Abstract
In this paper, the influence of inclusion complexation with β-cyclodextrin (β-CD) on the photostability of antazoline, xylometazoline, and naphazoline in aqueous media was investigated. The photodegradation reaction of these drugs molecules was explored using UV–vis spectrophotometery-based kinetic analysis and high performance liquid chromatography (HPLC). Quantitative evaluation of the influence of β-CD was judged based on the observed rate constant (k obs), half-life time (t 0.5) and t 0.1 of the photodegradation reaction and the peak area of the corresponding analyte after photodegradation using HPLC separation. It has been demonstrated that the photostability of these selected imidazoline-based drugs has been enhanced upon forming inclusion complexes with β-CD in aqueous media. Moreover, high consistency regarding the photostability enhancement was obtained using both techniques. Hypothetical structure for 1:1 inclusion complexes was proposed based on molecular mechanics calculations, which in turn provide an insight for the energetically preferential structure of the inclusion complexes. The results obtained demonstrate that β-CD can be utilized as photostabilizer additive for enhancing the photostability of imidazoline-derived drugs molecules.
Similar content being viewed by others
References
Damiani, E., Tursilli, R., Casolari, A., Astolfi, P., Greci, L., Scalia, S.: Effect of complexation with randomly methylated β-cyclodextrin on the aqueous solubility, photostability and antioxidant activity of an indolinonic nitroxide radical. Free Radic. Res. 39, 41 (2005). doi:10.1080/10715760400023689
Ragnoa, G., Cione, F., Garofalo, A., Genchi, G., Ioele, G., Risoli, A., et al.: Design and monitoring of photostability systems foramlodipine dosage forms. Int. J. Pharm. 265, 125 (2003). doi:10.1016/j.ijpharm.2003.07.001
Valero, M., Esteban, B.: Effect of binary and ternary polyethylene glycol and/or β-cyclodextrin complexes on the photochemical and photosensitizing properties of Naproxen. J. Photochem. Photobiol. B Biol. 74, 151 (2004). doi:10.1016/j.jphotobiol.2004.03.004
Cosa, G.: Photodegradation and photosensitization in pharmaceutical products: assessing drug phototoxicity. Pure Appl. Chem. 76, 263 (2004). doi:10.1351/pac200476020263
Bayomi, M.A., Abanumay, K.A., Al-Angary, A.A.: Effect of inclusion complexation with cyclodextrins on photostability of nifedipine in solid state. Int. J. Pharm. 243, 107 (2002). doi:10.1016/S0378-5173(02)00263-6
Ahmad, I., Fasihullah, Q., Vaid, F.H.M.: Effect of light intensity and wavelengths on photodegradation reactions of riboflavin in aqueous solution. J. Photochem. Photobiol. B Biol. 82, 21 (2006). doi:10.1016/j.jphotobiol.2005.08.004
Tønnesen, H.H.: Formulation and stability testing of photolabile drugs. Int. J. Pharm. 225, 1 (2001). doi:10.1016/S0378-5173(01)00746-3
Desai, D.S., Abdelnasser, M.A., Rubitski, B.A., Varia, S.A.: Of uncoated tablets of sorivudine and nifedipine by incorporation of synthetic iron oxides. Int. J. Pharm. 103, 69 (1994). doi:10.1016/0378-5173(94)90204-6
Glass, B.D., Brown, M.E., Daya, S., Worthington, M.S., Drummond, P., Antunes, E., et al.: Influence of cyclodextrins on the photostability of selected drug molecules in solution and the solid-state. Int. J. Photoenergy 3, 205 (2001). doi:10.1155/S1110662X01000277
Biloti, D.N., Dos Reis, M.M., Ferreira, C., M.M, Pessine, F.B.T.: Photochemical behavior under UVA radiation of β-cyclodextrin included Parsol 1789 with a chemiometric approach. J. Mol. Struct. 480, 557 (1999). doi:10.1016/S0022-2860(98)00822-9
Brisaert, M., Gabriëls, M., Matthijs, V., Plaizier-Vercammen, J.: Liposomes with tretinoin: a physical and chemical evaluation. J. Pharm. Biomed. Anal. 26, 909 (2001). doi:10.1016/S0731-7085(01)00502-7
Cannors, K.A.: The stability of cyclodextrin complexes in aqueous solutions. Chem. Rev. 97, 1326 (1997)
Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743 (1998). doi:10.1021/cr970022c
Dodziuk, H.: Cyclodextrins and their complexes: chemistry, analytical methods, applications. Wiley, Weinheim (2006)
Petrusewicz, J., Kaliszan, R.: Human blood platelet alpha adrenoceptor in view of the effects of various imidazol(in)e drugs on aggregation. Gen. Pharm. 22, 819 (1991)
Parini, A., Moudanos, C.G., Pizzinat, N., Lanier, S.M.: The elusive family of imidazoline binding sites. Trends Pharmacol. Sci. 17, 13 (1996). doi:10.1016/0165-6147(96)81564-1
Kaliszan, W., Petrusewicz, J., Kaliszan, R.: Imidazoline receptors in relaxation of acetylcholine-constricted isolated rat jejunum. Pharm. Rep. 58, 700 (2006)
Sortino, S., Giuffrida, S., Scaiano, J.C.: Phototoxicity of naphazoline evidence that hydrated electrons, nitrogen-centered radicals, and OH radicals trigger DNA damage: a combined photocleavage and laser flash photolysis study. Chem. Res. Toxicol. 12, 971 (1997). doi:10.1021/tx9900526
Tanaka, M., Ohkubo, K., Fukuzumi, S.: Reductive DNA cleavage Induced by UVA photoirradiation of NADH without oxygen. J. Am. Chem. Soc. 128, 12372 (2006). doi:10.1021/ja065073i
Bosca, F., Miranda, M.: Photosensitizing drugs containing the benzophenone chromophore. J. Photochem. Photobiol. B Biol. 43, 1 (1998). doi:10.1016/S1011-1344(98)00062-1
Sortino, S., Cosa, G., Scaiano, J.C.: pH Effect on the efficiency of the photodeactivation pathways of naphazoline: a combined steady state and time resolved study. New J. Chem. 24, 59 (2000). doi:10.1039/b000712i
Dawoud, A.A., Al-Rawashdeh, N.F.: Spectrofluorometric, thermal, and molecular mechanics studies of the inclusion complexation of selected imidazoline-derived drugs with β-cyclodextrin in aqueous media. J. Incl. Phenom. Macrocycl. Chem. 60, 293 (2008). doi:10.1007/s10847-007-9377-1
Albini, A., Fasani, E. (eds.): Drugs photochemistry and photostability. Royal Society of Chemistry, Cambridge, UK (1998)
Tønnesen, H.H. (ed.): Photostability of drugs and drug formulations. CRC Press, Boca Raton, FL, USA (2004)
Acknowledgement
The financial support from the Graduate College of Scientific Research/Jordan University of Science and Technology is gratefully acknowledged. Also, we extend our appreciation to Al-Hekma Pharmaceuticals Co. and Amman Pharmaceutical Industries Co. for generously providing the drugs molecules used in this study.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Bani-Yaseen, A.D., Al-Rawashdeh, N.F. & Al-Momani, I. Influence of inclusion complexation with β-cyclodextrin on the photostability of selected imidazoline-derived drugs. J Incl Phenom Macrocycl Chem 63, 109–115 (2009). https://doi.org/10.1007/s10847-008-9493-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-008-9493-6