Magnetic Graphene Oxide Modified with a Surface-Active Ionic Liquid for Ultrasound-Assisted Solid-Phase Extraction (UA-SPE) to Preconcentrate Lenalidomide from Human Plasma with Determination by High-Performance Liquid Chromatography with Ultraviolet Detection (HPLC-UV)

References

• Adlnasab, L., M. Ezoddin, M. Shabanian, and B. Mahjoob. 2019. Development of ferrofluid mediated CLDH@Fe3O4@Tanic acid- based supramolecular solvent: Application in air-assisted dispersive micro solid phase extraction for preconcentration of diazinon and metalaxyl from various fruit juice samples. Microchemical Journal 146:1–11. doi:10.1016/j.microc.2018.12.020.
   Web of Science ®Google Scholar
• Ai, L., C. Zhang and Z. Chen. 2011. Removal of methylene blue from aqueous solution by a solvothermal-synthesized graphene/magnetite composite. Journal of Hazardous Materials 192:1515–1524. doi:10.1016/j.jhazmat.2011.06.068.
   Web of Science ®Google Scholar
• Aliyari, E., M. Alvand, and F. Shemirani. 2016. Modified surface-active ionic liquid-coated magnetic graphene oxide as a new magnetic solid phase extraction sorbent for preconcentration of trace nickel. RSC Advances 6 (69):64193–202. doi:10.1039/C6RA04163A.
   Web of Science ®Google Scholar
• Asgharinezhad, A. A., N. Mollazadeh, H. Ebrahimzadeh, F. Mirbabaei, and N. Shekari. 2014. Magnetic nanoparticles based dispersive micro-solid-phase extraction as a novel technique for coextraction of acidic and basic drugs from biological fluids and waste water. Journal of Chromatography A 1338:1–8. doi:10.1016/j.chroma.2014.02.027.
   PubMed Web of Science ®Google Scholar
• Banjare, M. K., R. Kurrey, T. Yadav, S. Sinha, L. M. L. Satnami, and K. K. Ghosh. 2017. A comparative study on the effect of imidazolium-based ionic liquid on self-aggregation of cationic, anionic and nonionic surfactants studied by surface tension, conductivity, fluorescence and FTIR spectroscopy. Journal of Molecular Liquids 241:622–32. doi:10.1016/j.molliq.2017.06.009.
   Web of Science ®Google Scholar
• Banerjee, C., S. Mandal, S. Ghosh, J. Kuchlyan, N. Kundu, and N. Sarkar. 2013. Unique characteristics of ionic liquids comprised of long-chain cations and anions: A new physical insight. The Journal of Physical Chemistry B 117 (14):3927–34. doi:10.1021/jp4015405.
   PubMed Web of Science ®Google Scholar
• Berg, S. L., M. S. Cairo, H. Russell, J. Ayello, A. M. Ingle, H. Lau, N. Chen, P. C. Adamson, and S. M. Blaney. 2011. Safety, pharmacokinetics, and immunomodulatory effects of lenalidomide in children and adolescents with relapsed/refractory solid tumors or myelodysplastic syndrome: A children’s oncology group phase I consortium report. Journal of Clinical Oncology 29 (3):316–23. doi:10.1200/JCO.2010.30.8387.
   PubMed Web of Science ®Google Scholar
• Blesic, M., M. H. Marques, N. V. Plechkova, K. R. Seddon, L. P. N. Rebelo, and A. Lopes. 2007. Self-aggregation of ionic liquids: Micelle formation in aqueous solution. Green Chemistry 9 (5):481. doi:10.1039/b615406a.
   Web of Science ®Google Scholar
• Cao, X., M. Lin, H. Wei, H. Yu, and L. Li. 2021. Effect of the modification of magnetic graphene oxide with ionic liquid on the adsorption of nonionic surfactant NP10EO. Environmental Science and Pollution Research International 28 (41):58629–39. doi:10.1007/s11356-021-14784-8.
   PubMed Web of Science ®Google Scholar
• Chang, S., T. Zeng, S. Gao, T. Xia, L. Huang, F. Zhang, and W. Chen. 2016. LC–MS/MS method for simultaneous determination of thalidomide, lenalidomide, cyclophosphamide, bortezomib, dexamethasone and adriamycin in serum of multiple myeloma patients. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 1028:111–9. doi:10.1016/j.jchromb.2016.06.009.
   PubMed Web of Science ®Google Scholar
• Darwish, I. A., N. Y. Khalil, A. H. Bakheit, and N. Z. Alzoman. 2012. A highly sensitive fluorimetric method for determination of lenalidomide in its bulk form and capsules via derivatization with fluorescamine. Chemistry Central Journal 6 (1):118–7. doi:10.1186/1752-153X-6-118.
   PubMedGoogle Scholar
• Freitas, A. A., K. Shimizu, and J. N. C. Lopes. 2014. Complex structure of ionic liquids: Molecular dynamics studies with different cation–anion combinations. Journal of Chemical & Engineering Data 59 (10):3120–9. doi:10.1021/je500197x.
   Web of Science ®Google Scholar
• Guglieri-López, B., A. Pérez-Pitarch, M. A. Martinez-Gómez, B. Porta-Oltra, M. Climente-Martí, and M. Merino-Sanjuán. 2016. A wide linearity range method for the determination of lenalidomide in plasma by gigh-performance liquid chromatography: Application to pharmacokinetic studies. Journal of Laboratory Automation 21 (6):806–10. doi:10.1177/2211068216636570.
   PubMedGoogle Scholar
• Hayes, R., G. G. Warr, and R. Atkin. 2015. Structure and nanostructure in ionic liquids. Chemical Reviews 115 (13):6357–426. doi:10.1021/cr500411q.
   PubMed Web of Science ®Google Scholar
• Hou, C., Q. Zhang, M. Zhu, Y. Li, and H. Wang. 2011. One-step synthesis of magnetically-functionalized reduced graphite sheets and their use in hydrogels. Carbon 49 (1):47–53. doi:10.1016/j.carbon.2010.08.040.
   Web of Science ®Google Scholar
• Kargar, S., D. Elhamifar, and A. Zarnegaryan. 2021. Ionic liquid modified graphene oxide supported Mo-complex: A novel, efficient and highly stable catalyst. Surfaces and Interfaces 23:100946. doi:10.1016/j.surfin.2021.100946.
   Web of Science ®Google Scholar
• Khalil, N. Y., I. A. Darwish, T. A. Wani, and A. R. A. Al-Majed. 2013. Trace determination of lenalidomide in plasma by non-extractive HPLC procedures with fluorescence detection after pre-column derivatization with fluorescamine. Chemistry Central Journal 7 (1):52–7. doi:10.1186/1752-153X-7-52.
   PubMedGoogle Scholar
• Kord, B., F. Movahedi, L. Adlnasab, and H. Masrouri. 2020. Influence of eco-friendly pretreatment of lignocellulosic biomass using ionic liquids on the interface adhesion and characteristics of polymer composite boards. Journal of Composite Materials 54 (25):3717–29. doi:10.1177/0021998320918345.
   Web of Science ®Google Scholar
• Kyzas, G. Z., N. A. Travlou, and E. A. Deliyanni. 2014. The role of chitosan as nanofiller of graphite oxide for the removal of toxic mercury ions. Colloids and Surfaces. B, Biointerfaces 113:467–76. doi:10.1016/j.colsurfb.2013.07.055.
   PubMed Web of Science ®Google Scholar
• Lin, J. H. 2018. The anionic surfactant/ionic liquids intercalated reduced graphene oxide for high-performance supercapacitors. Nanoscale Research Letters 13 (1):1–9. doi:10.1186/s11671-018-2636-9.
   PubMedGoogle Scholar
• Maher, H. M., N. Z. Alzoman, M. M. Alshehri, H. I. Aljohar, S. Shehata, M. Alossaimi, and N. O. Abanmy. 2015. Simultaneous determination of dexamethasone and lenalidomide in rat plasma by solid phase extraction and ultra-performance liquid chromatography-tandem mass spectrometry: Application to pharmacokinetic studies. RSC Advances 5 (119):98600–9. doi:10.1039/C5RA22339C.
   Web of Science ®Google Scholar
• Movahedi, F., H. Masrouri, and H. Tayyebi. 2018. Highly efficient adsorption behavior of benzoylthiourea functionalized graphene oxide with respect to the removal of Hg(II) from aqueous solutions: Isothermal, kinetic and thermodynamic studies. Research on Chemical Intermediates 44 (9):5419–38. doi:10.1007/s11164-018-3431-z.
   Web of Science ®Google Scholar
• Palumbo, A., J. S. Miguel, P. Sonneveld, P. Moreau, J. Drach, G. Morgan, and H. Einsele. 2008. Lenalidomide: A new therapy for multiple myeloma. Cancer Treatment Reviews 34 (3):283–91. doi:10.1016/j.ctrv.2007.12.005.
   PubMed Web of Science ®Google Scholar
• Pashaei, Y., F. Ghorbani-Bidkorbeh, and M. Shekarchi. 2017. Superparamagneticgraphene oxide-based dispersive-solid phase extraction for preconcentration and determination of tamsulosin hydrochloride in human plasma by high performance liquid chromatography-ultraviolet detection. Journal of Chromatography A 1499:21–9. doi:10.1016/j.chroma.2017.03.038.
   PubMed Web of Science ®Google Scholar
• Pino, V., C. Yao, and J. L. Anderson. 2009. Micellization and interfacial behavior of imidazoliumbased ionic liquids in organic solvent–water mixtures. Journal of Colloid and Interface Science 333 (2):548–56. doi:10.1016/j.jcis.2009.02.037.
   PubMed Web of Science ®Google Scholar
• Ranganathan, P., V. Gunasekaran, I. Singhvi, and M. J. Ansari. 2019. Development and validation of Lenalidomide in human plasma by LC-MS/MS. Saudi Journal of Biological Sciences 26 (7):1843–7. doi:10.1016/j.sjbs.2018.02.006.
   PubMed Web of Science ®Google Scholar
• Richardson, P. G., R. L. Schlossman, E. Weller, T. Hideshima, C. Mitsiades, F. Davies, R. LeBlanc, L. P. Catley, D. Doss, K. Kelly, et al. 2002. Immunomodulatory drug CC-5013 overcomes drug resistance and is well tolerated in patients with relapsed multiple myeloma. Blood 100 (9):3063–7. doi:10.1182/blood-2002-03-0996.
   PubMed Web of Science ®Google Scholar
• Rodríguez-Escontrela, I., I. Rodríguez-Palmeiro, O. Rodríguez, A. Arce, and A. Soto. 2016. Characterization and phase behavior of the surfactant ionic liquid tributylmethylphosphonium dodecylsulfate for enhanced oil recovery. Fluid Phase Equilibria 417:87–95. doi:10.1016/j.fluid.2016.02.021.
   Web of Science ®Google Scholar
• Shah, S. R., and T. M. Tran. 2007. Lenalidomide in myelodysplastic syndrome andmultiple myeloma. Drugs 67:1869–81.doi: 10.2165/00003495-200767130-00005.
   PubMed Web of Science ®Google Scholar
• Stolte, S., S. Steudte, A. Igartua, and P. Stepnowski. 2011. The biodegradation of ionic liquids the view from a chemical structure perspective. Current Organic Chemistry 15 (12):1946–73. doi:10.2174/138527211795703603.
   Web of Science ®Google Scholar
• Tariman, J. D. 2007. Lenalidomide: A new agent for patients with relapsed or refractory multiple myeloma. Clinical Journal of Oncology Nursing 11 (4):569–74. doi:10.1188/07.CJON.569-574.
   PubMedGoogle Scholar
• Valizadeh, H., M. Amiri, and F. Hosseinzadeh. 2012. Nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica for the diazotization of aniline derivatives and subsequent synthesis of azo dyes. Dyes and Pigments 92 (3):1308–13. doi:10.1016/j.dyepig.2011.09.013.
   Web of Science ®Google Scholar
• Wang, H, and Y. Wei. 2017. Magnetic graphene oxide modified by chloride imidazole ionicliquid for the high-efficiency adsorption of anionic dyes. RSC Advances 7 (15):9079–89. doi:10.1039/C6RA27530C.
   Web of Science ®Google Scholar
• Wang, S., Z. Zhang, B. Liu, and J. Li. 2013. Silica coated magnetic Fe3O4 nanoparticles supported phosphotungstic acid: A novel environmentally friendly catalyst for the synthesis of 5-ethoxy methyl furfural from 5-hydroxymethylfurfural and fructose. Catalysis Science & Technology 3 (8):2104–12. doi:10.1039/c3cy00223c.
   Web of Science ®Google Scholar
• Wasserscheid, P., R. van Hal, and A. Bösmann. 2002. 1-n-Butyl-3-methylimidazolium ([bmim]) Octylsulfate an even ‘greener’ ionic liquid. Green Chemistry 4 (4):400–4. doi:10.1039/B205425F.
   Web of Science ®Google Scholar
• Watteyn, A., H. Wyns, E. Plessers, E. Russo, S. De Baere, P. De Backer, and S. Croubels. 2013. Pharmacokinetics of dexamethasone after intravenous and intramuscular administration in broiler chickens. Veterinary Journal (London, England: 1997) 195 (2):216–20. doi:10.1016/j.tvjl.2012.06.026.
   PubMed Web of Science ®Google Scholar
• Wu, J., Y. Gao, W. Zhang, Y. Tan, A. Tang, Y. Men, and B. Tang. 2014a. Deep oxidation desulfurization with a new imidazole-type acidic ionic liquid polymer. RSC Advances 4 (102):58800–4. doi:10.1039/C4RA10577J.
   Web of Science ®Google Scholar
• Wu, Z., H. Zhong, X. Yuan, H. Wang, L. Wang, X. Chen, G. Zeng, and Y. Wu. 2014b. Adsorptive removal of methylene blue by rhamnolipid-functionalized graphene oxide from wastewater. Water Research 67:330–44. doi:10.1016/j.watres.2014.09.026.
   PubMed Web of Science ®Google Scholar
• Yarahmadi, E., K. Didehban, M. G. Sari, M. R. Saeb, M. Shabanian, F. Aryanasab, P. Zarrintaj, S. M. R. Paran, M. Mozafari, M. Rallini, et al. 2018. Development and curing potential of epoxy/starch-functionalized graphene oxide nanocomposite coatings. Progress in Organic Coatings 119:194–202. doi:10.1016/j.porgcoat.2018.03.001.
   Web of Science ®Google Scholar
• Zhang, Q., F. Yang, F. Tang, K. Zeng, K. Wu, Q. Cai, and S. Yao. 2010. Ionic liquid-coated Fe3O4 magnetic nanoparticles as an adsorbent of mixed hemimicelles solid-phase extraction for preconcentration of polycyclic aromatic hydrocarbons in environmental samples. The Analyst 135 (9):2426–33. doi:10.1039/c0an00245c.
   PubMed Web of Science ®Google Scholar