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(MPC) with 2-(Diisopropylamino)Ethyl Methacrylate (DPA), for Intracellular Delivery Applications

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(MPC) with 2-(Diisopropylamino)Ethyl Methacrylate (DPA), for Intracellular Delivery Applications J Mater Sci: Mater Med (2015) 26:150 DOI 10.1007/s10856-015-5480-9 DELIVERY SYSTEMS Nanoprecipitation of polymeric nanoparticle micelles based on 2-methacryloyloxyethyl phosphorylcholine (MPC) with 2-(diisopropylamino)ethyl methacrylate (DPA), for intracellular delivery applications 1 1 2 1 Jonathan P. Salvage • Christopher Thom • Andrew L. Lewis • Gary J. Phillips • Andrew W. Lloyd1 Received: 8 January 2015 / Accepted: 1 March 2015 Ó The Author(s) 2015. This article is published with open access at Springerlink.com Abstract Biodistribution of nanoparticle-based intracel- cellular toxicity, and an apparent cellular uptake was ob- lular delivery systems is mediated primarily by particle size served via confocal laser scanning microscopy. This paper and physicochemical properties. As such, overcoming the presents the first report of an optimised nanoprecipitation rapid removal of these by the reticuloendothelial system methodology for the formation of MPC–DPA nanoparticle remains a significant challenge. To date, a number of micelles, and in doing so achieved monodisperse systems copolymer nanoparticle systems based on 2-methacryloy- with the size and physicochemical characteristics seen as loxyethyl phosphorylcholine (MPC) with 2-(diisopropy- desirable for long circulating therapeutic delivery vehicles. lamino)ethyl methacrylate (DPA), displaying biomimetic and pH responsive properties, have been published, how- ever these have been predominately polymersome based, 1 Introduction whilst micelle systems have remained relatively unex- plored. This study utilised nanoprecipitation to investigate The research and development of systemically adminis- the effects of solvent and buffer choice upon micelle size trable nanoparticulate-based intracellular delivery systems and polydispersity, and found using methanol produced (NIDS) is driven by the need to overcome a number of key monodisperse micelles of circa 70 nm diameter, whilst challenges. The hurdles faced by NIDS include dilution ethanol produced polydisperse systems with nanoparticles induced micelle dissociation, resulting in dose dumping, of circa 128 nm diameter. The choice of aqueous buffer, and the more problematic rapid removal from the circula- dialysis of the systems, extended storage, and exposure to a tory blood stream by the reticuloendothelial system (RES), wide temperature range (5–70 °C) had no significant effect mediated by particle size and physichochemical properties on micelle size, and the systems were highly resistant to [1]. Whilst polymeric micelle systems have been shown to dilution, indicating excellent colloidal stability. Optimisa- be able to withstand dilution to low concentrations, and tion of the nanoprecipitation process, post precipitation, thus offer the potential for systemic stability [2, 3], over- was investigated, and model drugs successfully loaded coming the RES remains a challenge. The main organs of whilst maintaining system stability. Subsequent in vitro the RES, the liver, spleen, and bone marrow, facilitate the studies suggested that the micelles were of negligible removal of conventional NIDS within minutes of intra- venous injection [4]. Two major factors are involved in this rapid removal, & Jonathan P. Salvage (i) opsonisation of the particle, and (ii) particle size. Op- [email protected] sonisation of NIDS occurs rapidly after injection [5] re- 1 sulting in a surface layer of proteins on the NIDS which School of Pharmacy and Biomolecular Sciences, University promote recognition and phagocytosis by the macrophages of Brighton, Huxley Building, Lewes Road, Brighton BN2 4GJ, UK of the RES. Particle size of the NIDS can modulate both mechanical filtration and RES-based macrophage removal. 2 Biocompatibles UK Ltd, a BTG International plc Group Company, Innovation Group, Lakeview, Riverside Way, Micron size range particles face capillary filtration in the Watchmoor Park, Camberley GU15 3YL, UK lungs and spleen [6, 7], with particles of 1–2 lm having 123 150 Page 2 of 14 J Mater Sci: Mater Med (2015) 26:150 been shown to induce maximum phagocytosis [8]. There- best of our knowledge the first report of this MPC100– fore a sub-micron particle size is considered desirable for a DPA100 nanoprecipitated micelle system. long circulating NIDS. However particles above 200 nm are subject to mechanical filtration by the spleen [9], whilst those below 50 nm may be lost through the fenestrae that 2 Materials and methods occur throughout the capillary network of the liver, spleen, and bone marrow [10, 11]. Thus the range of particle sizes 2.1 MPC100–DPA100 diblock copolymer from 50 to 200 nm in diameter appears to offer the pro- spect of resistance to RES clearance. However, it has also The 100–100 diblock length copolymer, comprised of been suggested that the use of protective surface coating 2-methacryloyloxyethyl phosphorylcholine (MPC) with technologies to extend nanoparticle circulatory times is less 2-(diisopropylamino)ethyl methacrylate (DPA), was sup- effective for particles with diameters greater than 150 nm plied by Prof Steven Armes (University of Sheffield, UK), [9], are more effective for particles within a narrower 60 to having been synthesised via atom transfer radical 100 nm size range [12]. When a NIDS possesses long polymerisation (ATRP), and characterised with nuclear circulating properties, tumour targeting can be achieved via magnetic resonance (NMR) and gel permeation chro- the enhanced permeation and retention (EPR) effect, which matography (GPC), as detailed previously [17, 18], where will result in the passive accumulation of the NIDS at the 1H NMR and GPC indicated the block copolymer was well tumour site via the leaky vasculature [13]. The long cir- defined with Mn and polydispersity values of 51,000 and culating properties are desirable as it has been hypothesised 1.27 respectively. that a minimum of six hours are required for there to be effective EPR accumulation [14]. 2.2 Preparation of polymeric micelle systems A number of successful biomedical materials have been via nanoprecipitation successfully developed utilising phosphorylcholine (PC) [15] which possess biomimetic biocompatibility achieved 2.2.1 Solvent ratio, time, and dialysis effect by mimicking the surface of natural phospholipid mem- -1 brane bilayers [16]. This could, in principle, reduce the Solutions of the MPC100–DPA100 copolymer (40 mg ml ) protein adsorption and cell activation of NIDS containing were prepared in methanol (MeOH) (Fisher, UK) and PC, and therefore avoid macrophage-mediated RES ethanol (EtOH) (Fisher, UK), and MeOH:EtOH volume removal. combination ratios of 3:1, 1:1, and 1:3. Aliquots (100 ll) of Since the early reports of PC containing MPC–DPA these were added drop-wise, using a micropipette, to nanoparticle systems [17, 18], there has been significant 9.9 ml of phosphate buffer saline (PBS) (Oxoid, UK), pH progress on the development of these in the form of 7.4, stirring with a 1 cm magnetic flea (1,250 rpm, 2 min) polymeric vesicles, akin to liposomes, known as poly- and subsequently bath sonicated for 5 min. Final copoly- mersomes [19, 20], whereas research into their further mer concentration was 0.4 mg ml-1. The systems were development as micelle-based NIDS has been more limit- examined at time zero (t = 0) and at 6 weeks post micelle ed. Nevertheless, progress has been made with regard to formation (t = 6), (room temperature storage), and also pre demonstrating the continued potential for MPC–DPA and post 1 week of dialysis, (8 kDa molecular weight cut- based micelles to be effective NIDS [21, 22]. As such, this off) (BioDesign, USA), in PBS (pH 7.4) with daily PBS paper reports on the development of MPC100–DPA100 changes, using photon correlation spectroscopy (PCS). based micelle systems, which we have previously demon- strated possess some of the key attributes desirable in a 2.2.2 Solvent, buffer, hydrophobic loading, dilution, NIDS: including drug analogue loading and release, pH and temperature effect responsiveness, dilution stability, and low cellular toxicity; -1 but which were found to be below 50 nm in diameter, and Solutions of the MPC100–DPA100 copolymer (40 mg ml ) of a polydisperse nature, having been formed by via a pH were prepared in MeOH and EtOH with and without a titration method [17]. Herein this paper reports the novel model hydrophobic compound Orange OT dye (OOT) development and optimisation of a rapid and straightfor- (Sigma, UK), at a polymer to OOT mol ratio of 2:1. Ali- ward nanoprecipitation based method to achieve repro- quots (100 ll) of these were added drop-wise to 9.9 ml of ducible production of monodisperse MPC–DPA micelles. PBS, pH 7.4, or MCIlvaines buffer (McB) (in-house), pH In doing so, this study investigated the effects of solvent 7.4, stirring with a 1 cm magnetic flea (1,250 rpm, 2 min) and buffer choice, hydrophobic model drug loading, system and subsequently bath sonicated for 5 min. The systems temperature, and polymer concentration on the particle were examined for dilution and temperature stability using dynamics of the polymeric micelles formed, and is to the PCS. 123 J Mater Sci: Mater Med (2015) 26:150 Page 3 of 14 150 2.2.3 Stirring, sonication, and filtration effect 0.2 lm pore size syringe filters immediately prior to measurement to ensure sample quality. -1 Solutions of the MPC100–DPA100 copolymer (40 mg ml ) The solvent, buffer, hydrophobic compound loading, were prepared in MeOH, and aliquots (100 ll) of these dilution, and temperature effects on the systems were added drop-wise to 9.9 ml of PBS, pH 7.4, under the (Sect. 2.2.2) were examined using PCS, at 25 °C, to de- following preparation conditions: (A) no stirring, no termine Dh and system Pd in response to solvent and buffer sonication, no filtration, (B) no stirring, no sonication, variation, with and without OOT loaded in the systems. 0.22 lm pore size syringe filtered (Millipore), (C) stirring The dilution stability of the PBS systems was examined at (1,250 rpm, 2 min), sonication (5 min), no filtration, 25 °C, by measuring signal intensity (KCps), Dh and Pd in (D) stirring (1,250 rpm, 2 min), sonication (5 min), response to halving dilutions of the micelle solutions made 0.22 lm pore size syringe filtered.
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