Bioimpacts. 2017;7(3): 155-166.
doi: 10.15171/bi.2017.19
PMID: 29159143
PMCID: PMC5684507
Scopus ID: 85032025993
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Original Research

“Grafting-from” synthesis and characterization of poly (2-ethyl-2-oxazoline)-b-poly (benzyl L-glutamate) micellar nanoparticles for potential biomedical applications

Mohsen Salmanpour 1, Ali Tamaddon 2*, Gholamhossein Yousefi 1,2, Soliman Mohammadi-Samani 1,2

11Depa Department of Pharmaceutics, Shiraz School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran
2 Center for Nanotechnology in Drug Delivery, Shiraz University of Medical Sciences, Shiraz, Iran
*Corresponding author: Ali Tamaddon, amtamadon@gmail.com


Introduction: Recent advances in the field of poly (2-oxazolines) as bio-inspired synthetic pseudopeptides have proven their potential biomedical applications such as drug delivery and tissue engineering.
In order to fabricate a biodegradable micellar nanoparticle of poly (2-ethyl 2-oxazoline)-b-poly (benzyl L-glutamate) or pEOx-b-pBLG, “grafting-from” synthesis approach was used involving consecutive steps of cationic ring-opening polymerization of 2-ethyl-2-oxazoline, amine functionalization of pEOx using 1-Boc-piperazine and N-carboxyanhydride polymerization of γ-benzyl- L-glutamate. Following hydrolysis of the copolymer, the protecting γ-benzyl groups were removed yielding a double-hydrophilic block ionomer of pEOx-b-poly (L-glutamic acid). The polymers were characterized by FTIR, 1H-NMR, size exclusion chromatography and differential scanning calorimetry (DSC). Aqueous assembly of the polymers was investigated by pyrene assay, dynamic light scattering, and transmission electron microscopy. MTT cytotoxicity assay was also performed to determine the cytocompatibility in various tumor cell lines.
Results: The polymeric micelles presented a uni-modal size distribution with mean hydrodynamic diameter of 149.8 ± 10.6 nm and critical aggregation concentration of 60 µg/mL. The average molecular weight of pEOx increased from ~ 14 to 20 kDa for pEOx-b-poly (L-glutamic acid) as determined by light scattering (Debye plot), indicating a successful copolymerization. MTT assay showed little to no practical cytotoxicity at concentrations below 1 mg/mL.
Conclusion: Multi-step synthesis of pEOx-b-pBLG and subsequent alkaline hydrolysis were performed to obtain the block ionomer pEOx-b-poly (L-glutamic acid). Both pEOx-based copolymers can be considered for various potential applications such as loading and delivery of drugs, genes, and contrast agents either by chemical conjugation or physical loading.
Keywords: Grafting-from synthesis, Nano-assembly, Double hydrophilic block ionomer, Poly (2-oxazolines) functionalization, Ring-opening polymerization, Poly (L-glutamic acid)
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Submitted: 02 Aug 2017
Revision: 26 Aug 2017
Accepted: 28 Aug 2017
ePublished: 30 Aug 2017
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