Carbodiimide-mediated immobilization of serratiopeptidase on amino-, carboxyl-functionalized magnetic nanoparticles and characterization for target delivery
Source abstract
Abstract
A hybrid biomaterial of serratiopeptidase enzyme was prepared with magnetic nanoparticles (MNPs) via carboxyl and amino-functionalization and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) for direct immobilization. The average size of prepared MNPs was found to be 15.05 ± 3.06 nm. Attachment of amino and carboxyl groups was confirmed by Fourier transform infrared spectroscopy. X-ray diffraction confirmed the purity and phase integrity of Fe3O4. The MNPs and enzyme-loaded-MNPs (EMNPs) were of saturation magnetization 58 and 50 emu g−1, respectively. Thermogravimetric analysis of EDC-MNPs and EMNPs showed the presence of organic coating over MNPs. Serratiopeptidase immobilized on amino-functionalized magnetic nanoparticles showed loss of enzyme activity due to crosslinking of enzyme, while serratiopeptidase immobilized on carboxyl-functionalized magnetic nanoparticles was better and gave 115.78 mg protein g−1 MNPs, enzyme loading 168.32 U g−1 MNPs at optimized MNPs-to-enzyme ratio 1.0 mg mg−1. In vitro and in vivo studies showed that EMNPs with magnetic targeting is more effective in drug permeation and reduction in edema than free enzyme.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Enzyme Production and Characterization · Peptidase Inhibition and Analysis · Phytase and its Applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (67)
Show source-provided references
1. Al-Khateeb TH, Nusair Y (2008) Effect of the proteolytic enzyme serrapeptase on swelling, pain and trismus after surgical extraction of mandibular third molars. Int J Oral Maxillofac Surg 37(3):264–26810.1016/j.ijom.2007.11.011 ↗
2. Bi F, Zhang J, Su Y, Tang YC, Liu JN (2009) Chemical conjugation of urokinase to magnetic nanoparticles for targeted thrombolysis. Biomaterials 30(28):5125–513010.1016/j.biomaterials.2009.06.006 ↗
3. Cao H, He J, Deng L, Gao X (2009) Fabrication of cyclodextrin-functionalized superparamagnetic Fe3O4/amino-silane core-shell nanoparticles via layer-by-layer method. Appl Surf Sci 255(18):7974–798010.1016/j.apsusc.2009.04.199 ↗
4. Chen Y, Zhang Y (2011) Fluorescent quantification of amino groups on silica nanoparticle surfaces. Anal Bioanal Chem 399(7):2503–250910.1007/s00216-010-4622-7 ↗
5. Chen JP, Yang PC, Ma YH, Wu T (2011) Characterization of chitosan magnetic nanoparticles for in situ delivery of tissue plasminogen activator. Carbohydr Polym 84:364–37210.1016/j.carbpol.2010.11.052 ↗
6. Chen J-P, Yang P-C, Ma Y-H, Tu S-J, Lu Y-J (2012) Targeted delivery of tissue plasminogen activator by binding to silica-coated magnetic nanoparticle. Int J Nanomedicine 7:5137–514910.2147/IJN.S36197 ↗
7. Cheon YH, Kim GJ, Kim HS (2000) Stabilization of d-hydantoinase by intersubunit cross-linking. J Mol Catal B Enzym 11(1):29–3510.1016/S1381-1177(00)00193-4 ↗
8. Chertok B, David AE, Yang VC (2011) Brain tumor targeting of magnetic nanoparticles for potential drug delivery: effect of administration route and magnetic field topography. J Control Release 155(3):393–39910.1016/j.jconrel.2011.06.033 ↗
9. Dandamudi S, Campbell RB (2007) The drug loading, cytotoxicty and tumor vascular targeting characteristics of magnetite in magnetic drug targeting. Biomaterials 28(31):4673–468310.1016/j.biomaterials.2007.07.024 ↗
10. El-Shafey A, Tolic N, Young MM, Sale K, Smith RD, Kery V (2006) “Zero-length” cross-linking in solid state as an approach for analysis of protein–protein interactions. Protein Sci 15(3):429–44010.1110/ps.051685706 ↗
11. Faraji M, Yamini Y, Rezaee M (2010) Magnetic nanoparticles: synthesis, stabilization, functionalization, characterization and applications. J Iran Chem Soc 7(1):1–3710.1007/BF03245856 ↗
12. Food Chemical Codex Ve (2003) Institute of Health. National Academy of Science, Washington, DC, 2001:923–924
13. Gao F, Yan Z, Zhou J, Cai Y, Tang J (2012) Methotrexate-conjugated magnetic nanoparticles for thermochemotherapy and magnetic resonance imaging of tumor. J Nano Res 14(10):1–10
14. Hong R-Y, Li J-H, Zhang S-Z, Li H-Z, Zheng Y, Ding J-m, Wei D-G (2009) Preparation and characterization of silica-coated Fe3O4 nanoparticles used as precursor of ferrofluids. Appl Surf Sci 255(6):3485–349210.1016/j.apsusc.2008.09.071 ↗
15. Hsieh H-J, Liu P-C, Liao W-J (2000) Immobilization of invertase via carbohydrate moiety on chitosan to enhance its thermal stability. Biotechnol Lett 22(18):1459–146410.1023/A:1005602812037 ↗
16. Hu F, Neoh KG, Cen L, Kang E-T (2006) Cellular response to magnetic nanoparticles “PEGylated” via surface-initiated atom transfer radical polymerization. Biomacromolecules 7(3):809–81610.1021/bm050870e ↗
17. Hu B, Pan J, Yu H-L, Liu J-W, Xu J-H (2009) Immobilization of Serratia marcescens lipase onto amino-functionalized magnetic nanoparticles for repeated use in enzymatic synthesis of Diltiazem intermediate. Process Biochem 44(9):1019–102410.1016/j.procbio.2009.05.001 ↗
18. Huang G-J, Pan C-H, Liu F-C, Wu T-S, Wu C-H (2012) Anti-inflammatory effects of ethanolic extract of Antrodia salmonea in the lipopolysaccharide-stimulated RAW246.7 macrophages and the λ-carrageenan-induced paw edema model. Food Chem Toxicol 50(5):1485–149310.1016/j.fct.2012.01.041 ↗
19. Jiang Y, Guo C, Xia H, Mahmood I, Liu C, Liu H (2009) Magnetic nanoparticles supported ionic liquids for lipase immobilization: enzyme activity in catalyzing esterification. J Mol Catal B Enzym 58:103–10910.1016/j.molcatb.2008.12.001 ↗
20. Kalkan NA, Aksoy S, Aksoy EA, Hasirci N (2011) Preparation of chitosan-coated magnetite nanoparticles and application for immobilization of laccase. J Appl Polym Sci 123(2):707–71610.1002/app.34504 ↗
21. Kee W, Tan S, Lee V, Salmon Y (1989) The treatment of breast engorgement with Serrapeptase (Danzen): a randomised double-blind controlled trial. Singapore Med J 30(1):48–54
22. Kouassi GK, Irudayaraj J, McCarty G (2005) Examination of cholesterol oxidase attachment to magnetic nanoparticles. J Nanobiotechnol 3: http://www.jnanobiotechnology.com/content/3/1/110.1186/1477-3155-3-1 ↗
23. Krukemeyer MG, Krenn V, Jakobs M, Wagner W (2012) Magnetic drug targeting in a rhabdomyosarcoma rat model using magnetite-dextran composite nanoparticle-bound mitoxantrone and 0.6 tesla extracorporeal magnets sarcoma treatment in progress. J Drug Target 20(2):185–19310.3109/1061186X.2011.622399 ↗
24. Kumar R, Inbaraj BS, Chen BH (2010a) Surface modification of superparamagnetic iron nanoparticles with calcium salt of poly(γ-glutamic acid) as coating material. Mater Res Bull 45(11):1603–160710.1016/j.materresbull.2010.07.017 ↗
25. Kumar S, Mohan U, Kamble AL, Pawar S, Banerjee UC (2010b) Cross-linked enzyme aggregates of recombinant Pseudomonas putida nitrilase for enantioselective nitrile hydrolysis. Bioresour Technol 101(17):6856–685810.1016/j.biortech.2010.03.084 ↗
26. Kumar S, Jana AK, Dhamija I, Maiti M (2013a) Chitosan assisted immobilization of serratiopeptidase on magnetic nanoparticles, characterization and its targeted delivery in vitro and in vivo. J Drug Target. doi: 10.3109/1061186X.1062013.1844157
27. Kumar S, Jana AK, Dhamija I, Singla Y, Maiti M (2013b) Preparation, characterization and targeted delivery of serratiopeptidase immobilized on amino-functionalized magnetic nanoparticles. Eur J Pharm Biopharm. doi: 10.1016/j.ejpb.2013.1006.1019
28. Kv S, Devi GS, Mathew ST (2007) Liposomal formulations of serratiopeptidase: in vitro studies using PAMPA and caco-2 models. Mol Pharm 5(1):92–9710.1021/mp700090r ↗
29. Li B, Ma Y, Wang S, Moran PM (2005) A technique for preparing protein gradients on polymeric surfaces: effects on PC12 pheochromocytoma cells. Biomaterials 26(13):1487–149510.1016/j.biomaterials.2004.05.004 ↗
30. Li G-y, Jiang Y-r, Huang K-l, Ding P, Chen J (2008) Preparation and properties of magnetic Fe3O4-chitosan nanoparticles. J Alloys Compd 466:451–45610.1016/j.jallcom.2007.11.100 ↗
31. Liang Y–Y, Zhang L-M (2007) Bioconjugation of papain on superparamagnetic nanoparticles decorated with carboxymethylated chitosan. Biomacromolecules 8(5):1480–148610.1021/bm061091g ↗
32. Liang Y–Y, Zhang L-M, Li W, Chen R-F (2007) Polysaccharide-modified iron oxide nanoparticles as an effective magnetic affinity adsorbent for bovine serum albumin. Colloid Polym Sci 285(11):1193–119910.1007/s00396-007-1672-2 ↗
33. Lin Y, Wei Y, Sun Y, Wang J (2012) Synthesis and magnetic characterization of magnetite obtained by monowavelength visible light irradiation. Mater Res Bull 47(3):614–61810.1016/j.materresbull.2011.12.042 ↗
34. Longhi C, Scoarughi GL, Poggiali F, Cellini A, Carpentieri A, Seganti L, Pucci P, Amoresano A, Cocconcelli PS, Artini M, Costerton JW, Selan L (2008) Protease treatment affects both invasion ability and biofilm formation in Listeria monocytogenes. Microb Pathog 45(1):45–5210.1016/j.micpath.2008.01.007 ↗
35. Lopez RFV, Collett JH, Bentley MVLB (2000) Influence of cyclodextrin complexation on the in vitro permeation and skin metabolism of dexamethasone. Int J Pharm 200(1):127–13210.1016/S0378-5173(00)00365-3 ↗
36. Mahato RI, Narang AS, Thoma L, Miller DD (2003) Emerging trends in oral delivery of peptide and protein drugs. Crit Rev Ther Drug Carrier Syst 20:153–21410.1615/CritRevTherDrugCarrierSyst.v20.i23.30 ↗
37. Maheshwari M, Miglani G, Mali A, Paradkar A, Yamamura S, Kadam S (2006) Development of tetracycline-serratiopeptidase-containing periodontal gel: formulation and preliminary clinical study. AAPS PharmSciTech 7(3):E162–E17110.1208/pt070376 ↗
38. Majumder AB, Mondal K, Singh TP, Gupta MN (2008) Designing cross-linked lipase aggregates for optimum performance as biocatalysts. Biocatal Biotransform 26(3):235–24210.1080/10242420701685601 ↗
39. Marroquin-Segura R, Flores-Pimentel M, Carreon-Sanchez R, Garcia-Burciaga MM, Mora-Guevara JLA, Aguilar-Contreras A, Hernandez-Abad VJ (2009) The effect of the aqueous extract of Helietta parvifolia A. Gray (Rutaceae) stem bark on carrageenan-induced paw oedema and granuloma tissue formation in mice. J Ethnopharmacol 124(3):639–64110.1016/j.jep.2009.06.004 ↗
40. Maximov V, Reukov V, Vertegel AA (2009) Targeted delivery of therapeutic enzymes. J Drug Deliv Sci Tech 19(5):311–32010.1016/S1773-2247(09)50066-4 ↗
41. Mazzone A, Catalan M, Costanzo M (1990) Evaluation of serratiopeptidase in acute or chronic inflammation of otorhinolaryngology pathology: a multicentre, double blind, randomized trial versus placebo. J Int Med Res 18:379–38810.1177/030006059001800506 ↗
42. Nakamura S, Hashimoto Y, Mikami M, Yamanaka E, Soma T, Hino M, Azuma A, Kudoh S (2003) Effect of the proteolytic enzyme serrapeptase in patients with chronic airway disease. Respirology 8(3):316–32010.1046/j.1440-1843.2003.00482.x ↗
43. Namdeo M, Bajpai SK (2009) Immobilization of α-amylase onto cellulose-coated magnetite (CCM) nanoparticles and preliminary starch degradation study. J Mol Catal B Enzym 59:134–13910.1016/j.molcatb.2009.02.005 ↗
44. Nigam S, Barick KC, Bahadur D (2011) Development of citrate-stabilized Fe3O4 nanoparticles: conjugation and release of doxorubicin for therapeutic applications. J Magn Magn Mater 323(2):237–24310.1016/j.jmmm.2010.09.009 ↗
45. Novak L, Banyai I, Fleischer-Radu JE, Borbely J (2007) Direct amidation of poly (γ-glutamic acid) with benzylamine in dimethyl sulfoxide. Biomacromolecules 8(5):1624–163210.1021/bm0612182 ↗
46. Nowicka AM, Kowalczyk A, Jarzebinska A, Donten M, Krysinski P, Stojek Z, Augustin E, Mazerska Z (2013) Progress in targeting tumor cells by using drug-magnetic nanoparticles conjugate. Biomacromolecules. doi: 10.1021/bm301868f10.1021/bm301868f ↗
47. Panagariya A, Sharma A (1999) A preliminary trial of serratiopeptidase in patients with carpal tunnel Syndrome. J Assoc Physicians India 47(12):1170–1172
48. Pecova M, Sebela M, Markova Z, PolAkova K, Cuda J, Safarova K, Zboril R (2013) Thermostable trypsin conjugates immobilized to biogenic magnetite show a high operational stability and remarkable reusability for protein digestion. Nanotechnology 24(12):12510210.1088/0957-4484/24/12/125102 ↗
49. Peppas N (1985) Analysis of Fickian and non-Fickian drug release from polymers. Pharm Acta Helv 60(4):110–111
50. Petri-Fink A, Steitz B, Finka A, Salaklang J, Hofmann H (2008) Effect of cell media on polymer coated superparamagnetic iron oxide nanoparticles (SPIONs): colloidal stability, cytotoxicity, and cellular uptake studies. Eur J Pharm Biopharm 68(1):129–13710.1016/j.ejpb.2007.02.024 ↗
51. Rath G, Johal ES, Goyal AK (2011) Development of Serratiopeptidase and Metronidazole Based Alginate Microspheres for Wound Healing. Artif Cells Blood Substit Immobil Biotechnol 39(1):44–5010.3109/10731199.2010.494580 ↗
52. Ren L, Wang X, Wu H, Shang B, Wang J (2010) Conjugation of nattokinase and lumbrukinase with magnetic nanoparticles for the assay of their thrombolytic activities. J Mol Catal B Enzym 62(2):190–19610.1016/j.molcatb.2009.10.009 ↗
53. Sadeghi H, Hajhashemi V, Minaiyan M, Movahedian A, Talebi A (2011) A study on the mechanisms involving the anti-inflammatory effect of amitriptyline in carrageenan-induced paw edema in rats. Eur J Pharmacol 667:396–40110.1016/j.ejphar.2011.05.053 ↗
54. Shaw S-Y, Chen Y-J, Ou J–J, Ho L (2006) Preparation and characterization of Pseudomonas putida esterase immobilized on magnetic nanoparticles. Enzyme Microb Technol 39:1089–109510.1016/j.enzmictec.2006.02.025 ↗
55. ShiXing W, Sun W, Zhou Y (2010) Preparation of Cu2+/NTA-derivatized branch polyglycerol magnetic nanoparticles for protein adsorption. J Nano Res 12(7):2467–247210.1007/s11051-009-9812-x ↗
56. Shubayev VI, Pisanic Ii TR, Jin S (2009) Magnetic nanoparticles for theragnostics. Adv Drug Deliv Rev 61(6):467–47710.1016/j.addr.2009.03.007 ↗
57. Siepmann J, Peppas NA (2001) Modeling of drug release from delivery systems based on hydroxypropyl methylcellulose (HPMC). Adv Drug Deliv Rev 48:139–15710.1016/S0169-409X(01)00112-0 ↗
58. Tang T, Fan H, Ai S, Han R, Qiu Y (2011) Hemoglobin (Hb) immobilized on amino-modified magnetic nanoparticles for the catalytic removal of bisphenol A. Chemosphere 83(3):255–26410.1016/j.chemosphere.2010.12.075 ↗
59. Verma M, Barrow C, Puri M (2013) Nanobiotechnology as a novel paradigm for enzyme immobilisation and stabilisation with potential applications in biodiesel production. Appl Microbiol Biotechnol 97(1):23–3910.1007/s00253-012-4535-9 ↗
60. Vichasilp C, Nakagawa K, Sookwong P, Higuchi O, Kimura F, Miyazawa T (2012) A novel gelatin crosslinking method retards release of mulberry 1-deoxynojirimycin providing a prolonged hypoglycaemic effect. Food Chem 134(4):1823–183010.1016/j.foodchem.2012.03.086 ↗
61. Wang N, Guan Y, Yang L, Jia L, Wei X, Liu H, Guo C (2013) Magnetic nanoparticles (MNPs) covalently coated by PEO-PPO-PEO block copolymer for drug delivery. J Colloid Interface Sci 395:50–5710.1016/j.jcis.2012.11.062 ↗
62. Xu H, Song T, Bao X, Hu L (2005) Site-directed research of magnetic nanoparticles in magnetic drug targeting. J Magn Magn Mater 293(1):514–51910.1016/j.jmmm.2005.01.067 ↗
63. Yu C–C, Kuo Y–Y, Liang C-F, Chien W-T, Wu H-T, Chang T-C, Jan F-D, Lin C–C (2012) Site-specific immobilization of enzymes on magnetic nanoparticles and their use in organic synthesis. Bioconjug Chem 13(4):714–724
64. Zheng Z-H, Wei Y-Q, Yan S-Q, Li M-Z (2009) Preparation of porous silk fibroin materials cross-linked by carbodiimide (EDC). J Fib Bioeng Inform 2(3):162–16710.3993/jfbi12200904 ↗
65. Zhu H, Pan J, Hu B, Yu H-L, Xu J-H (2009) Immobilization of glycolate oxidase from Medicago falcata on magnetic nanoparticles for application in biosynthesis of glyoxylic acid. J Mol Catal B Enzym 61:174–17910.1016/j.molcatb.2009.06.007 ↗
66. Zhuo Y, Yuan P-X, Yuan R, Chai Y-Q, Hong C-L (2009) Bienzyme functionalized three-layer composite magnetic nanoparticles for electrochemical immunosensors. Biomaterials 30(12):2284–229010.1016/j.biomaterials.2009.01.002 ↗
67. Ziv-Polat O, Topaz M, Brosh T, Margel S (2010) Enhancement of incisional wound healing by thrombin conjugated iron oxide nanoparticles. Biomaterials 31(4):741–74710.1016/j.biomaterials.2009.09.093 ↗