Selective Dispersive Solid Phase Extraction of Ser-traline Using Surface Molecularly Imprinted Polymer Grafted on SiO2/Graphene Oxide

Authors

Department of Chemistry, College of Basic Science, Yadegar -e-Imam Khomeini (RAH) Shahre Rey Branch, Islamic Azad University, Tehran, Iran

Abstract

A surface molecularly imprinted dispersive solid phase extraction coupled with liquid chromatography–ultraviolet detection is proposed as a selective and fast clean-up technique for the determination of sertraline in biological sample. Surface sertraline-molecular imprinted polymer was grafted and synthesized on the SiO2/graphene oxide surface. Firstly SiO2 was coated on synthesized graphene oxide sheet using sol-gel technique. Prior to polymerization, the vinyl group was incorporated on to the surface of SiO2/graphene oxide to direct selective polymerization on the surface. Methacrylic acid, ethylene glycol dimethacrylate and ethanol were used as monomer, cross-linker and progen, respectively. Non-imprinted polymer was also prepared for comparing purposes. The properties of the molecular imprinted polymer were characterized using field emission-scanning electron microscopy and Fourier transform infrared spectroscopy methods. The surface molecular imprinted polymer was utilized as an adsorbent of dispersive solid phase extraction for separation and preconcentration of sertraline. The effects of the different parameters influencing the extraction efficiency, such as sample pH were investigated and optimized. The specificity of the molecular imprinted polymer over the non-imprinted polymer was examined in absence and presence of competitive drugs. Sertraline calibration curve showed linearity in the ranges 1–500 µg L-1. The limits of detection and quantification under optimized conditions were obtained 0.2 and 0.5 µg L-1. The within-day and between-day relative standard deviations (n=3) were 4.3 and 7.1%, respectively. Furthermore, the relative recoveries for spiked biological samples were above 92%.

Keywords


1. McEvory G.K., Litvak K., Welsh O.H. “Sertraline”. In DrugInformation, American Hospital Formulary Service: Bethesda, 1995.

2. Jain D.S., Sanyal M., Subbaiah G., Pande U.C., Shrivastav P., 2005. Rapid and sensitive method for the determination of sertraline in human plasma using liquid chromatography–tandem mass spectrometry (LC–MS/MS). J Chromatogr B. 829, 69-74.

3. Kim M.K., Jung H.B., Choi H.M., Woo S.J., Paeng K.J., Chung C.B., 2002. Rapid and sensitive determination of sertraline in human plasma using gas chromatography–mass spectrometry. J Chromatogr B. 769, 333-339.

4. Khraiwesh A., Papoutsis I., Nikolaou P., Pistos C., Spiliopoulou C., Athanaselis S., 2011. Development and validation of an EI-GC/MS method for the determination of sertraline and its major metabolite desmethyl-sertraline in blood. J Chromatogr B. 879, 2576-2582.

5. Huang S.W., Hsieh M.M., Chang Y.S., 2012. Sensitive determination of sertraline by capillary electrophoresis with dispersive liquid–liquid microextraction and field-amplified sample stacking. Talanta. 101, 460-464.

6. Beltran A., Caro E., Marce R.M., Cormack P.A.G., Sherrington D.C., Borrul F., 2007. Synthesis and application of a carbamazepine-imprinted polymer for solid-phase extraction from urine and wastewater. Anal Chim Acta. 597, 6-11.

7. Schaller D., Hilder E.F., Haddad P.R., 2006. Separation of antidepressants by capillary electrophoresis with in-line solid-phase extraction using a novel monolithic adsorbent. Anal Chim Acta. 556, 104-111.

8. Mandrioli R., Addolorata Saracino M., Ferrari S., Berardi D., Kenndler E., Augusta Raggi M., 2006. HPLC analysis of the second-generation antidepressant sertraline and its main metabolite N-desmethylsertraline in human plasma, J Chromatogr B. 836, 116-119.

9. Beltran A., Marce R.M., Cormack P.A.G., Borrull F., 2009. Synthesis by precipitation polymerisation of molecularly imprinted polymer microspheres for the selective extraction of carbamazepine and oxcarbazepine from human urine. J Chromatogr A. 1216, 2248-2253.

10. Duan Z.J., Fan L.P., Fang G.Z., Yi J.H., Wang S.J., 2011, Novel surface molecularly imprinted sol-gel polymer applied to the online solid phase extraction of methyl-3-quinoxaline-2-carboxylic acid and quinoxaline-2-carboxylic acid from pork muscle. Anal Bioanal Chem. 401, 2291-2299.

11. Yin Y.M., Chen X.F., Wang X.F., Liu Y., Liu H.L., Xie M.X., 2012. Dummy molecularly imprinted polymers on silica particles for selective solid-phase extraction of tetrabromobisphenol A from water samples. J Chromatogr A. 1220, 7-13.

12. Gao R.X., Kong X.A., Su F.H., He X.W., Chen L.X., Zhang Y.K., 2010. Synthesis and evaluation of molecularly imprinted core-shell carbon nanotubes for the determination of triclosan in environmental water samples. J Chromatogr A. 1217, 8095-8102.

13. Lasakova M., Jandera P., 2009. Molecularly imprinted polymers and their application in solid phase extraction. J Sep Sci. 32, 799-812.

14. Alexander C., Andersson H.S., Andersson L.I., Ansell R.J., Kirsch N., Nicholls I.A., 2006. Molecular imprinting science and technology. J Mol Recognit. 19, 106-180.

15. 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.

16. Turiel E., Martin-Esteban A., 2010. Molecularly imprinted polymers for sample preparation. Anal Chim Acta. 668, 87-99.

17. Shaikh H., Memon N., Khan H., Bhanger M.I., Nizamani S.M., 2012. Preparation and characterization of molecularly imprinted polymer for di (2-ethylhexyl) phthalate: Application to sample clean-up prior to gas chromatographic determination. J Chromatogr A. 1247, 125-133.

18. Fan Y.B., Yin Y.M., Jiang W.B., Chen Y.P., Yang J.W., Wu J., Xie M.X., 2014. Simultaneous determination of ten steroid hormones in animal origin food by matrix solid-phase dispersion and liquid chromatography-electrospray tandem mass spectrometry. Food Chem. 142, 170-177.

19. He J., Lv R., Zhu J., Lu K., 2010. Selective solid-phase extraction of dibutyl phthalate from soybean milk using molecular imprinted polymers. Anal Chim Acta. 661, 215-221.

20. He J., Lv R., Cheng J., Li Y., Xue J., Lu K., Wang F., 2010. Preparation and characterization of molecularly imprinted microspheres for dibutyl phthalate recognition in aqueous environment. J Sep Sci. 33, 3409-3414.

21. Lai J.P., Yang M.L., Niessner R., Knopp D., 2007. Molecularly imprinted microspheres and nanospheres for di(2-ethylhexyl)phthalate prepared by precipitation polymerization. Anal Bioanal Chem. 389, 405-412.

22. Song X., Li J., Xu S., Ying R., Ma J., Liao C., Liu D., Yu J., Chen L., 2012. Determination of 16 polycyclic aromatic hydrocarbons in seawater using molecularly imprinted solid-phase extraction coupled with gas chromatography-mass spectrometry. Talanta.  99, 75-82.

23. Tamayo F.G., Turiel E., Martin-Esteban A., 2007. Molecularly imprinted polymers for solid-phase extraction and solid-phase microextraction: recent developments and future trends. J Chromatogr A. 1152, 32-40.

24. Xu S., Lu H., Li J., Song X., Wang A., Chen L., Han Sh., 2013. Dummy Molecularly Imprinted Polymers-Capped CdTe Quantum Dots for the Fluorescent Sensing of 2, 4, 6-Trinitrotoluene. ACS Appl Mater Interfaces. 5, 8146-8154.

25. Singh V., Joung D., Zhai L., Das S.I. Khondaker S., Seal S., 2011. Graphene based materials: past, present and future. Prog Mater Sci. 56, 1178-1271.

26. Han Q., Wang Z., Xia J., Xia L., Chen S., Zhang X., Ding M., 2013. Graphene as an efficient sorbent for the SPE of organochlorine pesticides in water samples coupled with GC–MS. J Sep Sci. 36, 3586-3591.

27. Wang Z., Han Q., Xia J., Xia L., Ding M., Tang, 2013. Graphene-based solid-phase extraction disk for fast separation and preconcentration of trace polycyclic aromatic hydrocarbons from environmental water samples. J Sep Sci. 36, 1834-1842.

28. Han Q., Wang Z., Xia J., Zhang X., Wang H., Ding M., 2014. Application of graphene for the SPE clean-up of organophosphorus pesticides residues from apple juices. J Sep Sci. 37, 99-105.

29. Khalilian F., Amiri Hanzaki S., Yousefi M., 2015. Synthesis of a graphene-based nanocomposite for the dispersive solid-phase extraction of vancomycin from biological samples. J Sep Sci. 38, 975-981.

30. Zhang B.T., Zheng X., Li H.F., Lin J.M., 2013.
Application of carbon-based nanomaterials in sample preparation. Anal Chim Acta. 784, 1-17.

31. Su Sh., Chen B., He M., Hu B., 2014. Graphene oxide-silica composite coating hollow fiber solid phase microextraction online coupled with inductively coupled plasma mass spectrometry for the determination of trace heavy metals in environmental water samples. Talanta. 123, 1-9.

32. Halas N.J., 2008. Nanoscience under glass: the versatile chemistry of silica nanostructures. ACS Nano. 2, 179-183.

33. Li X., Chen Y., Mo S., Jia L., Shao X., 2014. Effect of surface modification on the stability and thermal conductivity of water-based SiO2-coated graphenenanofluid. Thermochim Acta. 595, 6-10.

34. Staudenmaier L., 1898. Verfahrenzurdarstellung der graphitsaure. Ber-Dtsch Chem Ges. 31, 1481-1487.

35. Goa Y., Yip H.L., Chen K.Sh., O’ Malley K.M., Acton O., Sun Y., Ting G., Chen H., Jen A.K., 2011, Surface Doping of Conjugated Polymers by Graphene Oxide and Its Application for Organic Electronic Devices. Adv Mater. 23, 1903-1908.

36. Zeng Y., Zhou Y., Kong L., Zhou T., Shi G., 2013. A novel composite of SiO2-coated graphene oxide and molecularly imprinted polymers for electrochemical sensing dopamine. Biosens Bioelectron. 45, 25-33.

37. Xue Y., Liu Y., Lu F., Qu J., Chen H., Dai L., 2012. Functionalization of graphene oxide with polyhedral oligomericsilsesquioxane (poss) for multifunctional applications. J Phys Chem Lett. 3, 1607-1612. 

38. Stankovich S., piner R.D., Nguyen S.T., Ruoff R.S., 2006. Synthesis and exfoliation of iso carbon-treated grapheme oxide nanoplatelets, Carbon. 44, 3342-3347.

40. Djozan D., Mahkam M., Ebrahimi B., 2009. Preparation and binding study of solidphasemicroextraction fiber on the basis of ametryn-imprinted polymer application to the selective extraction of persistent triazine herbicides in tap water, rice, maize and onion. J Chromatogr A. 1216, 2211-2219.

41. Sellergren B., Molecularly Imprinted Polymers Man Made Mimics of Antibodies and their Application in Analytical Chemistry, Elsevier Science: Amsterdam, 2003.

42. He L., Feng F., Wu J., 2005. Determination of Sertraline in Human Plasma by High-Performance Liquid Chromatography–Electrospray Ionization Mass Spectrometry and Method Validation. J Chromatogr Sci. 43, 532-535.

43. Rodríguez Flores J., Maria Conten to Salcedo A., Muñoz Fernández L., 2011. Rapid HPLC Method for Monitoring Relevant Residues of Pharmaceuticals Products in Environmental Samples. Am J Anal Chem. 2, 18-26.