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Preparation of stealth micellar nanoparticles of novel biodegradable and biocompatible brush copolymers with cholesteryl-modified PLA and PEG side chains

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Abstract

Novel amphiphilic brush copolymers, P(CPLAMA)-co-P(PEGMA), of cholesteryl poly(l-lactic acid) (CPLA) and poly(ethylene glycol) monomethyl ether (PEG) with determined hydrophobic/hydrophilic ratios were synthesized by the methacrylate (MA) macromonomer copolymerization method. Brush copolymers were prepared via both free radical polymerization (FRP) and atom transfer radical polymerization (ATRP). The copolymer compositions were determined by 1H NMR spectroscopy. The synthesized copolymers were used to prepare the micellar nanoparticles with hydrophobic CPLA and hydrophilic PEG forming the core and shell, respectively. The critical micelle concentration (CMC) values of the samples produced by FRP (brush copolymer 1) and ATRP (brush copolymer 2) were estimated to be approximately 0.9 and 0.7 mg/L in aqueous solution by a fluorescence probe technique, respectively. The transmission electron microscopy (TEM) images of micelles of the brush copolymers 1 and 2 showed that micelles were spherical in shape with a mean diameter of 111 and 32 nm, respectively. The results showed that the size of micelles became larger with the increase of the molecular weight of polymer and the relative content of the hydrophilic PEG as well. The drug loading efficiency and drug-releasing properties of the micelles were investigated by using naproxen as a hydrophobic model drug. The in vitro release of naproxen-loaded micelles with about 85–89 % loading efficiency and 17–18 % loading capacity was studied by a using dialysis method in phosphate-buffered solution at 37 °C. The drug-releasing characteristics exhibited a phase of slow release. On the basis of the results obtained, the proposed brush copolymers may be useful in various targeted drug delivery applications, especially those involving hydrophobic drugs.

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Acknowledgments

The authors would like to thank the Vice Chancellor of Research of Azarbaijan Shahid Madani University for financially supporting this research. The authors’ warm thanks are also extended to Dr. H. Abdolmohammad zadeh and Mr Rahim Mohammad Rezaee for their useful help.

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Authors and Affiliations

  1. Chemistry Department, Science Faculty, Azarbaijan Shahid Madani University, P.O. Box 53714-161, 5375171379, Tabriz, Iran

    Massoumeh Bagheri & Elham Bigdeli

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  1. Massoumeh Bagheri
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  2. Elham Bigdeli
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Correspondence to Massoumeh Bagheri.

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Bagheri, M., Bigdeli, E. Preparation of stealth micellar nanoparticles of novel biodegradable and biocompatible brush copolymers with cholesteryl-modified PLA and PEG side chains. J Polym Res 20, 84 (2013). https://doi.org/10.1007/s10965-013-0084-x

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  • DOI: https://doi.org/10.1007/s10965-013-0084-x

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