Int. J. Mol. Sci. 2013, 14(7), 13022-13041; doi:10.3390/ijms140713022
Article

β-Cyclodextrin Inclusion Complex to Improve Physicochemical Properties of Pipemidic Acid: Characterization and Bioactivity Evaluation

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Received: 13 May 2013; in revised form: 8 June 2013 / Accepted: 13 June 2013 / Published: 25 June 2013
(This article belongs to the Section Bioactives and Nutraceuticals)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The aptitude of cyclodextrins (CDs) to form host-guest complexes has prompted an increase in the development of new drug formulations. In this study, the inclusion complexes of pipemidic acid (HPPA), a therapeutic agent for urinary tract infections, with native β-CD were prepared in solid state by kneading method and confirmed by FT-IR and 1H NMR. The inclusion complex formation was also characterized in aqueous solution at different pH via UV-Vis titration and phase solubility studies obtaining the stability constant. The 1:1 stoichiometry was established by a Job plot and the inclusion mechanism was clarified using docking experiments. Finally, the antibacterial activity of HPPA and its inclusion complex was tested on P. aeruginosa, E. coli and S. aureus to determine the respective EC50s and EC90s. The results showed that the antibacterial activity of HPPA:β-CD against E. coli and S. aureus is higher than that of HPPA. Furthermore, HPPA and HPPA:β-CD, tested on human hepatoblastoma HepG2 and MCF-7 cell lines by MTT assay, exhibited, for the first time, antitumor activities, and the complex revealed a higher activity than that of HPPA. The use of β-CD allows an increase in the aqueous solubility of the drug, its bioavailability and then its bioactivity.
Keywords: β-cyclodextrin; pipemidic acid; inclusion complex; microbial activity; antitumoral activity
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MDPI and ACS Style

Iacovino, R.; Rapuano, F.; Caso, J.V.; Russo, A.; Lavorgna, M.; Russo, C.; Isidori, M.; Russo, L.; Malgieri, G.; Isernia, C. β-Cyclodextrin Inclusion Complex to Improve Physicochemical Properties of Pipemidic Acid: Characterization and Bioactivity Evaluation. Int. J. Mol. Sci. 2013, 14, 13022-13041.

AMA Style

Iacovino R, Rapuano F, Caso JV, Russo A, Lavorgna M, Russo C, Isidori M, Russo L, Malgieri G, Isernia C. β-Cyclodextrin Inclusion Complex to Improve Physicochemical Properties of Pipemidic Acid: Characterization and Bioactivity Evaluation. International Journal of Molecular Sciences. 2013; 14(7):13022-13041.

Chicago/Turabian Style

Iacovino, Rosa; Rapuano, Filomena; Caso, Jolanda V.; Russo, Agostino; Lavorgna, Margherita; Russo, Chiara; Isidori, Marina; Russo, Luigi; Malgieri, Gaetano; Isernia, Carla. 2013. "β-Cyclodextrin Inclusion Complex to Improve Physicochemical Properties of Pipemidic Acid: Characterization and Bioactivity Evaluation." Int. J. Mol. Sci. 14, no. 7: 13022-13041.


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