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01-09-2022 | Original Research

Cellulose-based functional polycarbonates as degradable enzyme carriers

Authors: Chunyang Bao, Jing Chen, Yan Wang, Tao Yang, Xiaoling Xu, Qiang Zhang

Published in: Cellulose | Issue 16/2022

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Abstract

Cellulose-based matrices are expected to be ideal enzyme carriers due to their sustainability and biocompatibility. However, the linkages between immobilized enzymes and celluloses often suffer from low-density and non-biodegradability, leading to inefficient loading of enzymes as well as persistent generation of solid wastes after reuse. In the present study, cellulose-based functional materials with degradable polycarbonates brushes have been successfully synthesized as enzyme carriers via ring-opening polymerization of 5-methyl-5-allyloxycarbonyl-1,3-dioxan-2-one (MAC) following with ally epoxidation of MAC units. After covalent bonding with laccase, the resulting HPC-PMAC-Laccase could assemble in aqueous solution to form spherical nanoparticles with an enzyme immobilization efficiency of 88%. The immobilized laccase showed more tolerance towards pH and high temperature compared with free laccase. Moreover, the immobilized laccase demonstrated effective removal efficiency of bisphenol A and reached 83% in 3 h. After repeated usage for 8 times, the HPC-PMAC-Laccase still maintained relatively high enzyme activity. Especially, the polycarbonates brushes in the enzyme carriers could be totally hydrolyzed in 12 h to achieve its degradable property.

Graphical abstract

Cellulose-based functional polycarbonates as degradable enzyme carriers.

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Bao C, Chen J, Li D, Zhang A, Zhang Q (2020) Synthesis of lipase-polymer conjugates by Cu(0)-mediated reversible deactivation radical polymerization: polymerization vs degradation. Polym Chem 11:1386–1392. https://doi.org/10.1039/C9PY01462DCrossRef

Bao C, Wang Y, Xu X, Li D, Chen J, Guan Z, Wang B, Hong M, Zhang J, Wang T, Zhang Q (2021) Reversible immobilization of laccase onto glycopolymer microspheres via protein-carbohydrate interaction for biodegradation of phenolic compounds. Bioresour Technol 342:126026. https://doi.org/10.1016/j.biortech.2021.126026CrossRefPubMed

Bayramoglu G, Karagoz B, Arica MY (2018) Cyclic-carbonate functionalized polymer brushes on polymeric microspheres: immobilized laccase for degradation of endocrine disturbing compounds. J Ind Eng Chem 60:407–417. https://doi.org/10.1016/j.jiec.2017.11.028CrossRef

Bilal M, Iqbal HMN, Barcelo D (2019) Mitigation of bisphenol a using an array of laccase-based robust bio-catalytic cues: a review. Sci Total Environ 689:160–177. https://doi.org/10.1016/j.scitotenv.2019.06.403CrossRefPubMed

Cao S, Xu H, Li X, Lou W, Zong M (2015) Papain@Magnetic nanocrystalline cellulose nanobiocatalyst: a highly efficient biocatalyst for dipeptide biosynthesis in deep eutectic solvents. ACS Sustain Chem Eng 3:1589–1599. https://doi.org/10.1021/acssuschemeng.5b00290CrossRef

Carlsson L, Ingverud T, Blomberg H, Carlmark A, Larsson PT, Malmström E (2015) Surface characteristics of cellulose nanoparticles grafted by surface-initiated ring-opening polymerization of ε-caprolactone. Cellulose 22:1063–1074. https://doi.org/10.1007/s10570-014-0510-1CrossRef

Celikbicak O, Bayramoglu G, Yılmaz M, Ersoy G, Bicak N, Salih B, Arica MY (2014) Immobilization of laccase on hairy polymer grafted zeolite particles: degradation of a model dye and product analysis with MALDI-ToF-MS. Microporous Mesoporous Mater 199:57–65. https://doi.org/10.1016/j.micromeso.2014.08.003CrossRef

Chen B, Hu J, Miller EM, Xie W, Cai M, Gross RA (2008) Candida antarctica lipase B chemically immobilized on epoxy-activated micro- and nanobeads: catalysts for polyester synthesis. Biomacromol 9:463–471. https://doi.org/10.1021/bm700949xCrossRef

Daronch NA, Kelbert M, Pereira CS, de Araújo PHH, de Oliveira D (2020) Elucidating the choice for a precise matrix for laccase immobilization: a review. Chem Eng J. https://doi.org/10.1016/j.cej.2020.125506CrossRef

Drozd R, Rakoczy R, Wasak A, Junka A, Fijalkowski K (2018) The application of magnetically modified bacterial cellulose for immobilization of laccase. Int J Biol Macromol 108:462–470. https://doi.org/10.1016/j.ijbiomac.2017.12.031CrossRefPubMed

Ende AEvd, Kravitz EJ, Harth E (2008) Approach to formation of multifunctional polyester particles in controlled nanoscopic dimensions. J Am Chem Soc 130:8706–8713. https://doi.org/10.1021/ja711417hCrossRefPubMed

Farhat W, Venditti R, Ayoub A, Prochazka F, Fernández-de-Alba C, Mignard N, Taha M, Becquart F (2018) Towards thermoplastic hemicellulose: chemistry and characteristics of poly(ε-caprolactone) grafting onto hemicellulose backbones. Mater Des 153:298–307. https://doi.org/10.1016/j.matdes.2018.05.013CrossRef

Fatemeh B, Jaleh V, Reza Ahangari C, Dariush N, Razieh Taghizadeh P (2021) A comparative analysis of different enzyme immobilization nanomaterials: progress, constraints and recent trends. Curr Med Chem 28:3980–4003. https://doi.org/10.2174/0929867328999201214225249CrossRef

Gennari A, Fuhr AJ, Volpato G, Volken de Souza CF (2020) Magnetic cellulose: versatile support for enzyme immobilization: a review. Carbohydr Polym 246:116646. https://doi.org/10.1016/j.carbpol.2020.116646CrossRefPubMed

Guo J, Liu X, Zhang X, Wu J, Chai C, Ma D, Chen Q, Xiang D, Ge W (2019) Immobilized lignin peroxidase on Fe₃O₄@SiO₂@polydopamine nanoparticles for degradation of organic pollutants. Int J Biol Macromol 138:433–440. https://doi.org/10.1016/j.ijbiomac.2019.07.105CrossRefPubMed

Haniffa M, Munawar K, Chee CY, Pramanik S, Halilu A, Illias HA, Rizwan M, Senthilnithy R, Mahanama KRR, Tripathy A, Azman MF (2021) Cellulose supported magnetic nanohybrids: Synthesis, physicomagnetic properties and biomedical applications-A review. Carbohydr Polym 267:118136. https://doi.org/10.1016/j.carbpol.2021.118136CrossRefPubMed

Hosseini SH, Hosseini SA, Zohreh N, Yaghoubi M, Pourjavadi A (2018) Covalent immobilization of cellulase using magnetic poly(ionic liquid) support: improvement of the enzyme activity and stability. J Agric Food Chem 66:789–798. https://doi.org/10.1021/acs.jafc.7b03922CrossRefPubMed

Je HH, Noh S, Hong SG, Ju Y, Kim J, Hwang DS (2017) Cellulose nanofibers for magnetically-separable and highly loaded enzyme immobilization. Chem Eng J 323:425–433. https://doi.org/10.1016/j.cej.2017.04.110CrossRef

Jehanno C, Pérez-Madrigal MM, Demarteau J, Sardon H, Dove AP (2019) Organocatalysis for depolymerisation. Polym Chem 10:172–186. https://doi.org/10.1039/c8py01284aCrossRef

Jiang T, Li Y, Lv Y, Cheng Y, He F, Zhuo R (2013) Amphiphilic polycarbonate conjugates of doxorubicin with pH-sensitive hydrazone linker for controlled release. Colloids Surf B Biointerfaces 111:542–548. https://doi.org/10.1016/j.colsurfb.2013.06.054CrossRefPubMed

Johannes C, Majcherczyk A (2000) Laccase activity tests and laccase inhibitors. J Biotechnol 78:193–199. https://doi.org/10.1016/S0168-1656(00)00208-XCrossRefPubMed

Jun L, Yon L, Mubarak NM, Bing CH, Pan S, Danquah MK, Abdullah EC, Khalid M (2019) An overview of immobilized enzyme technologies for dye and phenolic removal from wastewater. J Environ Chem Eng 7:102961. https://doi.org/10.1016/j.jece.2019.102961CrossRef

Kalantari M, Yu M, Yang Y, Strounina E, Gu Z, Huang X, Zhang J, Song H, Yu C (2016) Tailoring mesoporous-silica nanoparticles for robust immobilization of lipase and biocatalysis. Nano Res 10:605–617. https://doi.org/10.1007/s12274-016-1320-6CrossRef

Klemm D, Heublein B, Fink HP, Bohn A (2005) Cellulose: fascinating biopolymer and sustainable raw material. Angew Chem Int Ed Engl 44:3358–3393. https://doi.org/10.1002/anie.200460587CrossRefPubMed

Lassouane F, Ait-Amar H, Amrani S, Rodriguez-Couto S (2019) A promising laccase immobilization approach for Bisphenol A removal from aqueous solutions. Bioresour Technol 271:360–367. https://doi.org/10.1016/j.biortech.2018.09.129CrossRefPubMed

Le Devedec F, Boucher H, Dubins D, Allen C (2018) Factors controlling drug release in cross-linked poly(valerolactone) based matrices. Mol Pharm 15:1565–1577. https://doi.org/10.1021/acs.molpharmaceut.7b01102CrossRefPubMed

Liu K, Du H, Zheng T, Liu H, Zhang M, Zhang R, Li H, Xie H, Zhang X, Ma M, Si C (2021) Recent advances in cellulose and its derivatives for oilfield applications. Carbohydr Polym 259:117740. https://doi.org/10.1016/j.carbpol.2021.117740CrossRefPubMed

Luan Q, Zhang H, Lei Y, Cai Y, Bao Y, Li Y, Tang H, Li X (2021) Microporous regenerated cellulose-based macrogels for covalent immobilization of enzymes. Cellulose 28:5735–5744. https://doi.org/10.1007/s10570-021-03887-7CrossRef

Luo X, Zhang L (2010) Immobilization of Penicillin G Acylase in Epoxy-Activated Magnetic Cellulose microspheres for improvement of biocatalytic stability and activities. Biomacromol 11:2896–2903. https://doi.org/10.1021/bm100642yCrossRef

Lv M, Ma X, Anderson DP, Chang PR (2017) Immobilization of urease onto cellulose spheres for the selective removal of urea. Cellulose 25:233–243. https://doi.org/10.1007/s10570-017-1592-3CrossRef

Mateo C, Abian O, Fernandez-Lafuente R, Guisan JM (2000) Increase in conformational stability of enzymes immobilized on epoxy-activated supports by favoring additional multipoint covalent attachment. Enzyme Microb Technol 26:509–515. https://doi.org/10.1016/s0141-0229(99)00188-xCrossRefPubMed

Mateo C, Grazú V, Pessela BCC, Montes T, Palomo JM, Torres R, López-Gallego F, Fernández-Lafuente R, Guisán JM (2007) Advances in the design of new epoxy supports for enzyme immobilization–stabilization. Biochem Soc Trans 35:1593–1601. https://doi.org/10.1042/BST0351593CrossRefPubMed

Olofsson K, Malkoch M, Hult A (2016) Facile synthesis of dopa-functional polycarbonates via thiol-Ene-coupling chemistry towards self-healing gels. J Polym Sci Part A Polym Chem 54:2370–2378. https://doi.org/10.1002/pola.28111CrossRef

Pelegri-O’Day EM, Bhattacharya A, Theopold N, Ko JH, Maynard HD (2020) Synthesis of Zwitterionic and trehalose polymers with variable degradation rates and stabilization of insulin. Biomacromol 21:2147–2154. https://doi.org/10.1021/acs.biomac.0c00133CrossRef

Qiu X, Wang Y, Xue Y, Li W, Hu Y (2020) Laccase immobilized on magnetic nanoparticles modified by amino-functionalized ionic liquid via dialdehyde starch for phenolic compounds biodegradation. Chem Eng J 391:123564. https://doi.org/10.1016/j.cej.2019.123564CrossRef

Qiu X, Wang S, Miao S, Suo H, Xu H, Hu Y (2021) Co-immobilization of laccase and ABTS onto amino-functionalized ionic liquid-modified magnetic chitosan nanoparticles for pollutants removal. J Hazard Mater 401:123353. https://doi.org/10.1016/j.jhazmat.2020.123353CrossRefPubMed

Rouhani S, Rostami A, Salimi A, Pourshiani O (2018) Graphene oxide/CuFe₂O₄ nanocomposite as a novel scaffold for the immobilization of laccase and its application as a recyclable nanobiocatalyst for the green synthesis of arylsulfonyl benzenediols. Biochem Eng J 133:1–11. https://doi.org/10.1016/j.bej.2018.01.004CrossRef

Sassolas A, Blum LJ, Leca-Bouvier BD (2012) Immobilization strategies to develop enzymatic biosensors. Biotechnol Adv 30:489–511. https://doi.org/10.1016/j.biotechadv.2011.09.003CrossRefPubMed

Shokri Z, Seidi F, Karami S, Li C, Saeb MR, Xiao H (2021) Laccase immobilization onto natural polysaccharides for biosensing and biodegradation. Carbohydr Polym 262:117963. https://doi.org/10.1016/j.carbpol.2021.117963CrossRefPubMed

Siró I, Plackett D (2010) Microfibrillated cellulose and new nanocomposite materials: a review. Cellulose 17:459–494. https://doi.org/10.1007/s10570-010-9405-yCrossRef

Smith PK, Krohn RI, Hermanson GT, Mallia AK, Gartner FH, Provenzano MD, Fujimoto EK, Goeke NM, Olson BJ, Klenk DC (1985) Measurement of protein using bicinchoninic acid. Anal Biochem 150:76–85. https://doi.org/10.1016/0003-2697(85)90442-7CrossRefPubMed

Stanisz M, Klapiszewski Ł, Jesionowski T (2020) Recent advances in the fabrication and application of biopolymer-based micro- and nanostructures: a comprehensive review. Chem Eng J. https://doi.org/10.1016/j.cej.2020.125409CrossRef

Stevens DM, Tempelaar S, Dove AP, Harth E (2012) Nanosponge formation from organocatalytically synthesized Poly(carbonate) copolymers. ACS Macro Lett 1:915–918. https://doi.org/10.1021/mz300179rCrossRefPubMedPubMedCentral

Suo H, Xu L, Xue Y, Qiu X, Huang H, Hu Y (2020) Ionic liquids-modified cellulose coated magnetic nanoparticles for enzyme immobilization: improvement of catalytic performance. Carbohydr Polym 234:115914. https://doi.org/10.1016/j.carbpol.2020.115914CrossRefPubMed

Tan J, Tay J, Hedrick J, Yang YY (2020) Synthetic macromolecules as therapeutics that overcome resistance in cancer and microbial infection. Biomaterials 252:120078. https://doi.org/10.1016/j.biomaterials.2020.120078CrossRefPubMed

Tian H, He J (2016) Cellulose as a scaffold for self-assembly: from basic research to real applications. Langmuir 32:12269–12282. https://doi.org/10.1021/acs.langmuir.6b02033CrossRefPubMed

Wang CF, Lin YX, Jiang T, He F, Zhuo RX (2009) Polyethylenimine-grafted polycarbonates as biodegradable polycations for gene delivery. Biomaterials 30:4824–4832. https://doi.org/10.1016/j.biomaterials.2009.05.053CrossRefPubMed

Wang D, Ding W, Zhou K, Guo S, Zhang Q, Haddleton DM (2018) Coating titania nanoparticles with epoxy-containing catechol polymers via Cu(0)-living radical polymerization as intelligent enzyme carriers. Biomacromol 19:2979–2990. https://doi.org/10.1021/acs.biomac.8b00544CrossRef

Weishaupt R, Siqueira G, Schubert M, Tingaut P, Maniura-Weber K, Zimmermann T, Thony-Meyer L, Faccio G, Ihssen J (2015) TEMPO-oxidized nanofibrillated cellulose as a high density carrier for bioactive molecules. Biomacromol 16:3640–3650. https://doi.org/10.1021/acs.biomac.5b01100CrossRef

Wu D, Feng Q, Xu T, Wei A, Fong H (2018) Electrospun blend nanofiber membrane consisting of polyurethane, amidoxime polyarcylonitrile, and β-cyclodextrin as high-performance carrier/support for efficient and reusable immobilization of laccase. Chem Eng J 331:517–526. https://doi.org/10.1016/j.cej.2017.08.129CrossRef

Xu R, Cui J, Tang R, Li F, Zhang B (2017) Removal of 2,4,6-trichlorophenol by laccase immobilized on nano-copper incorporated electrospun fibrous membrane-high efficiency, stability and reusability. Chem Eng J 326:647–655. https://doi.org/10.1016/j.cej.2017.05.083CrossRef

Yamaguchi H, Miyazaki M (2021) Laccase aggregates via poly-lysine-supported immobilization onto PEGA resin, with efficient activity and high operational stability and can be used to degrade endocrine-disrupting chemicals. Catal Sci Technol 11:934–942. https://doi.org/10.1039/d0cy01413cCrossRef

Yuan W, Yuan J, Zhang F, Xie X (2007) Syntheses, characterization, and in vitro degradation of Ethyl Cellulose-graft-poly(ε-caprolactone)-block-poly(l-lactide) copolymers by sequential ring-opening polymerization. Biomacromol 8:1101–1108. https://doi.org/10.1021/bm0610018CrossRef

Yuan H, Chen L, Hong F, Zhu M (2018) Evaluation of nanocellulose carriers produced by four different bacterial strains for laccase immobilization. Carbohydr Polym 196:457–464. https://doi.org/10.1016/j.carbpol.2018.05.055CrossRefPubMed

Zahirinejad S, Hemmati R, Homaei A, Dinari A, Hosseinkhani S, Mohammadi S, Vianello F (2021) Nano-organic supports for enzyme immobilization: scopes and perspectives. Colloids Surf B Biointerfaces 204:111774. https://doi.org/10.1016/j.colsurfb.2021.111774CrossRefPubMed

Zhang Q, Anastasaki A, Li G, Haddleton AJ, Wilson P, Haddleton DM (2014) Multiblock sequence-controlled glycopolymers via Cu(0)-LRP following efficient thiol-halogen, thiol-epoxy and CuAAC reactions. Polym Chem 5:3876–3883. https://doi.org/10.1039/c4py00320aCrossRef

Zhang D, Peng L, Wang Y, Li Y (2015) Lipase immobilization on epoxy-activated poly(vinyl acetate-acrylamide) microspheres. Colloids Surf B Biointerfaces 129:206–210. https://doi.org/10.1016/j.colsurfb.2015.03.056CrossRefPubMed

Zhang H, Luo J, Li S, Wei Y, Wan Y (2018) Biocatalytic membrane based on polydopamine coating: a platform for studying immobilization mechanisms. Langmuir 34:2585–2594. https://doi.org/10.1021/acs.langmuir.7b02860CrossRefPubMed

Zhou W, Wang L, Yu H, Zain-ul-Abdin YX, Chen Q, Wang J (2016) Synthesis of a novel ferrocene-based epoxy compound and its burning rate catalytic property. RSC Adv 6:53679–53687. https://doi.org/10.1039/c6ra07616eCrossRef

Zhou W, Zhang W, Cai Y (2021) Laccase immobilization for water purification: a comprehensive review. Chem Eng J. https://doi.org/10.1016/j.cej.2020.126272CrossRefPubMed

Title: Cellulose-based functional polycarbonates as degradable enzyme carriers
Authors: Chunyang Bao
Jing Chen
Yan Wang
Tao Yang
Xiaoling Xu
Qiang Zhang
Publication date: 01-09-2022
Publisher: Springer Netherlands
Published in: Cellulose / Issue 16/2022
Print ISSN: 0969-0239
Electronic ISSN: 1572-882X
DOI: https://doi.org/10.1007/s10570-022-04810-4

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