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Open AccessArticle

Alpha- and Beta-Cyclodextrin Inclusion Complexes with 5-Fluorouracil: Characterization and Cytotoxic Activity Evaluation

Department of Environmental, Biological and Pharmaceutical Sciences and Technologies, Second University of Naples, via Antonio Vivaldi 43, 81100 Caserta, Italy
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Bernard Martel
Molecules 2016, 21(12), 1644;
Received: 10 November 2016 / Revised: 24 November 2016 / Accepted: 25 November 2016 / Published: 1 December 2016
(This article belongs to the Special Issue Cyclodextrin Chemistry)
Cyclodextrins are natural macrocyclic oligosaccharides able to form inclusion complexes with a wide variety of guests, affecting their physicochemical and pharmaceutical properties. In order to obtain an improvement of the bioavailability and solubility of 5-fluorouracil, a pyrimidine analogue used as chemotherapeutic agent in the treatment of the colon, liver, and stomac cancers, the drug was complexed with alpha- and beta-cyclodextrin. The inclusion complexes were prepared in the solid state by kneading method and characterized by Fourier transform-infrared (FT-IR) spectroscopy and X-ray powder diffractometry. In solution, the 1:1 stoichiometry for all the inclusion complexes was established by the Job plot method and the binding constants were determined at different pHs by UV-VIS titration. Furthermore, the cytotoxic activity of 5-fluorouracil and its complexation products were evaluated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay on MCF-7 (breast cancer cell line), Hep G2 (hepatocyte carcinoma cell line), Caco-2 (colon adenocarcinoma cell line), and A-549 (alveolar basal epithelial carcinoma cell line). The results showed that both inclusion complexes increased the 5-fluorouracil capability of inhibiting cell growth. In particular, 5-fluorouracil complexed with beta-cyclodextrin had the highest cytotoxic activity on MCF-7; with alpha-cyclodextrin the highest cytotoxic activity was observed on A-549. The IC50 values were equal to 31 and 73 µM at 72 h, respectively. Our results underline the possibility of using these inclusion complexes in pharmaceutical formulations for improving 5-fluorouracil therapeutic efficacy. View Full-Text
Keywords: cyclodextrin; 5-fluorouracil; inclusion complex; cytotoxicity cyclodextrin; 5-fluorouracil; inclusion complex; cytotoxicity
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Di Donato, C.; Lavorgna, M.; Fattorusso, R.; Isernia, C.; Isidori, M.; Malgieri, G.; Piscitelli, C.; Russo, C.; Russo, L.; Iacovino, R. Alpha- and Beta-Cyclodextrin Inclusion Complexes with 5-Fluorouracil: Characterization and Cytotoxic Activity Evaluation. Molecules 2016, 21, 1644.

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