Abstract
Adamantane drugs (e.g., memantine, rimantadine, and amantadine) consist of a core tricyclodecane with different substituents. Memantine is used for treatment of Alzheimer’s disease, while rimantadine and amantadine are recommended for influenza A infection. Additionally, amantadine is clinically used for Parkinson’s disease. Analysis of adamantine drugs by optical detection requires some derivatization due to the lack of chromophores or fluorophores in their structures. This procedure is performed to enhance their detectability, but it can be time- and labor-intensive. This work focuses on developments of a simple and fast technique for the analysis of these drugs in a microplate platform. Derivatization was achieved in 50 mM borate buffer (pH 11.0) using a stoichiometric ratio between the analyte and fluorescamine (as a derivatizing reagent) of 1:10 and a reaction time of 10 min. The fluorescent derivatives were determined in a 96-well microplate using excitation and emission wavelengths at 385 and 485 nm, respectively. The method showed good linearity (r2 > 0.968), repeatability (RSDs of < 2.6%), and accuracy (% recovery 96.2–101.1 with RSD < 4.5%) with acceptable limits of detection (< 3 µM) and quantitation (< 10 µM). The method was successfully applied for the determination of the drugs in pharmaceutical formulations.
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De Bernardo S, Weigele M, Toome V, Manhart K, Leimgruber W, Böhlen P et al (1974) Studies on the reaction of fluorescamine with primary amines. Arch Biochem Biophys 163(1):390–399. https://doi.org/10.1016/0003-9861(74)90490-1
Duh T-H, Wu H-L, Pan C-W, Kou H-S (2005) Fluorimetric liquid chromatographic analysis of amantadine in urine and pharmaceutical formulation. J Chromatogr A 1088(1):175–181. https://doi.org/10.1016/j.chroma.2005.04.011
Hsin-Hua Y, Yuan-Han Y, Su-Hwei C (2010) Simultaneous determination of memantine and amantadine in human plasma as fluorescein derivatives by micellar electrokinetic chromatography with laser-induced fluorescence detection and its clinical application. Electrophoresis 31(11):1903–1911. https://doi.org/10.1002/elps.201000001
Konda RK, Challa BR, Chandu BR, Chandrasekhar KB (2012) Bioanalytical method development and validation of memantine in human plasma by high performance liquid chromatography with tandem mass spectrometry: application to bioequivalence study. J Anal Methods Chem. https://doi.org/10.1155/2012/101249
Leis HJ, Windischhofer W (2012) Determination of memantine in human plasma by GC using negative ion chemical ionization MS detection after derivatization with a new reagent. Microchim Acta 178(3):309–314. https://doi.org/10.1007/s00604-012-0840-3
Mahmoud AM, Khalil NY, Darwish IA, Aboul-Fadl T (2009) Selective spectrophotometric and spectrofluorometric methods for the determination of amantadine hydrochloride in capsules and plasma via derivatization with 1,2-naphthoquinone-4-sulphonate. Int J Anal Chem. https://doi.org/10.1155/2009/810104
Mei-Fen X, Wei Z, Xin-Yi T, Yi-Le C, Yi C, Yan L et al (2011) High-performance liquid chromatographic determination of memantine hydrochloride in rat plasma using sensitive fluorometric derivatization. J Sep Sci 34(3):241–246. https://doi.org/10.1002/jssc.201000579
Michail K, Daabees H, Beltagy Y, Elkhalek MA, Khamis M (2013) High-performance liquid chromatographic determination of memantine in human urine following solid-phase extraction and precolumn derivatization. J AOAC Int 96(6):1302–1307. https://doi.org/10.1155/2015/672183
Michal D, Veronika P, David S (2016) Optimization of o-phtaldialdehyde/2-mercaptoethanol postcolumn reaction for the hydrophilic interaction liquid chromatography determination of memantine utilizing a silica hydride stationary phase. J Sep Sci 39(16):3145–3155. https://doi.org/10.1002/jssc.201600489
Prapatpong P, Prutthiwanasan B, Nuchtavorn N, Buranaphalin S, Suntornsuk L (2017) Brompheniramine as a novel probe for indirect UV detection and its application for the capillary electrophoresis of adamantane drugs. J Sep Sci 40(5):1184–1192. https://doi.org/10.1002/jssc.201601162
Sawant TB, Wakchaure VS, Rakibe UK, Musmade PB, Chaudhari BR, Mane DV (2017) The development and validation of novel, simple high-performance liquid chromatographic method with refractive index detector for quantification of memantine hydrochloride in dissolution samples. J Chromatogr Sci 55(6):603–609. https://doi.org/10.1093/chromsci/bmx013
Sobczak A, Muszalska I, Rohowska P, Inerowicz T, Dotka H, Jelinska A (2013) Determination of adamantane derivatives in pharmaceutical formulations by using spectrophotometric UV-Vis method. Drug Dev Ind Pharm 39(5):657–661. https://doi.org/10.3109/03639045.2012.684391
Suckow RF, Zhang MF, Collins ED, Fischman MW, Cooper TB (1999) Sensitive and selective liquid chromatographic assay of memantine in plasma with fluorescence detection after pre-column derivatization. J Chromatogr B 729(1):217–224. https://doi.org/10.1016/S0378-4347(99)00157-7
The British Pharmacopoeia Commission (2019) British pharmacopoeia. The Stationery Office, London
The United State Pharmacopeial Convention (2019) The United States Pharmacopeia 42 The National Formulary 37. Rockville, MD
Toker SE, Olcay S, Çetin SM, Armağan Ö (2011) A new HPLC method with fluorescence detection for the determination of memantine in human plasma. J Sep Sci 34(19):2645–2649. https://doi.org/10.1002/jssc.201100489
Wu Y-L, Chen R-X, Xue Y, Yang T, Zhao J, Zhu Y (2014) Simultaneous determination of amantadine, rimantadine and memantine in chicken muscle using multi-walled carbon nanotubes as a reversed-dispersive solid phase extraction sorbent. J Chromatogr B 965:197–205. https://doi.org/10.1016/j.jchromb.2014.06.038
Yun Y, Pan M, Fang G, Yang Y, Guo T, Deng J et al (2017) Molecularly imprinted electrodeposition o-aminothiophenol sensor for selective and sensitive determination of amantadine in animal-derived foods. Sens Actuators B Chem 238:32–39. https://doi.org/10.1016/j.snb.2016.06.165
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The authors would like to acknowledge the financial and technical support from Faculty of Pharmacy, Mahidol University.
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Nuchtavorn, N., Sudprasert, C., Yurai, P. et al. A simple and rapid microplate fluorescence determination of adamantanes in pharmaceutical formulations. Chem. Pap. 74, 1859–1865 (2020). https://doi.org/10.1007/s11696-019-01035-x
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DOI: https://doi.org/10.1007/s11696-019-01035-x