Magnetic-Solid Phase Extraction of 5-Fluorouracil Using Newly Synthesized Surface-Imprinted Magnetic Hollow Porous Polymer

Authors

  • Nur Shahz Ereena Zulkifli Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM, Johor Bahru, Johor, Malaysia
  • Aemi Syazwani Abdul Keyon Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM, Johor Bahru, Johor, Malaysia
  • Khairil Juhanni Abd Karim Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM, Johor Bahru, Johor, Malaysia
  • Noorfatimah Yahaya Department of Toxicology, Advanced Medical and Dental Institute (AMDI), Universiti Sains Malaysia, 13200, Bertam Kepala Batas, Penang, Malaysia

DOI:

https://doi.org/10.11113/jomalisc.v3.49

Keywords:

Molecularly imprinted polymer, magnetic-solid phase extraction, 5-fluorouracil, capillary electrophoresis

Abstract

A magnetic hollow porous molecularly imprinted polymer (MHPMIP) was developed using a surface imprinting technique (mesoporous MCM-48 as a core). Its potential as a magnetic-solid phase extraction (MSPE) sorbent for the extraction of 5-fluorouracil (5-FU) anticancer drug was investigated to overcome some drawbacks caused by conventional SPE sorbents. Although SPE offers advantages such as rapidity and simplicity, the issues of low selectivity and sensitivity still remain unsolved. Moreover, the current determination methods of 5-FU in water samples are seriously disadvantaged due to major matrix interferences. Thus, extensive sample preparation is required before instrumental analysis. The MHPMIP was synthesized via precipitation polymerization using a functional monomer, methacrylic acid (MAA), crosslinking agent, ethylene glycol dimethacrylate (EGDMA), an initiator 4,4’-azobis (4-cyanopentanoic acid) (ACPA), and also the template, 5-FU. The specific surface area of MHPMIP was determined to be 63.47 m2/g with a pore volume of 0.2325 cm3/g using Brunauer-Emmett-Teller (BET) method. The MHPMIP possessed a good adsorption capacity of 2.089 mg/g. The adsorption capacity of 5-FU was significantly higher than that of the non-imprinted one (MHPNIP) (0.02324 mg/g). Coupled with FASI-CZE, the MSPE using the MHPMIP as sorbent showed that it could extract 5-FU from wastewater samples at low ppm levels. The limit of detection (LOD) and the limit of quantitation (LOQ) of the MSPE-FASI-CZE method was found to be 3.228 and 9.782 mg/L, respectively, in the linear concentration range of 5 to 15 mg/L with a good correlation (R2 = 0.9973). A recovery up to 105.7% (RSD% 9.428, n = 3) was obtained for 5-FU (5 mg/L) spiked in real samples.

References

Wormington, A.M., De María, M., Kurita, H.G., Bisesi Jr, J.H., Denslow, N.D., Martyniuk, C.J., 2020. Antineoplastic Agents: Environmental Prevalence and Adverse Outcomes in Aquatic Organisms, Environmental Toxicology and Chemistry, 39(5), 967-985.

Mullot, J.-U., Karolak, S., Fontova, A., Huart, B., Levi, Y., 2009. Development and Validation of a Sensitive and Selective Method Using Gc/Ms-Ms for Quantification of 5-Fluorouracil in Hospital Wastewater, Analytical and Bioanalytical Chemistry, 394(8), 2203-2212.

Białk-Bielińska, A., Mulkiewicz, E., Stokowski, M., Stolte, S., Stepnowski, P., 2017. Acute Aquatic Toxicity Assessment of Six Anti-Cancer Drugs and One Metabolite Using Biotest Battery – Biological Effects and Stability under Test Conditions, Chemosphere, 189, 689-698.

Serna-Galvis, E.A., Silva-Agredo, J., Botero-Coy, A.M., Moncayo-Lasso, A., Hernández, F., Torres-Palma, R.A., 2019. Effective Elimination of Fifteen Relevant Pharmaceuticals in Hospital Wastewater from Colombia by Combination of a Biological System with a Sonochemical Process, Science of The Total Environment, 670, 623-632.

Zounr, R.A., Khuhawar, M.Y., Khuhawar, T.M.J., Lanjwani, M.F., Khuhawar, M.Y., 2022. GC Determination of Fluorouracil in Serum by Using Hexafluroroacetylacetone as Derivatizing Reagent, Journal of Chromatographic Science, 60(5), 409-413.

Ebratkhahan, M., Zarei, M., Babaei, T., Hosseini, M.G., Hosseini, M.M., Fathipour, Z., 2022. Efficient Electrochemical Removal of 5-Fluorouracil Pharmaceutical from Wastewater by Mixed Metal Oxides Via Anodic Oxidation Process, Chemosphere, 296, 134007.

Youssef, S.H., Afinjuomo, F., Song, Y., Garg, S., 2021. Development of a Novel Chromatographic Method for Concurrent Determination of 5-Fluorouracil and Cisplatin: Validation, Greenness Evaluation, and Application on Drug-Eluting Film, Microchemical Journal, 168, 106510.

Gopinath, P., Veluswami, S., Thangarajan, R., Gopisetty, G., 2018. Rp-Hplc-Uv Method for Estimation of Fluorouracil–Epirubicin–Cyclophosphamide and Their Metabolite Mixtures in Human Plasma (Matrix), Journal of Chromatographic Science, 56(6), 488-497.

Shiokawa, R., Lee, X.-P., Yamada, M., Fujishiro, M., Sakamaki, H., Hasegawa, C., Ishida, H., Ikeda, K., Fujita, K.-i., Iwabuchi, S., Onda, H., Kumazawa, T., Sasaki, Y., Sato, K., Matsuyama, T., 2019. High-Throughput Method to Analyze Tegafur and 5-Fluorouracil in Human Tears and Plasma Using Hydrophilic Interaction Liquid Chromatography/Tandem Mass Spectrometry, Rapid Communications in Mass Spectrometry, 33(24), 1906-1914.

Kosjek, T., Heath, E., 2011. Occurrence, Fate and Determination of Cytostatic Pharmaceuticals in the Environment, TrAC Trends in Analytical Chemistry, 30(7), 1065-1087.

Nussbaumer, S., Bonnabry, P., Veuthey, J.-L., Fleury-Souverain, S., 2011. Analysis of Anticancer Drugs: A Review, Talanta, 85(5), 2265-2289.

Kartsova, L.A., Bessonova, E.A., 2009. Preconcentration Techniques in Capillary Electrophoresis, Journal of Analytical Chemistry, 64(4), 326-337.

Tang, S., Zhang, H., Lee, H.K., 2016. Advances in Sample Extraction, Analytical Chemistry, 88(1), 228-249.

Madikizela, L.M., Tavengwa, N.T., Chimuka, L., 2018. Applications of Molecularly Imprinted Polymers for Solid-Phase Extraction of Non-Steroidal Anti-Inflammatory Drugs and Analgesics from Environmental Waters and Biological Samples, J Pharm Biomed Anal, 147, 624-633.

Pietrogrande, M.C., Demaria, G., Russo, M., 2023. Determination of Particulate Polycyclic Aromatic Hydrocarbons in Ambient Air by Gas Chromatography-Mass Spectrometry after Molecularly Imprinted Polymer Extraction, Journal of Environmental Sciences, 124, 644-654

Fu, Y., Pessagno, F., Manesiotis, P., Borrull, F., Fontanals, N., Maria Marcé, R., 2022. Preparation and Evaluation of Molecularly Imprinted Polymers as Selective Spe Sorbents for the Determination of Cathinones in River Water, Microchemical Journal, 175, 107100.

Marć, M., Panuszko, A., Namieśnik, J., Wieczorek, P.P., 2018. Preparation and Characterization of Dummy-Template Molecularly Imprinted Polymers as Potential Sorbents for the Recognition of Selected Polybrominated Diphenyl Ethers, Analytica Chimica Acta, 1030, 77-95.

Zhao, Y., Bi, C., He, X., Chen, L., Zhang, Y., 2015. Preparation of Molecularly Imprinted Polymers Based on Magnetic Carbon Nanotubes for Determination of Sulfamethoxazole in Food Samples, RSC Advances, 5(86), 70309-70318.

Dai, X., Wang, D., Li, H., Chen, Y., Gong, Z., Xiang, H., Shi, S., Chen, X., 2017. Hollow Porous Ionic Liquids Composite Polymers Based Solid Phase Extraction Coupled Online with High Performance Liquid Chromatography for Selective Analysis of Hydrophilic Hydroxybenzoic Acids from Complex Samples, Journal of Chromatography A, 1484, 7-13.

Attallah, O.A., Al-Ghobashy, M.A., Ayoub, A.T., Nebsen, M., 2018. Magnetic Molecularly Imprinted Polymer Nanoparticles for Simultaneous Extraction and Determination of 6-Mercaptopurine and Its Active Metabolite Thioguanine in Human Plasma, Journal of Chromatography A, 1561, 28-38.

Shan, S., Ma, Y., Sun, C., Guo, X., Zheng, H., Xu, X., Qin, L., Hu, J., 2021. A Novel Magnetic Solid-Phase Extraction Method for Detection of 14 Heterocyclic Aromatic Amines by Uplc-Ms/Ms in Meat Products, Food Chemistry, 337, 127630.

Rocío-Bautista, P., Pino, V., Extraction Methods Facilitated by the Use of Magnetic Nanoparticles, Analytical Separation Science, pp. 1681-1724. https://doi.org/https://doi.org/10.1002/9783527678129.assep061.

Adlnasab, L., Ezoddin, M., Shojaei, R.A., Aryanasab, F., 2018. Ultrasonic-Assisted Dispersive Micro Solid-Phase Extraction Based on Melamine-Phytate Supermolecular Aggregate as a Novel Bio-Inspired Magnetic Sorbent for Preconcentration of Anticancer Drugs in Biological Samples Prior to Hplc-Uv Analysis, Journal of Chromatography B, 1095, 226-234.

Kazemi, S., Sarabi, A.A., Abdouss, M., 2016. Synthesis and Characterization of Magnetic Molecularly Imprinted Polymer Nanoparticles for Controlled Release of Letrozole, Korean Journal of Chemical Engineering, 33(11), 3289-3297.

Puoci, F., Iemma, F., Cirillo, G., Picci, N., Matricardi, P., Alhaiqu, F., 2007. Molecularly Imprinted Polymers for 5-Fluorouracil Release in Biological Fluids, Molecules, 12(4), 805-14.

Chen, L., Xu, S., Li, J., 2011. Recent Advances in Molecular Imprinting Technology: Current Status, Challenges and Highlighted Applications, Chemical Society Reviews, 40(5), 2922-2942.

Rezaei, B., Rahmanian, O., 2011. Nanolayer Treatment to Realize Suitable Configuration for Electrochemical Allopurinol Sensor Based on Molecular Imprinting Recognition Sites on Multiwall Carbon Nanotube Surface, Sensors and Actuators B: Chemical, 160(1), 99-104.

Wei, S., Molinelli, A., Mizaikoff, B., 2006. Molecularly Imprinted Micro and Nanospheres for the Selective Recognition of 17β-Estradiol, Biosensors and Bioelectronics, 21(10), 1943-1951.

Lu, A.-H., Salabas, E.L., Schüth, F., 2007. Magnetic Nanoparticles: Synthesis, Protection, Functionalization, and Application, Angewandte Chemie International Edition, 46(8), 1222-1244.

Zhang, X.-B., Li, J., You, B., Yong, G.-P., Tong, H.-W., Liu, S.-M., 2012. Hollow Porous Molecularly Imprinted Polymer Nanosphere for Fast and Efficient Recognition of Bisphenol A, RSC Advances, 2(26), 9778-9780.

Forough, M., Farhadi, K., Molaei, R., Khalili, H., Shakeri, R., Zamani, A., Matin, A.A., 2017. Capillary Electrophoresis with Online Stacking in Combination with Agnps@Mcm-41 Reinforced Hollow Fiber Solid-Liquid Phase Microextraction for Quantitative Analysis of Capecitabine and Its Main Metabolite 5-Fluorouracil in Plasma Samples Isolated from Cancer Patients, Journal of Chromatography B, 1040, 22-37.

Abdouss, M., Azodi-Deilami, S., Asadi, E., Shariatinia, Z., 2012. Synthesis of Molecularly Imprinted Polymer as a Sorbent for Solid Phase Extraction of Citalopram from Human Serum and Urine, Journal of Materials Science: Materials in Medicine, 23(6), 1543-1552.

Musa, M., Wan Ibrahim, W.A., Mohd Marsin, F., Abdul Keyon, A.S., Rashidi Nodeh, H., 2018. Graphene-Magnetite as Adsorbent for Magnetic Solid Phase Extraction of 4-Hydroxybenzoic Acid and 3,4-Dihydroxybenzoic Acid in Stingless Bee Honey, Food Chemistry, 265, 165-172.

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Published

2024-05-25

How to Cite

Zulkifli, N. S. E., Abdul Keyon, A. S., Abd Karim, K. J., & Yahaya, N. (2024). Magnetic-Solid Phase Extraction of 5-Fluorouracil Using Newly Synthesized Surface-Imprinted Magnetic Hollow Porous Polymer . Journal of Materials in Life Sciences (JOMALISC), 3(1), 8–20. https://doi.org/10.11113/jomalisc.v3.49

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