Abstract
Electrospinning is the most effective and efficient method for nanofiber production. In this study, polyvinyl alcohol (PVA)/β-cyclodextrin (β-CD) and PVA/β-CD/Mn2+ electrospun nanofibers were synthesized for use in arginase immobilization. The structural and morphological analysis of the β-cyclodextrin based nanofibers were determined by FTIR, XRD, TGA and SEM. Arginase was immobilized on the β-CD based nanofibers by adsorption and cross-linking methods. After immobilization β-CD based nanofibers (especially PVA/β-CD/Mn2+) demonstrated remarkable improvement in stability properties. When the free arginase lost almost all of its activity after 60 min at 80 °C, both arginase immobilized β-cyclodextrin based nanofibers protected nearly 80–90% activity at the same time. Arginase immobilized β-CD based nanofibers retained 95% of their activity in the acidic region, free arginase maintained only 10–20% of its activity. Arginase immobilized PVA/β-CD and PVA/β-CD/Mn2+ nanofibers protected approximately 50% of their activity after 16 and 20 reuses, respectively. L-ornithine production performance of arginase immobilized PVA/β-CD/Mn2+ nanofiber was found to be 64% even after 5th cycles.
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References
Salvatore F, Cimino F, d’Ayello-Caracciolo M, Cittadini D (1964) Mechanism of the protection by L-ornithine-L-aspartate mixture and by L-arginine in ammonia intoxication. Arch Biochem Biophys 107:499–503. https://doi.org/10.1016/0003-9861(64)90307-8
Blonde-Cynober F, Aussel C, Cynober L (2003) Use of ornithine α-ketoglutarate in clinical nutrition of elderly patients. Nutrition 19(1):73–75. https://doi.org/10.1016/S0899-9007(02)00849-3
Jalan R, Wright G, Davies NA, Hodges SJ (2007) L-Ornithine phenylacetate (OP): a novel treatment for hyperammonemia and hepatic encephalopathy. Med Hypotheses 69(5):1064–1069. https://doi.org/10.1016/j.mehy.2006.12.061
Demura S, Yamada T, Yamaji S, Komatsu M, Morishita K (2010) The effect of L-ornithine hydrochloride ingestion on human growth hormone secretion after strength training. Biosci Biotechnol Biochem 1:7–11. https://doi.org/10.4236/abb.2010.11002
Sugino T, Shirai T, Kajimoto Y, Kajimoto O (2008) L-Ornithine supplementation attenuates physical fatigue in healthy volunteers by modulating lipid and amino acid metabolism. Nutr Res 28(11):738–743. https://doi.org/10.1016/j.nutres.2008.08.008
Tokuyama E, Shibasaki T, Kawabe H, Mukai J, Okada S, Uchida T (2006) Bitterness suppression of BCAA solutions by L-ornithine. Chem Pharm Bull 54(9):1288–1292. https://doi.org/10.1248/cpb.54.1288
Huang K, Zhang T, Jiang B, Mu W, Miao M (2016) A coupled system involving arginase and urease for L-ornithine production. J Mol Catal B Enzym 133:303–310. https://doi.org/10.1016/j.molcatb.2017.01.018
Zhang X, Jin L, Xianhong Y, Fei W, Li Y, Zhezhe L, Yunyun L, Lixin M (2015) High-level expression of human arginase I in Pichia pastoris and its immobilization on chitosan to produce L-ornithine. BMC Biotechnol 15:66. https://doi.org/10.1186/s12896-015-0184-2
Lee SY, Shin HS, Park JS, Kim YH, Min J (2010) Proline reduces the binding of transcriptional regulator ArgR to upstream of argB in Corynebacterium glutamicum. Appl Microbiol Biotechnol 86:235–242. https://doi.org/10.1007/s00253-009-2264-5
El-Sayed AS, Shindia AA, Diab AA, Rady AM (2014) Purification and immobilization of L-arginase from thermotolerant Penicillium chrysogenum KJ185377.1; with unique kinetic properties as thermostable anticancer enzyme. Arch Pharm Res 37(10):1–10. https://doi.org/10.1007/s12272-014-0498-y
Strojny R, White H (1963) Preparation of ornithine from methyl 2,5-diazidovalerate. J Org Chem 28:1942–1943. https://doi.org/10.1021/jo01042a534
Esch F, Lin KI, Hills A, Zaman K, Baraban JM, Chatterjee S, Ratan RR (1998) Purification of a multipotent antideath activity from bovine liver and its identification as arginase: nitric oxideindependent inhibition of neuronal apoptosis. J Neurosci 18(11):4083–4095. https://doi.org/10.1523/JNEUROSCI.18-11-04083.1998
Ash DE, Cox JD, Christianson DW (1999) Arginase: a binuclear manganese metalloenzyme in manganese and its role in biological processes. In: Sigel A, Sigel H (eds) Metal ions in biological systems, Boca Raton, New York, pp 407–428. https://doi.org/10.1201/9781482289893
Wu G, Morris SM (1998) Arginine metabolism: nitric oxide and beyond. Biochem J 336:1–17. https://doi.org/10.1042/bj3360001
Aghaei H, Yasinian A, Taghizadeh A (2021) Covalent immobilization of lipase from Candida rugosa on epoxy-activated cloisite 30B as a new heterofunctional carrier and its application in the synthesis of banana flavor and production of biodiesel. Int J Biol Macromol 178:569–579. https://doi.org/10.1016/j.ijbiomac.2021.02.146
Tran DN, Balkus KJ (2011) Perspective of recent progress in immobilization of enzymes. ACS Catal 1:956–968. https://doi.org/10.1021/cs200124a
Mortazavi S, Aghaei H (2020) Make proper surfaces for immobilization of enzymes: Immobilization of lipase and α-amylase on modified Na-sepiolite. Int J Biol Macromol 164:1–12. https://doi.org/10.1016/j.ijbiomac.2020.07.103
Işık C, Arabaci G, Ispirli Doğaç Y, Deveci I, Teke M (2019) Synthesis and characterization of electrospun PVA/Zn2+ metal composite nanofibers for lipase immobilization with effective thermal, pH stabilities and reusability. Mater Sci Eng C 99:1226–1235. https://doi.org/10.1016/j.msec.2019.02.031
Nezhad MK, Aghaei H (2021) Tosylated cloisite as a new heterofunctional carrier for covalent immobilization of lipase and its utilization for production of biodiesel from waste frying oil. Renew Energy 164:876–888. https://doi.org/10.1016/j.renene.2020.09.117
Góra A, Sahay R, Thavasi V, Ramakrishna S (2011) Melt-electrospun fibers for advances in biomedical engineering, clean energy, filtration, and separation. Polym Rev 51(3):265–287. https://doi.org/10.1080/15583724.2011.594196
Xue J, Wu T, Dai Y, Xia Y (2019) Electrospinning and electrospun nanofibers: Methods, materials, and applications. Chem Rev 119:5298–5415. https://doi.org/10.1021/acs.chemrev.8b00593
Bhardwaj N, Kundu SC (2010) Electrospinning: a fascinating fiber fabrication technique. Biotechnol Adv 28:325–347. https://doi.org/10.1016/j.biotechadv.2010.01.004
Matthew DB, Dmitry L, Deepak T, Michel D (2007) Nano fiber based drug delivery; nanoparticulate drug delivery systems. Informa Healthcare 166:64–65
Verrect G, Chun I, Rosenblatt J, Peeters J, Dijck A (2003) Incorporation of drugs in an amorphous state in electrospun nanofibers composed of as water insoluble, non biodegradable polymer. J Control Release 92(3):349–360. https://doi.org/10.1016/S0168-3659(03)00342-0
Işık C, Ispirli Doğaç Y, Deveci I, Teke M (2020) Zn2+-Doped PVA Composite Electrospun Nanofiber for Upgrading of Enzymatic Properties of Acetylcholinesterase. ChemistrySelect 5(45):14380–14386. https://doi.org/10.1002/slct.202004006
Uyar T, Kingshott P, Besenbacher F (2008) Electrospinning of cyclodextrin-pseudopolyrotaxane nanofibers, Angew. Chemie 47:9108–9111. https://doi.org/10.1002/anie.200803352
Celebioglu A, Uyar T (2013) Electrospinning of nanofibers from non-polymeric systems: electrospun nanofibers from native cyclodextrins. J Colloid Interface Sci 404:1–7. https://doi.org/10.1016/j.jcis.2013.04.034
Crini G (2014) Review: a history of cyclodextrins. Chem Rev 114:10940–10975. https://doi.org/10.1021/cr500081p
Xiao P, Weibel N, Dudal Y, Corvini PFX, Shahgaldian P (2015) A cyclodextrin-based polymer for sensing diclofenac in water. J Hazard Mater 299:412–416. https://doi.org/10.1016/j.jhazmat.2015.06.047
Saallah S, Naim MN, Lenggoro IW, Mokhtar MN, Bakar NFA, Gen M (2016) Immobilisation of cyclodextrin glucanotransferase into polyvinyl alcohol (PVA) nanofibres via electrospinning. Biotechnol Rep 10:44–48. https://doi.org/10.1016/j.btre.2016.03.003
Amri C, Mudasir M, Siswanta D, Roto R (2016) In vitro hemocompatibility of PVA alginate ester as a candidate for hemodialysis membrane. Int J Biol Macromol 82:48–53. https://doi.org/10.1016/j.ijbiomac.2015.10.021
Bordage S, Pham TN, Zedet A, Gugglielmetti AS, Nappey M, Demougeot C, Girard-Thernier C (2017) Investigation of mammal arginase inhibitory properties of natural ubiquitous polyphenols by using an optimized colorimetric microplate assay. Planta Med 83:647–653. https://doi.org/10.1055/s-0042-118711
Corraliza IM, Campo ML, Soler G, Modolell M (1994) Determination of arginase activity in macrophages: A micromethod. J Immunol Methods 174:231–235. https://doi.org/10.1016/0022-1759(94)90027-2
Bradford NM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biolchem 72:248–254. https://doi.org/10.1016/0003-2697(76)90527-3
Gilmanl JW, VanderHart DL, Kashiwagi T (1995) In: Nelson GL (ed) Fire and Polymers II, 1st edn. ACS, Washington. https://doi.org/10.1021/bk-1995-0599.ch011
Tǎmǎşan M, Simon V (2012) Thermal and structural characterization of montmorillonite poly(vinyl alcohol) nanocomposites. J Optoelectron Adv Mater 14:1053–1058
Giordano F, Novak C, Moyano JR (2001) Thermal analysis of cyclodextrins and their inclusion compounds. Thermochim Acta 380:123–151. https://doi.org/10.1016/S0040-6031(01)00665-7
Shown I, Banerjee S, Ramchandran AV, Geckeler KE, Murthy CN (2010) Synthesis of cyclodextrin and sugar-based oligomers for the efavirenz drug delivery. Macromol Symp 287:51–59. https://doi.org/10.1002/masy.201050108
Abarca RL, Francisco JR, Guarda A, Galotto MJ, Bruna JE (2016) Characterization of beta-cyclodextrin inclusion complexes containing an essential oil component. Food Chem 196:968–975. https://doi.org/10.1016/j.foodchem.2015.10.023
Kayaci F, Sen HS, Durgun E, Uyar T (2014) Functional electrospun polymeric nanofibers incorporating geraniol–cyclodextrin inclusion complexes: High thermal stability and enhanced durability of geraniol. Food Res Int 62:424–431. https://doi.org/10.1016/j.foodres.2014.03.033
Zhang X, Liu J, Yu X, Wang F, Yi L, Li Z, Ma L (2015) High-level expression of human arginase I in Pichia pastoris and its immobilization on chitosan to produce L-ornithine. BMC Biotechnol 15:66. https://doi.org/10.1186/s12896-015-0184-2
Li M, Yang J, Qu H, Zhang Q, Bai F, Bai G (2014) Novel immobilization of arginase ı via cellulose–binding domain and its application in producing of L-ornitine. Appl Biochem Microbiol 50(1):43–48. https://doi.org/10.1134/S0003683813060112
Dala E, Szajani B (1994) Immobilization, characterization and laboratory-scale application of bovine liver arginase. Appl Biochem Biotechnol 49:203–215. https://doi.org/10.1007/BF02783058
Unissa R, Sudhakari M, Reddy ASK (2015) In vitro anticancer activity of L-arginase produced from Idiomarina sediminum; H1695. J Chem Pharm Res 7(9):764–770
Stasyuk N, Serkiz R, Mudry S, Gayda G, Zakalskiy A, Kovalchuk Y, Nisnevitch M (2011) Recombinant human arginase I immobilized on gold and silver nanoparticles: preparation and properties. Nanotechnol Dev 1(3e):11–15. https://doi.org/10.4081/nd.2011.e3
Ghiaci M, Aghaei H, Soleimanian S, Sedaghat ME (2009) Enzyme immobilization: Part 2: Immobilization of alkaline phosphatase on Na-bentonite and modified bentonite. Appl Clay Sci 43:308–316. https://doi.org/10.1016/j.clay.2008.09.011
Sedaghat ME, Ghiaci M, Aghaei H, Zad SS (2009) Enzyme immobilization. Part 3: Immobilization of α-amylase on Na-bentonite and modified bentonite. Appl Clay Sci 46:125–130. https://doi.org/10.1016/j.clay.2009.07.023
Pathak M, Devi A, Bhattacharyya KG, Sarma HK, Subudhid S, Lald B (2015) Production of a non-cytotoxic bioflocculant by a bacterium utilizing a petroleum hydrocarbon source and its application in heavy metal removal. RSC Adv 5:66037–66046. https://doi.org/10.1039/C5RA08636A
Acknowledgements
This study is a part of Ceyhun Işık’s PhD thesis and was supported by The Scientific and Technological Research Council of Turkey (Project no: TUBITAK‐218Z092) and Mugla Sitki Kocman University Research Fund (Project no: MUBAP 19/076/04/1).
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The authors would like to thank the The Scientific and Technological Research Council of Turkey (Project no: TUBITAK‐218Z092) and Mugla Sitki Kocman University Research Fund (Project no: MUBAP 19/076/04/1).
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Işik, C., Teke, M. β-cyclodextrin based electrospun nanofibers for arginase immobilization and its application in the production of L-ornithine. J Polym Res 29, 121 (2022). https://doi.org/10.1007/s10965-022-02968-w
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DOI: https://doi.org/10.1007/s10965-022-02968-w