Abstract
Thin films of trimethylsilyl cellulose are obtained by spin coating and regenerated to cellulose. The surface is activated with N,N′-carbonyldiimidazole and aminolysis with lysine is carried out in aqueous solution to yield a cellulose lysine carbamate film. The surface is analytically characterized by ATR-IR spectroscopy, zetapotential measurements, contact angle measurements, and atomic force microscopy. The amount of functional groups is determined by pH potentiometric titration as well as the ninhydrin test and is in the range of 25 pmolcm−2. Adsorption of bovine serum albumine (BSA) and fibrinogen on the cellulose film and the cellulose lysine carbamate surface is studied at different pH values by quartz crystal microbalance with dissipation monitoring (QCM-D). The adsorption of BSA is significantly reduced by modification with lysine. At physiological pH value (7.4) the adsorption of fibrinogen is even six times lower (1.0 mgm−2) compared to the pure cellulose surface. Thus, cellulose thin films with lysine moieties are promising candidates for hemo-compatible antifouling surfaces in the field of blood contacting devices.
Similar content being viewed by others
References
Alila S, Ferraria AM, do Rego AMB, Boufi S (2009) Controlled surface modification of cellulose fibers by amino derivatives using N,N′-carbonyldiimidazole as activator. Carbohydr Polym 77(3):553–562. https://doi.org/10.1016/j.carbpol.2009.01.028
Bellmann C, Caspari A, Albrecht V, Doan TTL, Mäder E, Luxbacher T, Kohl R (2005) Electrokinetic properties of natural fibres. Colloids Surf A 267(1–3):19–23. https://doi.org/10.1016/j.colsurfa.2005.06.033
Berglin M, Pinori E, Sellborn A, Andersson M, Hulander M, Elwing H (2009) Fibrinogen adsorption and conformational change on model polymers: novel aspects of mutual molecular rearrangement. Langmuir 25(10):5602–5608. https://doi.org/10.1021/la803686m
Boufi S, Vilar MR, Parra V, Ferraria AM, do Rego AMB (2008) Grafting of porphyrins on cellulose nanometric films. Langmuir 24(14):7309–7315. https://doi.org/10.1021/la800786s
Chen SF, Li LY, Zhao C, Zheng J (2010) Surface hydration: principles and applications toward low-fouling/nonfouling biomaterials. Polymer 51(23):5283–5293. https://doi.org/10.1016/j.polymer.2010.08.022
Curotto E, Aros F (1993) Quantitative determination of chitosan and the percentage of free amino groups. Anal Biochem 211(2):240–241. https://doi.org/10.1006/abio.1993.1263
Edwards JV, Batiste SL, Gibbins EM, Goheen SC (1999) Synthesis and activity of NH2- and COOH-terminal elastase recognition sequences on cotton. J Pept Res 54(6):536–543. https://doi.org/10.1034/j.1399-3011.1999.00134.x
Edwards JV, Prevost N, Sethumadhavan K, Ullah A, Condon B (2013) Peptide conjugated cellulose nanocrystals with sensitive human neutrophil elastase sensor activity. Cellulose 20(3):1223–1235. https://doi.org/10.1007/s10570-013-9901-y
Elschner T, Reishofer D, Kargl R, Griesser T, Heinze T, Stana-Kleinschek K (2016) Reactive cellulose-based thin films—a concept for multifunctional polysaccharide surfaces. RSC Adv 6(76):72,378–72,385 10.1039/c6ra14227c
Fujii S, Kido M, Sato M, Higaki Y, Hirai T, Ohta N, Kojio K, Takahara A (2015) pH-Responsive and selective protein adsorption on an amino acid-based zwitterionic polymer surface. Polym Chem 6(39):7053–7059. https://doi.org/10.1039/c5py00783f
Gericke M, Doliška A, Stana J, Liebert T, Heinze T, Stana-Kleinschek K (2011) Semi-synthetic polysaccharide sulfates as anticoagulant coatings for pet, 1-cellulose sulfate. Macromol Biosci 11(4):549–556. https://doi.org/10.1002/mabi.201000419
Indest T, Laine J, Kleinschek KS, Zemljič LF (2010) Adsorption of human serum albumin (HSA) on modified PET films monitored by QCM-D, XPS and AFM. Colloids Surf A 360(1–3):210–219. https://doi.org/10.1016/j.colsurfa.2010.03.003
Jedvert K, Elschner T, Heinze T (2017) Adsorption studies of amino cellulose on cellulosics. Macromol Mater Eng 302(7):1700,022. https://doi.org/10.1002/mame.201700022
Kumari S, Chauhan GS (2014) New cellulose-lysine schiff-base-based sensor-adsorbent for mercury ions. ACS Appl Mater Interfaces 6(8):5908–5917. https://doi.org/10.1021/am500820n
Li WC, Liu QS, Liu LY (2014) Amino acid-based zwitterionic polymers: antifouling properties and low cytotoxicity. J Biomater Sci Polym Ed 25(14–15):1730–1742. https://doi.org/10.1080/09205063.2014.948332
Liu QS, Singh A, Liu LY (2013) Amino acid-based zwitterionic poly(serine methacrylate) as an antifouling material. Biomacromolecules 14(1):226–231. https://doi.org/10.1021/bm301646y
Lord MS, Whitelock JM, Simmons A, Williams RL, Milthorpe BK (2014) Fibrinogen adsorption and platelet adhesion to silica surfaces with stochastic nanotopography. Biointerphases 9(4):041,002. https://doi.org/10.1116/1.4900993
Mohan T, Kargl R, Doliška A, Vesel A, Köstler S, Ribitsch V, Stana-Kleinschek K (2011) Wettability and surface composition of partly and fully regenerated cellulose thin films from trimethylsilyl cellulose. J Colloid Interface Sci 358(2):604–610. https://doi.org/10.1016/j.jcis.2011.03.022
Mohan T, Kargl R, Doliška A, Ehmann HMA, Ribitsch V, Stana-Kleinschek K (2013a) Enzymatic digestion of partially and fully regenerated cellulose model films from trimethylsilyl cellulose. Carbohydr Polym 93(1):191–198. https://doi.org/10.1016/j.carbpol.2012.02.033
Mohan T, Zarth CSP, Doliška A, Kargl R, Griesser T, Spirk S, Heinze T, Stana-Kleinschek K (2013b) Interactions of a cationic cellulose derivative with an ultrathin cellulose support. Carbohydr Polym 92(2):1046–1053. https://doi.org/10.1016/j.carbpol.2012.10.026
Mohan T, Findenig G, Hollbacher S, Cerny C, Ristic T, Kargl R, Spirk S, Maver U, Stana-Kleinschek K, Ribitsch V (2014) Interaction and enrichment of protein on cationic polysaccharide surfaces. Colloids Surf 123:533–B 541. https://doi.org/10.1016/j.colsurfb.2014.09.053
Mohan T, Niegelhell K, Zarth CSP, Kargl R, Kostler S, Ribitsch V, Heinze T, Spirk S, Stana-Kleinschek K (2014b) Triggering protein adsorption on tailored cationic cellulose surfaces. Biomacromolecules 15(11):3931–3941. https://doi.org/10.1021/bm500997s
Mohan T, Kargl R, Tradt KE, Kulterer MR, Bračič M, Hribernik S, Stana-Kleinschek K, Ribitsch V (2015) Antifouling coating of cellulose acetate thin films with polysaccharide multilayers. Carbohydr Polym 116:149–158. https://doi.org/10.1016/j.carbpol.2014.04.068
Prochazkova S, Varum KM, Ostgaard K (1999) Quantitative determination of chitosans by ninhydrin. Carbohydr Polym 38(2):115–122. https://doi.org/10.1016/S0144-8617(98)00108-8
Qin DJ, Zhang DL, Shao ZQ, Wang JQ, Mu KG, Liu YH, Zhao LB (2016) Short-chain amino acids functionalized cellulose nanofibers composite ultrafiltration membrane with enhanced properties. RSC Adv. https://doi.org/10.1039/c6ra14696a
Reischl M, Köstler S, Kellner G, Stana-Kleinschek K, Ribitsch V (2008) Oscillating streaming potential measurement system for macroscopic surfaces. Rev Sci Instrum 79(11):113,902. https://doi.org/10.1063/1.3020699
Ristic T, Mohan T, Kargl R, Hribernik S, Doliška A, Stana-Kleinschek K, Fras L (2014) A study on the interaction of cationized chitosan with cellulose surfaces. Cellulose 21(4):2315–2325. https://doi.org/10.1007/s10570-014-0267-6
Rosen JE, Gu FX (2011) Surface functionalization of silica nanoparticles with cysteine: a low-fouling zwitterionic surface. Langmuir 27(17):10,507–10,513. https://doi.org/10.1021/la201940r
Rowen JW, Blaine RL (1947) Sorption of nitrogen and water vapor on textile fibers. Ind Eng Chem 39(12):1659–1663. https://doi.org/10.1021/ie50456a029
Schaub M, Wenz G, Wegner G, Stein A, Klemm D (1993) Ultrathin films of cellulose on silicon-wafers. Adv Mater 5(12):919–922. https://doi.org/10.1002/adma.19930051209
Shi Q, Su YL, Chen WJ, Peng JM, Nie LY, Zhang L, Jiang ZY (2011) Grafting short-chain amino acids onto membrane surfaces to resist protein fouling. J Membr Sci 366(1–2):398–404. https://doi.org/10.1016/j.memsci.2010.10.032
Shiraishi K, Ohnishi T, Sugiyama K (1998) Preparation of poly(methyl methacrylate) microspheres modified with amino acid moieties. Macromol Chem Phys 199(9):2023–2028. https://doi.org/10.1002/macp.1998.021990934
Vatele JM (2004) Prenyl carbamates: preparation and deprotection. Tetrahedron 60(19):4251–4260. https://doi.org/10.1016/j.tet.2004.03.028
Wasilewska M, Adamczyk Z, Jachimska B (2009) Structure of fibrinogen in electrolyte solutions derived from dynamic light scattering (dls) and viscosity measurements. Langmuir 25(6):3698–3704. https://doi.org/10.1021/la803662a
Wertz CF, Santore MM (2002) Fibrinogen adsorption on hydrophilic and hydrophobic surfaces: geometrical and energetic aspects of interfacial relaxations. Langmuir 18(3):706–715. https://doi.org/10.1021/la011075z
Acknowledgments
The financial support of the German Research Foundation (DFG, Research Fellowship [Grant Number EL843/1-1]) is gratefully acknowledged. The authors thank Ana Bratuša and Tanja Kos for their experimental assistance.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Elschner, T., Bračič, M., Mohan, T. et al. Modification of cellulose thin films with lysine moieties: a promising approach to achieve antifouling performance. Cellulose 25, 537–547 (2018). https://doi.org/10.1007/s10570-017-1538-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-017-1538-9