Abstract
In this study, we used novel synthetic conditions of precipitation polymerization to obtain nanosized cyproterone molecularly imprinted polymers for application in the design of new drug delivery systems. The scanning electron microscopy images and Brunauer–Emmett–Teller analysis showed that molecularly imprinted polymer (MIP) prepared by acetonitrile exhibited particles at the nanoscale with a high degree of monodispersity, specific surface area of 246 m2 g−1, and pore volume of 1.24 cm3 g−1. In addition, drug release, binding properties, and dynamic light scattering of molecularly imprinted polymers were studied. Selectivity of MIPs was evaluated by comparing several substances with similar molecular structures to that of cyproterone. Controlled release of cyproterone from nanoparticles was investigated through in vitro dissolution tests and by measuring the absorbance by HPLC-UV. The pH dissolution media employed in controlled release studies were 1.0 at 37 °C for 5 h and then at pH 6.8 using the pH change method. Results show that MIPs have a better ability to control the cyproterone release in a physiological medium compared to the non molecularly imprinted polymers (NMIPs).
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References
Mosbach, K. (1994). Molecular imprinting. Trends in Biochemical Sciences, 19, 9–14.
Esfandyari-Manesh, M., Javanbakht, M., Atyabi, F., & Dinarvand, R. (2012). Synthesis and evaluation of uniformly sized carbamazepine-imprinted microspheres and nanospheres prepared with different mole ratios of methacrylic acid to methyl methacrylate for analytical and biomedical applications. Journal of Applied Polymer Science. doi:10.1002/app. 36288.
Tokonami, S., Shiigi, H., & Nagaoka, T. (2009). Review: micro- and nanosized molecularly imprinted polymers for high-throughput analytical applications. Analytica Chimica Acta, 641, 7–13.
Yang, G. L., Yin, J. F., & Li, Z. W. (2004). Chiral separation of nateglinide and its L-enantiomer on a molecularly imprinted polymer-based stationary phase. Chromatographia, 59, 705–708.
Ho, K. C., Yeh, W. M., Tung, T. S., & Liao, J. Y. (2005). Amperometric detection of morphine based on poly(3,4-ethylenedioxythiophene) immobilized molecularly imprinted polymer particles prepared by precipitation polymerization. Journal of Analytica Chimica Acta, 542, 90.
Javanbakht, M., Eynollahi Fard, S., Mohammadi, A., Abdouss, M., Ganjali, M. R., Norouzi, P., & Safaraliee, L. (2008). Molecularly imprinted polymer based potentiometric sensor for the determination of hydroxyzine in tablets and biological fluids. Analytica Chimica Acta, 612, 65.
Vallano, P. T., & Remcho, V. T. (2000). Highly selective separations by capillary electrochromatography: molecular imprint polymer sorbents. Journal of Chromatography. A, 887, 125.
Kamal, A., Kumar, B. A., Arifuddin, M., & Dastidar, S. G. (2003). Synthesis of 4β-amido and 4β-sulphonamido analogues of podophyllotoxin as potential antitumour agents. Bioorganic & Medicinal Chemistry, 11, 5135.
Puoci, F., Curcio, M., Cirillo, G., Lemma, F., Spizzirri, U. G., & Picci, N. (2008). Molecularly imprinted solid-phase extraction for cholesterol determination in cheese products. Food Chemistry, 106, 836.
Chen, W., Han, D. K., Ahn, K. D., & Kim, J. M. (2002). Molecularly imprinted polymers having amidine and imidazole functional groups as an enzyme-mimetic catalyst for ester hydrolysis. Macromolecular Research, 10, 122–126.
Suedee, R., Srichana, T., & Martin, G. (2000). Evaluation of matrices containing molecularly imprinted polymers in the enantioselective-controlled delivery of β-blockers. Journal of Controlled Release, 66, 135–147.
Sambe, H., Hoshina, K., Moadel, R., Wainer, W., & Haginaka, J. (2006). Uniformly-sized, molecularly imprinted polymers for nicotine by precipitation polymerization. Journal of Chromatography. A, 1134, 88–94.
Allender, C. J., Richardson, C., Woodhouse, B., Heard, C. M., & Brain, K. R. (2000). Pharmaceutical applications for molecularly imprinted polymers. International Journal of Pharmaceutics, 195, 39–43.
Ju, J. Y., Shin, C. S., Whitcombe, M. J., & Vulfson, E. N. (1999). Imprinted polymers as tools for the recovery of secondary metabolites produced by fermentation. Biotechnology and Bioengineering, 64, 232.
Alvarez-Lorenzo, C., & Concheiro, A. (2006). Molecularly imprinted materials as advanced excipients for drug delivery systems. Biotechnology Annual Review, 12, 225–268.
Hiratani, H., & Alvarez-Lorenzo, C. (2002). Timolol uptake and release by imprinted soft contact lenses made of N, N-diethylacrylamide and methacrylic acid. Journal of Controlled Release, 83, 223–230.
Alvarez-Lorenzo, C., & Concheiro, A. (2004). Molecularly imprinted polymers for drug delivery. Journal of Chromatography B, 804, 231–245.
Alvarez-Lorenzo, C., Yanez, F., Barreiro-Iglesias, R., & Concheiro, A. (2006). Imprinted soft contact lenses as norfloxacin delivery systems. Journal of Controlled Release, 113, 236–244.
Sellergren, B., & Allender, C. J. (2005). Molecularly imprinted polymers: a bridge to advanced drug delivery. Advanced Drug Delivery Reviews, 57, 1733–1741.
Wikimedia Foundation, Inc. (2012). Cyproterone. http://en.wikipedia.org/wiki/Cyproterone.
Azodi-Deilami, S., Abdouss, M., & Seyedi, S. R. (2010). Synthesis and characterization of molecularly imprinted polymer for controlled release of tramadol. Central European Journal of Chemistry, 8, 687–695.
Azodi-Deilami, S., Abdouss, M., & Javanbakh, M. (2011). The syntheses and characterization of molecularly imprinted polymer for controlled release of bromhexine. Applied Biochemistry and Biotechnology, 164, 133–147.
Abdouss, M., Asadi, E., Azodi-Deilami, S., Beik-Mohammadi, N., & Amir Aslanzadeh, S. (2011). Development and characterization of molecularly imprinted polymers for controlled release of citalopram. Journal of Materials Science. Materials in Medicine, 22, 2273–2281.
Azodi-Deilami, S., Abdouss, M., & Hasani, A. R. (2010). Preparation and utilization of a molecularly imprinted polymer for solid phase extraction of tramadol. Central European Journal of Chemistry, 8, 861–869.
Turchan, M., Jara-Ulloa, P., Bollo, S., Nunez-Vergara, L. J., Squella, J. A., & Alvarez-Lueje, A. (2007). Voltammetric behaviour of bromhexine and its determination in pharmaceuticals. Talanta, 73, 913.
Moffat, A. C. (2004). Clarkes analysis of drugs and poisons in pharmaceuticals (3rd ed., Vol. 2). London: Pharmaceutical.
Ciardelli, G., Cioni, B., Cristallini, C., Barbani, N., Silvestri, D., & Giusti, P. (2004). Acrylic polymeric nanospheres for the release and recognition of molecules of clinical interest. Biosensors and Bioelectronics, 20, 1083.
Martin, P., Jones, G. R., Stringer, F., & Wilson, I. D. (2003). Comparison of normal and reversed-phase solid phase extraction methods for extraction of beta-blockers from plasma using molecularly imprinted polymers. The Analysts Journal, 128, 345–350.
Nicholls, I. A. (1997). Combined hydrophobic and electrostatic interaction-based recognition in molecularly imprinted polymers. Recent Research in Development Pure and Applied Chemistry, 1, 133.
Mullet, W. M., Walles, M., Levsen, K., Borlak, J., & Pawliszyn, J. (2004). Multidimensional on-line sample preparation of verapamil and its metabolites by a molecularly imprinted polymer coupled to liquid chromatography–mass spectrometry. Journal of Chromatography B, 801, 297.
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Asadi, E., Azodi-Deilami, S., Abdouss, M. et al. Cyproterone Synthesis, Recognition and Controlled Release by Molecularly Imprinted Nanoparticle. Appl Biochem Biotechnol 167, 2076–2087 (2012). https://doi.org/10.1007/s12010-012-9748-y
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DOI: https://doi.org/10.1007/s12010-012-9748-y