Layer-by-layer coating of textile with two oppositely charged cyclodextrin polyelectrolytes for extended drug delivery
Jatupol Junthip
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorNicolas Tabary
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorFeng Chai
INSERM U1008, Controlled Drug Delivery Systems and Biomaterials, Lille, France
Search for more papers by this authorLaurent Leclercq
Université De Montpellier, Institut Des Biomolécules Max Mousseron (IBMM), UMR CNRS 5247, Montpellier, France
Search for more papers by this authorMickael Maton
INSERM U1008, Controlled Drug Delivery Systems and Biomaterials, Lille, France
Search for more papers by this authorFrederic Cazaux
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorChristel Neut
Inserm U995—Team 1, Faculté Des Sciences Pharmaceutiques Et Biologiques, Lille, France
Search for more papers by this authorLaurent Paccou
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorYannick Guinet
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorJean-Noel Staelens
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorMarc Bria
Université Lille 1, Centre Commun De Mesures RMN, Villeneuve D'ascq, France
Search for more papers by this authorDavid Landy
Université Du Littoral Côte D'opale, UCEIV, Dunkerque, France
Search for more papers by this authorAlain Hédoux
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorNicolas Blanchemain
INSERM U1008, Controlled Drug Delivery Systems and Biomaterials, Lille, France
Search for more papers by this authorBernard Martel
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorJatupol Junthip
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorNicolas Tabary
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorFeng Chai
INSERM U1008, Controlled Drug Delivery Systems and Biomaterials, Lille, France
Search for more papers by this authorLaurent Leclercq
Université De Montpellier, Institut Des Biomolécules Max Mousseron (IBMM), UMR CNRS 5247, Montpellier, France
Search for more papers by this authorMickael Maton
INSERM U1008, Controlled Drug Delivery Systems and Biomaterials, Lille, France
Search for more papers by this authorFrederic Cazaux
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorChristel Neut
Inserm U995—Team 1, Faculté Des Sciences Pharmaceutiques Et Biologiques, Lille, France
Search for more papers by this authorLaurent Paccou
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorYannick Guinet
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorJean-Noel Staelens
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorMarc Bria
Université Lille 1, Centre Commun De Mesures RMN, Villeneuve D'ascq, France
Search for more papers by this authorDavid Landy
Université Du Littoral Côte D'opale, UCEIV, Dunkerque, France
Search for more papers by this authorAlain Hédoux
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorNicolas Blanchemain
INSERM U1008, Controlled Drug Delivery Systems and Biomaterials, Lille, France
Search for more papers by this authorBernard Martel
Université Lille 1, Unité Matériaux Et Transformations (UMET) UMR CNRS 8207, Villeneuve D'ascq, France
Search for more papers by this authorAbstract
The coating of a nonwoven textile by polyelectrolyte multilayer film (PEM) issued from cationic and anionic β-cyclodextrin (βCD) polyelectrolytes according to the layer-by-layer (LbL) technique was successfully attempted. The tert-butyl benzoic acid (TBBA) was used as drug model to evaluate the loading capacity and sustained release properties of this PEM system. The build-up of the multilayer assembly was monitored in situ by optical waveguide lightmode spectroscopy (OWLS) on the one hand, and was assessed by gravimetry on the other hand when applied onto the textile substrate. In parallel, the complexation study of TBBA with both CD polyelectrolytes was also investigated by nuclear magnetic resonance (NMR) and isothermal titration calorimetry (ITC). The influence of thermal crosslinking of the multilayered coating on its stability and on TBBA release kinetics in phosphate buffered saline (PBS) at 37°C was studied. Finally, biological and microbiological tests were performed to investigate the cytocompatibility and the intrisic antibacterial activity of multilayer assemblies. © 2016 Wiley Periodicals, Inc. J Biomed Mater Res Part A: 104A: 1408–1424, 2016.
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References
- 1 Decher G, Eckle M, Schmitt J, Struth B. Layer-by-layer assembled multicomposite films. Curr Opin Colloid Interface Sci 1998; 3: 32–39.
- 2 Decher G, Hong JD, Schmitt J. Buildup of ultrathin multilayer films by a self-assembly process: III. Consecutively alternating adsorption of anionic and cationic polyelectrolytes on charged surfaces. Thin Solid Films 1992; 2: 210–211.
- 3 Boudou T, Crouzier T, Ren K, Blin G, Picart C. Multiple functionalities of polyelectrolyte multilayer films: New biomedical applications. Adv Mater 2010; 22: 441–467.
- 4 Gribova V, Auzely-Velty R, Picart C. Polyelectrolyte multilayer assemblies on materials surfaces: From cell adhesion to tissue engineering. Chem Mater 2011; 24: 854–869.
- 5 Hammond PT. Building biomedical materials layer-by-layer. Mater Today 2012; 15: 196–206.
- 6 Boulmedais F, Frisch B, Etienne O, Lavalle P, Picart C, Ogier J, Voegel JC, Schaaf P, Egles C. Polyelectrolyte multilayer films with pegylated polypeptides as a new type of anti-microbial protection for biomaterials. Biomaterials 2004; 25: 2003–2011.
- 7
Vautier D,
Karsten V,
Egles C,
Chluba J,
Schaaf P,
Voegel J-C,
Ogier J. Polyelectrolyte multilayer films modulate cytoskeletal organization in chondrosarcoma cells. J Biomater Sci Polym Ed 2002; 13: 712–731.
10.1163/156856202320269175 Google Scholar
- 8 Leonardo R, Silvia T, Irene B, Virginia P, Paolo D, Arianna M. Quantification of growth and differentiation of C2C12 skeletal muscle cells on PSS–PAH-based polyelectrolyte layer-by-layer nanofilms. Biomed Mater 2011; 6: 031001.
- 9 Phelps JA, Morisse S, Hindié M, Degat M-C, Pauthe E, Van Tassel PR. Nanofilm biomaterials: Localized cross-linking to optimize mechanical rigidity and bioactivity. Langmuir 2011; 27: 1123–1130.
- 10 Jewell CM, Lynn DM. Multilayered polyelectrolyte assemblies as platforms for the delivery of DNA and other nucleic acid-based therapeutics. Adv Drug Deliver Rev 2008; 60: 979–999.
- 11 Vrana NE, Erdemli O, Francius G, Fahs A, Rabineau M, Debry C, Tezcaner A, Keskin D, Lavalle P. Double entrapment of growth factors by nanoparticles loaded into polyelectrolyte multilayer films. J Mater Chem B 2014; 2: 999–1008.
- 12 Pavlukhina S, Sukhishvili S. Polymer assemblies for controlled delivery of bioactive molecules from surfaces. Adv Drug Deliver Rev 2011; 63: 822–836.
- 13 Johnston APR, Cortez C, Angelatos AS, Caruso F. Layer-by-layer engineered capsules and their applications. Curr Opin Colloid Interface Sci 2006; 11: 203–209.
- 14 Jessel N, Oulad-Abdelghani M, Meyer F, Lavalle P, Haîkel Y, Schaaf P, Voegel J-C. Multiple and time-scheduled in situ DNA delivery mediated by β-cyclodextrin embedded in a polyelectrolyte multilayer. Proc Natl Acad Sci USA 2006; 103: 8618–8621.
- 15 Lynn DM, Langer R. Degradable poly(β-amino esters): Synthesis, characterization, and self-assembly with plasmid DNA. J Am Chem Soc 2000; 122: 10761–10768.
- 16 Chen P, Wang X, Dong Y, Hu X. Development of a layer-by-layer assembled film on hydrogel for ocular drug delivery. Int J Polym Sci 2015; 2015: 9.
- 17 El Fagui A, Wintgens V, Gaillet C, Dubot P, Amiel C. Layer-by-layer coated PLA nanoparticles with oppositely charged β-cyclodextrin polymer for controlled delivery of lipophilic molecules. Macromol Chem Phys 2014.
- 18 Smith RC, Riollano M, Leung A, Hammond PT. Layer-by-layer platform technology for small-molecule delivery. Angew Chem Int Ed 2009; 48: 8974–8977.
- 19 Shukla A, Fuller RC, Hammond PT. Design of multi-drug release coatings targeting infection and inflammation. J Controlled Release 2011; 155: 159–166.
- 20 Leguen E, Chassepot A, Decher G, Schaaf P, Voegel J-C, Jessel N. Bioactive coatings based on polyelectrolyte multilayer architectures functionalized by embedded proteins, peptides or drugs. Biomol Eng 2007; 24: 33–41.
- 21 Martin A, Tabary N, Chai F, Leclercq L, Junthip J, Aubert-Viard F, Neut C, Weltrowski M, Blanchemain N, Martel B. Build-up of an antimicrobial multilayer coating on a textile support based on a methylene blue–poly(cyclodextrin) complex. Biomed Mater 2013; 8: 065006.
- 22 Chen X, Wu W, Guo Z, Xin J, Li J. Controlled insulin release from glucose-sensitive self-assembled multilayer films based on 21-arm star polymer. Biomaterials 2011; 32: 1759–1766.
- 23 Deng J, Liu X, Ma L, Cheng C, Shi W, Nie C, Zhao C. Heparin-mimicking multilayer coating on polymeric membrane via LbL assembly of cyclodextrin-based supramolecules. ACS Appl Mater Interfaces 2014; 6: 21603–21614.
- 24 Benkirane-Jessel N, Schwinté P, Falvey P, Darcy R, Haïkel Y, Schaaf P, Voegel JC, Ogier J. Build-up of polypeptide multilayer coatings with anti-inflammatory properties based on the embedding of piroxicam–cyclodextrin complexes. Adv Funct Mater 2004; 14: 174–182.
- 25 Martin A, Tabary N, Leclercq L, Junthip J, Degoutin S, Aubert-Viard F, Cazaux F, Lyskawa J, Janus L, Bria M, et al. Multilayered textile coating based on a β-cyclodextrin polyelectrolyte for the controlled release of drugs. Carbohydr Polym 2013; 93: 718–730.
- 26 Picart C. Polyelectrolyte multilayer films: From physico-chemical properties to the control of cellular processes. Curr Med Chem 2008; 15: 13. Available at: http://www.eurekaselect.com/66587/article#sthash.0vjkHkti.dpuf.
- 27 Rydzek G, Schaaf P, Voegel J-C, Jierry L, Boulmedais F. Strategies for covalently reticulated polymer multilayers. Soft Matter 2012; 8: 9738–9755.
- 28 Kilan K, Warszyński P. Thickness and permeability of multilayers containing alginate cross-linked by calcium ions. Electrochim Acta 2014; 144: 254–262.
- 29 Zhu H, Srivastava R, McShane MJ. Spontaneous loading of positively charged macromolecules into alginate-templated polyelectrolyte multilayer microcapsules. Biomacromolecules 2005; 6: 2221–2228.
- 30 Tengvall P, Jansson E, Askendal A, Thomsen P, Gretzer C. Preparation of multilayer plasma protein films on silicon by EDC/NHS coupling chemistry. Colloids Surf B 2003; 28: 261–272.
- 31 Richert L, Boulmedais F, Lavalle P, Mutterer J, Ferreux E, Decher G, Schaaf P, Voegel J-C, Picart C. Improvement of stability and cell adhesion properties of polyelectrolyte multilayer films by chemical cross-linking. Biomacromolecules 2003; 5: 284–294.
- 32 Panchagnula V, Kumar CV, Rusling JF. Ultrathin layered myoglobin−polyion films functional and stable at acidic pH values. J Am Chem Soc 2002; 124: 12515–12521.
- 33 Picart C, Elkaim R, Richert L, Audoin F, Arntz Y, Da Silva Cardoso M, Schaaf P, Voegel JC, Frisch B. Primary cell adhesion on RGD-functionalized and covalently crosslinked thin polyelectrolyte multilayer films. Adv Funct Mater 2005; 15: 83–94.
- 34 Chaubaroux C, Vrana E, Debry C, Schaaf P, Senger B, Voegel J-C, Haikel Y, Ringwald C, Hemmerlé J, Lavalle P, et al. Collagen-based fibrillar multilayer films cross-linked by a natural agent. Biomacromolecules 2012; 13: 2128–2135.
- 35 Hillberg AL, Holmes CA, Tabrizian M. Effect of genipin cross-linking on the cellular adhesion properties of layer-by-layer assembled polyelectrolyte films. Biomaterials 2009; 30: 4463–4470.
- 36 Moffat KL, Marra KG. Biodegradable poly(ethylene glycol) hydrogels crosslinked with genipin for tissue engineering applications. J Biomed Mater Res B Appl Biomater 2004; 71: 181–187.
- 37 Avrameas S, Ternynck T. The cross-linking of proteins with glutaraldehyde and its use for the preaparation of immunoadsorbernts. Immunochemistry 1969; 6: 53–66.
- 38 Feng X, Pelton R, Leduc M. Mechanical properties of polyelectrolyte complex films based on polyvinylamine and carboxymethyl cellulose. Ind Eng Chem Res 2006; 45: 6665–6671.
- 39 Ren K, Ji J, Shen J. Tunable DNA release from cross-linked ultrathin DNA/PLL multilayered films. Bioconjug Chem 2006; 17: 77–83.
- 40 Li B, Haynie DT. Multilayer biomimetics: Reversible covalent stabilization of a nanostructured biofilm. Biomacromolecules 2004; 5: 1667–1670.
- 41 Bernsmann F, Richert L, Senger B, Lavalle P, Voegel J-C, Schaaf P, Ball V. Use of dopamine polymerisation to produce free-standing membranes from (PLL-HA)n exponentially growing multilayer films. Soft Matter 2008; 4: 1621–1624.
- 42 Liu M, Yue X, Dai Z, Xing L, Ma F, Ren N. Stabilized hemocompatible coating of nitinol devices based on photo-cross-linked alginate/heparin multilayer. Langmuir 2007; 23: 9378–9385.
- 43 Olugebefola SC, Kuhlman WA, Rubner MF, Mayes AM. Photopatterned Nanoporosity in Polyelectrolyte Multilayer Films. Langmuir 2008; 24: 5172–5178.
- 44 Zhang X, Jiang C, Cheng M, Zhou Y, Zhu X, Nie J, Zhang Y, An Q, Shi F. Facile method for the fabrication of robust polyelectrolyte multilayers by post-photo-cross-linking of azido groups. Langmuir 2012; 28: 7096–7100.
- 45 Chien H-W, Chang T-Y, Tsai W-B. Spatial control of cellular adhesion using photo-crosslinked micropatterned polyelectrolyte multilayer films. Biomaterials 2009; 30: 2209–2218.
- 46 Gheith MK, Sinani VA, Wicksted JP, Matts RL, Kotov NA. Single-walled carbon nanotube polyelectrolyte multilayers and freestanding films as a biocompatible platform for neuroprosthetic implants. Adv Mater 2005; 17: 2663–2670.
- 47 Podsiadlo P, Tang Z, Shim BS, Kotov NA. Counterintuitive effect of molecular strength and role of molecular rigidity on mechanical properties of layer-by-layer assembled nanocomposites. Nano Lett 2007; 7: 1224–1231.
- 48 Harris JJ, DeRose PM, Bruening ML. Synthesis of passivating, nylon-like coatings through cross-linking of ultrathin polyelectrolyte films. J Am Chem Soc 1999; 121: 1978–1979.
- 49 Dai J, Jensen AW, Mohanty DK, Erndt J, Bruening ML. Controlling the permeability of multilayered polyelectrolyte films through derivatization, cross-linking, and hydrolysis. Langmuir 2001; 17: 931–937.
- 50 Yang SY, Rubner MF. Micropatterning of polymer thin films with ph-sensitive and cross-linkable hydrogen-bonded polyelectrolyte multilayers. J Am Chem Soc 2002; 124: 2100–2101.
- 51 Ma Y, Sun J, Shen J. Ion-triggered exfoliation of layer-by-layer assembled poly(acrylic acid)/poly(allylamine hydrochloride) films from substrates: A facile way to prepare free-standing multilayer films. Chem Mater 2007; 19: 5058–5062.
- 52 Lee BJ, Kunitake T. Two-dimensional polymer networks of maleic acid copolymers and poly(allylamine) by the Langmuir-Blodgett technique. Langmuir 1994; 10: 557–562.
- 53 Jang W-S, Jensen AT, Lutkenhaus JL. Confinement effects on cross-linking within electrostatic layer-by-layer assemblies containing poly(allylamine hydrochloride) and poly(acrylic acid). Macromolecules 2010; 43: 9473–9479.
- 54 Khutoryanskaya OV, Potgieter M, Khutoryanskiy VV. Multilayered hydrogel coatings covalently-linked to glass surfaces showing a potential to mimic mucosal tissues. Soft Matter 2010; 6: 551–557.
- 55 Junthip J, Tabary N, Leclercq L, Martel B. Cationic β-cyclodextrin polymer applied to a dual cyclodextrin polyelectrolyte multilayer system. Carbohydr Polym 2015; 126: 156–167.
- 56 Martel B, Ruffin D, Weltrowski M, Lekchiri Y, Morcellet M. Water-soluble polymers and gels from the polycondensation between cyclodextrins and poly(carboxylic acid)s: A study of the preparation parameters. J Appl Polym Sci 2005; 97: 433–442.
- 57 Ducoroy L, Bacquet M, Martel B, Morcellet M. Removal of heavy metals from aqueous media by cation exchange nonwoven PET coated with β-cyclodextrin-polycarboxylic moieties. React Funct Polym 2008; 68: 594–600.
- 58 Kurrat R, Prenosil JE, Ramsden JJ. Kinetics of human and bovine serum albumin adsorption at silica–titania surfaces. J Colloid Interface Sci 1997; 185: 1–8.
- 59 Leclercq L, Modena E, Vert M. Adsorption of proteins at physiological concentrations on pegylated surfaces and the compatibilizing role of adsorbed albumin with respect to other proteins according to optical waveguide lightmode spectroscopy (OWLS). J Biomater Sci Polym Ed 2013; 24: 1499–1518.
- 60 Segura-Sanchez F, Bouchemal K, Lebas G, Vauthier C, Santos-Magalhaes NS, Ponchel G. Elucidation of the complexation mechanism between (+)-usnic acid and cyclodextrins studied by isothermal titration calorimetry and phase-solubility diagram experiments. J Mol Recognit 2009; 22: 232–241.
- 61 Bertaut E, Landy D. Improving ITC studies of cyclodextrin inclusion compounds by global analysis of conventional and non-conventional experiments. Beilstein J Org Chem 2014; 10: 2630–2641.
- 62 O'Brien J, Wilson I, Orton T, Pognan F. Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. Eur J Biochem 2000; 267: 5421–5426.
- 63 Martel B, Morcellet M, Ruffin D, Ducoroy L, Weltrowski M. Finishing of polyester fabrics with cyclodextrins and polycarboxylic acids as crosslinking agents. J Inclusion Phenom Macrocyclic Chem 2002; 44 :443–446.
- 64 Ducoroy L, Martel B, Bacquet B, Morcellet M. Ion exchange textiles from the finishing of PET fabrics with cyclodextrins and citric acid for the sorption of metallic cations in water. J Inclusion Phenom Macrocyclic Chem 2007; 57: 271–277.
- 65 Wenz G. Influence of intramolecular hydrogen bonds on the binding potential of methylated β-cyclodextrin derivatives. Beilstein J Org Chem 2012; 8: 1890–1895.
- 66 Weisser M, Nelles G, Wenz G, Mittler-Neher S. Guest-host interactions with immobilized cyclodextrins. Sens Actuators B 1997; 38: 58–67.
- 67 Másson M, Loftsson T, Jónsdóttir S, Fridriksdóttir H, Petersen DS. Stabilisation of ionic drugs through complexation with non-ionic and ionic cyclodextrins. Int J Pharm 1998; 164: 45–55.
- 68 Zia V, Rajewski RA, Stella VJ. Effect of cyclodextrin charge on complexation of neutral and charged substrates: Comparison of (SBE)7M-β-CD to HP-β-CD. Pharm Res 2001; 18: 667–673.
- 69 Liu Y, Cao R, Chen Y, He J-Y. Effect of β-cyclodextrin charge type on the molecular recognition thermodynamics of reactions with (ferrocenylmethyl)dimethylaminium derivatives. J Phys Chem B 2008; 112: 1445–1450.
- 70 Tian Y, Bromberg L, Lin SN, Alan Hatton T, Tam KC. Complexation and release of doxorubicin from its complexes with pluronic P85-b-poly(acrylic acid) block copolymers. J Controlled Release 2007; 121: 137–145.
- 71 Okimoto K, Rajewski R, Uekama K, Jona J, Stella V. The interaction of charged and uncharged drugs with neutral (HP-β-CD) and anionically charged (SBE7-β-CD) β-cyclodextrins. Pharm Res 1996; 13: 256–264.
- 72 Giglio V, Sgarlata C, Vecchio G. Novel amino-cyclodextrin cross-linked oligomer as efficient carrier for anionic drugs: A spectro-scopic and nanocalorimetric investigation. RSC Adv 2015;
- 73 Uppanan P, Channasanon S, Veeranondh S, Tanodekaew S. Synthesis of GTMAC modified chitin–PAA gel and evaluation of its biological properties. J Biomed Mater Res Part A 2011; 98: 185–191.
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