoparticles for Drug Delivery Systems. In: Coelho, J. (eds) Drug Delivery Systems: Advanced Technologies Potentially Applicable in Personalised Treatment. Advances in Predictive, Preventive and Personalised Medicine, vol 4. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-6010-3_11
Download citation
DOI: https://doi.org/10.1007/978-94-007-6010-3_11
Published:
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-007-6009-7
Online ISBN: 978-94-007-6010-3
eBook Packages: MedicineMedicine (R0)