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Molecules 2012, 17(5), 6056-6070; doi:10.3390/molecules17056056
Article

Physicochemical Characterization and Cytotoxic Activity Evaluation of Hydroxymethylferrocene:β-Cyclodextrin Inclusion Complex

1,* , 1
, 2
, 1
, 3
, 3
, 1
 and 1
1 Department of Environmental Science, Second University of Naples, via A.Vivaldi 43, 81100 Caserta, Italy 2 Department of Biological and Environmental Science, University of Sannio, via Port'Arsa, 11, 82100 Benevento, Italy 3 Department of Life Sciences, Second University of Naples, via A.Vivaldi 43, 81100 Caserta, Italy
* Author to whom correspondence should be addressed.
Received: 24 April 2012 / Revised: 14 May 2012 / Accepted: 15 May 2012 / Published: 21 May 2012
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Abstract

An inclusion complex of hydroxymethylferrocene (FeMeOH) with β-cyclodextrin (β-CD) was prepared in the solid state by different techniques such as physical mixture, coprecipitation, kneading and freeze-drying. The formation of the inclusion complex was confirmed by X-ray Powder Diffractometry and Fourier Transform-Infrared spectroscopy. In aqueous solution, the 1:1 stoichiometry was established by a Job plot. The inclusion complex formation was also investigated by NMR and the stability constant (Kb) of the complex was determined to be 478 M−1, which is in agreement with that obtained with UV-Vis tritation (Kb = 541.3 M−1). The phase solubility study showed a diagram classified as BS type and that the solubility of FeMeOH was slightly increased in the presence of β-CD. Furthermore, utilizing phase solubility diagram data, the Kb was estimated to be equal to 528.0 M−1. The cytotoxic activity of FeMeOH and its complexation product with β-CD was determined using the MTT-assay on MDA-MB-231 cell line, showing that the inclusion complex has a higher capability of inhibiting cell growth compared to that of pure FeMeOH.
Keywords: β-cyclodextrin; hydroxymethylferrocene; inclusion complex; stability constant; phase solubility diagram; cytotoxicity β-cyclodextrin; hydroxymethylferrocene; inclusion complex; stability constant; phase solubility diagram; cytotoxicity
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.

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MDPI and ACS Style

Iacovino, R.; Caso, J.V.; Rapuano, F.; Russo, A.; Isidori, M.; Lavorgna, M.; Malgieri, G.; Isernia, C. Physicochemical Characterization and Cytotoxic Activity Evaluation of Hydroxymethylferrocene:β-Cyclodextrin Inclusion Complex. Molecules 2012, 17, 6056-6070.

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