Abstract
New magnetic molecularly imprinted polyurethanes based on magnetic multi-walled carbon nanotubes (MMWNTs-MIPUs) were synthesized with specific selectivity toward ketoconazole (KTZ) as an anti-fungal drug. First, novel N-(4-carboxyphenyl) trimellitimide diisocyanate (NTDIS) was prepared from the reaction of trimellitic anhydride and 4-amino benzoic acid in two steps. Then, NTDIS was functionalized by β-cyclodextrin and methacrylic acid (MAA-NTDIS-β-CD). MAA-NTDIS-β-CD was used as a functional monomer, KTZ as a template, ethylene glycol dimethacrylate (EGDMA) as a cross-linking agent and 2,2′-azobisisobutyronitrile (AIBN) as initiator. Structure and properties of the prepared compounds were characterized by FTIR, 1H NMR, FESEM, XRD, VSM, BET, and EDX. The influence of parameters such as solution pH, contact time, temperature, and initial concentrations in controlled absorption of KTZ using MMWCNTs-MIPU and MMWCNTs-NIPU were evaluated. The kinetic data were measured using the pseudo-first-order and pseudo-second-order equation. The pseudo-second-order equation displayed the best fit for the kinetic studies (R2 0.9958). The adsorption equilibrium of KTZ using MMWCNTs-MIPU could be well-defined with the Langmuir isotherm model, and the maximum adsorption capacity was calculated as 52.35 mg g–1. The prepared MMWCNTs-MIPU can be simply separated by an external magnetic field and, MMWCNTs-MIPU can be used after six filtration-regeneration cycles.
Similar content being viewed by others
References
Van der Meer J, Keuning J, Scheijgrond H, Heykants J, Cutsem JV, Brugmans J (1980) The influence of gastric acidity on the bio-availability of ketoconazole. J Antimicrob Chemother 6:552–554
El-Shabouri SR, Emara KM, Khashaba PY, Mohamed AM (1998) Charge-transfer complexation for spectrophotometric assay of certain imidazole antifungal drugs. Anal Lett 31:1367–1385
Esclusa-Diaz M, Guimaraens-Méndez M, Pérez-Marcos M, Vila-Jato J, Torres-Labandeira J (1996) Characterization and in vitro dissolution behaviour of ketoconazole/β-and 2-hydroxypropyl-β-cyclodextrin inclusion compounds. Int J Pharm 143:203–210
Corcoran J, Winter MJ, Tyler CR (2010) Pharmaceuticals in the aquatic environment: a critical review of the evidence for health effects in fish. Crit Rev Toxicol 40:287–304
Imiete IE, Viacheslovovna Alekseeva N (2018) Reverse osmosis purification: a case study of the Niger Delta region. Water Sci 32:129–137
Hunsom M, Pruksathorn K, Damronglerd S, Vergnes H, Duverneuil P (2005) Electrochemical treatment of heavy metals (Cu2+, Cr6+, Ni2+) from industrial effluent and modeling of copper reduction. Water Res 39:610–616
Seo S, Sung B, Kim G, Chu K, Um C, Yun S, Ra Y, Ko K (2010) Removal of heavy metals in an abandoned mine drainage via ozone oxidation: a pilot-scale operation. Water Sci Technol 62:2115–2120
Walker DJ, Hurl S (2002) The reduction of heavy metals in a stormwater wetland. Ecol Eng 18:407–414
Gu B, Brown GM, Chiang C-C (2007) Treatment of perchlorate-contaminated groundwater using highly selective, regenerable ion-exchange technologies. Environ Sci Technol 41:6277–6282
Chen L, Xu S, Li J (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev 40:2922–2942
Piletsky S, Panasyuk T, Piletskaya E, Nicholls IA, Ulbricht M (1999) Receptor and transport properties of imprinted polymer membranes: a review. J Membr Sci 157:263–278
Gao D, Wang D-D, Fu Q-F, Wang L-J, Zhang K-L, Yang F-Q, Xia Z-N (2018) Preparation and evaluation of magnetic molecularly imprinted polymers for the specific enrichment of phloridzin. Talanta 178:299–307
Azizi A, Bottaro CS (2020) A critical review of molecularly imprinted polymers for the analysis of organic pollutants in environmental water samples. J Chromatogr A 1614:460603
Haginaka J (2008) Monodispersed, molecularly imprinted polymers as affinity-based chromatography media. J Chromatogr B 866:3–13
Ding S, Lyu Z, Niu X, Zhou Y, Liu D, Falahati M, Du D, Lin Y (2020) Integrating ionic liquids with molecular imprinting technology for biorecognition and biosensing: a review. Biosens Bioelectron 149:111830
Kiasat AR, Nazari S (2012) Magnetic nanoparticles grafted with β-cyclodextrin–polyurethane polymer as a novel nanomagnetic polymer brush catalyst for nucleophilic substitution reactions of benzyl halides in water. J Mol Catal A Chem 365:80–86
Sobiech M, Maciejewska D, Luliński P (2020) Synthesis and characterization of poly(methacrylic acid-co-trimethylolpropane trimethacrylate) imprinted sorbent for analysis of biogenic amines. Mater Today Commun 22:100739
Fayazi M, Ghanei-Motlagh M, Taher M, Ghanei-Motlagh R, Salavati M (2016) Synthesis and application of a novel nanostructured ion-imprinted polymer for the preconcentration and determination of thallium(I) ions in water samples. J Hazard Mater 309:27–36
Fayazi M, Taher MA, Afzali D, Mostafavi A, Ghanei-Motlagh M (2016) Synthesis and application of novel ion-imprinted polymer coated magnetic multi-walled carbon nanotubes for selective solid phase extraction of lead(II) ions. Mater Sci Eng C 60:365–373
Mota JR, Bernad MB, Mayoral-Murillo J, Mora JG (2013) Synthesis and characterization of molecularly imprinted polymers with metallic zinc center for enrofloxacin recognition. React Funct Polym 73:1078–1085
Asadi E, Abdouss M, Leblanc RM, Ezzati N, Wilson JN, Kordestani D (2016) Synthesis, characterization and in vivo drug delivery study of a biodegradable nano-structured molecularly imprinted polymer based on cross-linker of fructose. Polymer 97:226–237
Udomsap D, Brisset H, Culioli G, Dollet P, Laatikainen K, Siren H, Branger C (2018) Electrochemical molecularly imprinted polymers as material for pollutant detection. Mater Today Commun 17:458–465
Jiang X, Tian W, Zhao C, Zhang H, Liu M (2007) A novel sol–gel-material prepared by a surface imprinting technique for the selective solid-phase extraction of bisphenol A. Talanta 72:119–125
Liu X, Wang Y, Wang J, Li L, Li R (2019) Hydrophilic molecularly imprinted dispersive solid-phase extraction coupled with liquid chromatography for determination of azoxystrobin residues in cucumber. Iran Polym J 28:725–734
Zhang Y-L, Zhang J, Dai C-M, Zhou X-F, Liu S-G (2013) Sorption of carbamazepine from water by magnetic molecularly imprinted polymers based on chitosan-Fe3O4. Carbohydr Polym 97:809–816
Surya SG, Khatoon S, Lahcen AA, Nguyen AT, Dzantiev BB, Tarannum N, Salama KN (2020) A chitosan gold nanoparticles molecularly imprinted polymer based ciprofloxacin sensor. RSC Adv 10:12823–12832
Huang D, Tang Z, Peng Z, Lai C, Zeng G, Zhang C, Xu P, Cheng M, Wan J, Wang R (2017) Fabrication of water-compatible molecularly imprinted polymer based on β-cyclodextrin modified magnetic chitosan and its application for selective removal of bisphenol A from aqueous solution. J Taiwan Inst Chem Eng 77:113–121
Li S, Wu X, Zhang Q, Li P (2016) Synergetic dual recognition and separation of the fungicide carbendazim by using magnetic nanoparticles carrying a molecularly imprinted polymer and immobilized β-cyclodextrin. Microchim Acta 183:1433–1439
Gong X-Y, Cao X-J (2011) Preparation of molecularly imprinted polymers for artemisinin based on the surfaces of silica gel. J Biotechnol 153:8–14
Rozaini MNH, Semail N-f, Saad B, Kamaruzaman S, Abdullah WN, Rahim NA, Miskam M, Loh SH, Yahaya N (2019) Molecularly imprinted silica gel incorporated with agarose polymer matrix as mixed matrix membrane for separation and preconcentration of sulfonamide antibiotics in water samples. Talanta 199:522–531
Wei X, Xu X, Qi W, Wu Y, Wang L (2017) Molecularly imprinted polymer/graphene oxide modified glassy carbon electrode for selective detection of sulfanilamide. Prog Nat Sci Mater Int 27:374–379
Cao N, Zhao F, Zeng B (2020) A novel self-enhanced electrochemiluminescence sensor based on PEI-CdS/Au@ SiO2@ RuDS and molecularly imprinted polymer for the highly sensitive detection of creatinine. Sens Actuators B Chem 306:127591
Xu K, Yang K, Liu J, Wang Y (2020) Study on metal magnetic memory signal of buried defect in fracture process. J Magn Magn Mater 498:166139
Yang W, Jiao F, Zhou L, Chen X, Jiang X (2013) Molecularly imprinted polymers coated on multi-walled carbon nanotubes through a simple indirect method for the determination of 2,4-dichlorophenoxyacetic acid in environmental water. Appl Surf Sci 284:692–699
Tilloy S, Bertoux F, Mortreux A, Monflier E (1999) Chemically modified β-cyclodextrins in biphasic catalysis: a fruitful contribution of the host–guest chemistry to the transition-metal catalyzed reactions. Catal Today 48:245–253
Bonnet P, Jaime C, Morin-Allory L (2001) α-, β-, and γ-cyclodextrin dimers. Molecular modeling studies by molecular mechanics and molecular dynamics simulations. J Org Chem 66:689–692
Becket G, Schep LJ, Tan MY (1999) Improvement of the in vitro dissolution of praziquantel by complexation with α-, β-and γ-cyclodextrins. Int J Pharm 179:65–71
Lichtenthaler FW, Immel S (1996) Molecular modelling of saccharides. Part 9. On the hydrophobic characteristics of cyclodextrins: computer-aided visualization of molecular lipophilicity patterns. Liebigs Ann 1996:27–37
Morin-Crini N, Crini G (2013) Environmental applications of water-insoluble β-cyclodextrin–epichlorohydrin polymers. Prog Polym Sci 38:344–368
Mhlanga SD, Mamba BB, Krause RW, Malefetse TJ (2007) Removal of organic contaminants from water using nanosponge cyclodextrin polyurethanes. J Chem Technol Biotechnol Int Res Proc Environ Clean Technol 82:382–388
Baruch-Teblum E, Mastai Y, Landfester K (2010) Miniemulsion polymerization of cyclodextrin nanospheres for water purification from organic pollutants. Eur Polym J 46:1671–1678
Adams F, Nxumalo E, Krause R, Hoek E, Mamba B (2014) Application of polysulfone/cyclodextrin mixed-matrix membranes in the removal of natural organic matter from water. Phys Chem Earth Parts A/B/C 67:71–78
Ye H, Zhang X, Zhao Z, Song B, Zhang Z, Song W (2017) Pervaporation performance of surface-modified zeolite/PU mixed matrix membranes for separation of phenol from water. Iran Polym J 26:193–203
Junthip J, Promma W, Sonsupap S, Boonyanusith C (2019) Adsorption of paraquat from water by insoluble cyclodextrin polymer crosslinked with 1,2,3,4-butanetetracarboxylic acid. Iran Polym J 28:213–223
Raeisi A, Allahyari F, Faghihi K, Hosseini-Ghazvini SM-B, Khaleghi M, Seidi F, Shabanian M (2020) A complete description on effect of β-cyclodextrin-ester as a bio-based additive for preparation of safe PVC: from synthesis to computational study. Mater Today Commun 22:100736
Raeisi A, Shabanian M, Faghihi K (2017) Preparation of β-cyclodextrin-ester network and new organo-modified LDH as dual additives of PVA: thermal, dynamic-mechanical and migration study. Prog Org Coat 111:402–415
Raeisi A, Faghihi K, Shabanian M (2017) Designed biocompatible nano-inhibitor based on poly(β-cyclodextrin-ester) for reduction of the DEHP migration from plasticized PVC. Carbohydr Polym 174:858–868
Arkas M, Allabashi R, Tsiourvas D, Mattausch E-M, Perfler R (2006) Organic/inorganic hybrid filters based on dendritic and cyclodextrin “nanosponges” for the removal of organic pollutants from water. Environ Sci Technol 40:2771–2777
Khodaverdi E, Aboumaashzadeh M, Tekie FSM, Hadizadeh F, Tabassi SAS, Mohajeri SA, Khashyarmanesh Z, Haghighi HM (2014) Sustained drug release using supramolecular hydrogels composed of cyclodextrin inclusion complexes with PCL/PEG multiple block copolymers. Iran Polym J 23:707–716
Yang Z, Zeng H, Zhou X, Ji H (2012) Mechanism into selective oxidation of cinnamaldehyde using β-cyclodextrin polymer as phase-transfer catalyst. Tetrahedron 68:5912–5919
Li X, Zhou M, Jia J, Jia Q (2018) A water-insoluble viologen-based β-cyclodextrin polymer for selective adsorption toward anionic dyes. React Funct Polym 126:20–26
Wewering F, Jouy F, Wissenbach DK, Gebauer S, Blüher M, Gebhardt R, Pirow R, von Bergen M, Kalkhof S, Luch A (2017) Characterization of chemical-induced sterile inflammation in vitro: application of the model compound ketoconazole in a human hepatic co-culture system. Arch Toxicol 91:799–810
Castro-Puyana M, García-Ruiz C, Cifuentes A, Crego AL, Marina ML (2006) Identification and quantitation of cis-ketoconazole impurity by capillary zone electrophoresis–mass spectrometry. J Chromatogr A 1114:170–177
da Silva RCS, Mano V, Pereira AC, de Figueiredo EC, Borges KB (2016) Development of pipette tip-based on molecularly imprinted polymer micro-solid phase extraction for selective enantioselective determination of (−)-(2S, 4R) and (+)-(2R, 4S) ketoconazole in human urine samples prior to HPLC-DAD. Anal Methods 8:4075–4085
Faghihi K, Gholizadeh M (2009) Rapid synthesis of new poly(amide-imide) s based on N-(4-carboxy phenyl) trimellitimide and hydantoin derivatives under microwave irradiation. Turk J Chem 33:87–97
Yeganeh H, Tamami B, Ghazi I (2002) Synthesis and properties of novel diisocyanate based optically active polyimides. Eur Polym J38:2179–2185
Sreenivasan K (1996) Grafting of β-cyclodextrin-modified 2-hydroxyethyl methacrylate onto polyurethane. J Appl Polym Sci 60:2245–2249
Sreenivasan K (1998) Synthesis and evaluation of a beta cyclodextrin-based molecularly imprinted copolymer. J Appl Polym Sci 70:15–18
Fayazi M, Taher MA, Afzali D, Mostafavi A (2015) Preparation of molecularly imprinted polymer coated magnetic multi-walled carbon nanotubes for selective removal of dibenzothiophene. Mater Sci Semiconduct Proc 40:501–507
Dil NN, Sadeghi M (2018) Free radical synthesis of nanosilver/gelatin-poly(acrylic acid) nanocomposite hydrogels employed for antibacterial activity and removal of Cu(II) metal ions. J Hazard Mater 351:38–53
Arvand M, Hassannezhad M (2014) Magnetic core–shell Fe3O4@SiO2/MWCNT nanocomposite modified carbon paste electrode for amplified electrochemical sensing of uric acid. Mater Sci Eng C 36:160–167
Langmuir I (1918) The adsorption of gases on plane surfaces of glass, mica and platinum. J Am Chem Soc 40:1361–1403
Bulut E, Özacar M, Şengil İA (2008) Equilibrium and kinetic data and process design for adsorption of Congo Red onto bentonite. J Hazard Mater 154:613–622
Freundlich H (1907) Über die adsorption in lösungen. Zeitschrift für Phys Chem 57:385–470
Li Z-C, Fan H-T, Zhang Y, Chen M-X, Yu Z-Y, Cao X-Q, Sun T (2011) Cd(II)-imprinted polymer sorbents prepared by combination of surface imprinting technique with hydrothermal assisted sol–gel process for selective removal of cadmium(II) from aqueous solution. Chem Eng J 171:703–710
Abdel-Halim E, Al-Deyab SS (2014) Preparation of poly(acrylic acid)/starch hydrogel and its application for cadmium ion removal from aqueous solutions. React Funct Polym 75:1–8
Acknowledgements
We gratefully acknowledge the financial support of this work from the Research Council of Arak University.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Soleimani, M., Faghihi, K. Selective adsorption of ketoconazole from aqueous solutions using a new molecularly imprinted polyurethane coated magnetic multiwall carbon nanotubes. Iran Polym J 29, 785–798 (2020). https://doi.org/10.1007/s13726-020-00839-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13726-020-00839-z