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Quantitation of naproxen by quenching of phosphorescence from a ternary complex of 2-bromo-6-methoxynaphthalene and α-cyclodextrin

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Abstract

A unique method, based on the measurement of phosphorescence lifetimes, is reported for use in analytically detecting the widely used anti-inflammatory drug naproxen. The reciprocal phosphorescence lifetime of a ternary complex containing α-cyclodextrin and 2-bromo-6-methoxynaphthalene increases linearly with naproxen concentration and has a quenching constant of 2.1 ± 0.05 × 106 M−1 s−1. Similar behavior is observed for quenching by the sodium salt of naproxen that has a quenching constant of 1.8 × 106 ± 0.05 M−1 s−1. The experimental sensitivity is sufficient to permit measurements of naproxen concentrations differing by 11 μg/ml. Phosphorescence lifetime measurements reveal that the quenching mechanism does not involve displacement of the unrelaxed triplet-state guest molecule by naproxen from the complex and may occur by energy transfer or electron transfer.

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References

  1. Dromgoole, S.H., Furst, D.E.: Drugs for Rheumatic Disease. In: Paulus, H.E., Furst, D.E., Dromgoole, S.H. (eds.) Drugs for Rheumatic Disease, pp. 347–364. Churchill Livingstone, New York (1987)

  2. Ward, J.R.: Nonsteroidal (nonsalicylate) anti-inflammatory drugs. In: Roth, S.H., Callabro, J.J., Paulus, H.E., Wilkens, R.F. (eds.) Rheumatic Therapeutics, pp. 383–396. McGraw-Hill, New York (1985)

  3. Kearney, P.M., Baigent, C., Godwin, J., Halls, H., Emberson, J.R., Patrono, C.: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis meta-analysis of randomized trials. Br. Med. J. 332(7553), 1302–1305 (2006)

    Article  CAS  Google Scholar 

  4. Markku, A.: Fluorometric determination of naproxen in serum. J. Pharm. Sci. 66, 433–434 (1977)

    Article  Google Scholar 

  5. Fernández-Sánchez, J.F., Segura-Carretero, A., Cruces-Blanco, C., Fernández-Gutiérrez, A.: Room-temperature luminescence optosensings based on immobilized active principles actives. Application to nafronyl and naproxen determination in pharmaceutical preparations and biological fluids. Anal. Chim. Acta 462, 217–224 (2002)

    Article  Google Scholar 

  6. Rapido Martinez, I., Villanueva Camañas, R.M., Garcia-Alvarez-Coque, M.C.: Micelle-stabilized room-temperature phosphorimetric procedure for the determination of naproxen and propranolol in pharmaceutical preparations. Analyst 119, 1093–1097 (1994)

    Article  Google Scholar 

  7. Arancibia, J.A., Escandar, G.M.: Determination of naproxen in pharmaceutical preparations by room-temperature phosphorescence. A comparative study of several organized media. Analyst 126, 917–922 (2001)

    Article  CAS  Google Scholar 

  8. Carretero, A.S., Cruces-Blanco, C., Ramirez, M.I., Diaz, G.B.C., Fernández-Gutiérrez, A.: Simple and rapid determination of the drug naproxen in pharmaceutical preparations by heavy atom-induced room temperature phosphorescence. Talanta 50, 401–407 (1999)

    Article  Google Scholar 

  9. Cline Love, L.J., Grayeski, M.L., Noroski, J.: Room-temperature phosphorescence, sensitized phosphorescence and fluorescence of licit and illicit drugs enhanced by organized media. Anal. Chim. Acta 170, 3–12 (1985)

    Article  Google Scholar 

  10. Hamai, S.J.: Room-temperature phosphorescence of 6-bromo-2-naphthol included by α-cyclodextrin in aqueous solution. J. Chem. Soc., Chem. Commun. 2243–2244 (1994)

  11. Hamai, S.J.: Inclusion complexes and the room-temperature phosphorescence of 6-bromo-2-naphthol in aerated aqueous solution of α-cyclodextrin. J. Phys. Chem. 99, 12109–12114 (1995)

    Article  CAS  Google Scholar 

  12. Grabner, G., Rechthaler, K., Mayer, B., Köhler, G., Rotkiewicz, K.: Solvent influences on the photophysics of naphthalene: fluorescence and triplet state properties in aqueous solutions and in cyclodextrin complexes. J. Phys. Chem. A 104, 1365–1376 (2000)

    Article  CAS  Google Scholar 

  13. Brewster, R.E., Teresa, B.F., Schuh, M.D.: Inclusion complexes of 6-bromo-2-naphthol (guest) and α-cyclodextrin (host): Thermodynamics of the binary complex and first-reported dynamics of a triplet-state guest/host2 complex. J. Phys. Chem. A 107, 10521–10526 (2003)

    Article  CAS  Google Scholar 

  14. Brewster, R.E., Kidd, M.J., Schuh, M.D.: Optical thermometer based on the stability of a phosphorescent 6-bromo-2-naphthol/α-cyclodextrin2 ternary complex. J. Chem. Soc., Chem. Commun. 1134–1135 (2001)

  15. Martinez, L.J., Scaiano, J.C.: Characterization of the transient intermediates generated from the photosensitization of nabumetone: A comparison with naproxen. Photochem. Photobiol. 68, 646–651 (1998)

    Article  CAS  Google Scholar 

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Acknowledgement

This research was supported by the National Science Foundation under grant number 0240213 for which the authors express their gratitude.

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  1. Department of Chemistry, Davidson College, POB 7120, Davidson, NC, 28035-7120, USA

    R. Owen Bussey III & Merlyn D. Schuh

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  1. R. Owen Bussey III
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  2. Merlyn D. Schuh
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Correspondence to Merlyn D. Schuh.

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Bussey, R.O., Schuh, M.D. Quantitation of naproxen by quenching of phosphorescence from a ternary complex of 2-bromo-6-methoxynaphthalene and α-cyclodextrin. J Incl Phenom Macrocycl Chem 57, 163–167 (2007). https://doi.org/10.1007/s10847-006-9202-2

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  • DOI: https://doi.org/10.1007/s10847-006-9202-2

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