Abstract
A simple and highly sensitive method based on hollow fiber liquid phase microextraction combined with high-performance liquid chromatography and fluorescence detection has been developed for simultaneous separation, preconcentration, and determination of naproxen and nabumetone from water, wastewater, milk, and biological samples. Parameters affecting the microextraction efficiency were evaluated and optimized. Under optimum conditions (extractant (14 μL of 1-undecanol), sample pH (3.0), extraction time (20 min), stirring rate (600 rpm), temperature (45 °C), potassium chloride concentration (4.0 %) and sample volume (9 mL)), the limits of detection based on (S/N = 3) were 1.3 ng L−1 for naproxen and 2.9 ng L−1 for nabumetone. The intra- and inter-assay relative standard deviations for naproxen and nabumetone were in the ranges of 3.2–6.1 % and 6.5–9.5 %, respectively. The calibration curves were linear in concentration ranges of 4.0–300.0 ng L−1 and 9.0–300.0 ng L−1 for naproxen and nabumetone, respectively, with good coefficient of determination (r 2 > 0.999). The method was successfully applied to the determination of naproxen and nabumetone in cow milk, water, wastewater, human plasma, and urine samples.
Similar content being viewed by others
References
Adhoum N, Monser L, Toumi M, Boujlel K (2003) Determination of naproxen in pharmaceuticals by differential pulse voltammetry at a platinum electrode. Anal Chim Acta 495:69–75
Adlnasab L, Ebrahimzadeh H, Yamini Y, Mirzajani F (2010) Optimization of a novel method based on solidification of floating organic droplet by high-performance liquid chromatography for evaluation of antifungal drugs in biological samples. Talanta 83:370–378
Aguilar-Arteaga K, Rodriguez JA, Miranda JM, Medina J, Barrado E (2010) Determination of non-steroidal anti-inflammatory drugs in wastewaters by magnetic matrix solid phase dispersion–HPLC. Talanta 80:1152–1157
Alshana U, Goger NG, Ertas N (2013) Dispersive liquid–liquid microextraction combined with field-amplified sample stacking in capillary electrophoresis for the determination of non-steroidal anti-inflammatory drugs in milk and dairy products. Food Chem 138:890–897
Amiri Pebdani A, Haji Shabani AM, Dadfarnia S, Khodadoust S (2015) Solid phase microextraction of diclofenac using molecularly imprinted polymer sorbent in hollow fiber combined with fiber optic-linear array spectrophotometry. Spectrochim Acta, Part A 147:26–30
Aresta A, Carbonara T, Palmisano F, Zambonin CG (2006) Profiling urinary metabolites of naproxen by liquid chromatography–electrospray mass spectrometry. J Pharm Biomed Anal 41:1312–1316
Asadi M, Dadfarnia S, Haji Shabani AM, Abbasi B (2015a) Simultaneous extraction and quantification of lamotrigine, phenobarbital and phenytoin in human plasma and urine samples using solidified floating organic drop microextraction and high performance liquid chromatography. J Sep Sci 38:2510–2516
Asadi M, Haji Shabani AM, Dadfarnia S, Abbasi B (2015b) Solidified floating organic drop microextraction combined with high performance liquid chromatography for the determination of carbamazepine in human plasma and urine samples. Chin J Chromatogr 33:634–641
Bagheri H, Saber A, Mousavi SR (2004) Immersed solvent microextraction of phenol and chlorophenols from water samples followed by gas chromatography-mass spectrometry. J Chromatogr A 1046:27–33
Bordagaray A, Garcia-Arrona R, Millán E (2014) Determination of triazole fungicides in liquid samples using ultrasound-assisted emulsification microextraction with solidification of floating organic droplet followed by high-performance liquid chromatography. Food Anal Methods 7:1195–1203
Breitner JCS, Welsh KA, Helms MJ, Gaskell PC, Gau BA, Roses AD, Pericak-Vance MA, Saunders AM (1995) Delayed onset of Alzheimer’s disease with non-steroidal anti-inflammatory and histamine H2 blocking drugs. Neurobiol Aging 16:523–530
Campillo N, Vinas P, Ferez-Melgarejo G, Hernandez-Cordoba M (2013) Dispersive liquid–liquid microextraction for the determination of macrocyclic lactones in milk by liquid chromatography with diode array detection and atmospheric pressure chemical ionization ion-trap tandem mass spectrometry. J Chromatogr A 1282:20–26
Costi EM, Goryacheva I, Sicilia MD, Rubio S, Bendito DP (2008) Supramolecular solid-phase extraction of ibuprofen and naproxen from sewage based on the formation of mixed supramolecular aggregates prior to their liquid chromatographic/photometric determination. J Chromatogr A 1210:1–7
Dadfarnia S, Haji Shabani AM (2014) Choice of solvent in liquid-phase microextraction. In: Pena-Pereira F (ed) Miniaturization in sample preparation. De Gruyter Open Ltd, Warsaw/Berlin, pp 253–275
Dadfarnia S, Haji Shabani AM (2010) Recent development in liquid phase microextraction for determination of trace level concentration of metals—a review. Anal Chim Acta 658:107–119
Enteshari M, Mohammadi A, Nayebzadeh K, Azadniya E (2014) Optimization of headspace single-drop microextraction coupled with gas chromatography–mass spectrometry for determining volatile oxidation compounds in mayonnaise by response surface methodology. Food Anal Methods 7:438–448
Gallo P, Fabbrocino S, Dowling G, Salini M, Fiori M, Perretta G, Serpe L (2010) Confirmatory analysis of non-steroidal anti-inflammatory drugs in bovine milk by high-performance liquid chromatography with fluorescence detection. J Chromatogr A 1217:2832–2839
Gallo P, Fabbrocino S, Vinci F, Fiori M, Danese V, Serpe L (2008) Confirmatory identification of sixteen non-steroidal anti-inflammatory drug residues in raw milk by liquid chromatography coupled with ion trap mass spectrometry. Rapid Commun Mass Spectrom 22:841–854
Hossien-poor-Zaryabi M, Chamsaz M, Heidari T, Arbab Zavar MH, Behbahani M, Salarian M (2014) Application of dispersive liquid–liquid microextraction using mean centering of ratio spectra method for trace determination of mercury in food and environmental samples. Food Anal Methods 7:352–359
Hu T, Peng T, Li XJ, Chen DD, Dai HH, Deng XJ, Yue ZF, Wang GM, Shen JZ, Xia X, Ding SY, Zhou YN, Zhu AL, Jiang HY (2012) Simultaneous determination of thirty non-steroidal anti-inflammatory drug residues in swine muscle by ultra-high-performance liquid chromatography with tandem mass spectrometry. J Chromatogr A 1219:104–113
Jeannot MA, Cantwell FF (1996) Solvent microextraction into a single drop. Anal Chem 68:2236–2240
Ji Y, Du Z, Zhang H, Zhang Y (2014) Rapid analysis of non-steroidal anti-inflammatory drugs in tap water and drinks by ionic liquid dispersive liquid-liquid microextraction coupled to ultra-high performance supercritical fluid chromatography. Anal Methods 6:7294–7304
Keyhanian F, Alizadeh N, Fallah Shojaie A (2014) Spectrophotometric determination of naproxen as ion-pair with bromophenol blue in bulk, pharmaceutical preparation and human serum samples. Curr Chem Lett 3:15–22
Kobylinska K, Barlinska M, Kobylinska M (2003) Analysis of nabumetone in human plasma by HPLC. Application to single dose pharmacokinetic studies. J Pharm Biomed Anal 32:323–328
Mikami E, Goto T, Ohno T, Matsumoto H, Nishida M (2000) Simultaneous analysis of naproxen, nabumetone and its major metabolite 6-methoxy-2-naphthylacetic acid in pharmaceuticals and human urine by high-performance liquid chromatography. J Pharm Biomed Anal 23:917–925
Murillo Pulgarín JA, Alanon Molina A, Martínez Ferreras F (2012) Simultaneous determination of nabumetone and its principal metabolite in medicines and human urine by time-resolved fluorescence. Analyst (Cambridge, U K) 137:144–5152
Pan Z, Huang X, Zhong Y, Wang L, Zhu D, Li L (2015) Three-phase hollow-fiber microextraction combined with ion-pair high-performance liquid chromatography for the simultaneous determination of five components of compound α-ketoacid tablets in human urine. J Sep Sci 38:1499–1506
Pedersen-Bjergaard S, Rasmussen KE (1999) Liquid-liquid-liquid microextraction for sample preparation of biological fluids prior to capillary electrophoresis. Anal Chem 71:2650–2656
Pereira FP, Lavilla I, Bendicho C (2009) Miniaturized preconcentration methods based on liquid-liquid extraction and their application in inorganic ultratrace analysis and speciation: a review. Spectrochim Acta B 64:1–15
Phillips TM, Wellner EF (2006) Measurement of naproxen in human plasma by chip-based immunoaffinity capillary electrophoresis. Biomed Chromatogr 20:662–667
Santos JL, Aparicio I, Alonso E, Callejón M (2005) Simultaneous determination of pharmaceutically active compounds in wastewater samples by solid phase extraction and high-performance liquid chromatography with diode array and fluorescence detectors. Anal Chim Acta 550:116–122
Sarafraz-Yazdi A, Amiri A, Rounaghi G, Eshtiagh-Hosseini H (2012a) Determination of non-steroidal anti-inflammatory drugs in water samples by solid-phase microextraction based sol–gel technique using poly (ethylene glycol) grafted multi-walled carbon nanotubes coated fiber. Anal Chim Acta 720:134–141
Sarafraz-yazdi A, Assadi H, Es’haghi Z, Danesh NM (2012b) Preconcentration of non-steroidal anti-inflammatory drugs in water using dispersive liquid-liquid and single-drop microextraction with high-performance liquid chromatography. J Sep Sci 35:2476–2483
Shariati-Feizabadi S, Yamini Y, Bahramifar N (2003) Headspace solvent microextraction and gas chromatographic determination of some polycyclic aromatic hydrocarbons in water samples. Anal Chim Acta 489:21–31
Tao Y, Liu JF, Hu XL, Li HC, Wang T, Jiang GB (2009) Hollow fiber supported ionic liquid membrane microextraction for determination of sulfonamides in environmental water samples by high-performance liquid chromatography. J Chromatogr A 1216:6259–6266
Wu YL, Hu B (2009) Simultaneous determination of several phytohormones in natural coconut juice by hollow fiber-based liquid-liquid-liquid microextraction-high performance liquid chromatography. J Chromatogr A 1216:7657–7663
Yamini Y, Faraji M, Ghambarian M (2015) Hollow-fiber liquid-phase microextraction followed by gas chromatography flame ionization detection for the determination of amitraz in honey and water samples. Food Anal Methods 8:758–766
Yilmaz B, Sahin H, Erdem AF (2014) Determination of naproxen in human plasma by GC-MS. J Sep Sci 37:997–1003
Zhang Y, Xu H (2014) Determination of triazoles in tea samples using dispersive solid phase extraction combined with dispersive liquid-liquid microextraction followed by liquid chromatography–tandem mass spectrometry. Food Anal Methods 7:189–196
Zhou J, Zhang Q, Sun JB, Sun XL, Zeng P (2014) Two-phase hollow fiber liquid phase microextraction based on magnetofluid for simultaneous determination of echinacoside, tubuloside B, acteoside and isoacteoside in rat plasma after oral administration of cistanche salsa extract by high performance liquid chromatography. J Pharm Biomed Anal 94:30–35
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Funding
This study was not funded by any organization.
Conflict of Interest
Mohammad Asadi declares that he has no conflict of interest. Shayessteh Dadfarnia declares that she has no conflict of interest. Ali Mohammad Haji Shabani declares that he has no conflict of interest. Bijan Abbasi declares that he has no conflict of interest.
Ethical Approval
All applicable international, national, and/or institutional guidelines for the care and use of animals were followed. This article does not contain any studies with human participants performed by any of the authors.
Informed Consent
Not applicable.
Rights and permissions
About this article
Cite this article
Asadi, M., Dadfarnia, S., Haji Shabani, A.M. et al. Hollow Fiber Liquid Phase Microextraction Method Combined with High-Performance Liquid Chromatography for Simultaneous Separation and Determination of Ultra-Trace Amounts of Naproxen and Nabumetone in Cow Milk, Water, and Biological Samples. Food Anal. Methods 9, 2762–2772 (2016). https://doi.org/10.1007/s12161-016-0449-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12161-016-0449-y