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Environmental Analysis

Selective Determination of n-Hexane and Methyl Ethyl Ketone (MEK) in Urine by Magnetic-Silica Aerogel-Based Molecularly Imprinted Polymers (MIPs) with Gas Chromatography – Flame Ionization Detection (GC-FID)

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Pages 1292-1311 | Received 17 Aug 2022, Accepted 21 Sep 2022, Published online: 30 Sep 2022

References

  • American Conference of Governmental Industrial Hygienists. 2021. Threshold limit values for chemical substances and physical agents and biological exposure indices. Accessed February 17, 2022. http://www.acgih.org/tlv-bei-guidelines/.
  • Ansari, S. 2017. Application of magnetic molecularly imprinted polymer as a versatile and highly selective tool in food and environmental analysis: Recent developments and trends. TrAC Trends in Analytical Chemistry 90:89–106. doi:10.1016/j.trac.2017.03.001.
  • Chambers, D. M., B. C. Blount, D. O. McElprang, M. G. Waterhouse, and J. C. Morrow. 2008. Picogram measurement of volatile n-alkanes (n-hexane through n-dodecane) in blood using solid-phase microextraction to assess nonoccupational petroleum-based fuel exposure. Analytical Chemistry 80 (12):4666–74. doi:10.1021/ac800065d.
  • Chen, W., Z. Wang, S. Gu, and J. Wang. 2019. Detection of hexanal in humid circumstances using hydrophobic molecularly imprinted polymers composite. Sensors and Actuators B: Chemical 291:141–7. doi:10.1016/j.snb.2019.04.065.
  • Cosnier, F., S. Grossmann, H. Nunge, C. Brochard, S. Muller, A.-M. Lambert-Xolin, S. Sebillaud, B. Rieger, A. Thomas, M.-J. Décret, et al. 2018. Metabolism of inhaled methylethylketone in rats. Drug and Chemical Toxicology 41 (1):42–50. doi:10.1080/01480545.2017.1289220.
  • dos Santos, C. R., M. M. Passarelli, and E. de Souza Nascimento. 2002. Evaluation of 2, 5-hexanedione in urine of workers exposed to n-hexane in Brazilian shoe factories. Journal of Chromatography B 778 (1–2):237–44.
  • Fedtke, N., and H. M. Bolt. 1986. Methodological investigations on the determination of n-hexane metabolites in urine. International Archives of Occupational and Environmental Health 57 (2):149–58. doi:10.1007/BF00381383.
  • Fernandes, R. S., M. Dinc, I. M. Raimundo, Jr, and B. Mizaikoff. 2018. Synthesis and characterization of porous surface molecularly imprinted silica microsphere for selective extraction of ascorbic acid. Microporous and Mesoporous Materials 264:28–34. doi:10.1016/j.micromeso.2017.07.019.
  • Gargouri, I., M. Khadhraoui, C. Nisse, A. Leroyer, M. L. Masmoudi, P. Frimat, D. Marzin, B. Elleuch, and D. Zmirou-Navier. 2011. A case study on co-exposure to a mixture of organic solvents in a Tunisian adhesive-producing company. Journal of Occupational Medicine and Toxicology (London, England) 6 (1):28. doi:10.1186/1745-6673-6-28.
  • Ghafari, J., M. Vahabi, S. F. Dehghan, and R. Zendehdel. 2020. Inside-tube solid-phase microextraction as an interlink between solid-phase microextraction and needle device for n-hexane evaluation in air and urine headspace. Biomedical Chromatography : BMC 34 (10):e4924. doi:10.1002/bmc.4924.
  • Gomes, P. C. F., É. D. D. Andrea, C. B. Mendes, and M. E. P. B. Siqueira. 2010. Determination of benzene, toluene and n-hexane in urine and blood by headspace solid-phase microextration/gas-chromatography for the biomonitoring of occupational exposure. Journal of the Brazilian Chemical Society 21 (1):119–26. doi:10.1590/S0103-50532010000100018.
  • Gori, G., G. B. Bartolucci, A. Sturaro, G. Parvoli, L. Doretti, R. Troiano, and B. Casetta. 1995. High-performance liquid chromatographic determination of urinary 2, 5-hexanedione as mono-2, 4-dinitrophenylhydrazone using ultraviolet detection. Journal of Chromatography B: Biomedical Sciences and Applications 673 (2):165–72. doi:10.1016/0378-4347(95)00257-X.
  • Gori, G., P. Meneghetti, A. Sturaro, G. Parvoli, L. Doretti, and G. B. Bartolucci. 1995. High performance liquid chromatographic determination of methyl ethyl ketone in urine as its 3-methyl-2-benzothiazolinone hydrazone derivative. Chromatographia 40 (5–6):336–40. doi:10.1007/BF02290366.
  • Hu, C., Z. Yang, F. Yan, and B. Sun. 2019. Extraction of the toluene exposure biomarkers hippuric acid and methylhippuric acid using a magnetic molecularly imprinted polymer, and their quantitation by LC-MS/MS. Mikrochimica Acta 186 (3):135. doi:10.1007/s00604-019-3239-6.
  • Huang, D.-L., R.-Z. Wang, Y.-G. Liu, G.-M. Zeng, C. Lai, P. Xu, B.-A. Lu, J.-J. Xu, C. Wang, and C. Huang. 2015. Application of molecularly imprinted polymers in wastewater treatment: A review. Environmental Science and Pollution Research International 22 (2):963–77. doi:10.1007/s11356-014-3599-8.
  • Imbriani, M., and S. Ghittori. 2005. Gases and organic solvents in urine as biomarkers of occupational exposure: A review. International Archives of Occupational and Environmental Health 78 (1):1–19. doi:10.1007/s00420-004-0544-z.
  • Jakubowski, M., and M. Trzcinka-Ochocka. 2005. Biological Monitoring of Exposure: Trends and Key Developments. Journal of Occupational Health 47 (1):22–48. doi:10.1539/joh.47.22.
  • Jalili, V., A. Barkhordari, and M. Heidari. 2019. The role of aerogel-based sorbents in microextraction techniques. Microchemical Journal 147:948–54. doi:10.1016/j.microc.2019.04.028.
  • Jalilian, N., H. Ebrahimzadeh, A. A. Asgharinezhad, and P. Khodayari. 2021. Magnetic molecularly imprinted polymer for the selective dispersive micro solid phase extraction of phenolphthalein in urine samples and herbal slimming capsules prior to HPLC-PDA analysis. Microchemical Journal 160:105712. doi:10.1016/j.microc.2020.105712.
  • Kežić, S., and A. C. Monster. 1991. Determination of 2, 5-hexanedione in urine and serum by gas chromatography after derivatization with O-(pentafluorobenzyl) hydroxylamine and solid-phase extraction. Journal of Chromatography B: Biomedical Sciences and Applications 563 (1):199–204. doi:10.1016/0378-4347(91)80296-O.
  • Kim, M.-S., H. R. Park, M. Park, S. J. Kim, M. Kwon, B. P. Yu, H. Y. Chung, H. S. Kim, S. J. Kwack, T. S. Kang, et al. 2009. Neurotoxic effect of 2, 5-hexanedione on neural progenitor cells and hippocampal neurogenesis. Toxicology 260 (1–3):97–103. doi:10.1016/j.tox.2009.03.013.
  • Kolaei, M., K. Dashtian, Z. Rafiee, and M. Ghaedi. 2016. Ultrasonic-assisted magnetic solid phase extraction of morphine in urine samples by new imprinted polymer-supported on MWCNT-Fe3O4-NPs: Central composite design optimization. Ultrasonics Sonochemistry 33:240–8. doi:10.1016/j.ultsonch.2016.05.003.
  • Köse, K., D. Y. Kehribar, and L. Uzun. 2021. Molecularly imprinted polymers in toxicology: A literature survey for the last 5 years. Environmental Science and Pollution Research International 28 (27):35437–71. doi:10.1007/s11356-021-14510-4.
  • Kutlu, G., Y. B. Gomceli, T. Sonmez, and L. E. Inan. 2009. Peripheral neuropathy and visual evoked potential changes in workers exposed to n-hexane. Journal of Clinical Neuroscience 16 (10):1296–9. doi:10.1016/j.jocn.2008.12.021.
  • Landarani, M., A. A. Asgharinezhad, and H. Ebrahimzadeh. 2020. A magnetic ion-imprinted polymer composed of silica-coated magnetic nanoparticles and polymerized 4-vinyl pyridine and 2, 6-diaminopyridine for selective extraction and determination of lead ions. New Journal of Chemistry 44 (18):7561–8. doi:10.1039/D0NJ01109F.
  • Long, Z., W. Xu, Y. Lu, and H. Qiu. 2016. Nanosilica-based molecularly imprinted polymer nanoshell for specific recognition and determination of rhodamine B in red wine and beverages. Journal of Chromatography B 1029–1030:230–8. doi:10.1016/j.jchromb.2016.06.030.
  • Martín-Esteban, A. 2013. Molecularly-imprinted polymers as a versatile, highly selective tool in sample preparation. TrAC Trends in Analytical Chemistry 45:169–81. doi:10.1016/j.trac.2012.09.023.
  • Mayan, O., J. P. Teixeira, and A. F. Pires. 2001. Biological monitoring of n-hexane exposure in Portuguese shoe manufacturing workers. Applied Occupational and Environmental Hygiene 16 (7):736–41. doi:10.1080/10473220116711.
  • McDermott, C., A. Allshire, F. N. van Pelt, and J. J. A. Heffron. 2007. Sub-chronic toxicity of low concentrations of industrial volatile organic pollutants in vitro. Toxicology and Applied Pharmacology 219 (1):85–94. doi:10.1016/j.taap.2006.12.004.
  • Mitra, S. 2004. Sample preparation techniques in analytical chemistry. Vol. 237. Hoboken, NJ: John Wiley & Sons.
  • National Institute for Occupational Safety and Health. 2014. Method: 8319. Acetone and methyl ethyl ketone in urine. Accessed August 05, 2021. https://www.cdc.gov/niosh/docs/2003-154/pdfs/8319.pdf.
  • National Research Council. 2013. Acute exposure guideline levels for selected airborne chemicals. Vol. 14. National Academies Press, Washington, DC.
  • Nolasco, D. M., A. Gusmão, and M. E. P. B. D. Siqueira. 2007. Urinary 2, 5-hexanedione in workers exposed to n-hexane: Influence of the sample treatment. Química Nova 30 (4):805–8. doi:10.1590/S0100-40422007000400009.
  • Oliveira, A. F. F., P. P. Maia, M. J. N. Paiva, and M. E. P. B. Siqueira. 2009. Determination of 2, 5-hexanedione in urine by headspace solid-phase microextraction and gas chromatography. Journal of Analytical Toxicology 33 (4):223–8. doi:10.1093/jat/33.4.223.
  • Oțelea, M., C. Handra, and A. Rașcu. 2015. Registered cases of occupational n-hexane intoxication in Bucharest. Romanian Journal of Legal Medicine 23 (4):279–84. doi:10.4323/rjlm.2015.279.
  • Pacenti, M., S. Dugheri, P. Traldi, F. Degli Esposti, N. Perchiazzi, E. Franchi, M. Calamante, I. Kikic, P. Alessi, A. Bonacchi, et al. 2010. New automated and high-throughput quantitative analysis of urinary ketones by multifiber exchange-solid phase microextraction coupled to fast gas chromatography/negative chemical-electron ionization/mass spectrometry. Journal of Automated Methods & Management in Chemistry 2010 (1):972926–13. doi:10.1155/2010/972926.
  • Panjali, Z., A. A. Asgharinezhad, H. Ebrahimzadeh, S. Karami, M. Loni, M. Rezvani, R. Yarahmadi, and S. J. Shahtaheri. 2015. Development of a selective sorbent based on a magnetic ion imprinted polymer for the preconcentration and FAAS determination of urinary cadmium. Analytical Methods 7 (8):3618–24. doi:10.1039/C4AY03066D.
  • Petrarulo, M., S. Pellegrino, and E. Testa. 1992. High-performance liquid chromatographic microassay for methyl ethyl ketone in urine as the 2,4-dinitrophenylhydrazone derivative. Journal of Chromatography B: Biomedical Sciences and Applications 579 (2):324–8. doi:10.1016/0378-4347(92)80398-A.
  • Piovesana, S., A. L. Capriotti, C. Cavaliere, K. Sparnacci, V. Gianotti, M. Laus, D. Antonioli, and A. Laganà. 2020. Magnetic molecularly imprinted multishell particles for zearalenone recognition. Polymer 188:122102. doi:10.1016/j.polymer.2019.122102.
  • Pourjavadi, A., Z. M. Tehrani, and S. Jokar. 2015. Functionalized mesoporous silica-coated magnetic graphene oxide by polyglycerol-g-polycaprolactone with pH-responsive behavior: Designed for targeted and controlled doxorubicin delivery. Journal of Industrial and Engineering Chemistry 28:45–53. doi:10.1016/j.jiec.2015.01.021.
  • Prieto-Castelló, M. J., M. L. Hernández-Viadel, A. Cardona, D. Marhuenda, and V. Felipo. 2007. Activation of soluble guanylate cyclase by nitric oxide is increased in lymphocytes from both rats chronically exposed to 2, 5-hexanedione and workers chronically exposed to n-hexane. Toxicology 229 (1–2):73–8. doi:10.1016/j.tox.2006.10.002.
  • Saad, N., M. Chaaban, D. Patra, A. Ghanem, and H. El-Rassy. 2020. Molecularly imprinted phenyl-functionalized silica aerogels: Selective adsorbents for methylxanthines and PAHs. Microporous and Mesoporous Materials 292:109759. doi:10.1016/j.micromeso.2019.109759.
  • Shibata, E., G. Johanson, A. Löf, L. Ernstgård, E. Gullstrand, and K. Sigvardsson. 2002. Changes in n-hexane toxicokinetics in short-term single exposure due to co-exposure to methyl ethyl ketone in volunteers. International Archives of Occupational and Environmental Health 75 (6):399–405. doi:10.1007/s00420-002-0325-5.
  • Tian, X., C. She, Z. Qi, and X. Xu. 2019. Magnetic-graphene oxide based molecularly imprinted polymers for selective extraction of microsystin-LR prior to the determination by HPLC. Microchemical Journal 146:1126–33. doi:10.1016/j.microc.2019.02.033.
  • Torres, M. E., L. L. Gonçalves, M. R. Bronze, A. P. M. dos Santos, M. C. Batoréu, and M. L. Mateus. 2014. Alternative biomarkers of n-hexane exposure: Characterization of aminoderived pyrroles and thiol-pyrrole conjugates in urine of rats exposed to 2, 5-hexanedione. Toxicology Letters 224 (1):54–63. doi:10.1016/j.toxlet.2013.10.011.
  • Toudeshki, R. M., S. Dadfarnia, and A. M. H. Shabani. 2019. Surface molecularly imprinted polymer on magnetic multi-walled carbon nanotubes for selective recognition and preconcentration of metformin in biological fluids prior to its sensitive chemiluminescence determination: Central composite design optimization. Analytica Chimica Acta 1089:78–89. doi:10.1016/j.aca.2019.08.070.
  • Xie, L., J. Guo, Y. Zhang, Y. Hu, Q. You, and S. Shi. 2015. Novel molecular imprinted polymers over magnetic mesoporous silica microspheres for selective and efficient determination of protocatechuic acid in Syzygium aromaticum. Food Chemistry 178:18–25. doi:10.1016/j.foodchem.2015.01.069.
  • Xing-Fu, P., Q. Ya-Ling, Z. Wei, T. Hong-Fang, R. Zheng, W. Bang-Hua, H. Han-Lin, Z. Yu-Xin, and Y. Hui-Fang. 2016. Determination of total urinary 2, 5-hexanedione in the Chinese general population. Environmental Research 150:645–50. doi:10.1016/j.envres.2016.05.030.
  • Yu, R., D. Hattis, E. M. Landaw, and J. R. Froines. 2002. Toxicokinetic interaction of 2, 5-hexanedione and methyl ethyl ketone. Archives of Toxicology 75 (11–12):643–52. doi:10.1007/s00204-001-0298-2.
  • Zendehdel, R., M. Parsarad, E. A. Gandomani, Z. Panjali, A. Rafieepour, Z. Mohammadi, Z. Moradpour, M. Vahabi, M. M. Alipour, and R. Gholamiarjenaki. 2021. Risk assessment of chemical mixtures by benchmark dose-principle component analysis approach in occupational exposure. Environmental Science and Pollution Research 28 (41):58781–6. doi:10.1007/s11356-021-14815-4.
  • Zeverdegani, S. K., A. Bahrami, M. Rismanchian, and F. G. Shahna. 2016. Extraction of toluene and methyl ethyl ketone from aquatic samples with NTD technique and nano sorb. Iran Occupational Health 13 (2):10–6.
  • Zhang, M., J. Zeng, Y. Wang, and X. Chen. 2013. Developments and trends of molecularly imprinted solid-phase microextraction. Journal of Chromatographic Science 51 (7):577–86. doi:10.1093/chromsci/bms260.

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