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

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

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 (CC BY 3.0).

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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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