Photo-responsive polymer nanocapsules

This work reports on the preparation of UV-light responsive nanocapsules based on cross-linked polyamide, obtained by miniemulsion interfacial polymerization. The photo-triggered E-Z transition of azobenzene moieties of the polymer backbone enabled controlled release of encapsulated molecules. Appropriate selection of emulsion conditions allowed tailoring size distribution of the resulting nanocapsules. The light responsiveness of the nanocapsule systems has been evaluated by monitoring size change and release of a fluorescent probe upon UV irradiation, and an unambiguous relationship between capsule size and release kinetics has been highlighted. In particular, the smaller the capsule size, the faster the achieved release. Therefore, the photoresponsiveness of the nanosized capsule systems can be modulated by a proper selection of emulsion and processing parameters. The significance of the reported results lies in the size control of the encapsulating particles, which in turn enables to tailor their swelling kinetics, and to precisely design light-controlled release systems.

[1]  S. Guterres,et al.  Tretinoin-loaded nanocapsules: Preparation, physicochemical characterization, and photostability study. , 2008, International journal of pharmaceutics.

[2]  G. B. Henegouwen,et al.  Protection Against UV‐Induced Reactive Intermediates in Human Cells and Mouse Skin by Glutathione Precursors: A Comparison of N‐Acetylcysteine and Glutathione Ethylester , 1998, Photochemistry and photobiology.

[3]  H. Möhwald,et al.  A novel method for encapsulation of poorly water-soluble drugs: precipitation in polyelectrolyte multilayer shells. , 2002, International journal of pharmaceutics.

[4]  P. Mishra,et al.  Dual coated erodible microcapsules for modified release of diclofenac sodium. , 2004, European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.

[5]  S. Ameerunisha,et al.  Characterization of simple photoresponsive systems and their applications to metal ion transport , 1995 .

[6]  I. Ferrocino,et al.  Nanocomposite polymer films containing carvacrol for antimicrobial active packaging , 2009 .

[7]  H. J. Dorman,et al.  Antimicrobial agents from plants: antibacterial activity of plant volatile oils , 2000, Journal of applied microbiology.

[8]  T. Mason,et al.  Time-Dependent Nanoemulsion Droplet Size Reduction By Evaporative Ripening , 2010 .

[9]  R. García-Valls,et al.  Synthesis, characterization, and photoresponsive behavior of new azobenzene‐containing polyethers , 2009 .

[10]  J. Asua Challenges for industrialization of miniemulsion polymerization , 2014 .

[11]  M. Antonietti,et al.  Miniemulsion Polymerization with Cationic and Nonionic Surfactants: A Very Efficient Use of Surfactants for Heterophase Polymerization , 1999 .

[12]  Gleb B. Sukhorukov,et al.  Optically driven encapsulation using novel polymeric hollow shells containing an azobenzene polymer , 2007 .

[13]  H. Möhwald,et al.  Polymeric microcapsules with light responsive properties for encapsulation and release. , 2010, Advances in colloid and interface science.

[14]  T. Riley,et al.  Antimicrobial activity of essential oils and other plant extracts , 1999, Journal of applied microbiology.

[15]  David J Brayden,et al.  Binding and uptake of biodegradable poly-DL-lactide micro- and nanoparticles in intestinal epithelia. , 1998, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[16]  A. R. Kulkarni,et al.  Biodegradable polymeric nanoparticles as drug delivery devices. , 2001, Journal of controlled release : official journal of the Controlled Release Society.

[17]  K. Bogdanowicz,et al.  Preparation and characterization of light-sensitive microcapsules based on a liquid crystalline polyester. , 2013, Langmuir : the ACS journal of surfaces and colloids.

[18]  Jiucun Chen,et al.  Synthesis and characterization of silica nanoparticles with well-defined thermoresponsive PNIPAM via a combination of RAFT and click chemistry. , 2011, ACS applied materials & interfaces.

[19]  Yang Liu,et al.  Gas phase growth of wurtzite ZnS nanobelts on a large scale , 2013 .

[20]  E. T. Kimura,et al.  Acute toxicity and limits of solvent residue for sixteen organic solvents. , 1971, Toxicology and applied pharmacology.

[21]  D. Poncelet,et al.  Microencapsulation by interfacial polymerisation: membrane formation and structure , 2015, Journal of microencapsulation.

[22]  V. Ambrogi,et al.  Light-Responsive Polymer Micro- and Nano-Capsules , 2016, Polymers.

[23]  Hongfei Lin,et al.  Advanced micro/nanocapsules for self-healing smart anticorrosion coatings , 2015 .

[24]  Masami Hagiya,et al.  Robust and photocontrollable DNA capsules using azobenzenes. , 2010, Nano letters.

[25]  H. Fessi,et al.  Nanocapsules of biodegradable polymers: preparation and characterization by direct high resolution electron microscopy , 2002 .

[26]  S. Jafari,et al.  Optimization of nano-emulsions production by microfluidization , 2007 .

[27]  Weiping Cai,et al.  Fabrication of self-standing silver nanoplate arrays by seed-decorated electrochemical route and their structure-induced properties , 2013 .

[28]  B. Mu,et al.  Superparamagnetic Temperature-Responsive Ionic-Cross-Linked Polymeric Hybrid Nanocapsules via Self-Templating Approach , 2012 .

[29]  D. Quintanar-Guerrero,et al.  Preparation techniques and mechanisms of formation of biodegradable nanoparticles from preformed polymers. , 1998, Drug development and industrial pharmacy.

[30]  Mark E. Davis,et al.  Nanoparticle therapeutics: an emerging treatment modality for cancer , 2008, Nature Reviews Drug Discovery.

[31]  B. Hyman,et al.  Nanoparticles enhance brain delivery of blood–brain barrier-impermeable probes for in vivo optical and magnetic resonance imaging , 2011, Proceedings of the National Academy of Sciences.

[32]  Junlian Huang,et al.  Preparation of liquid-core nanocapsules from poly[(ethylene oxide)-co-glycidol] with multiple hydrophobic linoleates at an oil-water interface and its encapsulation of pyrene. , 2007, Biomacromolecules.

[33]  H. Abolghasemi,et al.  The effects of a surfactant on mean drop size in a mixer-settler extractor , 2009 .

[34]  J. Aguilera,et al.  Influence of particle size on the in vitro digestibility of protein-coated lipid nanoparticles. , 2012, Journal of colloid and interface science.

[35]  Zhiqiang Fan,et al.  Facile fabrication of polymer nanocapsules with cross-linked organic-inorganic hybrid walls. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[36]  R. García-Valls,et al.  Light-induced switching of the wettability of novel asymmetrical poly(vinyl alcohol)-co-ethylene membranes blended with azobenzene polymers. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[37]  Chunhui Huang,et al.  Fluorophore-photochrome co-embedded polymer nanoparticles for photoswitchable fluorescence bioimaging , 2012, Nano Research.

[38]  L. Lyon,et al.  Photoinduced Phase Transitions in Poly(N-isopropylacrylamide) Microgels , 2004 .

[39]  B. Mu,et al.  Preparation of Photo-Sensitive Degradable Polymeric Nanocapsules from Dendrimer Grafted Nano-Silica Templates , 2011 .

[40]  Y. Ng,et al.  Factors influencing the preparation of hollow polymer-graphene oxide microcapsules via Pickering miniemulsion polymerization , 2015 .

[41]  Rosaria Ciriminna,et al.  Sol-gel microencapsulation of odorants and flavors: opening the route to sustainable fragrances and aromas. , 2013, Chemical Society reviews.

[42]  L. Gerschenson,et al.  Development of Edible Films and Coatings with Antimicrobial Activity , 2011 .

[43]  Xing-hong Zhang,et al.  Fabrication of polymer nanocapsules with controllable oligo(ethylene glycol) densities, permeation properties and robustly crosslinked walls. , 2013, ACS applied materials & interfaces.

[44]  S. Rajasekaran,et al.  Treatment of Local Anesthetic-Induced Cardiotoxicity Using Drug Scavenging Nanoparticles. , 2004, Nano letters.

[45]  A. Russo,et al.  Effectiveness of a novel insect-repellent food packaging incorporating essential oils against the red flour beetle (Tribolium castaneum) , 2013 .

[46]  J. Gómez-Estaca,et al.  Advances in antioxidant active food packaging , 2014 .

[47]  K. Horie,et al.  Photochemistry in polymer solids. 9. Photoisomerization of azobenzene in a polycarbonate film , 1989 .

[48]  E. Veldhuizen,et al.  Synergy between essential oil components and antibiotics: a review , 2014, Critical reviews in microbiology.

[49]  Z. Cao,et al.  Synthesis of nanostructured materials in inverse miniemulsions and their applications. , 2013, Nanoscale.

[50]  Wah Chiu,et al.  Remotely triggered liposome release by near-infrared light absorption via hollow gold nanoshells. , 2008, Journal of the American Chemical Society.

[51]  S. Burt,et al.  Essential oils: their antibacterial properties and potential applications in foods--a review. , 2004, International journal of food microbiology.

[52]  O. Poncelet,et al.  A comparative study of non-covalent encapsulation methods for organic dyes into silica nanoparticles , 2011 .

[53]  F. D. Prez,et al.  Polyurea microcapsules with a photocleavable shell: UV-triggered release , 2013 .

[54]  M. Isman Pesticides Based on Plant Essential Oils: Phytochemical and Practical Considerations , 2016 .

[55]  R. García-Valls,et al.  Preparation of a new lightly cross-linked liquid crystalline polyamide by interfacial polymerization. Application to the obtainment of microcapsules with photo-triggered release , 2009 .

[56]  D. Kalemba,et al.  Antibacterial and antifungal properties of essential oils. , 2003, Current medicinal chemistry.

[57]  Chuanglong He,et al.  Effect of pH-responsive alginate/chitosan multilayers coating on delivery efficiency, cellular uptake and biodistribution of mesoporous silica nanoparticles based nanocarriers. , 2014, ACS applied materials & interfaces.

[58]  Patrick Couvreur,et al.  Stimuli-responsive nanocarriers for drug delivery. , 2013, Nature materials.

[59]  Mary M. Caruso,et al.  Robust, double-walled microcapsules for self-healing polymeric materials. , 2010, ACS applied materials & interfaces.

[60]  Limu Wang,et al.  Microfluidic device for controllable chemical release via field-actuated membrane incorporating nanoparticles , 2013 .

[61]  K. Landfester,et al.  pH-Sensitive Nanocapsules with Barrier Properties: Fragrance Encapsulation and Controlled Release , 2014 .

[62]  R. Moreira,et al.  Poly (DL-lactide-co-glycolide) (PLGA) nanoparticles with entrapped trans-cinnamaldehyde and eugenol for antimicrobial delivery applications. , 2011, Journal of food science.

[63]  S. Kanazawa,et al.  Photochemically reversible liquefaction and solidification of multiazobenzene sugar-alcohol derivatives and application to reworkable adhesives. , 2014, ACS applied materials & interfaces.

[64]  Q. Zhong,et al.  Thymol nanoencapsulated by sodium caseinate: physical and antilisterial properties. , 2014, Journal of agricultural and food chemistry.

[65]  F Bakkali,et al.  Biological effects of essential oils--a review. , 2008, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[66]  M. Malinconico,et al.  Cationic copolymers nanoparticles for nonviral gene vectors: synthesis, characterization, and application in gene delivery. , 2010, Journal of biomedical materials research. Part A.

[67]  A. Elaissari,et al.  Nanotechnology olymer-based nanocapsules for drug delivery , 2009 .

[68]  H. Möhwald,et al.  Mesoporous silica nanoparticles for active corrosion protection. , 2011, ACS nano.

[69]  Emanuel Fleige,et al.  Stimuli-responsive polymeric nanocarriers for the controlled transport of active compounds: concepts and applications. , 2012, Advanced drug delivery reviews.

[70]  Yasutaka Matsuo,et al.  Sub-100 nm gold nanoparticle vesicles as a drug delivery carrier enabling rapid drug release upon light irradiation. , 2013, ACS applied materials & interfaces.

[71]  Shuo Chen,et al.  A photo, temperature, and pH responsive spiropyran-functionalized polymer: Synthesis, self-assembly and controlled release , 2016 .

[72]  G. Sukhorukov,et al.  UV-induced disruption of microcapsules with azobenzene groups. , 2014, Soft matter.

[73]  Kunihito Koumoto,et al.  Magnetoresponsive smart capsules formed with polyelectrolytes, lipid bilayers and magnetic nanoparticles. , 2010, ACS applied materials & interfaces.

[74]  H. Möhwald,et al.  Influence of the Ionic Strength on the Polyelectrolyte Multilayers' Permeability , 2003 .