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Effect of surface properties of mesoporous silica on adsorption of mesoionic compound molsidomine

Published online by Cambridge University Press:  17 October 2012

N.A. Alyoshina  and
E.V. Parfenyuk
N.A. Alyoshina
Affiliation:
G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, Ivanovo, 153045, Russia
E.V. Parfenyuk*
Affiliation:
G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, Ivanovo, 153045, Russia
*
a)Address all correspondence to this author. e-mail: evp@isc-ras.ru
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Abstract

Molsidomine is one of the sydnonimine class of antianginal drugs that due to its structure exhibits both dipolar nature and aromatic properties. To select efficient carrier for the drug, unmodified and modified mesoporous silica materials were synthesized using phenyltriethoxysilane and 3-aminopropyltriethoxysilane via cocondensation and grafting routes. Synthesis of the mesoporous silica materials via cocondensation was carried out in the presence of D-glucose as pore-forming agent. Equilibrium isotherms for the adsorption of mesoionic compound molsidomine on the mesoporous silica materials were analyzed by the Langmuir, Freundlich, Redlich-Peterson and Langmuir–Freundlich (Sips) models. Langmuir model is found to be the best to explain the equilibrium data. Comparative study of the adsorption properties of the unmodified and modified mesoporous silica materials demonstrated that the phenyl-modified silica materials are the most efficient adsorbents for molsidomine. They exhibit the highest adsorption capacity and affinity in relation to the mesoionic compound.

Keywords

adsorptionsurface chemistrybiomaterial
Type
Articles
Information
Journal of Materials Research , Volume 27 , Issue 22 , 22 November 2012 , pp. 2858 - 2866
Copyright
Copyright © Materials Research Society 2012

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References

REFERENCES

Vallet-Regi, M., Balas, F., and Acros, D.: Mesoporous materials for drug delivery. Angew. Chem. Int. Ed. 46, 7548 (2007).CrossRefGoogle ScholarPubMed
Slowing, I.I., Vivero-Escoto, J.L., Wu, C.W., and Lin, V.S-Y.: Mesoporous silica nanoparticles as controlled release drug delivery and gene transfection carriers. Adv. Drug Delivery Rev. 60, 1278 (2008).CrossRefGoogle ScholarPubMed
Rigby, S.P., Fairhead, M., and van der Walle, C.F.: Engineering silica particles as oral drug delivery vehicles. Curr. Pharm. Des. 14, 1821 (2008).CrossRefGoogle ScholarPubMed
Badami, B.V.: Mesoionic compounds. An unconventional class of aromatic heterocycles. Resonance 11, 40 (2006).CrossRefGoogle Scholar
Yashunskii, V.G. and Kholodov, L.E.: The chemistry of sydnone imines. Russ. Chem. Rev. 49, 28 (1980).CrossRefGoogle Scholar
Streel, B., Ceccato, A., Peerboom, C., Zimmer, C., Sibenaler, R., and Maes, P.: Determination of molsidomine and its active metabolite in human plasma using liquid chromatography with tandem mass spectrometric detection. J. Chromatogr. A 819, 113 (1998).CrossRefGoogle ScholarPubMed
Luliński, P. and Maciejewska, D.: Examination of imprinting process with molsidomine as a template. Molecules 14, 2212 (2009).CrossRefGoogle ScholarPubMed
Iler, R.K.: The Chemistry of Silica (Wiley, New York, 1979), p. 245.Google Scholar
Kim, J., Seidler, P., Wan, L.S., and Fill, C.: Formation, structure, and reactivity of amino-terminated organic films on silicon substrates. J. Colloid Interface Sci. 329, 114 (2009).CrossRefGoogle ScholarPubMed
Wei, Y., Xu, J., Dong, H., Dong, J.H., Qiu, K., and Jansen-Varnum, S.A.: Preparation and physisorption characterization of D-glucose-templated mesoporous silica sol-gel materials. Chem. Mater. 11, 2023 (1999).CrossRefGoogle Scholar
Dong, H.: Organic-inorganic hybrid mesoporous silica materials and their application as host matrix for protein molecules. Ph.D. Thesis, Drexel University, Philadelphia, PA, 2002.Google Scholar
Song, S-W., Hidajat, K., and Kawi, S.: Functionalized SBA-15 materials as carriers for controlled drug delivery: influence of surface properties on matrix-drug interactions. Langmuir 21, 9568 (2005).CrossRefGoogle ScholarPubMed
Wang, G., Otuonye, A.N., Blair, E.A., Denton, K., Tao, Z., and Asefa, T.: Functionalized mesoporous materials for adsorption and release of different drug molecules: A comparative study. J. Solid State Chem. 182, 1649 (2009).CrossRefGoogle Scholar
Yang, L., Weng, S., Ferraro, J.R., and Wu, J.: Far infrared study of some mono- and disaccharides. Vib. Spectrosc. 25, 57 (2001).CrossRefGoogle Scholar
Zhbankov, R.G., Andrianov, V.M., Ratajczak, C., and Marchewka, M.: Vibrational spectra and stereochemistry of mono- and polysaccharides. II. D-glucose and D-galactose α-anomers. Glucitol. Galactitol. Russ. J. Struct. Chem. 36, 430 (1995).Google Scholar
Slade, R.C.T., Bambrough, C.M., and Williams, R.T.: An incoherent inelastic neutron scattering investigation of the vibrational spectrum of phenyl-modified (C6H5–) mesoporous silica and its variations in the presence of sorbed benzene (C6H6) and of sorbed deuteriobenzene (C6D6). Phys. Chem. Chem. Phys. 4, 5394 (2002).CrossRefGoogle Scholar
Kitadai, N., Yokoyama, T., and Nakashima, S.: ATR-IR spectroscopic study of L-lysine adsorption on amorphous silica. J. Colloid Interface Sci. 329, 31 (2009).CrossRefGoogle ScholarPubMed
Sing, K.S.N., Everett, D.H., Haul, R.A.W., Moscou, L., Pierotti, R.A., Rouquerol, J., and Siemieniewska, T.: Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity (Recommendations 1984). Pure Appl. Chem. 57, 603 (1985).CrossRefGoogle Scholar
Rosenholm, J.M. and Lindén, M.: Towards establishing structure–activity relationships for mesoporous silica in drug delivery applications. J. Controlled Release 128, 157 (2008).CrossRefGoogle ScholarPubMed
Hughes, M.A.: The structure-function relationship of silica polyamine composites. Ph.D. Thesis, The University of Montana, Missoula, MT, 2007.Google Scholar
Aksu, Z., Idil Tatli, A., and Tunc, Ö.: A comparative adsorption/biosorption study of acid blue 161: Effect of temperature on equilibrium and kinetic parameters. Chem. Eng. J. 142, 23 (2008).CrossRefGoogle Scholar
Chen, Z., Pierre, D., Hea, H., Tanc, S., Pham-Huyd, C., Honga, H., and Huang, J.: Adsorption behavior of epirubicin hydrochloride on carboxylated carbon nanotubes. Int. J. Pharm. 405, 153 (2011).CrossRefGoogle ScholarPubMed
Liu, Z., Fan, A.C., and Rakhra, K.: Supramolecular stacking of doxorubicin on carbon nanotubes for in vitro cancer therapy. Angew. Chem. Int. Ed. 121, 7804 (2009).CrossRefGoogle Scholar
Hu, Q., Li, J.J., Hao, Z.P., Li, L.D., and Qiao, S.Z.: Dynamic adsorption of volatile organic compounds on organofunctionalized SBA-15 materials. Chem. Eng. J. 149, 281 (2009).CrossRefGoogle Scholar
Brühwiler, D.: Postsynthetic functionalization of mesoporous silica. Nanoscale 2, 887 (2010).CrossRefGoogle ScholarPubMed
Darga, A., Kecht, J., and Bein, T.: Probing the intrapore surface of phenyl-substituted nanoscale mesoporous silica piezoelectric sorption measurements in thin films. Langmuir 23, 12915 (2007).CrossRefGoogle ScholarPubMed
Parida, S.K., Dash, S., Patel, S., and Mishra, B.K.: Adsorption of organic molecules on silica surface. Adv. Colloid Interface Sci. 121, 77 (2006).CrossRefGoogle ScholarPubMed