Direct synthesis of Poly(Ԑ-Caprolactone)-block-poly (glycidyl methacrylate) copolymer and its usage as a potential nano micelles carrier for hydrophobic drugs

Journal of the Indian Chemical Society - Tập 99 - Trang 100537 - 2022
Deepak Poddar1, Ankita Singh1, Smriti Bansal1, Sanjeeve Thakur1, Purnima Jain1
1Department of Chemistry, Netaji Subhas University of Technology, Dwarka Sector 3, New Delhi, 110078, India

Tài liệu tham khảo

Riess, 2003, Micellization of block copolymers, Prog. Polym. Sci., 28, 1107, 10.1016/S0079-6700(03)00015-7 Nishiyama, 2006, Current state, achievements, and future prospects of polymeric micelles as nanocarriers for drug and gene delivery, Pharmacol. Ther., 112, 630, 10.1016/j.pharmthera.2006.05.006 Lu, 2013, Polymeric micelles and alternative nanonized delivery vehicles for poorly soluble drugs, Int. J. Pharm., 453, 198, 10.1016/j.ijpharm.2012.08.042 Allen, 1999, Nano-engineering block copolymer aggregates for drug delivery, Colloids Surf. B Biointerfaces, 16, 3, 10.1016/S0927-7765(99)00058-2 Cai, 2007, Micelles of different morphologies - advantages of worm-like filomicelles of PEO-PCL in paclitaxel delivery, Pharm. Res. (N. Y.), 24, 2099, 10.1007/s11095-007-9335-z Brinkhuis, 2011, Polymeric vesicles in biomedical applications, Polym. Chem., 2, 1449, 10.1039/c1py00061f Hedrick, 1998, Dendrimer-like star block and amphiphilic copolymers by combination of ring opening and atom transfer radical polymerization, Macromolecules, 31, 8691, 10.1021/ma980932b Nottelet, 2008, Novel amphiphilic degradable poly(ε-caprolactone)-graft-poly(4-vinyl pyridine), poly(ε-caprolactone)-graft-poly(dimethylaminoethyl methacrylate) and water-soluble derivatives, Macromol. Rapid Commun., 29, 743, 10.1002/marc.200800037 Ma, 2012, Construction of paclitaxel-loaded poly (2-hydroxyethyl methacrylate)-g-poly (lactide)- 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine copolymer nanoparticle delivery system and evaluation of its anticancer activity, Int. J. Nanomed., 7, 1313 Wang, 2011, Synthesis and self-assembly of novel amphiphilic copolymers poly(lactic acid)-block-poly(ascorbyl acrylate), J. Polym. Sci. Part A Polym Chem, 49, 3988, 10.1002/pola.24840 Yoncheva, 2015, Cationic triblock copolymer micelles enhance antioxidant activity, intracellular uptake and cytotoxicity of curcumin, Int. J. Pharm., 490, 298, 10.1016/j.ijpharm.2015.05.057 Gao, 2014, Nanotechnology-based intelligent drug design for cancer metastasis treatment, Biotechnol. Adv., 32, 761, 10.1016/j.biotechadv.2013.10.013 Domurado, 2007, Bioresorbable polyelectrolyte amphiphiles as nanosized carriers for lipophilic drug solubilization and delivery, J. Biomater. Sci. Polym. Ed., 18, 287, 10.1163/156856207779996940 Albertsson, 2003, Recent developments in ring opening polymerization of lactones for biomedical applications, Biomacromolecules, 4, 1466, 10.1021/bm034247a Shi, 2005, Stealth MePEG-PCL micelles: effects of polymer composition on micelle physicochemical characteristics, in vitro drug release, in vivo pharmacokinetics in rats and biodistribution in S180 tumor bearing mice, Colloid Polym. Sci., 283, 954, 10.1007/s00396-004-1243-8 Pohlmann, 2013, Poly(ε-caprolactone) microcapsules and nanocapsules in drug delivery, Expet Opin. Drug Deliv., 10, 623, 10.1517/17425247.2013.769956 Inoue, 1998, An AB block copolymer of oligo(methyl methacrylate) and poly(acrylic acid) for micellar delivery of hydrophobic drags, J. Contr. Release, 51, 221, 10.1016/S0168-3659(97)00172-7 Huang, 2003, Synthesis and characterization of block copolymers of ε-caprolactone and DL-lactide initiated by ethylene glycol or poly(ethylene glycol), Macromol. Chem. Phys., 204, 1994, 10.1002/macp.200350054 Quaglia, 2006, Nanoscopic core-shell drug carriers made of amphiphilic triblock and star-diblock copolymers, Int. J. Pharm., 324, 56, 10.1016/j.ijpharm.2006.07.020 Ponsart, 2002, Study of the grafting of bromoacetylated α-hydroxyω-methoxypoly(ethyleneglycol) onto anionically activated poly(ε-caprolactone), J. Bioact. Compat Polym., 17, 417, 10.1177/088391102030911 Riva, 2007, Combination of ring-opening polymerization and “click chemistry”: toward functionalization and grafting of poly(ε-caprolactone), Macromolecules, 40, 796, 10.1021/ma0624090 Liu, 2004, Synthesis and characterization of chitosan-graft-polycaprolactone copolymers, Eur. Polym. J., 40, 2739, 10.1016/j.eurpolymj.2004.07.016 Jeong, 2002, Polymer micelle-like aggregates of novel amphiphilic biodegradable poly(asparagine) grafted with poly(caprolactone), Polymer (Guildf), 44, 583, 10.1016/S0032-3861(02)00816-9 Nottelet, 2007, Novel amphiphilic poly(E-caprolactone)-g-poly(L-lysine) degradable copolymers, Biomacromolecules, 8, 2594, 10.1021/bm700449c Van De Watering, 1998, A mechanistic study of the hydrolytic stability of poly(2-(dimethylamino)ethyl methacrylate), Macromolecules, 31, 8063, 10.1021/ma980689g Van Steenis, 2003, Preparation and characterization of folate-targeted pEG-coated pDMAEMA-based polyplexes, J. Contr. Release, 87, 167, 10.1016/S0168-3659(02)00361-9 Liu, 2004, Polymer grafting via ATRP initiated from macroinitiator synthesized on surface, Langmuir, 20, 6710, 10.1021/la049465j Dou, 2006, Fabrication, characterization and drug loading of pH-dependent multi-morpho- logical nanoparticles based on cellulose Hongjing, Polym. Int., 55, 961 Xu, 2005, Covalent immobilization of glucose oxidase on well-defined poly(glycidyl methacrylate)-Si(111) hybrids from surface-initiated atom-transfer radical polymerization, Biomacromolecules, 6, 1012, 10.1021/bm0493178 Matsumura, 2008, Stability and utility of pyridyl disulfide functionality in RAFT and conventional radical polymerizations, J. Polym. Sci. Part A Polym Chem, 46, 7207, 10.1002/pola.23028 Bagheri, 2014, pH-responsive stealth micelles composed of cholesterol-modified PLA as a nano-carrier for controlled drug release, Prog Biomater, 3, 10.1007/s40204-014-0022-y Bagheri, 2013, Synthesis, characterization, and micellization of cholesteryl-modified amphiphilic poly(L-lactide)-block-poly(glycidyl methacrylate) as a nanocarrier for hydrophobic drugs, J. Polym. Res., 20, 10.1007/s10965-012-0059-3 Wang, 2011, Novel PEG-graft-PLA nanoparticles with the potential for encapsulation and controlled release of hydrophobic and hydrophilic medications in aqueous medium, Int. J. Nanomed., 6, 1443 Karami, 2016, Naproxen conjugated mPEG-PCL micelles for dual triggered drug delivery, Mater. Sci. Eng. C, 61, 665, 10.1016/j.msec.2015.12.067 Munjal, 2018, Core/shell nanoassembly of amphiphilic naproxen-polyethylene glycol: synthesis, characterisation and evaluation as drug delivery system, IET Nanobiotechnol., 12, 814, 10.1049/iet-nbt.2017.0219 Melgert, 1998, Targeting of naproxen covalently linked to HSA to sinusoidal cell types of the liver, J. Drug Target., 5, 329, 10.3109/10611869808997861 Haas, 1997, Drug-targeting to the kidney: renal delivery and degradation of a naproxen-lysozyme conjugate in vivo, Kidney Int., 52, 1693, 10.1038/ki.1997.504 Forte, 2016, Characterization of naproxen-polymer conjugates for drug-delivery, J. Biomater. Sci. Polym. Ed., 27, 69, 10.1080/09205063.2015.1108637 Jankova, 2005, Star polymers by ATRP of styrene and acrylates employing multifunctional initiators, J. Polym. Sci. Part A Polym Chem, 43, 3748, 10.1002/pola.20834 Habaue, 2003, Chemospecific ring-opening polymerization of α-methylenemacrolides, Polymer (Guildf), 44, 5195, 10.1016/S0032-3861(03)00491-9 Wan, 2006, Size-controlled preparation of magnetite nanoparticles in the presence of graft copolymers, J. Mater. Chem., 16, 298, 10.1039/B512605C Matyjaszewski, 2001, Atom transfer radical polymerization, Chem. Rev., 101, 2921, 10.1021/cr940534g Bagheri, 2020, Polycaprolactone/graphene nanocomposites: synthesis, characterization and mechanical properties of electrospun nanofibers, J. Inorg. Organomet. Polym. Mater., 30, 1566, 10.1007/s10904-019-01340-8 Franco, 2017, PCL-b-P(MMA-co-DMAEMA)2 new triblock copolymer for novel pH-sensitive nanocapsules intended for drug delivery to tumors, React. Funct. Polym., 119, 116, 10.1016/j.reactfunctpolym.2017.08.010