A strong adhesive block polymer coating for antifouling of large molecular weight protein

doi:10.1016/j.cjche.2017.04.007

Abstract

Abstract: Some proteins secreted by microorganisms have large molecularweights.Wereport here an approach to prepare coating by multilayer polymers for antifouling of proteins, especially the proteins with a large molecular weight. Stainless steel was used as the model substrate. The substrate was first coatedwith a hybrid polymer film, which was formed by simultaneous hydrolytic polycondensation of 3-aminopropyltriethoxysilane and polymerization of dopamine (HPAPD). After grafting the macroinitiator 2-bromoisobutyryl bromide, the block polymer brushes PMMA-b-PHEMA were grafted. Three proteins were used to test protein adsorption and antifouling behavior of the coating, including recombinant green fluorescent (54 kDa), recombinant R-transaminase (2×90 kDa), and recombinant catalase (4×98 kDa). It is demonstrated that the block polymer brushes not only can prevent the adsorption of small molecular weight proteins, but also can significantly reduce the adsorption of the large molecular weight proteins.

Key words: Antifouling, Protein, Block polymer, Surface, Polymerization

摘要： Some proteins secreted by microorganisms have large molecularweights.Wereport here an approach to prepare coating by multilayer polymers for antifouling of proteins, especially the proteins with a large molecular weight. Stainless steel was used as the model substrate. The substrate was first coatedwith a hybrid polymer film, which was formed by simultaneous hydrolytic polycondensation of 3-aminopropyltriethoxysilane and polymerization of dopamine (HPAPD). After grafting the macroinitiator 2-bromoisobutyryl bromide, the block polymer brushes PMMA-b-PHEMA were grafted. Three proteins were used to test protein adsorption and antifouling behavior of the coating, including recombinant green fluorescent (54 kDa), recombinant R-transaminase (2×90 kDa), and recombinant catalase (4×98 kDa). It is demonstrated that the block polymer brushes not only can prevent the adsorption of small molecular weight proteins, but also can significantly reduce the adsorption of the large molecular weight proteins.

关键词: Antifouling, Protein, Block polymer, Surface, Polymerization

Xianling Meng, Xia Jiang, Peijun Ji. A strong adhesive block polymer coating for antifouling of large molecular weight protein[J]. Chin.J.Chem.Eng., 2017, 25(12): 1831-1837.

Xianling Meng, Xia Jiang, Peijun Ji. A strong adhesive block polymer coating for antifouling of large molecular weight protein[J]. Chinese Journal of Chemical Engineering, 2017, 25(12): 1831-1837.

References

[1] E. Molena, C. Credi, C. De Marco, M. Levi, S. Turri, G. Simeone, Protein antifouling and fouling-release in perfluoropolyether surfaces, Appl. Surf. Sci. 309 (2014) 160-167.

[2] S. Zheng, Q. Yang, B.Mi, Novel antifouling surface with improved hemocompatibility by immobilization of polyzwitterions onto silicon via click chemistry, Appl. Surf. Sci. 363 (2016) 619-626.

[3] K.J. Lee, M.A. Lee,W. Hwang, H. Park, K.H. Lee, Deacylated lipopolysaccharides inhibit biofilm formation by Gram-negative bacteria, Biofouling 32 (2016) 711-723.

[4] M. Pérez, M. Sánchez, M. Stupak, M. Garcia, M.T. Rojo de Almeida, J.C. Oberti, J.A. Palermo, G. Blustein, Antifouling activity of celastroids isolated from Maytenus species, natural and sustainable alternatives for marine coatings, Ind. Eng. Chem. Res. 53 (2014) 7655-7659.

[5] X. Zhan, G. Zhang, X. Chen, R. He, Q.H. Zhang, F.Q. Chen, Improvement of antifouling and antibacterial properties of poly(ether sulfone) UFmembrane by blendingwith a multifunctional comb copolymer, Ind. Eng. Chem. Res. 54 (2015) 11312-11318.

[6] H. Yuan, B. Qian, W. Zhang, M. Lan, Protein adsorption resistance of PVP-modified polyurethane film prepared by surface-initiated atom transfer radical polymerization, Appl. Surf. Sci. 363 (2016) 483-489.

[8] H. Chen, C. Zhao, M.Z. Zhang, Q. Chen, J. Ma, J. Zheng, Molecular understanding and structural-based design of polyacrylamides and polyacrylates as antifouling materials, Langmuir 32 (2016) 3315-3330.

[9] H.O. Ham, S.H. Park, J.W. Kurutz, I.G. Szleifer, P.B. Messersmith, Antifouling glycocalyx-mimetic peptoids, J. Am. Chem. Soc. 135 (2013) 13015-13022.

[10] C. Falentin-Daudré, E. Faure, T. Svaldo-Lanero, F. Farina, C. Jérome, C.V.D. Weerdt, J. Martial, A.S. Duwez, C. Detrembleur, Antibacterial polyelectrolyte micelles for coating stainless steel, Langmuir 28 (2012) 7233-7241.

[11] X.Y. Zhu, D. Janczewski, S.S.C. Lee, S.L.M. Teo, G.J. Vancso, Cross-linked polyelectrolyte multilayers for marine antifouling applications, ACS Appl. Mater. Interfaces 5 (2013) 5961-5968.

[12] J.C. Yang, C. Zhao, I.F. Hsieh, S. Subramanian, L. Liu, G. Cheng, L. Li, S.Z.D. Cheng, J. Zheng, Strong resistance of poly(ethylene glycol) based L-tyrosine polyurethanes to protein adsorption and cell adhesion, Polym. Int. 61 (2012) 616-621.

[13] J. Wu, S. Chen, Investigation of the hydration of nonfouling material poly(ethylene glycol) by low-field Nuclear Magnetic Resonance, Langmuir 28 (2012) 2137-2144.

[14] S. Tugulu, H.A. Klok, Stability and nonfouling properties of poly(poly(ethylene glycol) methacrylate) brushes under cell culture conditions, Biomacromolecules 9 (2008) 906-912.

[15] M. Meibler, A. Taden, H.G. Börner, Enzyme-triggered antifouling coatings: switching bioconjugate adsorption via proteolytically cleavable interfering domains, ACS Macro Lett. 5 (2016) 583-587.

[16] J.M. Peng, Y.L. Su,W.J. Chen, X.T. Zhao, Z.Y. Jiang, Y. Dong, Y. Zhang, J.Z. Liu, X.C. Fan, Antifouling membranes prepared by a solvent-free approach via bulk polymerization of 2-hydroxyethyl methacrylate, Ind. Eng. Chem. Res. 52 (2013) 13137-13145.

[17] W.J. Yang, T. Cai, K.G. Neoh, E.T. Kang, Biomimetic anchors for antifouling and antibacterial polymer brushes on stainless steel, Langmuir 27 (2011) 7065-7076.

[18] K.K. Goli, O.J. Rojas, J. Genzer, Formation and antifouling properties of amphiphilic coatings on polypropylene fibers, Biomacromolecules 13 (2012) 3769-3779.

[19] K. Chen, S.X. Zhou, L.M.Wu, Self-repairing nonfouling polyurethane coatings via 3Dgrafting of PEG-b-PHEMA-b-PMPC copolymer, RSC Adv. 5 (2015) 104907-104914.

[20] C. Xu, X. Hu, J.Wang, Y.M. Zhang, X.J. Liu, B.B. Xie, C. Yao, Y. Li, X.S. Li, Library of antifouling surfaces derived from natural amino acids by click reaction, ACS Appl. Mater. Interfaces 7 (2015) 17337-17345.

[21] Z.L. Zhao, H.G. Ni, Z.Y. Han, T.F. Jiang, Y.Y. Xu, X.L. Lu, P. Ye, Effect of surface compositional heterogeneities and microphase segregation of fluorinated amphiphilic copolymers on antifouling performance, ACS Appl. Mater. Interfaces 5 (2013) 7808-7818.

[22] Y.X. Zhang, N. Islam, R.G. Carbonell, O.J. Rojas, Specific binding of immunoglobulin G with bioactive short peptides supported on antifouling copolymer layers for detection in quartz crystal microgravimetry and surface plasmon resonance, Anal. Chem. 85 (2013) 1106-1113.

[23] D. Bhatia, I. Bourven, S. Simon, F. Bordas, E.D. vanHullebusch, S. Rossano, P.N.L. Lens, G. Guibaud, Fluorescence detection to determine proteins and humic-like substances fingerprints of exopolymeric substances (EPS) from biological sludges performed by size exclusion chromatography (SEC), Bioresour. Technol. 131 (2013) 159-165.

[24] M. Lejars, A.Margaillan, C. Bressy, Fouling release coatings: a nontoxic alternative to biocidal antifouling coatings, Chem. Rev. 112 (2012) 4347-4390.

[25] W.J. Yang, T. Cai, K.G. Neoh, E.T. Kang, Barnacle cement as surface anchor for “clicking” of antifouling and antimicrobial polymer brushes on stainless steel, Biomacromolecules 14 (2013) 2041-2051.

[26] J. Yuan, J.Q. Meng, Y.L. Kang, Q.Y. Du, Y.F. Zhang, Facile surface glycosylation of PVDF microporousmembrane via direct surface-initiated AGET ATRP and improvement of antifouling property and biocompatibility, Appl. Surf. Sci. 258 (2012) 2856-2863.

[27] B.C. Zhu, S. Edmondson, Polydopamine-melanin initiators for surface-initiated ATRP, Polymer 52 (2011) 2141-2149.

[28] D.R. Kester, I.W. Duedall, D.N. Connors, R.M. Pytkowicz, Preparation of artificial seawater, Limnol. Oceanogr. 12 (1967) 176-179.

[29] M. Minier, M. Salmain, N. Yacoubi, L. Barbes, C. Méthivier, S. Zanna, C.M. Pradier, Covalent immobilization of lysozyme on stainless steel. Interface spectroscopic characterization and measurement of enzymatic activity, Langmuir 21 (2005) 5957-5965.

[30] H. Lee, S.M. Dellatore,W.M. Miller, P.B. Messersmith,Mussel-inspired surface chemistry for multifunctional coatings, Science 318 (2007) 426-430.

[31] O.P. Georgievski, D. Verreault, M.O. Diesner, V. Proks, S. Heissler, F. Rypacek, P. Koelsch, Nonfouling poly(ethylene oxide) layers end-tethered to polydopamine, Langmuir 28 (2012) 14273-14283.

[32] M. Tsuboi, S. Takahashi, J. Harda, Infrared and Raman spectra of nucleic acids. Vibration in the base residues, Physicochemical Properties of Nucleic Acids, second ed.Academic Press, New York, 1973.

[33] R.A. Zangmeister, T.A. Morris, M.J. Tarlov, Characterization of polydopamine thin films deposited at short times by autoxidation of dopamine, Langmuir 29 (2013) 8619-8628.

[34] R. Silverstein, G. Bassler, R. Morrill, Spectrometric Identification of Organic Compounds, John Wiley & Sons, New York, 1981.

[35] G. De, B. Karmakar, D. Ganguli, Hydrolysis-condensation reactions of TEOS in the presence of acetic acid leading to the generation of glass-like silica microspheres in solution at room temperature, J. Mater. Chem. 10 (2000) 2289-2400.

[36] P. Innocenzi, G. Brusatin, M. Guglielmi, R. Bertani, New synthetic route to (3-glycidoxypropyl)trimethoxysilane-based hybrid organic-inorganic materials, Chem. Mater. 11 (1999) 1672-1679.

[37] J. Sun, K. Du, L. Fu, J. Gao, H. Zhang,W. Feng, P. Ji, Sodium hexadecyl sulfate as an interfacial substance adjusting the adsorption of a protein on carbon nanotubes, ACS Appl. Mater. Interfaces 6 (2014) 15132-15139.

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