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Abstract
A sensitive time-resolved luminescence method for the determination of flubiprofen (FLP) in methanol and in aqueous solution is described. The method is based on the luminescence sensitization of terbium (Tb3+ ) by the formation of a ternary complex with FLP in the presence of 4,7 diphenyl 1,10 phenanthroline (DPP) as co-ligand, and Tween-20 as surfactant. The signal for Tb-FLP-DPP was monitored at λex = 285 nm and λem = 552 nm. Optimum conditions for the formation of the complex in an aqueous system were TRIS buffer, pH 8.0, DPP (2.5Å~10−7 M), Tween-20 (0.30%) and 4Å~10-5 mol L-1 of Tb3+ which allowed the determination of 20–1000 ng mL-1 of FLP with a limit of detection (LOD) of 10 ng mL-1 . The relative standard deviations of the method ranged between 0.6 and 1.4% indicating excellent reproducibility of the method. The proposed method was successfully applied for the assays of FLP in pharmaceutical formulations and spiked tap water samples with average recoveries of 87% – 95%.
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References
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- Chen, Y., Sun, J., Huang, Z., Liao, H., Peng, S., Lehmann, J. and Zhang, Y. Design, synthesis and evaluation of tacrine–flubiprofen–nitrate trihybrids as novel anti-Alzheimer’s disease agents. Bio. Med. Chem., 2013, 21, 2462-2470.
- Al-Obaid, A.M. and Moian, M.S. Analytical Profiles of Drug Substances and Experiments” Vol. 22, Ed. Britair, H.G. Academic Press, New York, 1993, p431.
- Sajeev, C., Jadhav, P.R., RaviShankar, D. and Saha, R.N. Determination of flubiprofen in pharmaceutical formulations by UV spectrophotometry and liquid chromatography. Anal. Chim. Acta, 2002, 463, 207-217.
- Jin, Y.X., Tang, Y.H. and Zeng, S. Analysis of flubiprofen, ketoprofen and etodolac enantiomers by precolumn derivatization RP-HPLC and application to drug-protein binding in human plasma. J. Pharm. Biomed. Anal. 2008, 46, 953-958.
- Guo C.C, Tang,Y.H., Hu, H.H, Yu, L.U., Jiang, H.H. and Zeng, S. Analysis of chiral non-steroidal antiinflammatory drugs flubiprofen, ketoprofen and etodolac binding with HAS. J. Pharm. Anal., 2011, 1, 184- 190.
- Kumirska, J., Plenis, A., Łukaszewicz, P., Caban, M., Migowska,N., Białk-Bielińska, A., Czerwicka, M. and Stepnowski, P. Chemometric optimization of derivatization reactions prior to gas chromatography-mass spectrometry analysis. J. Chromatogr. A, 2013, 1296, 164-178.
- Mei, J., Xu, J.R., Xiao, Y.R., Zhang, Q.R. and Feng, Y.Q., Immobilized phospholipid capillary electrophoresis for study of drug–membrane interactions and prediction of drug activity. Talanta, 2008, 75, 104-110.
- Arnoud, N. and Georges, J. Investigation of the luminescence properties of terbium-anthranilate complexes and applications to the determination of anthranilic acid derivatives in aqueous solutions. Anal. Chim. Acta, 2003, 476, 149-157.
- Panadero, S., Gómez-Hens, A. and Pérez-Bendito, D. Kinetic determination of salicylic acid, diflunisal and their mixture based on lanthanide-sensitized luminescence. Anal. Chim. Acta, 1996, 329, 135-149.
- Agüilar-Caballos, M.P. Gòmez-Henz, A. and Pèrez-Bendito, D. Simultaneous determination of benzoic acid and saccharin in soft drinks by using lanthanide-sensitized luminescence. Analyst, 1999, 124, 1079-1085.
- Caro de la Torre, M.A. and Gömez-Henz, A. Evaluation of terbium(III) sensitized luminescence with benzenepolycarboxylic acids: determination of terepthalic acid in drinks samples. Anal. Chim. Acta, 2000, 407, 53-60.
- Al-Kindy, S.M.Z. and Suliman F.E.O. Determination of ibuprofen in pharmaceutical formulations using terbium sensitized luminescence. Lumin., 2007, 22, 294-301.
- Al-Kindy, S.M.Z., Al-Harasi Z., Suliman F.E.O., Al-Hamadi A. and Pillay A. Terbium sensitized luminescence for the determination of ketoprofen in pharmaceutical formulations. J. Fluoresc., 2009, 19, 249- 255.
- Lis, S. Analytical applications of lanthanide luminescence in solution Chem.Anal. (Warsaw), 1993, 38, 443- 454.
- Steemers, F.J., Verboom,W., Renihoudt, D.N., Vander, E.B. and Verhoeven, J.W. New sensitizer-modified calixarenes enabling near-UV excitation of complexed luminescent lanthanide ions. J. Am. Chem. Soc., 1995, 117, 9408-9414.
- Werts, M.H.V., Hofstraat, J.H., Geurts, F.A.J. and Verhoeven, J.W. Fluorescein and eosin as sensitizing chromophores in near-infrared luminescent ytterbium(III), neodymium(III) and erbium(III) chelates. Chem. Phys. Lett., 1997, 276, 196-201.
- Dang, F., Li, Y. and Liu, W. The new fluorescence enhancement system Tb-N-(2-pyridinyl) ketoacetamide- Et3N-Zn and its application. Spectro. Chim. Acta A, 2007, 66, 676-680.
- Qin, W., Zhang, Y., Liu, W. and Tan, M. Synthesis and infrared and fluorescence spectral properties of luminescent terbium and europium complexes with open-chain carboxylate crown ethers. Spectro. Chim. Acta A, 2003, 59, 3085-3092.
- Ansari, A.A., Singh, N., Khan, A.F., Singh, S.P. and Iftikhar, K. Solvent effect on optical properties of hydrated lanthanide tris–acetylacetone. J. Lumin., 2007, 127, 446-452.
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References
Cipriano, M., Björklund, E., Wilson, A., Congiu, C., Onnis, V. and Fowler, C.J. Inhibition of fatty acid amide hydrolase and cyclooxygenase by the N-(3-methylpyridin-2-yl)amide derivatives of flubiprofen and naproxen. Eur. J. Pharm., 2013, 720, 383-390.
Chen, Y., Sun, J., Huang, Z., Liao, H., Peng, S., Lehmann, J. and Zhang, Y. Design, synthesis and evaluation of tacrine–flubiprofen–nitrate trihybrids as novel anti-Alzheimer’s disease agents. Bio. Med. Chem., 2013, 21, 2462-2470.
Al-Obaid, A.M. and Moian, M.S. Analytical Profiles of Drug Substances and Experiments” Vol. 22, Ed. Britair, H.G. Academic Press, New York, 1993, p431.
Sajeev, C., Jadhav, P.R., RaviShankar, D. and Saha, R.N. Determination of flubiprofen in pharmaceutical formulations by UV spectrophotometry and liquid chromatography. Anal. Chim. Acta, 2002, 463, 207-217.
Jin, Y.X., Tang, Y.H. and Zeng, S. Analysis of flubiprofen, ketoprofen and etodolac enantiomers by precolumn derivatization RP-HPLC and application to drug-protein binding in human plasma. J. Pharm. Biomed. Anal. 2008, 46, 953-958.
Guo C.C, Tang,Y.H., Hu, H.H, Yu, L.U., Jiang, H.H. and Zeng, S. Analysis of chiral non-steroidal antiinflammatory drugs flubiprofen, ketoprofen and etodolac binding with HAS. J. Pharm. Anal., 2011, 1, 184- 190.
Kumirska, J., Plenis, A., Łukaszewicz, P., Caban, M., Migowska,N., Białk-Bielińska, A., Czerwicka, M. and Stepnowski, P. Chemometric optimization of derivatization reactions prior to gas chromatography-mass spectrometry analysis. J. Chromatogr. A, 2013, 1296, 164-178.
Mei, J., Xu, J.R., Xiao, Y.R., Zhang, Q.R. and Feng, Y.Q., Immobilized phospholipid capillary electrophoresis for study of drug–membrane interactions and prediction of drug activity. Talanta, 2008, 75, 104-110.
Arnoud, N. and Georges, J. Investigation of the luminescence properties of terbium-anthranilate complexes and applications to the determination of anthranilic acid derivatives in aqueous solutions. Anal. Chim. Acta, 2003, 476, 149-157.
Panadero, S., Gómez-Hens, A. and Pérez-Bendito, D. Kinetic determination of salicylic acid, diflunisal and their mixture based on lanthanide-sensitized luminescence. Anal. Chim. Acta, 1996, 329, 135-149.
Agüilar-Caballos, M.P. Gòmez-Henz, A. and Pèrez-Bendito, D. Simultaneous determination of benzoic acid and saccharin in soft drinks by using lanthanide-sensitized luminescence. Analyst, 1999, 124, 1079-1085.
Caro de la Torre, M.A. and Gömez-Henz, A. Evaluation of terbium(III) sensitized luminescence with benzenepolycarboxylic acids: determination of terepthalic acid in drinks samples. Anal. Chim. Acta, 2000, 407, 53-60.
Al-Kindy, S.M.Z. and Suliman F.E.O. Determination of ibuprofen in pharmaceutical formulations using terbium sensitized luminescence. Lumin., 2007, 22, 294-301.
Al-Kindy, S.M.Z., Al-Harasi Z., Suliman F.E.O., Al-Hamadi A. and Pillay A. Terbium sensitized luminescence for the determination of ketoprofen in pharmaceutical formulations. J. Fluoresc., 2009, 19, 249- 255.
Lis, S. Analytical applications of lanthanide luminescence in solution Chem.Anal. (Warsaw), 1993, 38, 443- 454.
Steemers, F.J., Verboom,W., Renihoudt, D.N., Vander, E.B. and Verhoeven, J.W. New sensitizer-modified calixarenes enabling near-UV excitation of complexed luminescent lanthanide ions. J. Am. Chem. Soc., 1995, 117, 9408-9414.
Werts, M.H.V., Hofstraat, J.H., Geurts, F.A.J. and Verhoeven, J.W. Fluorescein and eosin as sensitizing chromophores in near-infrared luminescent ytterbium(III), neodymium(III) and erbium(III) chelates. Chem. Phys. Lett., 1997, 276, 196-201.
Dang, F., Li, Y. and Liu, W. The new fluorescence enhancement system Tb-N-(2-pyridinyl) ketoacetamide- Et3N-Zn and its application. Spectro. Chim. Acta A, 2007, 66, 676-680.
Qin, W., Zhang, Y., Liu, W. and Tan, M. Synthesis and infrared and fluorescence spectral properties of luminescent terbium and europium complexes with open-chain carboxylate crown ethers. Spectro. Chim. Acta A, 2003, 59, 3085-3092.
Ansari, A.A., Singh, N., Khan, A.F., Singh, S.P. and Iftikhar, K. Solvent effect on optical properties of hydrated lanthanide tris–acetylacetone. J. Lumin., 2007, 127, 446-452.
Rosen, M.J. Solubilization by solution surfactants: micellar catalysis. In Surfactants and Interfacial Phenomena, (3rd Edn.) Wiley: New York, 2004, 178-207.