Novel Analytical Study For The Charge-Transfer Reactions Of Omeprazole With 2,3-Dichloro-Naphthoquinone And 2,3,5,6-Tetrabromo- 1,4-Benzoquinone: Application For The Development Of Microwell Assay Of Omeprazole
DOI:
https://doi.org/10.24297/jac.v15i1.7003Keywords:
Omeprazole, 2,3-dichloronaphthoquinone, bromanil, Charge-transfer complexes, KineticsAbstract
Novel analytical study was performed in order to develop and validate new high-throughput microwell-based spectrophotometric assays for determination of omeprazole (OMZ) in its pharmaceutical formulations. The proposed assays were based on the charge-transfer (CT) reaction of OMZ with 2,3-dichloronaphthoquinone (DCNQ) and 2,3,5,6-tetrabromo-1,4-benzo-quinone (BROM). In the present study, the CT reactions was carried out in microwell plates as reaction vessels in order to increase the automation of the assays and the efficiency of its use in quality control laboratories (QCLs). All factors affecting the CT reactions were carefully studied, and the conditions were optimized. Kinetics and stoichiometry of the CT reactions were investigated, and the mechanism was postulated. Activation energy of the CT reactions was determined and found to be 13.87 and 16.27 Kcal mol−1 for the reaction of OMZ with DCNQ and BROM, respectively. The initial rate and fixed time methods were applied for generating the calibration graphs for determination of OMZ concentrations. Under the optimum conditions, the linear range was 0.145 – 1.45 x 10-4 and 1.45 – 7.25 x 10-4 M with LOD of 0.6 and 6.0 microgram ml-1 for DCNQ and BROM, respectively. Analytical performance of the proposed methods, in terms of accuracy and precision, was statistically validated and the results were satisfactory; RSD was <2.8% for both repeatability and reproducibility. The proposed methods were successfully applied to the analysis of OMZ in its dosage forms and the recovery results (98.64 – 100.6 ± 0.25 -2.74 %) were comparable with those of the reported method. The developed method may provide a safer and economic tool for the analysis of OMZ in QCLs.
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References
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[2] Bosch. M. E., Ruiz. S., A. J., S´anchez. R. F. and Bosch. O. C. Analytical methodologies for the determination of omeprazole: an overview. J Pharm Biomed Anal. 44: 831–844 (2007).
[3] Yoshida. N., Yoshikawa. T., Tanaka. Y., Fujita. N., Kassai. K., Naito. Y. and Kondo. M. Aliment Pharmacol Ther. 14: 74–81 (2000).
[4] United States Pharmacopeia 24 United States Pharmacopeial Convention The Board of Trustess. p 1217 (2000).
[5] Ahmed. S. and Atia. N. N. Simultaneous determination of triple therapy for Helicobacter pylori in human plasma by reversed phase chromatography with online wavelength switching Spectrochim. Acta A Mol Biomol Spectrosc.136: 1380-1387 (2015).
[6] Nalwade. S. U., Reddy. V. R., Rao. D. D. and Morisetti. N. K. A validated stability indicating ultra-performance liquid chromatographic method for determination of impurities in Esomeprazole magnesium gastro resistant tablets. J Pharm Biomed Anal. 57: 109-14 (2012).
[7] Gor. P., Alnouti. Y. and Reed. G A. Buspirone fexofenadine and omeprazole: quantification of probe drugs and their metabolites in human plasma. J Pharm Biomed Anal. 55: 1127-35 (2011).
[8] Barreiro. J. C., Vanzolini. K. L., Madureira. T. V., Tiritan. M. E. and Cass. Q. B. A column-switching method for quantification of the enantiomers of omeprazole in native matrices of waste and estuarine water samples. Talanta. 82: 384-91 ( 2010).
[9] Rambla-Alegre. M., Esteve-Romero. J. and Carda-Broch. S. Analysis of omeprazole and its main metabolites by liquid chromatography using hybrid micellar mobile phases. Anal Chim Acta. 633: 250-6 (2009).
[10] Ma. J., Wang. S., Zhang. M., Zhang. Q., Zhou. Y., Lin. C., Lin. G. and Wang. X. Simultaneous determination of bupropion metroprolol midazolam phenacetin omeprazole and tolbutamide in rat plasma by UPLC-MS/MS and its application to cytochrome P450 activity study in rats. Biomed Chromatogr .29: 1203–1212 doi: 10 1002/bmc 3409 (2015).
[11] Gopinath. S., Kumar. R. S., Shankar. M. B. and Danabal. P. Development and validation of a sensitive and high-throughput LC-MS/MS method for the simultaneous determination of esomeprazole and naproxen in human plasma. Biomed Chromatogr. 27: 894-9 (2013).
[12] Li. Z., Yao. J., Zhang. Z. and Zhang. L. Simultaneous determination of omeprazole and domperidone in dog plasma by LC-MS method. J Chromatogr Sci. 47: 881-4 (2009).
[13] Nevado. J. J., Peñalvo. G. C., Dorado. R. M. and Robledo. V. R. Simultaneous determination of omeprazole and their main metabolites in human urine samples by capillary electrophoresis using electrospray ionization-mass spectrometry detection. J Pharm Biomed Anal. 92: 211-9 (2014).
[14] Estevez. P., Flor. S., Boscolo. O., Tripodi. V. and Lucangioli. S. Development and validation of a capillary electrophoresis method for determination of enantiomeric purity and related substances of esomeprazole in raw material and pellets Electrophoresis. 35: 804-10 (2014).
[15] Qaisi. A. M., Tutunji. M. F. and Tutunji. L. F. Acid decomposition of omeprazole in the absence of thiol: a differential pulse polarographic study at the static mercury drop electrode (SMDE). J Pharm Sci. 95: 384–391 (2006).
[16] Shahrokhian. S., Ghalkhani. M., Bayat. M. and Ghorbani-Bidkorbeh. F. Voltammetric Behavior and Determination of Trace Amounts of Omeprazole Using an Edge-plane Pyrolytic Graphite Electrode Iran J Pharm Res. 14: 465-71 (2015).
[17] Shaghaghi. M., Manzoori. J. L. and Jouyban. A. Indirect spectrofluorometric determination of omeprazole by its quenching effect on the fluorescence of Tb3+-110-phenanthroline complex in presence of bis (2-ethylhexyl) sulfosuccinate sodium in capsule formulations. DARU. 16: 256-260 (2008).
[18] Peralta. C. M., Fernandez. L. P. and Masi. A. N. Precision improvement for omeprazole determination through stability evaluation Drug Test Analysis. 4: 48–52 (2012).
[19] Mahmoud. A. and Ahmed. S. A validated high-throughput fluorimetric method for determination of omeprazole in quality control laboratory via charge transfer sensitized fluorescence. J Fluorescence. 26: 521-529 (2016).
[20] Dhumal. S. N., Dikshit. P. M., Ubharay. I. I., Mascarcuhas. B. M. and Gaitonde. C. U. Individual UV-spectrophotometric assays of trazodone hydrochloride and omeprazole from separate pharmacetical dosages Indian Drugs. 28: 565–567 (1991).
[21] Sastry. C. S. P., Naidu. P. Y. and Murty. S. S. N. Spectrophotometric methods for the determination of omeprazole in bulk form and pharmaceutical formulations. Talanta. 44: 1211–1217 (1997). [22] El-Kousy. N. M. and Bebawy. L. I. Stability-indicating methods for determining omeprazole and octylonium bromide in the presence of their degradation products. J AOAC Int. 82: 599–606 (1999).
[23] Salama. F., El-Abasawy. N., Abdel Razeq. S. A., Ismail. M. M. F. and Fouad. M. M. Validation of the spectrophotometric determination of omeprazole and pantoprazole sodium via their metal chelates. J Pharm Biomed Anal. 33: 411–421 (2003).
[24] Lotfy. H. M. and Hagazy. M. A. Comparative study of novel spectrophotometric methods manipulating ratio spectra: an application on pharmaceutical ternary mixture of omeprazole tinidazole and clarithromycin Spectrochim. Acta A. 96: 259-70 (2012).
[25] Mahmoud. A. M. New sensitive kinetic spectrophotometric methods for determination of omeprazole in dosage forms . Int J Anal Chem. 2009: 1-11 (2009).
[26] Crouch. S. R., Cullen. T. F., Scheeline. A. and Kirkor. E. S. Kinetic Determinations and Some Kinetic Aspects of Analytical Chemistry. Anal Chem. 70: 53R-106R (1998).
[27] Kuznetsov. A. M. and Ulstrup. J. Electron Transfer in Chemistry and Biology: An Introduction to the Theory John Wiley & Sons New York. (1999).
[28] Pandeswaran. M. and Elango. K. P. Spectroscopic studies on the interaction of cimetidine drug with biologically significant r- and p-acceptors Spectrochim. Acta Part A. 75: 1462–1469 http:// dx doi org/10 1016/j saa 2010 01 017 (2010).
[29] Pandeeswaran. M. and Elango. K. P. Spectroscopic studies on the molecular complex of the drug atenolol with iodine. J Solution Chem. 38: 1558–1572 http://dx doi org/10 1007/s10953-009-9467-3 (2009).
[30] Foster. R. Organic Charge Transfer Complexes Academic Press New York USA. (1969).
[31] Khashaba. P. Y., El-Shabouri. S. R., Emara. K. M. and Mohamed. A. M. J Pharm Biomed Anal. 22: 363–376 (2000).
[32] Bebawy. L., El Kelani. K., Abdel Fattah. L. and Ahmad. A. Study of 77'88'-tetracyanoquinodimethane charge transfer complexes with some n-donating drugs. J Pharm Sci. 86 1030-1033 (1997).
[33] El-Kousy. N. M. and Bebawy. L. I. Stability-indicating methods for determining omeprazole and octylonium bromide in the presence of their degradation products. J AOAC Int. 82: 599–606 (1999).
[34] International Conference on Harmonization ICH guideline Q2 (R1): Validation of Analytical Procedures: Text and Methodology London. (2005).
[35] Darwish. I. A. Kinetic spectrophotometric methods for determination of trimetazidine dihydrochloride. Anal Chim Acta. 551: 222–231 (2005 ).
[36] Taha. A. and Rücker. G. Utility of π-Acceptors in Alkaloid Assay. Arch Pharm. 310: 485-489 (1977).
[37] Darwish. I. A., Mahmoud. A. M. and Majed. A. R. A novel analytical approach for reducing the consumption of organic solvents in the charge transfer-based spectrophotometric analysis: Application in the analysis of certain antihypertensive drugs. Acta Pharmaceutica. 60: 493–501 (2010).
[38] Vogel’s Textbook of Practical Organic Chemistry. 5th edition Longman group UK Ltd England. pp 1442-1444 (1989).
[39] Dwivedi. P. C., Banga. A. K. and Gupta. A. Spectroscopic studies on the interaction of cimetidine drug with biologically significant σ- and π-acceptors Electrochim. Acta. 28: 801 (1983).
[40] Job. P. Ann Chem. (1936). 16: 97 In “Advanced Physicochemical Experiments†2nd edition Oliner and Boyd Edinburgh. P 54 (1964 ).
[41] Martin. A. N., Swarbrick. J. and Cammarata. A. Physical Pharmacy third ed Lee and Febiger Philadelphia. pp 371-374 344–346 (1983).
[42] Benesi. H. A. and Hildebrand. J. J Am Chem Soc. (1949). 71: 2703 through Physical Pharmacy fourth ed Lea & Febiger Philadelphia London. pp 266–267 (1993).
[43] Ewing. G. W. In Instrumental methods of chemical analysis 5th ed Lippincott-Raven Philadelphia. pp 484-486 (1995).
[44] Heyden. Y. V., Nijhuis. A., Smeyers-Verbeke. J., Vandeginste. B. G. M. and Massart. D. L. Guidance for robustness/ruggedness tests in method validation. J Pharm Biomed Anal. 24: 723-753 (2004).
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Published
2018-03-12
How to Cite
Alkahtania, S. A., Mahmoud, A. M., & Al-Rubb, S. S. A. (2018). Novel Analytical Study For The Charge-Transfer Reactions Of Omeprazole With 2,3-Dichloro-Naphthoquinone And 2,3,5,6-Tetrabromo- 1,4-Benzoquinone: Application For The Development Of Microwell Assay Of Omeprazole. JOURNAL OF ADVANCES IN CHEMISTRY, 15(1), 6099–6115. https://doi.org/10.24297/jac.v15i1.7003
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